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Bestselling author Fabrice Testa is an exponential thinker, innovator, serial tech entrepreneur, business angel investor, trusted advisor, public speaker, author, and highly sought-after mentor. He has successfully founded, co-founded, or participated in the launch of multiple companies that created hundreds of jobs and generated multi millions in revenue. 

He is the creator of the Superpreneur Blueprint framework and has developed a set of cutting-edge strategies and tactics that enable super-entrepreneurs to materialize crazy ideas, build breakthrough ventures, and solve the world’s biggest problems. After helping more than 100 companies excel in their fields, Testa is making this proven methodology publicly available in Super-Entrepreneurship Decoded to help super-entrepreneurs everywhere transform our lives—and the planet.

This was such dynamic and informative chat. I highly recommend the book (which I read multiple times because it was that good) so make sure to follow the links to grab a copy yourself. 

Super-Entrepreneurship Decoded: https://amzn.to/3pYlL6M 

Connect with Fabrice at https://fabricetesta.com 

Follow Fabrice on Social Media here:

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Super Entrepreneur Instagram

Transcript powered by Happy Scribe

Welcome to the show. My name is Eric Wright. I’m the host for your DiscoPosse podcast. I hope that you liked this one as much as I did when I recorded it with Fabrice Testa. Fabrice is an author, an entrepreneur or an investor, and somebody who genuinely is using technology and business to bring good to the world. It was such a fantastic opportunity to really delve into his book Super Entrepreneurship Decoded. I loved it so much that I actually read it multiple times in preparation for the interview, and it was just that good.

So you definitely got to get a copy. Hit the links that are on the website episode page. You can also hit us up on the YouTube definitely reach out. I’m going to be running a contest on my YouTube channel. If you want to get a copy of this book, drop me a comment on the YouTube channel. It’s YouTube.com/c/DiscoPossePodcast and I’m going to be giving away a bunch of copies of this fantastic book. So just check the YouTube page for the details on that one. All right.

And before, speaking of, how do we make stuff like that happen? It goes without saying that the fine folks that make this podcast happen include people like VM Software who have been longtime supporters and who I support because they have a fantastic set of products. As far as data protection goes, they got you covered. Everything you need for your data protection needs, whether it’s in the cloud, whether it’s in containerized platforms, whether it’s SAS, whether it’s on premises, virtualized, even physical servers, all that stuff needs to be backed up and needs to be saved from things like ransomware and all sorts of naughty things that are going on in the world.

So, it could just be Pete in accounting that accidentally deletes a file. It could be somebody who erases a team’s message that shouldn’t have gone away. So get that stuff protected. All right, just go to vee.am/DiscoPosse and it’s just that easy, vee.am/DiscoPosse. And speaking of protection, make sure you protect your data when it’s in transit as well. Easy way to do that is you can use great products like ExpressVPN. The reason why I use VPN is because I like to make sure that I can do my best to protect my identity, protect my data.

And also it’s just fantastic for web testing. If I need to test like, remote location to make sure that it works as expected from different regions. So it’s really, really great. I use ExpressVPN for that very purpose. If you want to check it out yourself, go to tryexpressvpn.com/DiscoPosse and you can get it for yourself. All right. This is Fabrice Testa. I hope you like the show. He is amazing. Get his book.

Hey. Hello. It’s Fabrice Testa and you are listening to DiscoPosse podcast.

This is perfect. What a great way to start the year. This is fantastic. So Fabrice, thank you very much. I’ve been engulfed in the school of Fabrice now for a while. I was really pleased when I had the opportunity to put you on as a potential guest. And I really enjoyed. First, I read your most recent book, which is the Super Entrepreneurship Decoded. Fantastic book. Went a lot through the rest of your history, of course. And leading up to that book, you have so much to bring and you’ve brought so much to the world already.

But for folks that are brand new and who don’t already know you. Fabrice, if you don’t mind, let’s just get a quick bio. We’ll talk about the book and a really good exploration of this concept of the superpreneur.

Yes. Thanks Eric, for welcoming me on this show. Yes. So I’m Fabrice Testa, and actually I’m Belgian. I have also some origins from Italy. So I live in Belgium, but I work mostly. My business is mostly in Luxembourg, so in Europe and I have, of course, travel all over the world during my career. And basically I’m an entrepreneur. So I co-funded different companies in the space sector in the digitalization. One of them achieved 100 million Euro turnover, 200 people. Then this company was sold and after that I funded also a company in the satellite service company, Luxembourg.

And after three years that company was also sold. And after the sale of this company, I had no new entrepreneurial projects. So I started some new life as an investor, a business center. So I did different investments again in different technologies, space, artificial intelligence, ICT, et cetera. And then, I started also to be a coach and mentor to help other entrepreneurs because I wanted to give back somehow and to help other entrepreneurs by sharing my experience. And let’s say those successful strategies and tactics that was working for me.

I also created by that time a blueprint that I call the Superpreneur Blueprint to help entrepreneurs to become what I call superpreneur. And maybe we will discuss more about this and to solve some big problems by materializing crazy ideas. And actually I met a young Dutch entrepreneur in 2017 and he came with a crazy idea. So for me it was the opportunity to also be again involved in a kind of superpreneur venture. So we co-founded with other people in 2019, the company called Maana Electric that is also mentioned in my book.

And now this company is working well. So today I spent my time between this company as a co-founder and shareholder. I also spent time mentoring, coaching, speaking at several events to explain this super entrepreneurship movement that I launched. And I wrote a book, this book, Super-Entrepreneurship Decoded, because I think that one thing was missing in the Superpreneur Blueprint. It was a method, because the Superpreneur Blueprint gives the core pillars, the guiding principles and the key characteristic of this kind of venture, but it was not telling how to do it.

And so I try to analyze what super entrepreneurs and super achievers, how they do it. What is their secret to succeed? Why others fail? And in the book, I unveil five secrets that I think can help entrepreneurs to maximize their chances of success. Of course, it’s not a guarantee of success, but I think it’s a way to maximize the chances of success. They put all these five secrets around a method that I call the crazy method. So that’s a bit of my story and the origin of the book.

I really appreciated the beautiful use of acronyms. So, we’ll talk about crazy as a method. People think, is he meaning literally crazy? But it’s a perfect pairing because it allows us to assign a memorable name to it. And it’s not far off of, you know, these real sort of crazy and moonshot type of ideas. If we take it in this literal sense of the word and then a pathway to execution that’s been tested and proven that you’re bringing this methodology, you’re bringing a framework to the world that you’ve lived and experienced, which is, I think, one of the best things that people need to appreciate about the book.

This is not a Harvard Airplane NBA guide that you read between New York and Boston flights. This is a lived experience that’s brought down and distilled into effective, meaningful steps that you can implement with great analogous references that are meaningful and helpful. And, of course, likes to bring your personal experience. I trust it. I think Nassim Taleb says the greatest way to be a philosopher King is to be a King first and then a philosopher second. Too many times these days, when you go through the business section or these sort of self help sections, it’s a lot of people who are straight from school and their PhD year was writing from research.

And while it’s a beautiful thing, ten years later, when they go back and revisit their early work, they’re like, ‘Oh, wow. I was naïve a lot of times in what was written’. Your book, first of all, tells a beautiful story. And like I mentioned before, we talked, it is you telling the story. It really comes through as a person telling me how to achieve this from their own experience. And I said, it’s a refreshing change because I’ve read a lot of books of this style that aim to do this, and they often come back as the same three things that I already sort of knew, and it’s a little bit reinforcing, but it was very well done.

So I honestly can’t talk enough. We’ll have links, of course, in all the show notes for people, they should absolutely pick up the book.

Thanks, Eric. I really appreciate it. It’s always nice to hear nice words like this, but I think I wrote the book as I would like to read a book, because I also read a lot of non fiction books, maybe between 50 and 60 books, you know, per year. I like book support, entrepreneurship, business, etc. Some are very good, and some, I think are less good because it’s true that there are a lot of, maybe they tend to have some frameworks, et cetera. But you don’t see really how to apply it.

And what I wanted with the book is to give a very simple framework because I think the framework is very simple in essence. Now the difficulty is to apply it in real life, and it’s why I provide in the book worksheets so that people can apply, let’s say the principles of the book, try to answer a lot of questions and try to put in practice the principles of the book. And it’s also why I’m just launching by end of this month, a companion course to the book, which will be called The Crazy Method Launch online course.

And it’s an online coaching program on twelve weeks. Every week there will be a module and we are mostly following, let’s say, the method which is in the book, but I’m going really to dive deep into each of them, which of course, I could not do with the book, because in the book you are obliged a bit to scratch the surface, unfortunately. Because the book will be indigenous and will be much too big. But with the course, I think the people will have really the opportunity to go really, to dive deep into the principles of the book, to put in actions the method that I propose in the book, and hopefully like this, they can really materialize their breakthrough potential.

They can really have a solid plan if, for example, they want to launch this kind of breakthrough venture that I’m suggesting in the book.

The thing that we need to look at, too, and that’s why I appreciated the references throughout and very specific stories that are called on from other parts of the industry as well, is the proof in execution elsewhere. Right. It gives us a chance to have a reason. Why is the book built to last? One of the most popular ones is because it’s five familiar brands that we know, and that familiarity breeds the belief that I can achieve it. There’s something to be said about this, but when you get into the moonshot areas and these very big ideas, it’s a little more difficult to find meaningful, real existing references.

Looking back now, it’s funny that in two years, three years, you’ll look through those stories in the book and they’ll be like it’ll seem obvious, but at the time when you’re writing this, of course, these are still moonshots. We look at Elon Musk, not just in a single moonshot, but in multiple ventures that he’s achieved. You, of course, coming from supporting and investing in space technologies and being in that ecosystem, there’s a lot of these sort of hidden, there’s a hidden world that’s existing that most people are not going to be aware of until it’s already on their phone or wherever it is.

They just take for granted all of this other work that’s happening to support the thing that makes the news or that makes the big story. So I just realized, too, by actually coincidence, I was wearing a SpaceX shirt. My wife and I are both space fanatics. And last time I got a chance, we actually went to watch the Delta Four Orion launch in Florida. It was fantastic. There’s nothing like an in-person launch. And being aware of how seemingly unrealistic that idea is to most people and why the super entrepreneur has to and is somehow able to put that aside and say, this needs to get done.

And despite advice and despite doubt, we’re going to do things to get back to like this, it can be done. So maybe let’s start there describe to me Fabrice, what is the super entrepreneur or the superpreneur?

Yes, I think it’s a good question indeed, to start somehow the conversation. What I call super entrepreneurs are people that they want to solve some big problems. Because I explained in the book that in 2007 we enter in what I call ‘The Edge of Exponential Acceleration’. So everything is really going very fast. Mostly technology is going exponentially, which is a good thing, because today we have many technologies that have achieved a good level of maturity, and they are used by this kind of innovators and inventors to build some amazing solutions.

But at the same time, problems are also accelerating at an exponential pace of change. If you look at climate change and unfortunately, you know, these disasters in Colorado, for example, I strongly believe that this is a consequence of climate change. And we see that we have now more wildfires, more flooding et cetera. In Belgium, for example, we have terrible flooding in the summer. So I think that we must do something. And unfortunately, most of the conventional solutions have proven their limits. So it’s time for radical solutions, what we call crazy ideas, crazy solutions, solutions that initially seem impossible.

But what I try to always explain is that today at the edge of exponential acceleration, nothing is really impossible. And at the edge of the exponential acceleration, impossible becomes possible. And this kind of entrepreneurs, I call them super entrepreneurs because they probably believe that nothing is really impossible. And they are ready to dedicate ten years, 20 years of their lifetime to solve such kind of big problems and to come with some amazing solution that will solve this problem. And, for example, to give a very concrete example to your audience.

There is, for example, this guy in the book that I described, Joseph Pescounty. He is Italian but living in Barcelona, in Spain, and he discovered that he could use some technology used for 3D print human tissues, et cetera. That he could use the same technology to 3D print food and so now he’s using this technology to 3D print food. Imagine that today is, of course, still a very small scale. But imagine that tomorrow he can build machines, he can scale these machines to produce tons of food and 3D print tons of food.

This could be really a big solution for solving hunger around the world, because today, unfortunately, in the world many people, they have only access to one meal per day. So I think at the 21st century, we are always saying we live extra ordinary times, et cetera, which is true. But how can we admit that today in our civilization that some people, they have only access to one meal per day? So I think we need to come with some solutions. And it’s not with the traditional solutions that we will do it.

But with this kind of breakthrough solutions, it will be possible. And so it’s why I call them super entrepreneurs. And just to be clear, I don’t want to oppose one kind of entrepreneur to another kind of entrepreneur. I’m an entrepreneur, and I respect all kind of entrepreneurship. It’s just that these kind of people, I think they are super because they want to really solve big problems, to dedicate a big part of their lifetime to this, to work on moonshot things that others may think are impossible.

When I met this young entrepreneur, Joost van Oorschot, that is also in the book that came with this idea behind Maana Electric. When I met him first, my first reaction was also to say, wow, it’s crazy. He wants to turn sand into solar panels into a machine. This is impossible. So my first reaction and I’m also in this movement. But my first reaction was to say that’s impossible. So our first reaction, because we have a linear mind is to say it’s impossible. And if we go to an exponential mind, then we see the thing is possible, because in the exponential world, you know, if you can go ten times, if you have ten doublings, it’s a grow of 1000.

If it’s 20 doublings, it’s a grow of 1 million, you know. If it’s 30 doublings, is 1 billion growth. So it’s going very fast. And today we see with this progress of technologies that many things are possible. So I think we need to have a mind shift and to really shift our perspective and see. Okay, if I would have a magic wand, how I will solve this problem. And it’s what I recommend to innovators if you would like to solve this problem, what would you do? Don’t think that with possible solution.

Just imagine if you could do it or you will do it. Like, for example, I said this 3D printing machine, like we seen some science fiction movies, you know, that the food is printed or appears directly like this. And this is really something that we think with a magic wand that it could be possible. But today the reality is that it’s probably feasible and it will happen. I’m pretty sure that it will happen in the coming years that it will be at this time.

To take it back to this first principles thinking approach, which I think is obviously the fundamental to the folks that are achieving these sort of grand visions is because they’ve gotten rid of linear thinking. They have to shed the belief that everything is one to 1.1. It truly is this sort of zero to one. Go back to raw materials. And I think Elon Musk was recently on Alex Friedman podcast. He talked about that. The only way you can approach this is simply look at the costs of the raw materials, and the goal in the end, is always to the cost of manufacturing will be asymptotically close to zero above the raw materials.

And it’s just a matter of the work that you do to get closer to that raw material cost. And that’s ultimately what led to battery technologies. And we’re seeing this with solar. But you’ve proven it out right in that very idea that if you just said, well, we have to just make it slightly better than the current lithium manufacturing, right? That can’t be it. You had to go to what seems like a crazy idea, as Joost brings and say, okay, what if we actually could do this and then you realize you always could with the right, first mindset and then second, which is why the book is important, executing the approach in operations as well, because there’s lots of big ideas.

But then having the team, the growth, the understanding to financially survive to execution is where, it’s a long distance from idea to execution. So that’s why where do we learn this? Is it as rare as it seems to be able to have this thinking?

Yes, I think you are right, Eric. When I met again, when I met you the first time, I was thinking, okay, that’s impossible to transform sand into solar panels. All this will be impossible. But then I go just 1 minute after. Yeah, but let’s imagine that it can work. Okay. So I asked some people, do you think that it’s possible? And many people told me, look, it’s not against the laws of physics, in sand, you can find everything to transform it into Silicon and then into solar cells and glass.

So basically it’s possible from just a physique standpoint. And so this was for me, the confirmation. Okay, that’s probably possible. So now let’s dive a bit deeper into that. So I did my due diligence. I analyze more. I try to understand also the business model, et cetera. What was the plan? I was also impressed by your master plan. It’s a notion that I explain also in the book, what were the big goals, etcetera. And to be honest, we are just following the big milestones right now.

And then you are right. I think an idea remains an idea until it is materialized and so what I see so many times is entrepreneurs. They have a lot of ideas, et cetera. But they never take action, or if they take action, they take the bad action. So it’s why I always say first, you need to really know, okay, what do you want to achieve? What do you want to create in this world? What is your true purpose? Okay. And after that, you need to press your crazy ideas that these crazy ideas will really allow you to materialize somehow your big dreams and you have to dream big and bold.

Many people are unfortunately not audacious enough. These kind of super entrepreneurs or super achievers. They have dream. They have big dreams. They believe in their big dreams, and they are bold. They take the necessary actions to materialize their dreams. But you are right that the proper execution is key, because without a proper execution, without what I call a flawless execution, you cannot, unfortunately, materialize because these kind of moonshots are very complicated, to be honest, to be achieved, to be materialized. So it’s why it’s very important to have a flawless execution.

And these kind of super entrepreneurs and super achievers, they are master at execution. They really try to see anything that can help the business. And now the secret one of the secret to succeed this flawless execution is to have a good preparation. The preparation is key, but now you have not also to spend months and months just in preparation and never take action. So I think there is a good balance to have when you think that your plans are good enough, then you have to act and maybe to revise a little bit your plans, et cetera, iterate.

Of course, move forward because I see also a lot of entrepreneurs. They have big ideas. They create big plans, but at the end they have the fear to fail. Or maybe they try to perfection their plans, but at some point they never do it. And they have very nice pitch deck. Or they have very nice business plans, or they have even very nice products. But they never ask the customers about their products or they never try to sell their products. So they have fantastic products. But at some point they never question also the business case for the product.

Again, it’s nice to have big ideas, but you need to go from a big idea, from a dream to a plan and then to some execution. Again, it may seem very simple, and I think the basics of the business is simple. Business is what an entrepreneur is there to solve a problem with a product or service that you want to sell to some people and you make some profits. I think the basic of business are very simple. The realization is something which is more complicated because there are so many parameters and these kind of super entrepreneurs and super achievers, they have a holistic approach about how to manage the company and they try to minimize the flaws in every aspect of their business.

Now you bring up a very important point when without customer validation, this is quite often the death knell for product management and bringing products successfully to market, because if they wait too long before they expose to their buyer and their user and their true technical consumer, they go far down the path to what they believe is the correct thing to build or method to use. And then you have the double problem of number one. They’re now pot committed or too far invested into this. And so they then start to discount the customers ideas like, ‘oh, no, but you don’t understand. We know what we’re doing better. We built it.’

But then the counter problem exists now, Fabrice, where in moonshots, quite often the customer doesn’t exist in a way when you’ve got an idea, you have long plan as to when a customer will be able to test it. How does that gap get bridged in your experience dealing with very early emerging tech?

Yeah, that’s, of course, a good question. And it can be a problem, actually, it’s also something which is well known. And I re-explain also in the book is the technology adoption lifecycle. So initially I think for this kind of, because mostly what I describe in the book are what is called deep tech companies. So it’s really very long. Let’s say moonshot venture that will take probably 5 to 10, if not 20 years, because there is a lot of research and development up front, et cetera. And for these kind of deep tech companies, generally, what you need is to have the validation, at least a kind of validation or pre validation from early pioneers.

So early pioneers are really people that are visionary that love new things, et cetera. That maybe see beyond, they like futuristic things, et cetera. And let’s take the example of Lilium, for example. It’s a company also that I described in the book. What they want is to have a small electric plan to make inter regional, let’s say, or intercity flights. So this will be perfect. It’s a bit like also Uber Air. So it’s these kind of companies that want to make some flight taxis, et cetera.

And you are right. Is there today customers? No. But there are some people that they may question some people and say, look, if this would be available, will you take it? Will you be able to pay for it? And I think there are many people that will say, yeah, I love Uber Air. That for example, in LA, where there is a big traffic jam, maybe I would have the possibility to fly instead of going on the road. I will love it. And I will be ready to pay for it.

So I think you can always find some people that at least validate your, let’s say, your proposition. Now, the difficulty for this kind of companies is that after two pioneers or what we call the early majority that will adopt, let’s say, their product, it will be to go to the mass market. And they might be more complicated. But, yeah, it’s all the difficulty of creating a business that can scale et cetera. But there are some, of course, fully, some strategies to do this. But I think in the case of Lilian, for example, they now went on the stock market.

I think it’s on the Nasdaq, their value at 1.5 billion. So the market believes in what they do. And I think there is a strong, let’s say, thinking among the population that, yes, this kind of solution at some point will take off, which is the right word will take off as long as, for example, the barriers related to air regulations, et cetera will be removed. But early validation is very important. And I like to give a very simple tip to start up, which is the Starbuck tip.

So if you have an idea, you go into Starbucks and you ask someone, ‘Look, I pay you your latte, but you spend ten minutes with me. I explain to you what I want to do, and you just give your honest feedback about what I want to do. If you think that it’s completely crazy, tell me that it’s completely crazy. If you think that you will never pay for it or that it will never work. Just let me know if you think that it’s amazing. Just let me know, et cetera.’

But you know what? Recently, a company in Luxembourg. I met them in an event and they talk about this idea. And I said, Did you validate your idea? “Oh, no, we don’t know exactly yet. We have not talked with potential customers yet, et cetera”. And I told them, look, go into a coffee shop and do this, and they did. And they receive an incredible validation of their solution. And many people said, look, if this would exist, it would be fantastic. And since then, they just won some prices, et cetera.

And they started doing well, because now they are convinced that there is a real market behind. So I do believe that early market validation is very important. But you are right that for this kind of companies, it’s not always easy. I think they have to focus on the pioneers, the early adopters, if at least they have this validation, it’s already a good sign. But after they will have some challenges, of course, for sure.

And I think an important thing that obviously plays out in the book. And with all the work you’re doing and the upcoming courses is, I often call it framework over firepower. That the old saying goes that plans are useless, but planning is essential and being able to adjust pivot, deal with changes in inputs. But if you do not have a framework in which you can apply these methods and you’re lucky more than you’re right in the execution. And this is the belief that we can just sort of throw.

If I scale my engineering team by 100, then I will suddenly be 100 times more productive. And it’s the mythical man month, as they often used to call it a mythical person month, of course, but more politically correct now, because you cannot just throw human firepower at it or money firepower necessarily and have it scale. The framework is incredibly important because then it becomes the methodology that anyone in your team can apply and that it also comes from vision and principle of the company. And I guess when you’re creating your own framework and you’re using your own method here Fabrice or you’re looking to entrepreneurs, especially as an angel investor, what is it that you look for in that, this is an idea and I trust these people to be able to scale towards this solution.

Look, before I make an investment. I use what I call the four T’s. And it’s not because my name is Testa. It’s around the T. And again, I like acronyms et cetera. But here it’s very mnemonic system for me to remember what is important. The first tier is technology. So is this technology really something breakthrough? Is it really something unique? Can this technology really create a big value? So that’s the first tier that I look into. Then I look at the second T, which is traction. And for me again, traction means market.

Is there a big market enough for this? Now, referring back to the previous question, sometimes it may be a bit complicated, but at least, is there some early pioneers, early adopters that, let’s say, that are quite excited about this solution and it’s what I call the traction. Then the third tier is the team. Is there a team able to materialize this big idea within this big market? Because for me, this is essential. It’s the execution. Is the team available today or maybe with some other people to execute the vision?

And then the fourth tier is the timing. Is it the right timing for it? Is it too early or is it too late? It’s a notion that I explain also in the book because I think this is really paramount. And there is a famous person that, unfortunately, I forgot his name. But he did an analysis of many ventures. What were their success factors, et cetera. And among, let’s say, all these startups et cetera. I think the video is available on YouTube. He found that, actually, timing was the key success factor.

So yeah, because why? Because sometimes some people, they have a very good idea, but they come too early and they are going to burn a lot of money before the market is ready. It’s maybe a bit the case, for example of Lilium, that I was talking about previously because I think they have a fantastic solution. But today the market is not fully ready, so they need a lot of cash. And it’s why, for example, they did an IPO to have enough cash. If you are too late for the market, the market is already over, and that’s done.

I think probably you will have some late people that might, let’s say, what we call the late majority that might eventually buy your solution. But the market is over. So it’s finished. So I think the proper market, the proper timing is very important. And what I have observed is that most of these super entrepreneurs, they are able to really sense, ‘Okay. What are the moods of the time? When is the right timing for it? And they launch the solution at the right timing. For example, I think Elon Musk, he was a master in that when he launched Tesla.

I think he really perceived that there was something missing on the market, that it was a time for electrical vehicle. But there was a need for some new kind of electrical vehicle, et cetera. He was right when he launched SpaceX. And you have dealt with SpaceX. It’s also in the right timing because there was all the start of the new space, et cetera. There was many projects of multi constellation, et cetera. And he was right to say, okay, if I can have a solution, which is maybe cheaper, et cetera, I can give a boost into this new space edge.

So I think the timing is very important. So I use these four T’s, the technology, I have the right technology, the right market, the right team, and the right timing. And for me, these are the basics after that. Of course, there are many things, but I think these are the four basics. And if at least a company has these four green lines into these four pillars, then for me, I can try to investigate a bit more.

Yeah, the timing is very interesting, and it’s often, it’s difficult to know until you run the other side of it. But if we take anecdotal experience, combine it with data, and I believe that we are going to be better. And we are today better at predicting that timing and ability to execute into that market. Of course, I brought up Built to Last. The funny thing about Built to Last is most of the stories in Built to Last actually led to pretty deep failures, years after the book had come out because the markets completely shifted away.

And it was sort of the idea that while they were successful in this pivot of those companies, they then failed to pivot soon after, and they suffered because of the belief that it was now stabilized. And they languished what they believed they already achieved what they needed to do to survive. But survival, like most things, is a continuous effort, especially in business when you’ve got funding. In the end, they often say it’s like startups fail for two simple reasons. The money runs out or the founders give up.

Yeah. Exactly. Dispute between the founders, or they give up or the lack of cash. Yes, these are the two main reasons, for sure.

But the four T’s that you talk about are the reason why the second part will occur most likely, right. Because we joke about pets.com and the original.com era. They all would have been fantastically valued and successful today, of course. But we’ve now succeeded on the backs of their failure. And I think that’s what as humans and as learners, in business and in tech, if we take those learnings and we say if given the right timing, if we change the approach, if we go back to first principles, could we bring this back to the market and be successful in it?

It’s good. I like that entrepreneurship as well as being celebrated. We saw a long period where it’s a bit of a tough word when you say the Uber of something. Right. Uber was this fantastic thing. But then it became synonymous with a negative view of the founder, of the specific founder. Right. That story was unfortunate because it truly did taint the incredible thing that was done to change the market to create something that just didn’t exist. And so I like that now entrepreneurship, we’re going to see more and more people that are successful with it, because I think further down towards the school system.

They’re studying these things instead of General Motors and Vodafone and the early technology creators as the case studies. They can now use case studies from the last five to ten years, which are fundamentally different than what we had 30 years ago, which were the case studies that were put in print and treated as the gospel of schooling, at least. And I’m curious on this one, Fabrice. Is there enough further down, even like in high school and secondary education, that is being done to make entrepreneurship a viable future for people?

I feel like we’re still not there yet, but I’m curious of your experience as well, talking to especially early founders.

Yes. I strongly believe that we need more entrepreneurship and not only to create profit ventures but also nonprofit ventures. I think anyway, the same principles of entrepreneurship can be applied also for nonprofit. So we need more people with an entrepreneurship spirit. I think when you have an entrepreneurship spirit, you can achieve anything you want in life because you have some capacity to convince others. You have some tolerance, let’s say, to risk. And maybe again, to things that are impossible. Things that are possible. And unfortunately, I don’t think that today the education system prepares enough for entrepreneurship, at least at primary or secondary school.

Of course, after that, there are some masters in entrepreneurship, et cetera. But yes, when the children are very young, I think there should be more kind of entrepreneurship, which is taught to our children. So, for example, to learn them, how to make great presentations, how to maybe have a small business which can be a profit or nonprofit, but at least to try to put in place of projects. So project management is very important. How to test their hypothesis, how to make experiments. That failure is not a problem.

I think there are many, many notions that could be to learn, for example, the exponential technologies. It may seem complicated, but it’s not, you know, a 3D printer is not so expensive and they could play with the 3D printer to build stuff, et cetera. AI, for example, coding in Python, et cetera. It’s also not expensive. So I think there are many things that could be taught in virtual reality, and that are sold today. This metaphors, et cetera. Again, just simple glasses, et cetera for virtual reality is not so expensive.

So I think today again, because in this age of exponential acceleration, we also seem a decrease of many costs, et cetera. So it’s the zero marginal cost society that has been well described by Jeremy Rifkin. And so, today many of these technologies are not so expensive if you want just to experiment a little bit. So why not to create in school some kind of living lapse where children, they can play with this. They can also try to put in place some projects and to pitch their projects in front of an audience, et cetera.

Maybe to fundraise also because sometimes they ask to the parents, or they ask to the teachers, but why not to the children themselves to try to fund raise for their school. And we should also learn the principles of personal finance to children because it’s something which is also not taught. And I think it’s unfortunate. So I think there is a lot to do in that space, unfortunately.

Yeah. You are speaking the words that I think of and said so well to this idea that there are things that we do not teach. And I guess there’s an assumption that the parents, it’s on the parents to teach these principles. But in the end, if it’s not promoted through the school system where they spend the majority of their time learning where that’s the most formal part of their day to day education. By the time the parents get around to it, they’ve spent a day learning or a day in some kind of programmatic method.

The last thing you’re going to do is suddenly, hey, let’s explore creating a pitch deck. And it’s funny that when I work with my kids and I recall here that you have kids as well.

Yeah. Four kids.

There you go. I know your number too. I’m the same. And my older kids when they would come to me for money, I would say, okay, what can we do? So that if I give you this money, we can turn it into a way that it can create more money. The first thing is what’s a repeatable thing that we can do. So rather than just go and buy this thing once and at least just to introduce critical thinking and them having to explain why they really wanted something to me.

They would often become more confident, like, okay, so I’ve got this idea. I need $40 for something. But I’ve got an idea. What I’m going to do is I’ve got a bunch of stuff in my closet. I’m going to maybe do a garage sale. And so I would say, well, tell you what, I’ll save you the trouble. We’re going to donate it. And I’ll give you the money so that we can win twice because you’re going to help somebody in need. And you’ve pitched your case.

I’m now your VC is when you give them, though, that freedom to create an idea and to push to get towards it, they feel good. And you can tell in the next thing they ask you. Now they’ve got an approach. They’ve got a method, right. So I think next time they go to their teacher, they’re going to say, I need more time on this. But here’s my proposal. I’m going to run a study group. This is entrepreneurship in the smallest way. I love that spirit, and you can see it in the kids.

They know it’s in them. It’s not for everybody for sure. There are many kids who they also think and act and learn differently. And we should support that as well. But for those kids that can take that to the next level, I really think we should be putting stuff in place to help them and nurture that.

No, I like it. And I try to do the same with my kids. For example, one of my son said, ‘There is this business that I know some friends. They do it’, et cetera. I said, you can do it, but I need some capital to start. I said, ‘Look, I will make your sponsor. I will give you the initial money and then you have to try. Then if you make profit, that’s fine. And let’s see how it works’, et cetera. I like it. But you are right.

The parents, of course, that maybe are educated can do it. But many parents probably are not businessmen, or they are not entrepreneurs. So maybe they just don’t think or they don’t have the knowledge to learn to their children. And it’s why at some point, the school should try to learn this kind of principles to the young generation, because I strongly believe that we need and it’s all, you know, my mission. I try to elevate a new generation of young entrepreneurs because I think that entrepreneurs can really shape a better future for humanity.

I think it’s through entrepreneurship, through building new things, et cetera, that we will build a better world, as I always say, build the world you love. I think if you wait, that others, build the world that you love for you, it will not happen. You have to do it. So what the book is also called with more doers more builders that can really shape a new world that will be better for the next generation. I’m a father of four kids, and what I want is that when I pass away, the world will be a bit better than the one that I knew because I want my children and my grandchildren that they live in a better world.

And so I think it’s a collective responsibility. So it’s why I call so this super entrepreneurship, a super entrepreneurship movement. I hope that many people will read the book. It will inspire them. Again, it’s not a guarantee of success, but maybe it will give ideas to some people. Okay. Maybe now it’s my time to start. I will follow some principle of the book, and I will try to take my chance because I think it’s never too late and we have one life. So why not to try at least?

Now, some people will fail. And I also had some failures like everyone that’s perfectly normal. But you need just to say, okay, I fail. What I can learn from this failure. And I can try differently next time. But maybe during this journey, some people will meet some investors or some team members, and maybe the next time they will do another venture with these investors or these team members, and it will work. So I think that’s normal. I think failure is part of the journey, but it’s not a reason to not try.

And I think we need more people that try new things, try to change how things are done. So we need more game changers at all, let’s say, levels of the society, we need more game changers, people that don’t accept the status course. I think there is too much acceptance. Let’s see how things are done. And again, at this age of exponential acceleration, everything is going fast and there is no reason why we could not do things differently and change how the world is going. Again, I think there are many things that are going well.

So I’m not pessimistic at all. I think we live probably much, much better than 100 years ago, for sure. But there are anyway, many problems. And I think it’s the collective responsibility of all of us to try to find some solutions to solve these problems.

Yes. An interesting quote is from Penn Jillette of the magician duo Penn and Teller. And he says two things are invariably true. The world is getting better and people think it’s getting worse. There’s an incredible amount of media attention to negative news stories. It’s very easy for that to spread and to us feel engulfed in this. But as you said by most measurable factors, we are better off economically, better off as far as distribution of food. There are many things we have a long way to go, and it happens by people like yourself and people like the superpreneurs and the people that are ready to give whatever to give back. We can continue to exponentially affect the world and at the same time making it commercially viable to run the organizations that can create these systems and solutions that can give back.

It’s an interesting dichotomy of celebrating sort of the free market capitalism to grow a business fund, development fund, research fund, delivery of new things, and then balance that with making sure that we give back. And I’m optimistic of what’s ahead. But I’m also careful about my optimism. Nothing is automatic for sure. You brought up a great point Fabrice. I’d like to quickly touch on this, too. Failure is an important part of the process, and we’ve all had levels of failure at some point in our life.

For those early entrepreneurs, do you find, is there any risk that a lack of exposure to failure can be problematic? I’d say for them as they begin this entrepreneur journey because they’re maybe not prepared for that first hit, that first thing that could set them back. How do you prepare somebody for adversity when they haven’t experienced it yet?

Yes. Look, let’s be honest. Who likes to fail? I think nobody. I think we all like to win and to never fail, that’s for sure. So I think unless you are wrong, I don’t know people that like to fail, but for me, it’s not a reason not to try. Now, all these super achievers or super entrepreneurs are they let’s say, overcome failures is through their massive transformative purpose. So they know what their true purpose is and they are fully committed to this. So it’s what gets them off the bed every morning and they know why they are doing this. For example, to solve hunger or to try to contribute to climate change, et cetera.

And it’s their strong motivation. So with this, they know that, okay. I have to try. I want to pursue my moonshot. It will take time. I will face setbacks. I will face many years. I will have failures, but I will need just to continue, because what I do is great. What I do can be great for humanity. So I need to just continue, even if I face some fears. I think for me their true purpose is their tool to always keep the true north and to always go, even if there is snow, there is rain, there is a lot of things.

They just continue on their track until they achieve their goals. And this is what I have observed. All these guys took Elon Musk and he waited probably 20 years before SpaceX is a great success. And many rockets just crashed and exploded. So he had a lot of failures. But he just continued. At some point he was almost broke. But he continued again and again. I think it’s just the secret. It’s only the secret to succeed is never give up. Like Winston Churchill was saying, never give up.

But I think it’s true. And these kind of super entrepreneurs and super achievers. They have a relentless, let’s say pursue of their dream or their objective. They will never give up until they reach their dream. Now, at some point, if they see that really, they need to take some other route to go to any way to achieve their dream, they will do it. They are not stupid too, so pivot or to try to change a bit and adapt the plans are also possible, for sure. But generally they are very relentless.

And even if everybody around said, look, you will never succeed, they just continue. Steve Jobs was well-known like this. He was saying, no, we will succeed, we will do it, et cetera. Everybody around was saying, no, it’s impossible. Again, it’s impossible. And he was saying, no, it’s possible. I think it’s really a question of mindset. And if you are fully convinced yourself, I think you can convince others. But if the founder says things that he will not succeed, I’m not sure that it’s going to work, et cetera.

How can he convince his team that it will work? So I think the best super entrepreneurs, they have a very strong belief that what they do will succeed and it’s all. They can convince investors, they can convince team members, they can convince customers because they say no, I’m sure it will work, it will work, et cetera. It’s what I’ve observed. I have known some guys, they were incredible. Even if everybody was believing that it will never work, they will continue. No, I’m sure it will work.

And they were demonstrating why it will work, etc. And they can bring some convincing arguments. Just people follow them. Why? Because dreaming is nice too. And so you try to also believe in these dreams too, because you want to be part of the big dream, because if you don’t have a big dream yourself, but you want to help someone else, maybe to make their dream come true. So I think that’s something which is fascinating.

Oh, definitely. And the most important thing and why I will implore people to pick up the book. And I’ll say that either through the blog or through social media, I want to make sure that people get access to this. So I’m going to offer up to buy up a few copies myself on people’s behalf and make sure that I get more people exposed to this. If you take something that’s executed successfully at scale and bring it down to a human level, that’s what makes day to day entrepreneurship accessible.

If we use the practices and the successes from incredible moonshots and bring them down where there’s less risk and there’s less things but use the methods. This is fantastic. It’s much harder to take traditional business methodologies and then scale them into an area where no one’s been exposed before. This is why it’s such a beautiful opportunity to take the lessons from the book and then put them into day to day. And when I read it, it immediately made me want to revisit a few things that I’ve got active.

I’m an advisor to a start up, and I’m doing other things, and it just lit up an incredible creative spark in me to shed the unnecessary things that are being worked on. And let’s go to core principles. Let’s go to what needs to get done. So I found it to be a very inspiring read, and I sure hope that other folks do. And it’s funny just to further that one thing you talk about SpaceX landing rockets. I use this in presentations all the time recently at a customer talking about how today’s stuff that we see as normal was not that case two years ago, even because Blue Origin, they sent people to the edge of space and back, and they landed the rocket.

So they land the first age of the rockets, and it wasn’t even in the news because it’s normal now. So SpaceX has normalized landing the first stage of a rocket, which was unfathomable five years ago.

Now for sure. And if I tell you that there is a way to land rockets without using any fuel, because SpaceX is using fuel to land rockets. But if I tell you that there is today, a means to do it without using any fuel. So a very sustainable way to reuse a rocket. Will you believe me or will you say that it’s impossible? I can tell you that it’s possible because I’m now part of a venture which is a German entrepreneur, fantastic super entrepreneur. And he just demonstrated very recently with a drop test on a small scale that it works.

It’s a kind of an inflatable parachute, if you want that enveloped, let’s say the rocket and it works, but it’s not using any kind of fuel, et cetera. And so it’s a fully sustainable solution to reuse rockets. So you see, it’s going so fast. What I wanted also to say maybe about the risk is that there are some techniques also to minimize the risk, and it’s part of the good preparation. And I explained a little bit in the book and in this course, the crazy method launchpad that will start end of this month.

I will also give much more explanation about these tools, but there are some tools that exist also to try to have a very good preparation to analyze all the possible risk, et cetera. So that again, the risk of failure still exists, but at least you try to minimize it. And I think that again, maybe some entrepreneurs are fearful to do something because they say it’s going to fail, and sometimes it’s a lack of preparation. I think if you are well prepared, if you have well evaluated risk, and if you see what I like, this principle of asymmetry of risk.

Okay. There are some risk, but they are minimal compared to the reward that can be provided by what I want to do, then it should be always the decision. Okay. I’m going to do it because what I’m going to do if I succeed will just be great for the planet. By the way, if I succeed, I can even have a billion dollar company. Why not? And the risk is quite small. Or at least I know what I can do because I have some backup plans, et cetera, to minimize the risk.

If eventually they would happen.

Well, I look forward to seeing the outcomes from the first cohorts in the crazy method launchpad, so Fabrice will stay close for folks who do want to get in touch with you. What’s the best way they can reach you in order to get in contact?

Yeah. So I think the best way is to go on my, I have two websites, but my main website is fabrictesta.com, where you can find all the information. You can reach out to me on this website. I have also another website, which is superpreneurblueprint.com. I’m also available on all social media networks, Facebook, Instagram, LinkedIn, YouTube. So just feel free to connect with me if you need some advice for your startup. If you need some mentoring, coaching if you want to follow this new course, if you want anything, I try always to be available for entrepreneurs because I love entrepreneurs and I want also to give back by helping them so that we built a better world.

That’s fantastic. Yeah, I wanted to spend some time talking to mentoring, but I didn’t want to take away from what we wanted to talk about here. Mentoring is incredibly close to home to myself as well, and I’ve definitely seen the advantages that come. And so thank you for giving back to the entrepreneur community. In doing that, it’s more and more. I’ve now spoken to a couple of hundred entrepreneurs through the course of this podcast life, and invariably the successful ones always say my success is because of the lessons that were given to me by others through mentoring and effectively, we can save each other risk.

We can save each other pain. We can share. It’s not all just about pat on the back. You’re doing a great job, kid, and that’s really not what mentoring is about. Mentoring is about having a good, critical voice partner to share ideas with, and I’ve seen it myself as a recipient and also in mentoring I’ve done in the community as well, so it’s great. Hopefully we’ll come back. I’d love to have you back on again in the future, and we can talk a bit more deeply about mentoring.

With pleasure, Eric. It was a great conversation, great questions. And I really enjoy very much this conversation. Thanks a lot for inviting me.

Ladies and gentlemen, Fabrice Testa. Thank you very much.

Bye-bye. Thanks.

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Charlie’s debut album Americana And Whatever’s Left is a story of heartbreak, loss and growth. We dive into the writing process, performing in a pandemic, and what inspires storytelling through music.

Big thanks to Charlie for joining me for the podcast and for performing for us as part of the show!

Check out Charlie Cope Americana and Whatever’s Left on Spotify here: https://open.spotify.com/album/5AyZ1iItYevoQRvBIHDYjt?si=QF0xwqO4S_aXwMUUdUiqKg&dl_branch=1

Listen to Charlie on Apple Music here: https://music.apple.com/us/artist/charlie-cope/1352517889 

Transcript powered by Happy Scribe

Welcome to the show. This is DiscoPosse podcast host, Eric Wright. Thank you very much for listening. We’ve had an amazing 2021 as far as the podcast listenership and really great response, so thank you all for coming along for the ride. This is a perfect, really neat soulful ending to the year, with the show featuring Charlie Cope. Charlie is a singer-songwriter and his brand new album Americana or Whatever’s Left has just been released. So this is a really cool opportunity to share in a storytelling experience through the power of music. I was really happy with the discussion I had with Charlie, so I hope you love this as much as I did and it even features some actual live music, or at least it was live when we recorded it. While it is not as awesome as his album, which you’ll have links to the Spotify and ways to listen to Charlie’s music, I definitely recommend. So hang tight. Listen to the song and the whole story. Charlie’s got such a fantastic story, that’s an absolute must listen. And speaking of must listen, please just take a second to think about what you need to do as far as supporting this podcast and supporting the great people that make this happen and support yourself in your own safety when it comes to data protection, to information protection, to info security, ransomware protection, this is the way to do it.

You can visit my fine friends over at Veeam Software. They’ve been super cool, not only in the amazing platform that they offer, which you can find, of course, by going to vee.am/DiscoPosse. On top of that, they’re a great team and they really are doing some fantastic stuff around cloud protection, on-premises data protection, physical servers, Cloud-Native with their CAST. And offering much more around SaaS, things like Teams and SharePoint. You need to protect your stuff. It’s real, right? Ransomware and all this crazy stuff is real. So go check it out, go to vee.am/DiscoPosse. And also protect your data in flight while you’re traveling around or even while you’re sitting at home. There are incredible amounts of risk in just your data being picked up, your identity being captured. A really great way to solve that is to use a VPN. I’m a user of ExpressVPN, so I highly recommend it and I’m really happy that they’re also supporters. So if you want to check that out, you can head over and try expressvpn.com/DiscoPosse.

Alright, let’s get to the good stuff. This is Charlie Cope.

Hey, this is Charlie Cope and you’re listening to the DiscoPosse Podcast.

So for the folks that are new to you, if you want to do me a favor, give a quick little bio. We’re going to talk about the new album. We’re going to talk about the industry in general and touring in a pandemic. And this is a lot of craziness that you’ve got to deal with right now. But, yeah, give us the elevator pitch and why people need to get your album. And I’m telling you, there’s links below. It is wicked good.

Thank you. My name is Charlie Cope. I’m an Americana singer based out of Texas, singer songwriter. I write all my own songs, and a couple of them are co writes. And like you said, I’ve been touring a lot, especially during the pandemic. And this album took me seven years to release, to write and create and live. And I’m hoping that a couple of people that have heard these songs might have lived through similar situations that may need a little bit more understanding in life, that need to feel a little bit less alone, might hear these songs and feel a little less alone in the world and maybe get a little connection between me and them and a couple of print stopping catchy songs along the way. It’s just a bonus.

It’s funny that you bring this up, right? Like the Americana style and your roots in that really come out. And it’s funny. I grew up as a kid, like just nothing but Highway Man records. So I grew up with Waylon and Willie and, like the classic stuff. My dad was really digging that the only guy that worked in the tech industry that had cowboy boots. It was kind of wild that I had this really diverse set of influences. And when I started playing my own music, it was funny because it comes out in this really strange diversity of my background of listening. And then my playing would swing and move around. Now far beyond me saying I’m a musician relative to the work that you’ve done and how much you’ve created. But it gives me a super, really good appreciation of bringing it through and maintaining your voice. But hearing the roots of it, it really just hits home to folks like me who grew up with a lot of that stuff.

Appreciate it. Yeah. I also grew up on that Willie and Waylon and the boys. When I was younger, I wanted to sing like Wayland Jennings, and I wanted to write music like Merle Haggard and lyrics like Chris Christopherson. Obviously, back then it was all country stuff. Now it’s a little bit more diverse Americana, like you said, kind of a bit of everything.

Well. And this is the thing maybe set the stage for folks that are fresh of the phrase. Right, because we went through, like, classic country, and then there was new country. And the new country is not new anymore because it’s old, new country. And you had that sort of wave of the next generation of it. And then Americana is this beautiful, sort of almost like a throwback, but it’s just a reminder to the origins of the whole genre.

So Americana music is basically just kind of everything old school, kind of put in pot and mixed together. It’s like a little bit of folk, bluegrass, rock and roll, blues, country. Like you said, I try to touch on every side of it as I could in this album, starting with, what about you obviously being a very big rock song and to use somebody, which is pretty country kind of folky, if your grandparents listen to it.

Yeah. The interesting thing of the music and the lyrics as a combination, the stories are super strong, and it’s amazing. I’ve always found that there’s so much stuff out there today in the sort of traditional, like, serious hits, one crowd, God bless them. Right. They’re making money and they’re still supporting the business. But I don’t even know the lyrics to any of the songs because you don’t need to. You just need to know the hook and it’s catchy. But what I found with listening to your songs is you really genuinely listen to the story. And then the more I play it, the more it’s you feel like that emo kid. Listen to the words, man, because it actually does have a real true start, middle finish as a storyteller. This is exciting to me that you can do it. And also, again, diversity of styles. Like you said, you got some stuff that’s more towards rock, and then you’ve got those real cool sort of bluegrass tones that are in there.

Yeah. Thank you. A lot of people ask me where the genres came from and, like the bluegrass, the rock and everything. And right now I’m wearing a David Bowie T-shirt, and that style really came from because I wanted to tell a story, like you said, but not just with the lyrics, also with the music itself. So taking What About You, the first song in the record, which is by far the most popular, is it kind of in the Kia-C? Kind of not, because I don’t want to talk to musician wise and people that aren’t musicians that understand, but it never really ends on a C major, so it never really has, like a period. It’s almost like you’re just talking for ever and ever. And I felt like that built anxiety. And that’s what I wanted to infer in that song and tell a story without the lyrics and then with the lyrics and then make them kind of come together and sometimes even make them say two different things at once.

The sort of the walking style of the story along with it reminded me even like the Stones Far Away, I was always one of those ones where it just has this beautiful rolling back tone. Like you almost picture just like the movie set going by behind them. And that’s what the music is. And then the story, and then it comes into the hook and then you’re in a song again, and then it goes back to story. I love that interplay and the style.

Yeah, for sure. A bunch of, I didn’t just want to have 14 stories. I wanted one big story and so it’s not really more 14 stories, it’s more like 14 chapters of the story. So there’s different parts and as you go through it, it gets more word I’m looking for. It gets more mature as it goes through because all my best songs are true stories. I’ve written around 1500 to 2000 songs now and all my best ones, when you’ve written that many, you’ve written them every which way but loose. But my best ones are always true stories and I was looking at them and trying to figure out what I was going to do for this album years ago and I was like, well, something just hit me. All my best songs are true stories and I’m going to sing about anything. Well then I know exactly what I’m going to sing about. And then I sent out to I think it was Prince or Michael Jackson that said if they would release an album with twelve songs, they’d write 120.

Yes.

Well, I figured I’m no Prince, I’m no Michael Jackson. So I wrote 1200 and I wanted to pick the top twelve and ended up being 14.

That’s an interesting thing to talk about the process of choosing the order because there’s this sort of this amalgam of music you’ve got in your back catalog, it’s in your head and you’ve played it everywhere and it’s in notebooks all over and snippets of recordings and to really bring it together as both individually small stories and then the real true overplay of this story throughout as a theme and it’s not easy. How do you approach that whole process with the truth?

It’s the best way to do it. I really believe in putting emotion and soul, heart and soul into what I do, really anything I do. And at first it was like I got to make a new album, I got to do this when I was younger and then I grew up a little bit and it wasn’t so much I need to make an album, I need to tell a story and that story was really the heart and soul of it and that was really just a big part of my life growing up, especially because now I’m only 20 years old and of course this has taken so long to create and that’s why I say seven years because that’s the span that I listed this from. For the most part, it wasn’t that hard getting the order down just because it was like, okay, well this happened and this happened, this happened. There was a few things I had to mix around in order to make it less complicated but that was relatively easier. But writing and rewriting and rewriting again, all these songs in order to make number two, connect with number eight more and have this come back at this and have this guitar riff and slipping away, match the trumpet riff and putting myself through and all this sort of thing.

And it all had artistic symbolism. It meant something. It wasn’t just there to be cool. It all meant something. That was definitely a lot harder than picking the order.

You’re interesting that you’ve mixed a lot of dynamics of sound, like instrument selection. You’ve got fantastic players who are supporting you through this. And I saw some of the making of recording stuff, and it’s like, especially recording and producing and mixing down during pandemic while touring and all the stuff going on. It’s a very different process than just kind of seven guys going into a studio for nine straight days and just banging, hanging it out. Like it’s a laborious process. But I love the mix of what makes you bring those different instruments sounds and those different styles in.

Well, like you said, the musicians are amazing. Most of me or the other guys, my backing band, and there’s a few extended members. We call those the other other guys. And they’re all fantastic musicians. But like I said earlier, they all have meetings. For example, the horns are more triumphant. That’s what they’re trying to symbolize triumphantness. And so, like in Big River to Cross, for example, there’s the big horn section that comes in on that song, and that’s supposed to seem like there’s a Big River to Cross being like, we have to break up and we have to in this and move on with our lives and, like this big goal that we’ve been trying to accomplish for so long. And then we finally do. And then I had also been putting myself through. It wasn’t a full horn section. It was much smaller. It was just a trumpet. But that also had symbolism with growing maturity. Same way with the rock and roll kind of. There’s sirens in my background. Living in a college town, it happens.

Yes. It’s sad to hear more often than you’d hope.

Yeah. But like the rock and roll side and let me go easy. And like, the guitar solo, in a lot of that was very kind of like a battle between good and evil. And also, depending on what part it is, it also symbolizes immaturity and growing up. And this story started when I was about 13, and this album where it ended, I was 18. So there’s a lot of immaturity there. Like I said, I try to be as honest as humanly possible in this album, and I think it definitely helped in being honest.

You’re wise beyond your years in the way that it comes through, and it’s always amazing to hear, like, just the strength and the depth of your voice. But more than that, like that, sometimes you could get away with just pure raw talent. Like, just the physical talent of singing is one thing, but there’s an emotion that’s buried inside it, and it’s hard. Like, when you think most folks you see that are blues artists, they got a few decades of hurt in them. So for you to come at it and to be able to give this kind of storytelling and to have seven years in at age 20, it’s a pretty heroic amount of work that you’ve been doing to put this stuff together. I imagine it was probably buried in you long before even 13.

I’ve always wanted to be a musician. As long as I can remember, it was pretty highly discouraged from friends and family as I think would probably be wise. It is now. But starting out wasn’t the most lucrative job, wasn’t the safest job by far. And a lot. I know I’m in the vast minority of musicians that can actually make a living and then some. And for a pretty long time, I wasn’t nothing against anybody that said I wouldn’t be able to make it or anything like that. Totally cool. It worked out for the best for me. So I’ve always wanted to be one and I just kind of put it off. I was also really shy. I’ve always had problems with self confidence. Still do. And just like, well, if they can’t make it, there’s no way I could ever make it. So I just kind of put it off for a really long time. But it was always there. And then I guess when I started when I was 13 and I kind of started falling in love with this one girl, and that was just kind of the whole story of an on again, off again relationship, especially trying to keep it under wraps, not being able to talk to anyone because it was secret.

I guess art is a great way for your own therapy. So it was almost just like I needed to get it out somehow. And a great way is to pretend like I made it up.

Yeah, that’s always the funny part. People don’t realize how much truth is buried in those words that you’re probably not supposed to reveal. And it’s like you’re like most of it is made up except for the parts that are all real. I always appreciate whenever Taylor Swift gets into a relationship, I’m all right. Two years to a new album. It’s just fantastic. She seems to be this wave of good relationship realize it doesn’t. Sadly, I shouldn’t make fun of it because it is, unfortunately, a bit of a feeder for really fantastic stories and music because that emotion gets poured into it. On that, though, the longevity of a song versus the longevity of the original emotion. What do you feel about this idea that you’re going to be playing songs that really meant something immediate and distinct when you were like 17 and you’re going to carry that 10, 15, 20 years down the road, you’re going to bring those songs up and it’s going to be a hit. Not the story of 17 year old Charlie, who is suffering.

Yeah, I’ve thought about that a lot. I think it was Joe Walsh said about one of his tunes that if I’ve known that was going to be the song I’d sing for the rest of my life, I would have written a different song. I don’t know, because the story hasn’t necessarily ended yet. So I’m kind of even though the last song, Best Thing Ever Made, that part of the story, ended when I was 18, when I just graduated high school. So it hasn’t really ended yet. And I totally thought it did but it totally did not.

Even you get surprised by the story sometimes.

Yeah. But I can’t talk too much about this, but when I was on tour, I was touring through Houston, and I’m from a really small town near Houston, so I got to be in town and I was there and kind of all hit me back. All those memories and stuff. I drove by my old school and all those roads we used to speak down in private and those 30 miles an hour roads, we all used to go 85 on all that sort of thing. And even though it’s changing a lot, that really small town in just a very short amount of time, all those memories and feelings and even songs I forgot I wrote, came back. And when I actually got to meet again with some of these people and figured out that, oh, crap, this story kept going because I actually met with someone special a few times. And I remember that night I had a show because I got into an argument with her, and I had a show in Houston, a really small joint. It was called the 202 Main just in Conroe outside Houston. And I put on probably the best show I put on all year.

It was just a little one man show joint, but it was definitely top five. And I’ve been looking back on that show like, man, I got to do that again. I don’t know if that emotion is ever going to go away. Every time I sing these songs, I think about how I wrote them, how I felt after I wrote them, how I feel about them now, at least in the short span of time, because I realized that could be a different story when I’m 40 years old. But as of right now, the emotions haven’t gone away. I don’t really see them going away anytime soon.

This is where the collaboration stuff comes into, because there’s a real emotion to pairing with somebody and co writing, and you really hear it and feel their contribution to it through that. I mean, I pulled on the old country roots, too. I remember watching as a kid, Honeysuckle Rose, and I love that movie. It’s a Willie Nelson, which is basically like a biography of him. This idea of going on tour with a girl but realizing his wife was like, I was that girl. And I see how you’re looking at that girl now. So I know something’s going on because I was the one that took you from somebody else. And I don’t want you to do that to me because it’s Willie’s band. I always loved that he would just use his guys and watching this thing of the moment that they’re on stage, and then they connect, and it’s there. That emotion comes even with just connecting with the audience, with connecting with the drive on the way to the venue. And you’re like, oh, man, that’s that pizza joint that we used to go to. And I remember having this big argument out there, and just like, that kicks in, and all of a sudden you’re on stage and you close your eyes and that’s it.

That memory just takes over.

Yeah, man. And that’s really why I’m doing this. I’m trying to connect the audience. Like I said in the beginning, it’s a big deal. So if I can carry that emotion through the rest of my career and into the audience and into the bands and everything, well, then I guess I did something right.

When you’re performing, how adaptive is the performance? Because obviously you got it set up by you guys and there could be nobody in the room, and you can nail down the songs. You’ve already got the music’s in you, the stories in you, you’re ready to perform. You guys rehearse. Everybody knows that. It’s funny. Just like any job. It’s like, I know I can pull this off, but then situationally things adjust. How much do you do? Things like move around set list or extend parts of the song. How much do you like to mix that in?

A whole lot. I actually try to never play the same song the same way twice, especially with the band. I throw in extra verses. I put in new lyrics that’s more for, like, the acoustic stuff when there’s not a whole lot else you can do. But I’ll modulate it. I’ll add in extra instruments, take instruments out. I always make it fun. I try to make it because I don’t want people to think if I wanted to hear this song, I could just listen to his album on my phone, come out to the show, and it’s always different. It’s always more fun. I’ll get people’s names from the audience. I’ll slip their names into the song just for the hell of it. I’ll even write songs on the stage with the band. They’ll be like, you give me a word. Okay? Flowers. You give me a word. Umbrella. All right. This one’s called Flowers and Umbrellas.

That’s awesome.

It’s always different. And the set lists are different every night, which makes practice extremely hard, but it makes the shows extremely fun.

I remember doing medley’s when I was in, I would never want to play, like, a whole song. We would do our original stuff. And the funny thing, actually, the story the name of DiscoPosse, where this came from, that we were in this heavy band. And we were sort of like toolish, very melodic, heavy music. So you got that style. And then what we would do is we would open our own band with our own bands, but we would put on, like, funky wigs, and we would play really heavy versions of disco songs. So I called it the DiscoPosse. And we would just play Wild Cherry and Chic and just like me, or just rocking out with a seven string, and it was a blast. And then you would just go get a couple of drinks. Now you’re relaxed and you play your original stuff, and people really kind of playing originals sometimes when you go into these small venues is a good sign. If you want to go to the bathroom, now is a great time because you’re not going to know what the song sounds like. But they would know that we were there twice, and they would really kind of dig into it.

But that was the thing is, playing stuff that was dynamic. You start to play and you see. You can see the room. You can feel it, not like just the vibe wasn’t right. And so we would switch up and just like, go with it. And you had to know. You had to be ready to kind of throw away the set list, because there’s nothing worse than if you’re just like, the next song in our list is X. And if they didn’t like the last one, and this sounds just like it, why in the hell are you playing? Figure out what they want to hear.

You got to be able to adapt.

If you were to say, the first song that you played end to end, that you wanted the room to say, check this out, I learned this song. What was the one that made you ready? This is it. I’m a performer. I learned this whole goddamn song.

Actually. You know what? I think it was an original. I do remember it because it has followed me around for years. It was a God-awful song. It’s called Angel. I didn’t really know how to play guitar. I knew, like a chord and a half, and I was 14. And so I played a few of my first open mics and that sort of thing. Nothing real. And I actually did have, like two gigs just through some people I knew. They had, like, some charity events, so I got a few bucks for that. But Angel, that was it. When I was 16, I made a terrible record. It’s terrible. You can check it out. It’s awful. I wouldn’t suggest it.

You definitely know I’m putting things into that one now.

Yeah, well, it’s not that great, but I knew nothing about music. Nothing like Americana or Whatever’s Left. But it was called Good Time Charlie. And the first song on it was Angel, and it was pretty awful. I’ve actually rewritten all those songs just to see if I could just to make them suck a little less. Actually, they don’t suck that much anymore. But the original recordings you can look at, they’re all awful. It was Angel. I was so proud of that. Terrible.

That’s the other thing, right? Evolution of the music is something that I remembered going through. Like I said, my singer in the band, he’s just got this notes, like, basically like a poetry sell book with weird stuff all over it. And he would just be like, all right, tapping into a rhythm, you’re like, okay, cool, let’s just go dig. And he’s like. He remembers a word and he’s like, all right, find some sentence, some phrase that he wrote. And then from there we would like, carry on. And we would do stuff. And I remember recording on this, like, , sorry, I’m an old dude. So I recorded on four track, old school cassettes, putting four tracks and then bouncing it down on physical tracks, which means that basically you get bleed between the tracks, so it just destroys the dynamics of it. But hey, to us, it was like, Holy crap, we recorded a song and we actually managed to squeeze in layered guitars and stuff, but we would do this, and then you would record it, and then a month later, you almost forget how that song was recorded because you’d listen to something else and it would start to adapt, and then you realize, like, oh, man, that’s the real song.

Like, it’s living, it’s breathing, it’s organic. And that’s actually one of the best things because the emotion just gets carried forward into a new vessel, I guess.

Yeah, I think that if you release it, I know that’s different. Just keeping it on a track in your bedroom. But if you release it out to the world and it’s on the radio and stuff and people hear it and connect with it, it grows even, because obviously I can’t change them now. They’re there. I mean, I could do a remastered version one day, but that’s them. I also think that they evolve and they grow and they’re living in a different sense. By the way people look at them all the time. People come up and tell me, Use Somebody is my wife’s song or whatever, and they’ll tell me why. And they’ll give me their little life story, and I’m just thinking, and I’m telling them, that’s great, terrific. Thank you. But I’m just thinking, I don’t know how the hell you got that. That’s not a great song to have with you and your wife, man. You didn’t listen to that song properly, but it has a different meaning and a different connotation to them. So beautiful that this thing that I wrote so specifically about my life could mean something so similar to somebody in a completely different situation.

And I did have that intent to give it a little bit of vagueness so that could happen. Yeah, it took off so much further than I thought it ever could.

Well, this is the interesting thing. You’re handing it to the listener for them to interpret, and you have to sort of surrender to how it’s going to be interpreted. That’s got to be a weird feeling, because he almost was like, no, man, it’s not what’s about. Like poetry, songwriting, artistry. When the artist is not there, we’re all like, oh, yeah, this is what he meant when he drew it. You could see the shades of yellow that were in the sun and the sunflowers in the side of France. And you’re like, no, just the dude’s kid really like yellow.

So that’s like yellow.

But you’re doing that. You have to effectively give this thing and then listen to how people enjoy it and interpret it. What’s that like?

It’s like I made something that’s better than myself. I don’t know. Like, I’m Dr. Frankenstein and now the monster is designing skyscrapers crap. You did a better job than I did. I made you and you can barely talk. It’s humbling and a little awkward at first sometimes. I once played acoustic show, just a little one man show, and I think it was in Fort Worth. And some people came out and they were sitting in the middle, so I couldn’t really tell who it was. And at the acoustic show, sometimes we’ll tell little stories. And I wrote this. I was on the road and about this, and that. Not all the time, just sometimes. And some lady went, no, it’s not. I’m like, okay. And I just started playing it. I didn’t even know what to say. I wrote it. I don’t know what to say.

Fair enough. Good point. You got me.

You get heckled at a show that’s definitely a new. But it is amazing to see how people can connect it to their experience at that time. Just in the same way that when you drove by your high school, you remember the car you had, you remember the music that was on the radio every morning for the last semester that you were there. Like, there’s all this connective memories that are there that are very situational, that are very specific. And then years go by and they’re there. They’re always there. Like, some of it leads and fades. But it really is funny how, now that you’re the guy that’s creating that point in time experience that you have and giving it to somebody, in 15 years, they’re going to be driving by their high school going like, man, I remember listening to that Charlie Cope album, and this was like, I got some stuff done in that car or whatever it’s going to be, right?

It’s pretty amazing. I don’t always think about that. It doesn’t always hit me that these songs could. I definitely didn’t expect them to be as popular as they are. I didn’t expect them to get on the charts, much less seven of them. And so many different charts as well, and all around the world, and I see bands that are covering it and everything, and I didn’t expect it. I knew I’d get a couple of fans by this time in my career, but I didn’t think I’d have nearly as many as I do. It’s a little weird.

Yeah, well, it’s earned and deserved and all that. Charlie, when did you know this was your career?

It’s going to sound corny. When I told the girl, this is what I was going to do. When I told someone special, this is what I was going to do. I don’t know. She didn’t really say anything. She just kind of looked at me funny, and she had this look in her eyes I’ll never forget, we were kids a million years ago. And then I started showing her all my songs. She’s like, all right, Charlie, you need to shut the hell up now. But it was a cool feeling because she knew the first song, she knew it was about her, and it was kind of a really cool feeling. And then years later, when I started seeing people, they were telling me about the songs and how they feel for them. The career grew. I knew this is what I was probably, the only thing I was actually capable of doing and then finding more and more and more reasons to it. The career itself also was also a living entity and also grew, and so did my reasoning behind it.

The business is weird, especially now. People don’t get this that you going to produce and release an album. There’s lawyers, there’s craziness, there’s leaps of faith. There are contracts that you’re going to look back on in 20 years and weep about. You know, you hear some of the stories, even just the simplest things, like co writing credits and songwriting credits, like stuff like that. I remember hearing Billy Corgan talking about it. He’s like, Be careful what decisions you make at the start, because 15 years in, when you’re the one getting the check, and the five people that are on tour with you for 15 years aren’t getting the same check. There’s a very weird thing about being the voice, the songwriter, the creator, and having a great support and crew. But you have to think about weird future stuff when you don’t even know it’s real yet as you’re like, just trying to get yourself out there. That’s got to be a strange sensation of seeing it as a business while also just being a performer.

Yeah. And especially in my head, I’m still that 14, overweight kid with the goofy haircut. So I don’t necessarily think I need to get my band some NDAs, because when I give them the schedule for the next album, we can’t tell that on the radio. We can’t tell that magazines or my mentor is like, hey, Charlie, I just bought a magazine. Your face is on it. Like, do you put it there? Put a sticky note? That’s a weird feeling. And then the whole business side, I don’t necessarily think of those things right away. It’s more of like, hey guys, you want to go grab a burger and I can show you the new songs that I have, not here’s your NDA before I show you these songs. It’s very weird. But, luckily, I have a lot of great mentors on the music side and the business side. And they’ve helped me out and I found those really early in my career. So I did have a jump start for when things start moving. I kind of already knew what I needed to go down.

Yeah. And especially in my head, I’m still that 14, overweight kid with the goofy haircut. So I don’t necessarily think I need to get my band some NDAs, because when I give them the schedule for the next album, we can’t tell that on the radio. We can’t tell that magazines or my mentor is like, hey, Charlie, I just bought a magazine. Your face is on it. Like, do you put it there? Put a sticky note? That’s a weird feeling. And then the whole business side, I don’t necessarily think of those things right away. It’s more of like, hey guys, you want to go grab a burger and I can show you the new songs that I have, not here’s your NDA before I show you these songs. It’s very weird. But, luckily, I have a lot of great mentors on the music side and the business side. And they’ve helped me out and I found those really early in my career. So I did have a jump start for when things start moving. I kind of already knew what I needed to go down.

How much of the scene sort of impacted your ability to get close to music? Because I’d say in Texas there’s definitely a very strong music scene and there seems to be an understanding of the talent that’s in the area. It’s a beautiful thing to go through there. There like Tennessee got its own scene. Of course you got New Orleans got its own style. Everybody’s got these very localized groups. But having sort of close proximity access to a real industry, not just big oil, but big music, it must have been helpful, I’d say, versus some poor guy that’s up in North Dakota just trying to make this happen.

Yeah, his neighbor lives a mile away. Yeah, it was a huge impact on me actually. So like I said earlier, mentors. I take mentors everywhere I can. I’m always trying to learn something. No matter how much I think I know about something, I don’t know much about it. And especially like we said earlier, this business is very weird and constantly adapting. So advice that I had or lived by or even gave just a year ago might not be true anymore, especially with Covid. So a lot of my inspirations came from local musicians, probably even more so than Tom Petty or Bob Dylan that I might have grew up listening to. I think those local guys, especially around Houston, I think around Dallas, but Fort Worth is a little bit more country. Around Houston, there’s a lot more blues and there’s a lot more Americana. So it’s really folky, kind of John Prine is big Townes Van Zandt is huge. So listening to those guys, that’s a lot of storytelling there. And really intricate lyrics hanging out with those guys. And like this person taught me how to write a set list and this person taught me how to put on a show other than the music.

And this person, my buddy Van Buchanan taught me how to write a catchy song, right. Actually, I met Van at JP Hops House, which is one of my favorite bars in the whole world. Weird thing to say when you’re 20 and it’s been one of my favorite bars since I was a lot younger. I don’t want to say how younger cause I don’t want to get them in trouble. I wouldn’t drink there. I would just go there to play, but some of the top singer songwriters come around and they’ll hang out every now and then. I was part of the National Summer Association. I was part of the Houston Summer Association. A few other things, too. And just everyone would go there and play. And it was just like one of the hot spots. I would go do that and do open mics before I had a bunch of gigs. I would even do, like, seven or eight open mics in one day. Just so I was like, okay, this song was too slow. They said it needs to be faster. This one was too fast, it needs to be slower. And this person did this, and this person did that.

I try to learn from everywhere I could go. So the scene around there was very big.

The interesting thing, too, is the weird transparency to the writing process. There is a lot of that, right? And some people, maybe especially later in their career, they’re like, no, ef oh, y’all. This is what the song is going to sound like, whether you like it or not. This is how it’s going out. But early on, as you find that voice, find your style and figure it out, sometimes just through that creative process, you got to test it and audience testing. It’s like comedians do this all the time, right? They go out and they just do little, like eight minute spots here and there. And even big, huge comedians. Chappelle shows up at The Comedy Store and he’ll do ten minutes, which really blows up the poor bugger who’s on after him didn’t know that he was going to show up. But then that material gets matured and tested and worked on. And then sometimes it’s the room that’s wrong. Sometimes it’s you that’s wrong. Sometimes it’s the timing that’s wrong. And then over time, all of sudden, a you’re like, all right, now I’ve got this song that’s really ready, and it’s kind of automatic at that point.

But do you like that collaborative audience style writing?

Oh, yeah. It’s called road testing. Yeah, it’s really important. I’ve done it on every one of these songs, some more than others. Yeah, that’s really important because I’m trying to connect with the audience. I know that’s different from a show to a studio, but I’m trying to connect with them. So to get their opinion on it is so huge and especially because I’m always asking everybody’s opinion, even if they don’t know anything about music. So whoever I ask, I always take it with a grain of salt. But that’s really important, especially for me, because like I said, I’ve always had an issue with self confidence. So I’m like, I don’t know, does this work? Does this work? And then, Charlie, that’s like one of your best songs ever. Okay, cool. I’m always asking them, and I’m always very cautious about my music. I don’t want to release crap that I think is good. No one else does. So I’m always road testing it, and it helps them evolve a whole lot.

Have you ever known that someone was just wrong?

They’ve given me some terrible advice. I’ve had one of them, won’t say who, won’t say who, but one person said and was telling me something. I was like, oh, well, actually, that’s illegal. You can’t do that. But I saw a TV show about it. Yeah. There’s a sitcom about a rapper. And I just like, okay, I’m not going to argue with you. He’s like, I know more than you because I watched this sitcom. I was like, okay? I’m a professional. Cool. I’ll take your word for it. I got to run, though. I’ve had people and family tell me to stop playing shows for money, start playing gigs for free. But that’s an interesting approach. Ton of people told me to quit so many times, it got so annoying the amount of times they would tell me to quit. Not every one of them, of course. A lot of, like, my grandfather on my mom’s side bought me my first guitar, and he was the first person to tell me, I can make it. He’s even on the album.

Wow, that’s awesome.

Yeah. I got him in the intro track with the clapping, so I got him on that. But yeah, a couple of them are just, like, terrible advice. Drop out of college, get a regular job. It’s like, okay, well, at least get a regular job as, like, a waiter or in fast food or something until you really make it big and just hold off on the music. Why would I do that? Even at this point, I was probably 18. I was like, make less money than I am now. Why and hold off on the career? It doesn’t make any sense, but it’s all good. You always have to take it all with a grain of salt.

Yeah. And you think about every musician, every artist, every creator has had somebody just say, like, trash, right? Like, somebody got the First Kiss album. They’re like, I’m just not hearing a hit here. That was one of the famous Joan Jett, talks about this thing of going to, like, shopping. I love rock and roll to 40 different record producers, and they’re all like, I just can’t imagine hearing this on the radio. And today she’s probably still getting six figure checks for it.

It’s a great song, but if you really think of it, like, try to step back, it’s a great song. I love Joan Jett. One of my favorites, but it’s so extremely cheesy.

Right. Yeah.

This is the interesting thing, too. Have you got songs that people love that you hate or not hate as a bit of a dark word, but songs that you’re like? I wish people didn’t like this as much as they did, because I kind of feel like it’s either boxed into a period of time or maybe the style wasn’t quite how you want it.

Breaking Down Never Felt So Good is one of mine. And that’s a great song. I love to play it. It hurts my arms to play it, but it’s a great song. It’s really fast. It hurts, especially the poor drummer, because he’s going to town on that tambourine. When we play it live, it’s longer. So that one. But if you do it at, like, a one man show or like, a two-man show or something like that, it’s not always as good that way. So I’ll get, like, people to clap along and stuff. But if the crowd isn’t as responsive, it just doesn’t work as well. So I don’t play it in that event. Like you say, you got to update the set list in those.

Yeah.

But sometimes people just, like, request it. I’ve even had people request it, like, three times in one four hour show. The crowd was so not into it. It was just a one man show. So I didn’t have the band. I was like, don’t think okay, because, I mean, I wrote it. So if I get a song request for one that I wrote, it’s kind of hard to avoid playing that, but it’s also just a pain to play, and I got to do all the solos by myself.

If I’m playing acoustically, that don’t get no easier.

No, sir. No, that’s it. The acoustic fretboard and string tension is not designed for that kind of playing. There are guys that I’m always amazed. There’s a guy who’s a subway musician in Toronto where I was raised, and I remember going through every day, and he would play. It’s like bitter cold. He’s wearing fingerless gloves, and he’s playing this crazy, like, high speed, like, Spanish Flamingo stuff. And then he’s, but then it turns out he also played, like, Heavy Duty, like, prog rock as well. And he started playing on an acoustic, and he’s like, I can’t do this, dude. You break down fast. And he plays all the time. And he’s like, no, this is not good for your soul or body to do this.

I have several guitars on the stage, but one of my main guitars, one with a lot of the pictures with Jesse. Either custom strings, so they’re really thick and they’re really heavy. Yeah, they’re hardly guitar strings. They’re more like steel bridge cables.

What’s the gauge on that from? This is where we nerd out for all the people that if you want to tap out for a few minutes, we’re going to nerd out on some guitar tech. You can even hear you fighting to bend. Like, you know that. Those are some thick strings. But what a beautiful tone, though.

Oh, yeah. Love this guitar. I named her after Jesse Coulter.

Oh, yeah. Very cool.

Yeah. All my guitars have names. Oh, yeah. We’re going to nerd out over here.

There you go. Just because I got a collection of guitars around to show you. This is when my wife got this for me and I was actually particularly proud of this one. So it’s hard to see, it’s not going to focus. That’s signed by Ed Sheeran and it says ‘Please Play, Don’t Display’. Yes, sir. I play this thing all the time. This is a Martin, it’s like a baby guitar. This is Ed Sheeran’s, like model. I think Ed Sheeran must be 4ft tall because this is tiny. It’s just like a little wee guitar. So it feels funny because I play a seven string. So when I pick up even a six string, I feel like Jimmy Hendrix’s hands wrapping around the neck. So this thing, it feels like junior size. But it’s fantastic to sound like this little tiny Martin guitar. But it’s just like just big thick sound and I love the warmth of it.

‘Please Play. Do not Display’. I like that. I might steal that.

That is. You got to put that on someone’s guitar.

I’ve signed plenty of guitars, man. It always freaks me out. Are you sure you want me? Do you want me to sign your beer can or something? I do that a lot.

That’s an interesting thing too, right? Is that there’s this different level that you get, right? Because some people want you to sign a thing. It has both a meaning in that moment and they see this longevity of the meaning. And it’s really amazing to be able to mean that to somebody, right? That’s got to be pretty well. And then at the same time you’re just like, this is like a $3,000 guitar, dude. Maybe you should, can I sign a piece of paper? Like maybe a book or something?

Yeah. One of my biggest fears is like I’m going to misspell their name on their guitar.

With a nice big thick Sharpie.

Yeah, exactly. I would feel like such a tool if I did that. You could see me. If there’s like every now and then at the bigger shows, there’ll be like a line of a couple of people that want me to sign stuff and they’ll take pictures of me and stuff. You can see the panic in my eyes.

Now this is the fun part because I know there’s nothing worse than be like dance for me. Right? Because you, come on, we want to talk. But at the same time, I don’t even know the legality of, ‘can I play your songs’? If you’re playing your songs on my podcast, am I going to get busted for a DMCA? I don’t know how that all works.

You have my permission. You can play my music as much as you like.

There you go, folks. That’s for the lawyers. There you go. Charlie, it’d be a real honor if you want to play a little bit for us. I would love to mix up. Be the first time I’ve ever had a live player on the podcast. And we can jump back into some more of the tech.

Sure. Do you have a favorite?

No. You know what I’m going to say. This is artist pick. If you had the song that you wanted people to know that this is the start of your listing journey, throw down.

Make sure I’m in tune. I’m not.

This is half the battle.

Yeah. At least I’m inside, not out in the cold.

There’s nothing worse than playing outdoor gigs. And you’re like, this is not going to go well. Temperature changes make a mess.

Your fingers turn the sausages.

Yeah, I’m in New Jersey now, but I grew up in Toronto and it was disturbing. We’d go and play outdoor games. You’re sitting around a campfire. See, your guitar is, like, hot on the front. Your back is cold from the winter and it’s a bad scene that I’ve got an old Seagull guitar, which is basically almost the same style as a Martin. It’s an open top, so not laminated. This thing has been through wars. I still have the price tag on it. I bought it when I was, like 22, so it’s like 25 years old. And I still love this guitar, but, man, it’s a miracle it’s still with me these days. And the action is still, like, super low. It’s a beautiful play. I’m a big fan of it.

I see, like, William Prince playing outdoor in the snow on New Year’s Eve in Canada. I was like, oh, God, not just the guitar, but also your vocals. I’m wearing a Carhartt if I’m outside and like, anything below 70.

All right, ladies and gentlemen, there you go. I got to say, Charlie Cope.

Can you hear the guitar okay?

Yeah, it’s actually pretty cool. The cool thing, the signal wire platform that I use, it actually plays pretty cleanly and technically I can actually talk while you’re playing. And it records both. It’s not like Zoom, where it cuts out one when someone else starts talking. It actually multiplexes audio. That’s another nerd bit for the folks that are used to networking and speedy recording, but, yeah, that’s why it doesn’t cut off as bad. Zoom is horrible to play on because any change in dynamics, it tries to auto adjust and it just blows up the dynamics.

Very cool. Yeah. So we talked about the best tape ever made, a couple of times. See if I can get work. We’ll do a little different version.

You heard that’s driving stop.

Yes.

And if we work out, our story was riddled with disaster. We were never meant to make it anyway.

I look back and all I see is the laughter. So I showed you Willie Nelson’s song.

I love it. Beautiful.

My voice might be a little bit out of tune. I didn’t warm up or anything.

No, I know that’s the worst, too. It’s one thing as a guitarist, you can always sort of mess with your fingers and get ready. Thank you for being on the spot and nailing it too. That was very cool. I tell you a perfect setup because one of my favorite questions that I love to ask people, which I’m very sure I stole from somebody like Tim Ferriss. And it is thematic to the song. What is the worst thing that’s happened to you that you’re the most thankful for?

Good one.

One worst thing that’s happened to me that I’m thankful for. It might not all be great, but I was going to say it might not all be great, but it all worked out in the end. So none of it’s terrible, but there’s quite a bit of terrible stuff. I mean, as you can probably tell if you Google me enough, look up on the magazines. A lot of people know I have my history battling addiction and I was homeless for a little while. But actually the homeless thing wasn’t that bad at all. I also don’t want to spoil any future songs.

It’s all good.

I had some problems with this girl and she had some problems in her personal life, and it just killed me to see her and her struggling with her own problems. But I think that made both of us a lot stronger. And if she didn’t have to deal with those problems, she would have been able to brace the ones that were coming. I know that didn’t really happen to me, but seeing someone that I love struggle, it’s definitely worse than anything that could ever happen to myself.

That’s good. That’s why you never open with that question.

Or end. That would be a weird ender, too.

And you shared before about your personal journey and some of the challenges you faced. And this industry, the music industry, I say this industry like I’m in it, but I know of it. And I got a lot of friends that are in the music industry and performers and everything, TV, radio, it’s just on a good day. It’s a weird life because it’s very non structured. It requires you to build a lot of coping mechanisms to normalcy. Right? Like there is no normal by the standard definition. And it’s funny when you see a lot of folks, right? People see like Dave Mustain from Megadeth, and he speaks three languages and he talks about all his philosophies, read and writing, and people are like, but you’re the lead singer in a heavy metal band. This dude’s got a lot of free time and he’s fighting addiction. So he has built a lot of coping mechanisms and things that allowed him to compensate for time. I could be on the tour bus and then going into the city copping and then heading back to the bus, or I can read a goddamn Shakespeare and really get into something that keeps me busy.

So when you go into an industry that is non structured, where you have to sort of build your own safety into your life, how does that work?

Well, I took control of a lot. I don’t really like depending on others, especially in this industry. I mean, there’s been so many times when people have asked me some other groups, some soul and pop singers and blues band, we were all going to go on tour together, and they came to me, they approached me, they gave me all the numbers, and we even had contracts. And then the whole tour kind of fell apart. I knew I had contracts, I could have done something. But it’s not like I was being taken advantage of or anything like that. So it unfortunately fell apart. So I rolled with it. I just said, no worries. Keep me in mind in the future. Let me know if you need anything, that sort of thing. Keep in touch. And we didn’t. But I really dislike depending on other people. I’m very independent. I’m a very independent person. So I did everything myself. So all the tours that I go on now, they’re my tours, and if I run in, they do sometimes intersect with other people’s tours. Parker McCollum and Lynn Clark Green and Random King and stuff like that, we will intersect.

But it’s always, if I’m on tour, it’s my tour, at least for the next few years. So when I’m the boss, I have so much more control. I don’t have complete control, but I have a lot more control. And I think the people that work for me, my promoters and agents and musicians, I think they realize that I am extremely professional in what I do. I’m also a man of my word. And so I will go above and beyond to see what I mean. I mean what I say. And sometimes, like I said, things happen, COVID happens. I don’t think anyone really has.

No one had that in their plan.

Yeah, only a couple of people really gave me a hard time. Like, why does this happen like this? Well, COVID. 90% of people are like, okay, that’s cool. No problem. Understandable. But I try to take control as much as I could and be very professional. And I also expect and ask that everyone that works with me try to do the same. I hold that very, somebody’s word means a whole lot to me. So I’m a very trusting person, but I think I am where I am because I learn everywhere I go and I get mentors and all that.

So I’m a trusting person, but I’m also going to learn. So if your word falls apart a bunch of times, I’m going to learn, unfortunately, as it may be. So I try to take as much control as I can, even if that’s not necessarily the healthiest way to deal with it.

I’ll say it’s not even as much control as responsibility. You put the responsibility on yourself, but because you’re giving back into it, right? It’s not just I’m taking controls and I don’t trust anybody. You’re taking controls, and I’m ultimately responsible for the outcome here. And I’m going to depend on other people occasionally, but I want them to be responsible. And if they fail to meet that bar, then the responsibility goes back to me. So it’s a weird thing that we still talk about the word control. And some people say, like, Charlie, you’re controlling because you do everything. There’s a very big difference between control and responsibility. Control is power. Responsibility is ownership. Big difference.

I definitely don’t have much power, but I definitely have a whole bunch of ownership.

You sure own the outcomes.

Yeah.

But it’s a huge lift because it’s not just you. You’ve got performers, AR, PR people. You’ve got contracts to uphold. You’ve got to take care of your body, take care of yourself to perform all the time. People don’t get like, if I get sick, I just call in sick. You’re out on the road, you’re sick. You’re gargling lemon and salt water and spewing it out your nose and doing weird stuff to flush your sinuses in between sets because you can’t stop. That’s nuts.

We have protocols. If any of the band members ever get sick on the road, we have protocols for that, because as a singer, that’s the worst thing that can happen. So terrible.

I remember hearing that was a funny thing. Billy Corgan was on. He was getting interviewed. I think he was on Opie and Anthony, they were in New York. They’re a talk show. And like, 40 minutes into the interview, the guy’s like, yeah, sorry, there’s water everywhere. Because I’ve been sick for two straight days. I’m just trying to stay hydrated. And Corgan just says to him, perfect. This is a great time to tell me, because it’s not like my voice is my job. I’ve been sitting in this tiny little glass room with you for 40 minutes, and you’re breathing on me, you bastard.

When I was in the Hill Country, like, Hill Country area of Texas on tour, I played 23 hours in eight days. I think it was like 13 gigs or something. I don’t know, something like that. It was 23 hours in eight days. And so I was sick as a dog because I can’t eat the day of a show until afterwards because it’ll mess up my voice.

Yeah.

So I wasn’t eating because I was having multiple shows in a day. I wasn’t eating until really late at night. And if I had a morning gig, then I’m not going to be able to eat. And I wasn’t sleeping because I also had to do all the business side stuff and soon to come and everything. So I was sick as a dog, and I got tested for COVID, and it was negative. So cool. But it was just like, you probably should try sleeping. I’m like, well, I can’t. I was terribly sick for, like, two weeks because I couldn’t get better because I couldn’t sleep, so I couldn’t heal. It was terrible.

It’s the strain on your voice. It’s a muscle, right. And it’s like people who have sore muscles, they take an Advil or Tylenol, whatever. There is no Advil for your throat. You can ultimately try it, right? Yeah, that’s right. The catch with having to do this, especially you’re doing morning gigs, you do morning radio for an evening gig and they want you to perform. It’s really hard to just be on all the time. And sometimes when you’re touring, that’s it. There is no real break.

Yeah, I’m a workaholic at this point. I have a very addictive personality. I’ve actually been awake for 48 hours, give or take. I’ve been working a lot since this will come out in December. So I can say this. We have two tours next year.

Unbelievable. Congratulations in advance, man. It must feel good to know that the road is calling again.

In many ways, yes. Absolutely love it. In other ways, like getting sick for two weeks because I can’t heal, that one sucks. The cheap Airbnb. The road is really weird because it’s trying to, like a coping mechanism. Kind of like you said. One night you could play for 1500 people. People could scream your name. You could be signing guitars. Music legends that you grew up listening to could just be hanging out in the green room and want to jam with you. And that’s just an amazing feeling. That could be like your Friday night and then your Saturday night, you could be playing in a small dive bar for 25 people. It’s such a weird, and it could be the very next night. It’s so weird. And just trying to cope with that, that just huge high and huge lows as you’re just trying to make a living and connect with people and do whatever you’re trying to do in your music or your job. And then just the ups and the downs are just so much bigger than any other ups and downs in any most normal jobs. And I think a lot of musicians try to cope with that.

And the workload with chemical dependence, it’s definitely an easy thing to get into.

Yeah, that’s the challenge. And it’s just there people say, I don’t understand why people don’t even have to be a real pro musician. I used to do Tuesday night gigs that sound like, you’re playing with four other bands and there’s 25 people and then you realize it’s because it’s the bands and their girlfriends. That’s the 25 you’re playing for, but you’re playing for half price drink tickets. You’re not even getting paid. But it was like, hey, it’s just time on stage. It’s practice, it’s fun. Sometimes people show up, you never know. And even in those situations, you could see in the peer level, it was very easy to get into much more than just the beer behind the bar. And I was lucky enough to avoid that culture altogether. But it’s a tough and active choice that you got to make all the time. People don’t realize that it’s such a weird. Like, it’s intrinsic. It’s actually buried in the lifestyle.

Yeah. And it’s free. I don’t want to give peer pressure because everyone says that, but at some point it’s almost like just excessive guerilla marketing. I almost bought a T-shirt for, like, $80 yesterday. I was like, what am I doing? What am I doing? These aren’t even ten just because I see the ad everywhere I go. I was like, you know what? I don’t have any nice T-shirts. It’s just everywhere. And when you’re on the road, it really is everywhere. And that’s one of those things that it’s my tour bus. It’s got my face on it, or at least part of my face on it, because the wrapping didn’t come out great and it’s all mine. And I don’t care what you do, as long as you’re safe and it doesn’t affect the show. It’s none of my business, but I can take some control, some responsibility for it. Again, like you said, two different things, but I can. Okay. Hey, man, at this show, I’ve played this venue before with another group. They do have a lot of things going on backstage. Also, you’re going to meet a couple of celebrities, and it’s such a weird toss up.

And I know that they’re like, yeah, let’s do some coke with the “leave his name” celebrity. And then it’s totally something I get and something I’ve done so much more than any human being should have, but at least I did it got through. It got sober, the last time I got sober. And I can use it as an experience, even if I am a little bit terrified of it now. I can look back with experience and know how. And also, I mean, you meet so many people that they could be OD-ing or getting into dangerous situations or something like that. And like, hold up, I know exactly what to do.

Yeah. It’s kind of sad that you end up having to be part-time paramedic. You almost got to be ready for that kind of stuff. A lot of people don’t get off those buses.

Yeah, we have some clauses. Like I said, it’s on my business, but I do have a van, and anyone that needs a ride is encouraged. I used to say driving under the influence is cool as long as you can handle it. I don’t think that anymore. I’ve seen it go very bad, especially with musician egos. It can go very bad, even if it’s a home gig. We do have to drive sometimes an hour or two just for a home gig, and it can go bad. 02:00 A.M.

Oh, that’s it. And all it takes is just, it’s very easy. Yeah, you’re already tired, you’re amped up, you get a couple of drinks. Even like, comedians do this all the time. Like, I’m in a plane to New York, just going to drive back to Boston and it’s like that’s a three-hour drive, even if the ultimate intoxication, you’re just going to fall asleep. No other stuff. Like, there’s a lot of dangers that are present that are not normal for most people. And you have to think about stuff that’s very different, which goes to that thing of responsibility. And I appreciate you can tell in the way you even tell the story of it, how much it impacts and it’s inside you. So you got a lot of success. And I guess there’s the fun question, when will you be able to say, I’ve made it? What’s your mark?

Unfortunately, I don’t think myself as a person, I don’t think I’m capable, and I don’t think myself as a businessman, I don’t think I’m able to figure different things. But as a person, I don’t think I’m capable, because no matter how many people come up to Walmart and say, you’re the music dude, I just can’t see myself as someone who’s like a big deal. And that’s not even how my view has made it. My goal is to connect with people. And so there’s not a number on that. I don’t think there’s any real possible way to connect with everybody. So there isn’t a number. It’s not how many people come out to the shows or how much money or tour billboards have my face on them right now. The numbers too, by the way, not right now in total, but it’s just connecting with people. So I don’t think there’s ever that number to get to. I don’t think I’ll ever be able to actually make it. My little crusade of love, peace, and Kumbayah.

I think it’s cool because even if you do get to whatever the next level is, your personal responsibility won’t let you stop. And it’s a beautiful thing when you can take your band with you, bring other people. You can support a team of PR people around to be able to actually employ people and do what you love. And I got a huge respect for you for doing this. It’s really amazing and it shows in the music. It’s really fantastic. You’re a fantastic performer and writer, and if you hadn’t done that bad album, then this would be your bad album. So you got it out of the way.

I’m hoping that ten years down the road, I’ll think the same one about this one, because that just means I grew. I got better. That’s what I’m hoping.

Well, Charlie, you got a lot more than ten glorious and well earned years ahead of you, especially you got seven in there already and you’re 20, so it’s a good start. You’re not even able to drink legally. At most these places, they got to fire you in the back door and try and hide you from the bouncers. That’s always a weird thing too, right? When you’re playing and you’re under legal age, it’s like they can obviously do it. They can furnish you getting in and out, but there’s like all sorts of weird stuff that gets wrapped around that one, I imagine.

Well, I’ve had this beard on and off, actually since I was 14. So the beard and my hair is up in a bun now, so that helps, too. So it’s so weird because the bouncers have no idea how old I am. Nobody knows how old I am, unless they look at the magazine stuff. I’ve had like bouncers and venue owners hang out with me. Because I’ll hang out sometimes after the venue closes and they’ll just be complaining about these kids trying to sneak in. And I’m like, 16, I’m like, man, these college kids and like, I’m a sophomore in high school and I’m just like, they’re terrible.

I remember going to this. I grew up in this tiny little town. It was like a farm town and everybody knew everybody, right? Literally, like it’s a 2000 person town. And there’s a place called the Village Inn which is like the perfect name for the local drinking hole. And I would go into the Village Inn all the time and I remembered going there for like a year and a half and then celebrating my 19th birthday in Canada, drinking age is 19. And watching you pull out your driver’s license for real now. And they’re like, hey, what’s the big occasion, like turning 19th day? And they’re like, wait a minute. I reckon, I know you. You’ve been going here for a long time.

It’s all good.

We won’t tell anybody’s story. We’ll save that until the statute of limitation runs out.

There you go.

Charlie, thank you very much. This has been a real pleasure. And there you go, folks. charliecopemusic.com, lots of great links down below. Get the album and if you can’t afford the album, I’ll buy you the goddamn album. It’s that good. There’s lots of ways you can get it. So do so support amazing musicians and the whole ecosystem and, Charlie, I hope to see you on the road. Hopefully one day, I’ll be able to bump into you backstage somewhere on the 2022 tour. Now that the world is opening up a little bit, It’s been a real pleasure here to chat.

Yeah. Thanks again for having me on.

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Jennifer Byrne is the CEO of Arrived Workforce Connections. Previously Jennifer was responsible for market expansion initiatives leveraging business model and technology innovation for government, healthcare, and education providers around the globe at Microsoft after joining as the Chief Security Officer for the Worldwide Public Sector Division in 2014.

Prior to Microsoft, Jennifer was a leader in Cybersecurity, having held technical, sales and executive positions at companies such as Intel, McAfee and Symantec. She began her career in technology as an Information Security Analyst and Engineer serving US Government clients.

Her first career, which remains her passion today, was in the non-profit world working with under-served populations.

We discuss how to use tech innovation for optimizing the human experience, the importance of tech access to underserved communities, and how we can all do something small every day to make a difference. 

Thank you and congratulations to Jennifer on her new role as CEO!

Transcript powered by Happy Scribe

Welcome to the show. My name is Eric Wright. I’m gonna be your host for the DiscoPosse podcast. This is a really enjoyable episode featuring Jennifer Bryne.

Jennifer. Between the time we recorded and now when we released, we can proudly say that we can say Congratulations to Jennifer on becoming the CEO of Arrived Workforce Connections. Jennifer has such a storied history in the industry, but more than anything, the reason why she’s been successful both in work and in life is because how she gives back in her approach to thinking about what can we do to give, especially to underserved communities and to the broader community.

This is a great discussion and we cover a lot of ground. We didn’t get a chance to go specifically into her new role as CEO because it was in the works and had not yet been announced when we recorded. So big thanks to Jennifer for giving me the chance to record while she’s in the throes of transition. And Congratulations again. So please do follow the link and reach out to Jennifer and give her a good shout out and a Congratulations. I got to give another shout out.

Speaking of, to the fine folks that make this podcast happen and to really celebrate a fantastic year we’ve all had together. So remember when you have anything in the world of data, in the world of compute, in the world of cloud, you need to protect those assets. How do you do it? Go to the people that have you covered for everything you need for your data protection needs, whether it’s On-Prem, whether it’s in the Cloud, whether it’s Cloud-Native. They’ve got stuff for SAAS, they’ve got your team’s protection SharePoint. You name it.

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So let’s celebrate this together. So go to vee.am/DiscoPosse. And while you’re protecting, make sure you protect your data in transit as well. If you’re not using a VPN, you definitely need to think about why this is so important. We’re in a dangerous world. Let’s make sure we reduce the risk exposure when you’re surfing the Internet. Whether it’s out in the world or even at home, go to tryexpressvpn.com/DiscoPosse. You can check out ExpressVPN. I’m a user. I’m a customer. I really like it. So go check it out.

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Hey, this is Jennifer Byrne. I am the President of Digital Future Consulting and the former CTO of Microsoft US division and about to start a new venture as the CEO. And you are listening to the DiscoPosse podcast.

Jennifer, thank you very much. This is very exciting for me for a variety of reasons and, of course, for my listeners. But selfishly, I think I really do the podcast just so I can meet amazing people like yourself. You’ve got a really strong sort of storied career. You’ve done stuff that I find really inspiring in your approach to the way that you treat people, the way that you empower others, the way that we can use technology. And you talk so much about empowerment through technology. And this is near and dear to my heart because I’m a nerd at heart, and I love technology, and I love the Nerd Bits, and I love getting excited about it.

But I also have to see that what really gets me is what we can do with it. And so we’ll talk a lot about the path to digital transformation and the human empowerment that we can create along the way. But anyway, let me first of all, for folks that are new to you. Jennifer, if you want to give a quick introduction, and then we’ll talk about, first of all, digital future consulting and of course, much more that you’ve got going on.

Yeah. Thank you. Eric. I’m excited to be here, too. This is why I love to be on podcast because this is when you get to talk about all your favorite topics. So the big anchor in my career was the years I spent at Microsoft as the CTO, ultimately of the US division. Although my first CTO role at Microsoft was in the industry team, and I joined Microsoft in 2014 as the chief security officer for the public sector group. Because I’d spent the previous 20 odd years in cybersecurity at Intel McAfee Symantec into startup and way back when I was an InfoSec analyst working for government agencies back in the late 90s.

So that’s my career. I left Microsoft when I had felt like I’d put in my time in big corporate America and felt a calling to do something a little bit different. I had run a couple of innovation projects in my last role as CTO focused on digital skills, and it really started out really simple because we needed more people to know how to use Azure. You cannot drive cloud consumption when there aren’t enough employees in your customers environment than no Azure. But you start to pull the thread on that one, and it’s really not about Azure.

It’s about the skills that you need in order to learn Azure. And then it’s a bigger skills conversation. And all of a sudden, you’re outside of the walls of your customers environment and you’re into communities thinking broadly like, how do we get skills to happen? Because the world is getting more digital and you don’t know that any better than you do when you’re in this industry trying to make that possible. And then it just kind of occurred to me as I’m sitting in communities like Louisville, Kentucky and Houston and Syracuse, New York, that there is this unintended consequence of technology that I think, Eric, you know, and all of us who have been in this industry, we’ve been in the business of talking about how amazing technology is and all the fantastic things they can do in the world, how many problems it can solve.

And it is largely a positive passion that we all believe in. And yet the unintended consequences that it creates a need for skills that a lot of people don’t have. So how do we solve that? And by the way, that skills gap follows socioeconomic, existing socioeconomic rifts in society. And so it is a problem that takes more than technologists to solve. But it felt like a worthy thing to be doing. So when I left Corporate America, I decided I would spend a little time in the future workspace.

So I started a small consulting agency and I work with startups and advise companies. And that’s super fun. It keeps me fresh and also spend a lot of time just doing research and talking and thinking about future work, which has led to a role as a CEO and a company that is playing a small role in that space. So anyway, that’s the nickel tour around me and my career.

Well, there’s so much to, so many threads to pull on. And I think you hit this really strong thing that especially as technologists, where it’s a bit of a bubble. I get concerned about the echo chamber of raw technologists who are all on Twitter, and they’re all at the events. And we all sort of like chatter amongst each other. And that’s fantastic as a way for us to kind of like, build new things. But for people that don’t know what SoMa is in the Bay Area, and there’s so much of this country and of the world that’s beyond the very tech centric Silicon Valley, the New York Bank sectors, like all this amazing stuff in between.

As a technologist, I would go to events, and I would talk about how we’re into other areas, right? I go to Wisconsin. This is one thing that was amazing to me. You go to Wisconsin, there’s these incredible technology companies. And at first I was like, just like the stupid, arrogant guy that lived in the city too many years. I was like, That’s funny. Whenever I reference Wisconsin, I always think of like a dairy farm or something like this, like people with cheese hats.

By the way, that does happen in Wisconsin.

But it was humbling to realize that they have really done leaps and bounds of advancement in how they’re leveraging technology to do a lot of these flyover state things that the rest of the tech ecosystem kind of forgets, goes on. And I was happy when I realized I’m like, this is what matters. These are the stories that need to be told, not how I can get Bank of New York Mellon to go from VMs to containers. That’s neat. But when I can talk about people that never worked in tech suddenly becoming programmers and using no code and using the cloud.

And they were from all sorts of diverse backgrounds. That’s the exciting part to me. And I love that you’ve done research in this area as well, and you’re really working hard to broaden your audience.

Thank you so much. I love what you said about Wisconsin because the specific epiphany I had, and it happened in Louisville, Kentucky, when I was at a ribbon cutting event for a makerspace. It’s like a nonprofit and they renovated it, and they created these conference rooms, and they were really just in the business of helping very small entrepreneurs build the things that they wanted to build. And I had this, as a Microsoft executive, you’re there to stand at a podium and say kind words. We’d sponsored some of this.

I loved the project, but we give them some dollars. That was really, some total of what we did was lend our name, our credibility, give some dollars. I flew out to Louisville, and that was what we were going to do. And it was so clear to me that that was actually just in the broader context of things. Such a small contribution to the grander picture of a really healthy, inclusive digital future because the real work was being done by the people in the facility. The real work happens at the ground floor on the street level.

And I was spending all my time on the 28th floor of a beautiful building in Bellevue, Washington, thinking about programs and thinking broadly and top-down. And I got all the attention. I got all the attention, but I wasn’t really the solution. So when you get down to the street level, if you’re in Wisconsin and people have real problems and they’re vary from a technologist perspective, they’re great problems because they’re discrete problems. They’re bounded. So you can attach technology to a problem at that level and actually generate a difference.

The distance between action and reaction and a small problem is very short. The distance between action and reaction and a really big macroeconomic or global problem or something that would be worthy of a corporate initiative is very long. So if you want to measure impact, then get down into the street and start doing stuff, and that was really when I thought, okay, I can see how this stage of my career could come to a really wonderful and positive end. And I could have the beginning of something else that would be fulfilling for me and also just measurable enough for me to feel like I was making a difference.

This is the interesting dichotomy of, as you said, becoming sort of the face and voice of technology and transformation and all these things. We have to have the evangelists and the advocates and whatever the title is going to be next year when we’re no longer developer advocates are no longer cool. Whatever the new thing is going to be. And it’s this weird thing that I sort of struggle with all the time of being able to get out and meet with people and listen to them. When I do a keynote, it’s to listen to 500 people, to watch their reaction as we’re talking about something and change the way that I tell a story and change the way that I look at what’s next based on that live reaction.

Plus, after the fact we get to talk to people on the ground and you really hear what’s true. It’s very easy to get this Ivory Tower super presenter mode in. But now the advantage you get is pairing that opportunity where you can write books and be a speaker and do all these things and do the ribbon cuttings and then also really be mindful and humble about who’s really doing it. Like you said, this is the true sort of boots on the ground, the unsung heroes, the real transformation is all these other people.

So it’s just weird. I feel bad sometimes, in fact, a lot of friends of mine that are in the public speaking space, they’ve chosen just like to stop. We need to open the stage up for more people. The hard part is when you’re good at public speaking, you get asked to do more of it, and you’re sort of stuck. Like, Why is Robert Downey Jr. In a lot of movies? Because he’s a great actor. So is it his fault? I don’t, not that I’m Robert Downey Jr., for a poor example.

But I mean, I love that you’ve been able to strike this beautiful balance of being close to where it’s really happening. And I find people that have trouble. Sometimes they get a little hung on the idea of looking down from the stage.

It’s tough to find the right altitude. And I will say in defense of good speakers everywhere, that we all have to move forward together. And so it’s the three-legged stool analogy. Two legs just won’t do. So we all have to be doing all of it. And by the way, look, I’m in your podcast. I love to talk about this stuff. So it’s the daily drip of being able to talk about the things that matter, and hopefully in a way that’s helpful to other people is important for me, too.

When I got out of Microsoft and you just do a bunch of stuff and you’re trying to cycle through what I realized I was doing eventually was trying to find the right altitude. I didn’t want to just talk about the problem, but I didn’t want to get so down into the weeds that I was lost in something that felt like a passion project but wasn’t going to create some kind of impact on the world. And so then you sort of get into the problem space you’re in, what does the ecosystem look like?

A tech background really helps because it’s kind of a design thinking or systems approach to things where you’re trying to understand the inner work I was in the future workspace and am and thinking about how do we democratize access to skills, but also how do we change the power structure such that people themselves have the ability to leverage the things that make them better if it’s a skills course or whatever, into a better job, because that’s not how the job market works. It’s very top-down.

So if you’re at the bottom, you just wait for jobs to come to you by way of a job advertisement on Indeed. So if you want to go invest in yourself and get a new skill, it’s a really uncertain business model, right? I mean, that’s not how people think about it, but if you’re a business person you’re like, I don’t understand the ROI of that. That course is going to cost you $12,000 in a year, but you have no actual guaranteed return because you have no way of proactively advertising yourself.

The only platform that exists for that is LinkedIn, which is fabulous, but LinkedIn from a demographic’s perspective is the higher end of the job skills, sort of like in healthcare, treating what they call the worried well, the people who are already healthy and they just want to get healthier. Like LinkedIn is a proactive profile building platform is for people who already generally have a job and they want a better one. But we have this whole section of the workforce that doesn’t. They’re just struggling to get living wage who are very interested in building capabilities and experience that will provide a better path of the future.

But we don’t have a path for them to do so in a proactive way. And so that was when I started to understand in this skills job space what the ecosystem started to look like, where the power was, where the connection is, and then from there, you can figure out, okay, what could we do from a tech perspective to solve that? So that’s all my long, winding way of saying for me, I had to figure out what altitude I could be relevant in this process, and it took a year to get there.

What I respect about how you just described it and your approach to it was just that you have to take a hypothesis. You have to test the hypothesis. You have to live amongst the results and then bring that back to the hypothesis and effectively run it through this machine. And that’s really what makes, it’s very easy for the, I’ll say the pundits, as I call them, right? That it’s easy to sit back and talk about the future of X, but yet never be committed to saying this is how it’s going to go and then writing it down and saying, I’ll pay $1,000 if I’m wrong, like, you’re effectively skinning the game committed to the outcome because you are getting close to who will be affected by it. You’re looking for, especially a population that’s, like, under represented population.

It doesn’t even have to be such a sort of distinct niche. It is 30 plus percent of the United States as an example, and I’m Canadian. My funny accent gives me away sometimes, but I live in New Jersey. There’s so many people who, like, we take for granted. And I say we meaning the Twitterati, right? We’re complaining. Everyone’s talking about the great resignation, and it’s a proud thing. I’m like, yeah, that’s right. Because people are saying, like, oh, it’s disgusting that they’re going to make me go back to an office.

Did you go to Whole Foods today? Yeah. There’s 1000 people, that’s their office. Those people that made sure that you got your well crafted latte and your fancy artisanal steak. They don’t have a work from home option. We have to remember that as a community, it’s not just the community of, like, it’s the community of existence. It’s so easy for us to get just wrapped into, like, oh, yeah, Linkedin is for everybody. I love LinkedIn. I love that it’s a great tool, but it’s very easy for us to just say, like, oh, this box is the Earth.

Right. Yeah.

Totally. You know, I agree. That’s the challenge. It’s a big challenge. It feels like something that could make a difference. And I love when I see my own peers trying to solve the technical aspects of that problem. And many of them are whether that was the intent or not. Microsoft isn’t the only company. There are many that are trying to. IBM, as an example, are trying to democratize access to technology by abstracting the complexity out of it, which is the inspiration behind low code, no code, the abilities or capabilities and whatever platform you’re in.

And digital skills. All the companies are spending a ton of money to try to solve that problem. So I think it is something that we broadly recognize as an issue. The problem is that it is an issue that’s so intractable in its nature because it’s embedded into the kind of the economic structures of our society that you just need a lot of creativity and effort to make a difference. And, you know, I have two kids in their twenties. My daughter is an aspiring artist and works at a restaurant, and it’s tough to watch it.

My son is in his last year as a computer science major, so he’s figured out how to have a career that will pay money. But I’ve got an equally bright, hard working kid who didn’t make that choice, and she’s going to have a tougher road. And I see from her first hand how the world is not built to serve her in her needs given what she wants to do with her life, and that’s okay. Like she made her choices eyes wide open. But there’s stuff that we could fix that would make it better.

And it’s just not about handouts or anything. It’s really just about rethinking the problem in a new way. And if you can make your society healthier, everyone benefits, it is a shared infrastructure that we’re in after all. So that becomes very personal to me on that level. And trying to figure out how to solve it becomes super important.

Yeah. There’s a real challenge in that. The business world, especially the tech startup ecosystem, is very driven on quarter over quarter measurement and growth. But to have the long view, this is why philanthropy and corporate don’t line up in the pure money sense they often can, because it’s a tax deduction. And at least we’ve created a way in which that it can incent people to give back in that way. But what we really need to do is create programs and put people in front of people and show them, that story is there.

I think democratization is a great way to talk about it now. Like you can become a Twitch streamer and you only need to just do the thing that you did, right? It’s the potential is there, that is something like that. You can go on YouTube, you can learn to program through. You can take Harvard Business School courses on YouTube, right. We’ve created opportunity like as far as content and tech access, although Internet access is still not 100% available. Right. But connecting people and giving them a path.

I think this is what’s missing and like mentorship. So I’d love to get your thoughts on this. What have we got today that’s not being used, right? Because we haven’t connected people to show them how to embrace and leverage it.

Yeah. Well, I think it’s a slightly different problem depending on industry. And again, this goes back to your Wisconsin comment that we all think we understand that the edge of the horizon, as we see it, is the actual edge. And it’s not right. We all live in these universes. And so that question for people who are in whatever space where they can move toward Tuck In at Varleys, in the way we would describe it. Computing, right. Coding all those jobs is when there are things that we can do there.

And I think it has a lot to do with a bigger corporate investment and nontraditional learning skills. We could dissect that problem, and I’m very interested in it. There’s a job taxonomy of the future, piece of work that needs to be embraced by the Fortune 500s and 1000s so that HR and people managers recruiters can understand what they’re even hiring for, because once there’s clarity on what the job of the future looks like, there’s clarity on the skills required for the job in the future. And once you have that, you can start to rewrite job descriptions.

You can start to think about the way you recruit. You can start to signal out to potential candidates what they even need to do in order to be eligible for that job in the future. And I think that will sort itself out because you get smart people in that swath that understand the problem and can solve it. But there’s this other technology conversation that it’s easy for computing technologists to forget, which is that in a factory, automation in a factory means that somebody who is actually doing knobs and levers on a control panel is going to move to an iPad, and that iPad is going to require some level of digital context or fluency, that for you and I, might not be the biggest deal, but for people in industries, it will.

There’s a lot of manufacturing and light industrial that works on paper today because they haven’t had a business model to do anything else. Like the solutions factory, light industrial is really interesting if you look at it as an industry, because it’s a very long tail industry where you have a few companies that are big, but most of the revenue or a lot of it is driven through small, independently franchise. If you will branch factories or installations or smaller companies because they are providers to bigger companies, they don’t have a business model for adopting technology.

They don’t have the revenue to do it. And so it exists on paper. But as that automation flows down, you’re starting to require workers to have a level of digital skill that they don’t have. So a manufacturer of a conveyor belt technology that gets put into a factory might require a certification to use that technology. The certification, if you had, it might actually allow you to go find a job that pays $3 more an hour because it’s a little bit more advanced. That scenario exists in almost every industry and that’s technology, and those are digital skills and their digital skills importantly, that once obtained, actually provide a path toward a better living wage.

So for me, that’s the part of the problem that I’m most interested in. It’s ignored. And yet we’re talking about the people who, in aggregate, are the lifeblood of our economy. They are the people who make things and make things work. To your point, the folks in Whole Foods or the people solving real problems in Wisconsin. So I’m interested in that technology and how we help that profile of worker.

Yes. And I probably sound like a dark individual sometimes how much I sort of trash the peer group that I live amongst. But this is just because sometimes it bothers me that they don’t see beyond the rather often myopic view that they have of their frame of existence. And fair enough, it’s not even intentional. It’s just more that when you get people that are very outward about like this is what the world looks like. That’s what your view of the world looks like. It’s not really representative. The whole sort of learn to code as this trope of like, oh, that’s the future of work.

Right?

You need to learn to code like, no, it’s not possible for many people. I’m a technologist. I have a whole host of things that I probably would have had to take pills for when I was a kid ADHD and all this different stuff. And I’m also dyslexic, so it’s horrifying for me to write code. I do it, but more out of necessity. And I live with a wealth of anxiety while I’m doing it. And I have skills that most people never got exposed to. You know, I always say I grew up on a farm and I became a technologist, but that’s because my dad was a technologist who took the leap and got out of the farming and made this jump.

Most people don’t have that luxury to leave their ecosystem or their geography. They can’t leave where they live. There are a lot more limiting factors that are forgotten. I think sometimes, which is a little bit frustrating.

Agree. It’s a big problem. Anyway, it’s a lifetime of work. So I’m in an area where I don’t think I’ll ever run out of interesting things to talk about and good stuff to do. So Yay for me. Good job security.

That’s right. What’s a good example of something that you’ve really seen that strikes home, it’s like this is the power of people getting access to technology that you’ve recently seen that’s excited you.

Well, I mean, I haven’t seen it yet in the space I’m in, which is why I’m in the space I’m in, kind of thinking about the other industries where this hasn’t happened. But I’ll tell you, I follow a lot of nontraditional education providers, and I listen to their stories is kind of my daily good news. And so companies like General Assembly and there are many others, have a constant stream of success stories where people have made the leap from whatever they were doing that was not satisfying into jobs that are and, of course, those are tech jobs.

But I think it’s fantastic. So I think it is actually happening all around us. And if there weren’t a ground swell of that, however, the media may or may not be able to report on it. It’s a harder thing maybe to report on. I think it’s behind a lot of this great resignation, which itself, I think, is fantastic news. And it’s happening because people are looking around and they’re seeing their friends and their family or their peers make a leap and all they needed. It’s like all the little penguins are standing at the edge of the glacier, and they just need one of them to jump and everyone else is kind of following.

And I think that’s starting to happen. That’s behind the groundswell and the very fact that there is this great resignation, the very fact that people are, it’s kind of a take back the night moment are starting to say, yeah. No. I mean, sure, I had my unemployment benefits are out, by the way now, and I’m still not going to go back to that crappy job. Sorry. I’m going to figure it out, is exactly what is at the birth of any big social change. So I’m excited.

And, of course, because of my kids, I hear it all the time. I hear my daughter say, if you use the word gig one more time, I’m going to die. We know what that means, and we’re demanding something better. So I think there’s good news, even in the bad news, because it means that people are going to sort of accept, not stand for accepting less. You remember 20 years ago, the issues with the big box retailers, where there were all sorts of lawsuits and generally speaking, I think we all had this collective sigh like, oh, yeah.

It must be terrible to have a part time job in much of America because you don’t get your hours published. Even today. Did you know that they’re, like, 26 million workers who do not know their schedule more than a week in advance? How do you live a life when you can’t figure out what you’re going to be doing next week?

Yeah. When the alternative is you need to find a second part time job, but they’re constantly conflicting or you’re always up in the air. I remember the early days of working two retail jobs, and on Sunday you would find out the schedule for one. And on Monday, you’d find out the schedule for the other. And then I’d have to race to see if I could get shift coverage. And that was just me for part time jobs. But I was in school, so it didn’t hurt me. There are people that have families, but that’s their reality.

And it’s easy to forget sometimes that’s just so much millions. The sheer numbers. This one thing always boggles my mind is that if you just look at the sheer numbers, it’s very easy to lose track that, well, 300. That means that 307,000,000 people don’t have that problem. But there’s 26 million people that do. That’s a giant number. We should all be a little bit horrified. I love the great resignation from the idea. Somebody on not too long ago is Michelle Seiler Tucker, and she’s focused on helping people to build their business for sale, to how to get out of the business and make it viable for purchase.

And she goes through this whole program. And she says, the funny thing is we have these weird stats that we hear all the time that are like, 90% of startups fail and all this different stuff. And she’s like, Well, we’re actually lying when we say those things because according to the Small Business Administration for the past 24 months, in fact, 75% plus or, I forget the exact number of businesses, are thriving. And in fact, businesses that are more than 20 years old have a 90 plus percent failure rate.

So it’s actually the reverse that those of us who are like, I’m done, I’m going to build my own thing. I’m going to do my own thing. We are the next generation of statistics that haven’t been realized yet.

Well, as somebody who just took a CEO role in a company with not that many people in an early stage in market, but just barely, I am excited about that. That’s great. My odds are better than I thought they were.

Yeah. It’s an unfortunate trope that we take this old thing. It’s the same way that, its possession is nine tenths to the law and all these goofy sort of stats that we get tossed around almost like fortune cookie sayings that become wrong quickly, but they’re still printed somewhere. So we still call on them. I love this idea that, I’ve even seen through my own company that people that we hired as business development reps and BDRs or SDRs, their cut in basically dialing for dollars people, right? Like, they get on.

Like, they get on. They’re doing cold calling. And you see someone, you like, oh, he seems different, right? I couldn’t figure out this one seemed like he’s got something going on. And then I see him in LinkedIn, founding a new company. I’m like, oh, that’s neat. Then I see him launching a series A. I’m like, oh, yeah, that’s there. So what you’re creating now, Jennifer, is that small group of people. Those are also future founders that you’re probably empowering because they’ve seen that it can be done now. That’s magical to me.

Yeah, I think so, too. I think it’s exciting. We’ll see what that looks like in the future. If it becomes a competency to build a company. I don’t know how that works from a kind of macroeconomic perspective, but for sure, you do see your point around monetization, you do see so many more people thinking creatively about how to monetize themselves. So sometimes that shows up in our world as the founder of a tech company. But Twitch streaming the long tail of social media advertising. I think that it’s harder than it looks.

But there are a lot of people who are starting small businesses and figuring out how to effectively run them through social media platforms, which I also think is exciting. Upwork, Freelance. There’s a dark side to all those stories, but there’s a positive side to it as well that we’re starting to have a more distributed notion of what work looks like that not everybody has to work in a big company for the rest of their lives in a single career. We can do different things. So I think that’s exciting.

Yeah. And this is actually interesting that you brought that up, the idea that there is a dark side to many of these things as with anything. The hard part is that we’ve got such rapid access to that side of the story much faster than the good side. I remember when I was in Toronto and Uber was making its way into the city, and I was a nerd. I was like, that is really exciting. I can just get a car on my phone. It’s like, super cool. The people at my company, I worked at Raymond James at the time.

So I’ve got all these people that are running an investment firm, and they’re like, what is an Uber? They had no idea what I was talking about. I’m like, watch this. I hit a button and then Yukon XL pulls up on the road and door opens. Hop in, guys, we’re going to the party, and we would have this idea of, the disruption of it. And I was excited by the opportunity for disruption. Unfortunately, there are people that were not going to do financially well through it, and they would be facing challenges when it came to City Council trying to regulate it.

What ended up happening was you’d have, of course, very strong voices on either side. And you would hear people who would say, like, I’m a mother of three kids that are under six. I can get my mother in law to help me watch the kids from 09:00 p.m. Until two in the morning every night, and my husband takes care of them in the morning. So result, I get to work 5 hours a day and I make money and I feel safe.

You hear stories like this, it’s like she can’t work for a taxi. She can’t work at a regular job because it requires four till ten shifts. All of a sudden, we’ve got this incredible story again, counter. There are difficult sides of it as well. But like that opportunity, like Upwork and those opportunities now are there. I’m excited by it. But I also know that a lot of people don’t often see there’s risk and balance to kind of any new thing that we take on in this style.

Well, I think another way of saying that is that if you’re in the business of creating disruption, which is what Uber was in the business of doing and Airbnb and has become the North Star or the greatest aspiration for anybody who’s trying to be a founder of a tech company that matters, then the measure of your success may be that you cause so much disruption. You actually create unrest at social policy levels. Because I’ll tell you, I was at Microsoft when all that was happening, and I was traveling around the world talking to a lot of government leaders and ministries of finance in smaller countries.

And they wanted to know, like, the big question was Microsoft, what is your view on the uberization of work and technology. And what is the role of a tech company in that space? Because after all you’re creating a lot of this, and it’s actually causing a lot of unrest, especially in countries that have a little bit bigger of a social safety net and therefore more investment and a sense of responsibility for dramatic shifts in the way industry works. So it was a big thing to your point. I kept thinking, Well, this is a hard conversation, but if we just take the longer view, it’s probably going to end up in a good place because we are trying to solve the next generation or the next version of our problem.

But we’re making progress. There are as many success stories here as elsewhere. And let’s not forget that if you at all believe in free markets or in the wisdom of markets, there’s a reason why Uber was successful because they addressed an unmet need.

Right.

And it wasn’t even a technology, if you think about the components of the technology behind Uber, that’s not where the innovation was. The innovation was in the idea. And so personally, that’s my inspiration. If I want to go do something, of course, I want to be disruptive and make a big change. I’m not thinking I need to do it in technology. There are other technologists who will go be CEOs of companies that are in Cleantech or doing something crazy cool with AI. And that’s not me.

I think from an innovation perspective, you can just innovate by thinking of a fresh solution to an old problem and bring all the existing tech that already exists to play. And if you’re lucky, people get really uncomfortable. But you’re also making life better.

Yeah, because you hear it all the time. Like, these two sided markets are incredible. Their right for disruption. Next door really became a thing. It quietly was worth all of this money because it had such a vast growth. I had never heard of Nextdoor in my life. My mother-in-law. She’s like, I’ll go on Nextdoor and find something. We’re looking for a contractor. I’m like, what the heck is Nextdoor? Then I dig into it. I’m like, Good golly. This thing is worth billions, but it was just that, right?

A two sided marketplace. You had people that need to be serviced on either side. This is fantastic. Everything needs to be like, all it takes is a little bit of an idea, and you can close the gap. And what it satisfied for me was, I solved the problem. I needed to get a hose fixed and somebody else solved a problem. He’s trying to build his cottage and pay for his family. And so he found a little tiny gig that he could fit in in an afternoon.

And I didn’t need to write an ad in the paper for it. We’ve come a long way, and it’s magical that we can create this opportunity. I think I’m with you on Disruption. Sounds like a dark word sometimes, but it really means that in the same way that forests naturally will burn from that, you can only get new growth because if the forest continues to grow, it creates shade, which stops growth below the shade line. But it is hard to have that macro view when you’re micro affected.

And I think that’s what we become very overly attuned to is that this is affecting me now or someone I know now. And therefore I must have some kind of a feeling about this that’s bad.

Yeah. Really. Well said. We’re in exciting times, may you live in interesting times as the proverb sort of tongue-in-cheek says, right.

Yeah. And the thing that I really want more people to look at is how they can directly do things. And this is what I’d love to get your thought on. Jennifer, where can we, if we, as a people have, say, technology skills or something to share, where can we have a direct effect? Do you see the opportunity for us to empower people, to empower other people? I think this is the missing two sided market.

I mean, I have narrowed the list down to a few things. I think there are an endless number of things. It’s more of a mindset of do I take responsibility? What is my role in this problem? From there? There’s a lot of things that we can do. If you’re a hiring man, I’ll just throw it to you. If you are a hiring manager and I am a hiring manager now. And I’m finding myself saying, don’t be a hypocrite. Do what you think is the right thing to do.

Are you allowing yourself permission to look at novel skill sets when you’re looking for people? Because if we’re talking about a more I mean, ultimately, what we’re talking about is that we are going to live in a more digital world. And if we’re going to allow people an opportunity to survive and thrive in that world, but they don’t have a four year computer science degree, how are we going to address that? So looking at novel skill sets, allowing online certifications to be enough, looking at potential and broad capabilities rather than five years of Python and your previous job and a four year degree at this University, I think it’s hiring managers, the unsung hero of Middle America or middle management corporate America.

We really have a huge amount of influence on what the future of work looks like, even though you may not get any credit for it. So I think thinking about that, you have a very direct role to play in shaping the next generation of workers through your actions, and it will require risk, and it will require creativity, and it will require harder work. Diverse teams are harder to get to productivity as we know. So that’s something. I was always inspired. Microsoft was a fantastic company for many reasons, but also from a culture perspective, there was a culture of giving and giving back to communities.

I don’t know if it’s better or worse than any another company, but it was wonderful there. And I was so inspired that I had many hundreds of technical people on my team throughout my tenure there, and most of them if you ask them what they did in their free time, they were spending their Saturdays teaching robotics camps or coding skills and doing hackathons with kids and in their communities. And I think that is fantastic, especially when you get to underserved communities and communities of color or women or girls and STEM.

I think boys are just as important as girls, but wherever you find people who might need a little extra help getting yourself involved and I don’t think enough people are doing that. I would say also, I don’t see a lot of technologists in this policy conversation. We’re talking about getting really steeped into future of work, that would be something I’d rather see. And I guess my last point of advocacy would be for us to stop, to be very careful not to assume that technology is computing technology.

There are all sorts of solutions out there that are technology outside of our industry, and they are creating jobs. And if we can make sure that the people working on an offshore oil rig are adequately trained in the underlying technology concepts and the applications and use of their industry, that is a path forward in factories and event hospitality, health care, finance. There’s all sorts of non computing specific technology that the world needs to know how to use. And if we can give people those skills, we create a lift for everyone, so it doesn’t just have to be coding.

I think skills is such a great description of what we can empower like technology can be software, mechanical. It can be lots of different ways that we can create new ways to interact with systems. But systems isn’t always technology. There are people systems. There are very human systems that are out there that can be optimized, and I exploited to such. It sounds like a negative word, but exploited in, like, properly leveraged. So people in hospitality, even the simplest things. I used to be a shoe repair man, so I was a cobbler with a rare treat that you don’t get too many people that could say they’ve done that.

And I worked in a mall at the entrance to a subway and we had all this throughput. But the first thing I thought about was treat this like a system. How can I make sure that I can optimize the flow of people when it was rush hour, optimize the flow of shoes going through the system, right? Knowing how and teaching people who are not technologists, who I work with, how to think like a system. I taught them systems thinking. And I was at high school education.

I had no other than just my strange nerdish need to find optimization and everything. I got this, and I looked at the wall of stuff that we sold, and I started organizing. I’m like, what would entice somebody to come to the front of the store. And so I made the display differently. And I sort of built this journey through the little tiny store. And the funny thing was, six months later, we won a marketing award for a shoe repair by Cadillac Fairview, which is this big mall.

And they’re also pension fund as well. So the people that I worked with, what it taught them was that we’re amazing. We all have something we can do, something that we can reach for. And then the two guys that I worked with, went to get their own stores. And then one guy went independent, and he started his own shoe repair. That was entrepreneurship and even entrepreneurship with a paycheck just thinking about systems thinking and thinking about optimization and thinking of ways we can do that.

We created a better human experience for our customers and for each other, and no Comp-Sci degree required. It was pretty cool to see that we could pull that off.

I just literally love what you just said. That whole systems thinking approach, the idea of being able to discern a pattern out of chaos. If there was one higher level cognitive skill that I think in our education systems, we should be teaching, it’s that. And I’ve heard enough of these conversations that we’re all educators who agree, but I think they’re still in the minority. There’s this, I don’t know, this is going to be super geeky, so maybe not helpful. There’s this architect, a famous architect who I think was, I’m sure, a teacher at a University.

His name is Christopher Alexander, and he wrote this seminal book in architecture called The Timeless Way of Building. And I had a lead architect on my team at Microsoft who said, “You’ve got to read this book”, because what we don’t ever remember is that the underpinnings of anything we do when we’re designing a technology system are the very same underpinnings that architects use when they’re designing space or mechanical engineers are using when they’re designing roads and bridges. And they are all in their most fundamental elements, designed to reflect a human experience.

And it was a very big turning point for me to get clear on the fact that number one, technology is ultimately only ever an expression of our human experience, of the world around us. We just reflect ourselves in the things that we build, whether it’s a bridge or an application. But if you can start to cognitively, kind of grasp how to discern patterns, how to understand connections and relationships, then you’re much more equipped to understand the world, understand the problem you want to solve, understand where you fit in the world.

And I don’t think we do that enough. But that book, if you ever want to read a 400 page book on architecture. But he talked about how cities are built and how a house is built. A quick example. You intuitively know when the front door is in the right place of a house, we intuitively know this. We don’t need any training. And when it’s right, it’s when there is enough of a pathway to a front door. When it’s wrong, it’s where the front door is right on the street.

And the reason for that is that a house represents an intimate, personal space. And so the front door placement is a way of allowing us to slowly get closer to our space and allowing enough distance for people who are going to come into our space to do so in a slower and thoughtful space. You don’t want someone abruptly in your face in a first conversation, nor do you want them abruptly in your front door. And so it’s just a way of saying, oh, interesting. That’s why certain design elements in architecture makes sense to us.

It’s not because we know anything about architecture. It’s because we know everything about ourselves and technology is that way, too. But you can apply that thinking to anything. And I think then the world starts to get more understandable, like people get lost in the world of technology. We just feel like it’s passed us by or we don’t get it. And I’m here to say that you actually do get it, on some level. You actually totally understand it because it’s built on the same patterns that are echoed throughout your life.

And they’re human.

Yeah. This is the magical thing of seeing it. And actually, I always laugh at my favorite example is everyone smiles on it and will say, like bees when they create honeycombs, they’re perfectly hexagonal. Like, that’s amazing. It’s like bees know math. I’m like, I think you’ve got it backwards. These are patterns in nature that we’ve discovered, and we’ve built math to represent these things. And then we teach math as if that was the skill. But it’s actually the capturing of the pattern, not necessarily the learning of the task of measurement.

That was the zero to one thing that happened one day, the reason why the apple striking the head as being the sign of the start of gravity, whether real or not. As if the Apple knew what gravity was and just had to tell Isaac Newton, by the way, here you go, here’s an idea. It was a variety of things that suddenly was like, aha, but it was the recognition over years of looking for a pattern and then seeing it. And it can be very small things.

That’s why, even like, said servers in restaurants. A great friend of mine, he’s been working as a server, and he goes now like he has a SWAT team of servers. And they go into new restaurants like Gordon Ramsay’s little TV show where they like, ‘You’re doing it all wrong. And here’s how you do it’. And they teach people how to optimize the flow for customer experience, including the chefs and all these interactions. And he says, what do I teach people? He says, “I hand them this as the most bizarre book that you wouldn’t think you’d hand to a restauranteur.

But I give them The Goal by Eli Goldratt, which, if we are in technology, is the foundation of the Phoenix Project, which is the entire DevOps movement, is based out of this idea of how do we optimize flow. And Goldratt wrote this book, in I don’t even know, it was like the 60s or 70s. Talking about the manufacturing industry and lean manufacturing led to lean startups and lean development. And just like, we think that the bees know math, no. Here we are. So here’s somebody teaching a serving crew at a restaurant.

And then when it comes to taking on technology, those group of people, they start to look at this system now and go, you know, it’d be better is if this menu was done this way and they are now driving the experience for the developers and for the restauranteur and saying, like, ‘It’d be better if we put the system here’. And they are invested in their own outcome. But then, as a peer group, it raises us all to be able to just ask a question, don’t just come in and do it.

That’s the beauty. It’s like when your kids say, why, for the first time, you’re like, oh, that’s cute. And then it becomes very uncute because they ask why about everything.

So true.

But then you realize it’s beautiful because they are genuinely questioning it. And you’re like, I’m so happy you’re doing that.

It’s so good. I mean, we could just get super nerdy here, but it is a reminder that through our evolution, we are born optimized to understand the world at a very intuitive level, how that happens. Neurologists can have the nature nurture conversation that happens all the time in the AI spaces, you know, like, does the system have to start from scratch, or can it be built in with a few things to give it a head start? Because people are. Babies are born with the way we function neurologically is optimized to be a reflection of the world already around us.

And that’s why things make sense to people all the time. But it’s important because it is a mindset shift of, I start from a place if I can. The world is not foreign to me. Any manifestation of the world, technological or otherwise is not on some level foreign to me. It is simply an expression of the laws that I was born that were internalized in me the moment I was born, that we are optimized for the world.

And it’s just a matter of patience and understanding and study and observation that I can become more efficient and efficacious in that world that I start from a place that I can.

I’m curious, who are the people that you look to as more recent inspiration? Like we can always look to the philosophers of old and sort of our early teachers. But who do you see that you find is reflecting a new existence and doing it well, nowadays?

I think I look at people who are talking about this. So there’s a gentleman, Erik Brynjolfsson, who’s now at Stanford, and now I’m going to forget the name Stanford Digital, something other. He was at MIT, and he is an economist and technologist who talks about future work. And so much of what I understand is from his work. So I think everyone should follow him. But then there are the innovators, like the Elon Musk’s of the world. I know he’s overused, but the reality is there’s this charm of not getting so excited about the fact that he’s solving a big problem that I think is exactly that mindset of you have to get yourself into a space where you feel like if you just thought about things, use that kind of root cause analysis and ask a bunch of questions about why things work the way they are and uncover your assumptions about things that you actually can get to a very rich understanding of the world around you.

And from there understand how you can affect it. So I don’t follow a lot of people on a daily, weekly basis. But those are two. For the world itself, Ian Bremmer, I’m a huge Ian Bremmer fan. Nobody knows who is. He runs a group called the Eurasia Group. He talks about world and world politics, and I think he applies that kind of thinking to the realm of politics and policy and global affairs. And so I think maybe it’s more about people who I think use that mindset and apply it to whatever it is that they do that I’m inspired by.

I pulled over a book just because I literally wrote this down because I was listening to Antifragile. It’s Nassim Nicholas Taleb. Famous for Black Swan and a lot of things. And the one quote that jumped out of me says, to be a successful philosopher King, it’s better to start as a King and then become a philosopher. I find that it’s the practitioners that are truly creating the next philosophical discussions because before it was always from academia, then teaching the world how it’s supposed to work.

But I find this is an opportunity, we can turn it on its head. And much like you talked about Elon Musk. Right. First principles thinking even in the smallest format and things we do of like, why is it that we do this thing this particular way when you see people that are doing stuff in practice and they’re saying, I don’t want to go to an office, they’re saying I can become a gig worker. I can become my own landscaper. I can start my own shoe repair.

I can start a startup using no code and low code just because I’ve got a problem to solve. But it’s very much often people with lived experience that then just can take this and almost question the philosophers of old and say, I think we can do something here. I think where we’re going to see ten years from now, a lot of stuff going on that’s already happening, but it won’t be realized in public effectively until the next wave of startups kind of make it to whatever status is where we look for unicorns, or just the fact that longevity. We will see more longevity in small businesses, and people will see those new statistics.

And that’s the future of all of us. Actually, this is a fun part when you’re looking at the future of things, and we’ve clearly gone through very literally a Black Swan event with what’s gone through with the pandemic and what’s still continuing with the pandemic, of course. But are the things that you looked at five years ago that either are holding true or maybe even were accelerated because of the most recent 18 months that we’ve gone through.

I have to just take a second to go back to five years ago. So I’m literally like, wait, what year was it five years ago, 2017. Where was I then? I think that my understanding of how problems need to get solved on a small level kind of back at the very beginning of this conversation. That the boundaries of a problem matter that actually has a relationship to this whole democratization distribution of technology knowledge, because when you let everyone solve their own small problem, I think there’s a bigger aggregate effect than when you assume that only a few organizations or there’s a real centralization of problem solving capability and all the money and power and intention flows to that.

And I was seeing that in the context of a lot of the digital transformation projects that we were running, and if you go work for the big Fortune 50 at some level, you’ve got to get C-level people to sign up for projects that are extremely so expensive that the board has to approve. And they have very dubious ROI because it’s an innovation project. How do you know it? It’s an experiment. So it’s not that you don’t see it at that level, but they only work when they were inspired by people who are actually out in the field, whatever the field is in, whatever industry trying to get very specific about a problem.

And that was when I realized, oh, my gosh. The democratization of skills is important because you need to empower everyone to solve their small problem, and that’s going to create a shift in power. Right knowledge and efficacy being power if you let people solve problems and you give them technology, then they’ll do it. And of course, remember, I have a son who can Twitch and all that sort of stuff has been in my house for a while. So I’ve kind of seen that, too. So I’d say that would be the pattern that has stayed true, and I think it’s going to continue to shift.

I didn’t know it was going to look quite like this, though.

Having kids. I’ve got four kids and I’ve got 20, 18 and 5 and 2. So I’ve got quite a range of things that I’ve seen, and I sort of laugh now, people that have young kids, especially that we all know about sort of the YouTubers and these Blippi and Ryan’s Toy review. And there’s all these very popular things. And there’s one kid, who you look at his videos five years ago, and it was just basically filmed on an iPhone, not even a good iPhone, but an iPhone seven or six, whatever it was at the time.

And this year, he was in Fortune reporting 26 and a half million dollars in revenue.

Wow.

He’s eleven years old. There is very unicorn-like capabilities in exploiting these. Finding the pattern, exploiting the system that allows you access to uncover and use that pattern. And that’s kind of cool. The economy is so different now, but I think I’m like you. I like the democratization, and I think the last 18 months, though, not anybody in the world wouldn’t trade away. What we’ve had to go through as a society. What we have to do is find the best of what we did. And I think the great resignation startups moving to everybody’s mindset, people realizing you can just do things on the Internet and you can begin to generate revenue.

It’s a new economy, it’s a new world. The one thing we didn’t get a chance to talk to, but it’s still early on. So I’m going to have you back because I want to get your first few months of experience. So I have to say Congratulations in advance that as this is out and people are listening. You are the CEO of a new company and you’ve been involved, so, in the last couple of minutes here and I apologize. I don’t want to box you in, but just as a bit of a teaser to what’s coming up next for you, Jennifer.

Well, we’re going to go through a big rebranding renaming event, so I’m hesitant to talk about too many of the details here, but it’s a company that’s in this future workspace from an industry taxonomy perspective. You put us in the HR tech space, but I’m concerned about workers that are not in the tech industry. I’m concerned about workers who are not on LinkedIn, and I’m interested in how we can within the existing ecosystem of how people find work, which is through staffing, agencies and employers. How can we give people access to a proactive profile building capability that allows them to find work to go out and find work?

They advertise to agencies and employers based on the profile they build for themselves. So I got the advanced certification. I was making $18 an hour. My profile has changed. I have really great five star ratings from my last two employers. I’ve got a few verified skills, and now I think I could earn at least $23 an hour. How do you do that? What’s the platform in the marketplace that you build to do that? So the company is already kind of in that space and a little bit narrower because product market fit is important.

But that’s the aspiration of the company. And ultimately, I think it’s providing that LinkedIn active profile building capability to the rest of America, and then hopefully the rest of the world.

That’s amazing. And Congratulations on the big move. And I’m excited about the future there, inevitably, with you as part of the leadership team and then heading it up. They’ve got success ahead for them. And so it’ll be exciting to watch. So it’d be great to be able to see post rebrand. I know that’s always an interesting challenge for any organization, so it’s always fun that we get to be secretively leading up to it. But this will be, actually the said timing, as it were, this will probably be pretty close to when you go live.

So I’m excited about that. Jennifer, if anybody wants to reach you, of course, well, I have links to your website. And where can folks find you if they want to get connected?

Well, I think by the time this publishes, I’ll have a whole bunch of new contact information, but I am a big fan of LinkedIn. I use it and I’m on it all the time, and people reach out to me all the time there, and I always reply, so that would be probably the single best way to find me.

Excellent. You’re better human than I am. I’m the worst, because the thing I get the most at these days is people trying to sell me explainer videos on LinkedIn is particularly good for prospecting. And for whatever reason, once you have a very public voice, people see you as a great prospecting target for a lot of things.

Thank you. But I’m so grateful for that platform, so I really take it seriously. I do try to kind of be somewhat active. I post all my podcasts there. Not that everyone wants to listen to me. And I just try to be useful on the platform. And I try to be grateful for the people who reach out there because you never know any. Of course, there’s lots of sales pitches, but that’s okay.

And like you said, I’m really mindful of the effect that it can have. And really, the last job that I took, it was kind of funny. After I was at the company about three months, the human resources team, they phoned me up and they said, hey, Eric, we realized that we don’t have a resume of you. We’re supposed to have one on file. So can you do us a favor? Can you write up and send me a resume? Because that is the future of work for a lot of people that there is no more filing the CV and sending with a cover letter.

It was, somebody sort of found me on LinkedIn and they followed my blog and we met an event and I interviewed with a bunch of people. And the offer comes it was a very different world. But yet the old classic practices like, we’re supposed to have a resume on file somewhere just to say that we looked at it, which is crazy.

I know it’s kind of crazy. And when you get into the lower end of the wage scale, resumes are just not even necessary because you get people early in career. So I will say one of the features that we have is this video capability. So kind of like TikTok where I can film myself answering questions and in three minutes, a recruiter or a hiring manager can get a very good sense of. Can I show up? Can I talk? What have I done? What’s the look and feel?

What’s my authenticity? Am I real? I’m not even my actual person. So I think that’s the future, especially for a lot of those jobs where you just need to make sure, I’m going to be serving people. You need to make sure I can serve people.

Yeah, that’s right. I am very excited to dig in on this one. So there you go. Once the new name is unveiled, we can have you back on. We can do a deep dive into what you and the team are doing.

I would love that. Thank you. Such a fun conversation.

Great. Thank you very much.

Alright. Thanks, Eric.

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Kison Patel is the Founder and CEO of DealRoom, a project management software for complex financial transactions. Kison has over a decade of experience as an M&A advisor and developed DealRoom after experiencing first-hand a number of deep-seated, industry-wide inefficiencies and challenges.

We cover a ton of really great lessons on the productizing of process and how Kison has scaled teams and culture. If you’re a founder or anyone in a startup, these are solid lessons and Kison was a real pleasure to chat with.

Plus check out his podcast, book, and more at https://kisonpatel.com/ 

Transcript powered by Happy Scribe

Good morning, everybody or afternoon, wherever you are, whatever time it is you listen to this. This is the DiscoPosse podcast and you’re in for a treat because you’ve got Kison Patel from M&A Science. Kison is also a podcaster, a great content creator and somebody who really has a mindful approach to his sharing of information and really wants to help people. So this is a great discussion around the process of founding his original ideas and productizing them working with the team. We talk about culture. It’s a really great, wide ranging discussion.

In order to make great discussions like this happen, I do have to, of course, give you a shout out. And that is you all make this happen. We just blew past 100,000 views on the YouTube channel, so make sure you go check that out. And of course, who else makes this possible is our fine friends who support the podcast, including everything you need for your data protection needs from the friends at Veeam Software. I’m a fan because I’m actually using their platform myself for protecting my own real production data have done for a long time and worked with a ton of people in the community.

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All right.

This is Kison Patel. I hope you enjoy the show.

I’m Kison Patel with M&A Science, and you’re listening to the DiscoPosse podcast.

Thank you very much. This is going to be an area where we can cover a lot of exciting ground. You’re doing work through both the product side with what you’ve done with DealRoom, you’ve got more product work that you’ve done. You’re doing work on the actual activity of mergers and acquisition. You’ve got a huge important and stored background in that. And you are a prolific creator of contents both through, you’ve got your podcast, you’ve got video work that you’re doing, and thankfully, I get to share some video time with you, which is great.

And you’ve written a book. You are busy. You’ve got a great voice, not just on the microphone, but literally. I love the way that you bring content to this world. So with that, if you want to give a quick intro for folks that are new to you and we’ll talk about what you’re doing with M&A science and with DealRoom and much more.

Happy to. My name is Kison Patel and I come from a background doing M&A advisory. I did it for about ten years. Working originally with private owners of small businesses to buy, sell and then grew in the career to work with corporates on similar transactions at larger scale. Then the recession happened around 0607. We did a lot of reflection, found that out myself and aspiring to get into the software space, got involved with a start up that didn’t work out. But what it led me to was an understanding and the way that software engineers would use project management software to manage building software.

And then I took that inspiration and started the company DealRoom a bit later in 2012 as project management software for mergers and acquisitions. Then learn shortly after there’s a whole bunch of things that you need to learn that come along with it in terms of how to build software, properly build a good software, how to get market fit, how to really develop a go-to market and then rebuild your software for scale. Because once you start getting customers, you realize that little thing you originally built with wasn’t really built or stood up for scale.

So it was a lot of fun experience. I was really fortunate in that journey. A friend of mine in marketing was, hey, man, you should do a podcast. And I was like, what the hell is a podcast? Don’t worry about it, you’re the next big thing. And that was probably the best market advice I ever received. We started podcasting about five years ago with a podcast called M&A Science. I think the one thing is, I was fortunate enough to have a good marketing team that was really good at repurposing content.

We would take transcripts of these interviews, write blogs, eBooks, and then recently published our second book. And then that evolved into doing online events, which evolved into owning and operating an online school for M&A. So now we have a few different business lines today, back in a nutshell.

Yeah, well, this is what’s really sort of the key story when you talk about successful startups, and I’ve seen it. I’m lucky at the point that this will go out. We’re just past 200 episodes. So I’ve talked to a lot of founders and you’ve seen this consistency in the success is often taking real lived experience and then translating it into productizing and creating products that very genuinely map to experience that you’ve brought to that company. And it can be through as a technical founder or as a business lead founder and finding a technical co founder because of your really strong background in M&A, and then your willingness to bring it in the open through podcasting, people often say, like, Well, you’re giving all this stuff away. Why would I buy the book?

Well, I’ve read the book.

It’s fantastic, right? It’s a great read. Secondly, it’s a way to kind of continue to go back and reference like, okay, where am I at it? You hear about sort of The Magic Box principle as another popular book and the idea of where you are in the acquisition process. But then when it comes to DealRoom, I like this. You’ve brought together two important things. One, you brought business to a technical platform, and at the same time, you brought development learnings through that previous startup to how you are going to build and scale DealRoom.

So I really want to find where those two things came together. When did you know it was working, that it was going to bring these two things together, or what were those first few months in defining what DealRoom would be?

Okay. So this is a really good question here. When I look at where we’re at today and where we first started is very different. And I wouldn’t say the attribution success was so much of our M&A experience. That’s what got the foot in the door. And I would attribute 10% of our success today from that. The other 90% comes from being obsessed, being extremely, that’s our competitive edge is that we obsess over M&A. We can talk about it nonstop within our own organization. I’m constantly encouraging team members to learn about M&A, to be able to speak about it, understand the specific pain points challenges.

When we look at those early days, the problem you have when you come from the background and the industry is you bring a lot of assumptions with you. So with the experience that I worked in to, primarily worked in hospitality and small financial institutions, the experience I had in those markets is what I based a lot of the assumptions and how we should build a product and take it to market. And you’ll find out at some point either, ideally, sooner than later, that you’re wrong about a lot of those things.

And then the right thing to do is build the feedback loop really go through a process where you can validate your pain points that your problems you’re solving for. That’s a whole process of its own to be able to do that in an unbiased way because one, it’s our idea. We have some entitlement around it, and we tend to ask people for feedback that know us and they want to be nice and encourage us to follow and chase dreams and things of that sort. But that’s not what we want.

We want to identify who the cohort of customers are and we get the unbiased feedback on what are the key problems that you’re facing and understand how I see it and if it aligns. We went through that process about going through the first few months. We started with an idea of building a marketplace for M&A. We thought, here’s the lifecycle of deals. We’re going to start off with the very front end. Where do you find deals? How do buyers and sellers connect? And that’s where we found out we’re wrong about a lot of things.

We put this marketplace together. In the first year, Eric, we operated it. We had about 200 deals listed and 1200 users and realized we just build a sophisticated dumpster for deals. It wasn’t going to go very far. And it was at that time we realized we need to go back to the drawing board and step back because it was the typical thing as the founder, where you have ideas, you make an outline with what they call feature creep. You build this massive outline with 100 different features you wanted to do.

Then you’re like, all right, let’s start with the top and start building this front end stuff. We went back and took more. I think if you Google customer development interviews, there’s a lot of articles about it, and it kind of walks you through how do you validate the problem that you’re solving for. When we went through that exercise, and the goal for us was to do 40 of these interviews to really validate what we’re doing. And we realized one, finding deals wasn’t the biggest problem for the customers that we were looking to work with.

It was more on the management side. There was a lot around how do you get deals through the process, coordinate with so many different people and drive efficiency. It wasn’t so much managing the front end to find the deal, it was really managing everything in between, so close. So we shifted our focus and went through a whole other series of challenges because we focused on one market and had a lot of uphill challenges where we didn’t understand the competitive market, the legacy technology they were using, their sales model. A lot of whining and dining.

They’re just very relationship driven, and we’re trying to go to market as a light touch technology solution that wasn’t happening. You’re not competing against late dinners and nights out at the nightclub, ball game tickets with funny market.

There’s ‘no dinner at Nobu’ option on the checklist of buttons you can click, right?

Yeah. Like a free dinner with it. So it took us a little while we probably got into year two, three and realized our early adopters were actually corporates, we shifted our focus and started working with corporates back then, and our product evolved as you work with customers and continue the feedback loop where we started solving for the integration challenges after they buy a company need to integrate it. And now we’re more recently doing the pipeline management on the front end. And when I look at the product today, very little of it is from my original ideas, very little of it.

It’s 95% from customers. Or maybe there’s some little insight we got from engineers and problem solving. But, yeah, I don’t know, when I look at these companies or aspiring entrepreneurs today, it’s so much of what I emphasize is really assuring that you’re validating the problem you’re solving for and continue that feedback loop as you start modeling out solutions, even early mockups and keep getting feedback. And it allows you to show people you’ve committed to it. Identify your early customers, more importantly, give validation. So if you do go to market and raise money, there’s so much evidence that you’ve done to validate that.

Hey, I got this idea and I’ve talked to so many people. This is what I’ve learned. You know how to speak the industry language better, better speak on the problem you’re solving and how you’re going about solving it.

When you read every founding story of a company, it’s always like, this is chapter four, and it’s the pivot, right? And it’s funny that chapter one is about the founder. Chapter two is about how the cofounders meet and chapter three, this is where it was. It started in a Starbucks in San Francisco or Pete’s Coffee, I guess, is probably the more common thing. Or in Chicago, I’m not sure what the local favorite coffee joint is, but then chapter four is we realized we had to pivot, and it sounds like a shift in a timeline, like it happened on a weekend, but it’s a grueling process to be able to evaluate and make sure that you’re doing the right thing through that process.

When you began it, Kison, versus when you are on the other side of it. Where would the perception deviate from how long and how challenging that process would be to pivot into what your market approach was?

Good question. I think I remember asking a friend for advice about marketing, and he said, I don’t want you spending a dollar in marketing. I want you to go back to the drawing board because I don’t think your business model is where it needs to be to put marketing money into it. And he challenged me to go back and really validate the problems that we’re solving for. So it took some time because we really went back to the drawing board and did it in a different way.

We got out of the drawing room and went out and started talking to people, went through a whole series of interviews. I was fortunate I had interns that summer, so I had some extra help. And it’s nice when you have two people doing the interview, one person really focus on asking the questions.

Right.

And important to learn how to go about it because you want to approach it. Two things. One is being dumb, where you put away your assumptions, assume you’re wrong, assume you know nothing, so be dumb.

And then two, be curious. I think sometimes we get a little, we ask a question and move on to the next question. But that’s not being curious. Being curious is really getting in there. Like, why is that happening? Why do you have that problem? Well, why did so and so do that and digging in to really identify some root causes. I think that going through that and then being patient where you can know that, I’m not going to have a couple of conversations and change my mind or go make a big decision, like pivoting the company, but that we can make a commitment.

At the time, we committed to doing 40 of these interviews, and that’s what really led us to see a pattern from these different interviews. Then we started realizing that we needed to shift and focus in the area that matters most to the people we’re looking to sell to.

It’s a real challenging period, and especially in a founder’s life, because, like I said, you have a hypothesis and down the road, eventually, the hypothesis may not be, it’s not that it was wrong. It was just that in order to go to market, there may be something else. There’s a hidden treasure amongst the hypothesis that’s the actual marketable productized thing that you can bring. But it’s such a weird thing when someone just asks you that bold question of like, what if you just actually talk to somebody and found out whether they actually need to solve this problem.

Actually, ironically enough, in a merger with two large companies. At that time, I worked at Sunlight Financial and we were merging with Clarica, and I got brought into, they’re like, one of those, like, they tap you on the shoulder. Can you come over here and I need you to sign this paper and we’re just going to bring you in and chat with a few people. And I was one of the technologists that was in the architecture team, and we were suddenly in a room with these people like, oh, these are all these senior architects from this other organization.

Not hard to put together what’s about to happen? And so we were, as you said, right, bringing our assumptions, bringing our sort of bravado to, like, I know how to do this. And then after a couple of days, we actually brought in a fellow from Microsoft, and he was this young kid. When you say that, I’m like, I’m an older gentleman. I could say young kid proudly, he’s about 26 years old, and he was from the consulting services, and he walks in and literally, it’s like he walks in, puts his jacket down.

He looks at the diagram. He’s like, what are you trying to achieve here? So we need to bring these two directories together. And he just says, what if we just created the third directory and actually just got rid of these two altogether and just bring them up. And the brashness of that approach, like immediately, we were like, you’re torn because you’re like, I don’t like that I’ve got to give up what we just did. But you’re like, he’s probably right. And that’s what it was just like the fact that that question got asked by a third party allowed us to be free in accepting it.

And that’s what’s really hard to separate yourself from because you bring the hypothesis, you bring the team the idea, and then somebody comes from outside. And it’s such a beautiful moment when you’re like, you’re right. I should really think about this for a second.

True. You never asked too many questions.

No. And that’s it. And through that moment, I’ll say, right, you’ve been an M&A advisor for a long time. So how did it feel that all of a sudden you had probably been the person that would bring that question to many people, and all of a sudden it was being asked of you. What was that feeling like?

It’s so different now, coming from background, when you work with clients, you advise them on transactions, represent them as buyers, represent the sellers. So today we are a company that’s based on products around education and technology. So I feel like we’re the closest resemblance is to the people selling the picks and shovels to the gold miners during the rush days. We’re seeing a lot of increasing activity around M&A, a lot of interest around it. And different even, new sectors, even smaller companies are starting to think about acquisitions earlier.

For us, we provide a lot of educational resources around best practices. How do you go about doing this in a way that doesn’t disrupt the business so much that a lot of people get pissed off and quit and you lose a lot of value when that happens. And instead, keep everybody motivated and align so you can hit the goals that you originally planned with doing the acquisition. To, also the other technology part of our practice is setting up, which is now a lifecycle management solution that we can take all these.

A lot of times, there are companies using a bunch of Excel trackers and a lot of communications, primarily through email, and we’ll set it up in a nice stack. So there’s a single database to run your pipeline, run your diligence management, coordinate with all the folks you need to both internally, externally, enable good collaboration and also preparation for those integration activities and use that same environment so you can run and actually execute integration, and you don’t have any delays with team members having to relearn all this stuff.

They learned about the company already, and that’s been another great part in working with organizations and setting that up. And today, now we’re working with larger multinational companies like BP, Johnson & Johnson, Cardinal Health, Emerson. But it’s very different from going from one end where you work on a smaller transaction where you’re very hands on. You’re in the middle of the deal, directly, working with the client, the lawyers and really hands on making sure the deal gets through. Now to be on the other side, we got to work with the team, but we don’t have all the intensity or pressure that we do.

And I enjoy the problem solving part of it because you’re dealing with more, which you’re familiar with, Eric. With technical challenges combined with directories and things of that sort. And for us, we get to do it on more of the logistics through the whole process. So we don’t get into a lot of the technical integrity of the challenges with integrating companies. But it’s fun. I definitely like what we do now. I like the fact that we can come up with an idea or a way to solve a problem and scale it out, get it in front of a lot of people.

Well, that brings in the perfect sort of question around scaling. And you’ve talked in the past as a founder, sort of the right time to scale, which is probably one of the most common mistakes that people do. It’s this idea of like, going, when is the MVP ready? And that’s another one I hear all the time. People are like, if you think it’s ready, you waited too long. And also the challenge of, you’ve talked in the past about people that build for scale when they haven’t even gone to market.

And when you developed your platform, did you find that sweet spot where those things needed to line up?

I remember for us, a pivotal moment was when we had our site crashing almost every day and we had paying customers. I remember specifically, we had a 200 million dollar deal we’re managing, and it was so hectic and chaotic because they’re trusting us with managing a significant transaction. Our site keeps crashing. Bugs are popping up, and that was the point we knew, we need to build for scale. We ended up bringing in a CTO that helped re-architect, rebuild the product to follow a microservices architecture, build a team that knew how to write code for scale.

Now, it’s funny if we look back at that. I mean, remember, even Twitter was sort of famous in the early days for what they called the Fail Whale, right? And it would be down for hours at a time. Quite sometimes it was actually down for a couple of days at a time. They had active people they were bringing into this platform and it just couldn’t keep up. And it would just go down. Back then, there was no, is it down or is it just me.com, right? People just sort of generally accept it.

But now it’s funny if you launch DealRoom right now, and you had suffered that kind of an outage, the risk would be, I think, much different, the level of acceptance of people on the dependence of software and availability of that software. It’s integral. Now, what do you think if you had that sort of challenged moment right now, what would it look like to your customers and keeping them?

You know, that’s an interesting thing, because you see this thing happened in the market where companies can get hacked into, and nowadays you got to be prepared. It could be anything. Could be one employee fall for a phishing scheme and the same password everywhere. Now you’re very vulnerable. It’s a challenge of its own. It’s a challenge of its own to really manage. I think if we had to deal with it today, we’d have a lot of calls, but I think you’d rebound over it. If you look at all these organizations, like Solar Winds, some of these other firms, we have a big one with what was it, not AOL, Yahoo. That was Right-Media acquisition.

They had a big breach they had announced.

That’s right. Yeah. Worst possible time, right?

Yeah, it is. But like with the solar winds, it created a lot of awareness. I feel like it made it tougher for the startups out there that are working with large companies. Now they’re getting more scrutinized in terms of how they’re handling their security. But in terms of them, they definitely, like, bounce back. And the old saying that there’s no such thing as bad press. The older I get, the more I believe in that. You think about the news with Robin Hood and everything recently, and I’m like, unbuy their IPO.

I’m like, no, that’s all good. It doesn’t matter. It just got their name out there. And everyone in the world has heard of Robinhood. Now you can always take the bad character and become good. We’ve seen Microsoft go through it’s cycle in terms of how the market looked at it, and now they’ve completely turned it around. But as long as you’re in the news, you keep building brand equity. I think we would probably explode with our support if we had something like that to happen, but you’d recover from it.

I’m knocking on a lot of wood to make sure.

Let’s talk about going beyond product one. So you have DealRoom. You are doing a lot around the education and you’re wrapping stuff around it with M&A science, which is really cool. We’ll get into that. Actually, I’m really excited about that area. Then you sort of solve one problem, then you say, okay, well, now we’ve got to effectively build this. Everybody has a data room, right? We’ve gotten this problem solved with managing the flow of the diligence in the transaction. And so you’ve got other products that you’re developing.

So let’s talk about the rest of the portfolio.

Yeah, we have books. We look at them as products. We wrote a book called Agile M&A. It’s a fun book. The whole trend right now in software is taking Agile and making it as complex as you can with scaled Agile frameworks and things of that sort. And we did the opposite. We took the idea of Agile and dummied it down so even a high school kid could understand it. Since that’s where we got to make it for our finance folks to quickly understand as well. And the origination of it, too, was a lot of the things I noticed our own engineers were doing.

I kept correlating to my M&A experience and thought we should have done this. We should have managed diligence this way. This would have been way more efficient, made a lot more sense. I started blogging about it. I don’t think to this day, a single person has read those blogs, but it led me to interviewing Google and Atlassian where those ideas were validated. I brought up some of those examples and they’re like, yeah, we’re actually doing that. A lot of it stemming from the engineering culture.

Yeah.

That was a good wake up call that gave me inspiration, motivation to write a book, and try to put a case study behind it.

Then I remember, Christina, at Atlassian was like, don’t just write a book, make it a framework and look at our team plays. We took a lot of inspiration from Atlassian’s team plays and built around the idea of having game plans and plays and have actually encouraged practitioners in the industry to write their own little techniques. That was the bigger problem. Like even going back to starting the podcast. The idea of starting a podcast in our industry wasn’t simply to get talk time. It was aligning it with a mission where we noticed in working with these corporations, there was a lack of standardization.

All these large companies were working with had a very unique way of doing M&A, and that’s where we realized the bigger problem was the fragmentation of the industry. Everybody’s essentially working in a silo. It’s not like accounting or law, where there’s a lot of common bodies to reference and standardization. M&A didn’t have that. It’s just all Wild West. Everybody’s got their own way of doing it. And that led to the idea of, can we find what actually works? Can we throw some signs here and find where the proven techniques are, identify them, have some evidence around this.

With M&A, it’s difficult. It’s not quantitative. We’re not transferring currency, and we analyze a bunch of quantitative data. Instead, we do qualitative interviews, just like we were doing with those discovery to validate the problems we’re solving and how we’re going about the problems we’re trying to solve for and how we go about solving them. Now, it was about can we take that same approach? And we’re already learning so much around this, but interview practitioners in the industry and enable them to share their lessons learned and doing the same approach.

We’re doing a series of these interviews and identifying the patterns to really understand what are the key challenges practitioners face? How have they overcome them and what actually works? Do we see a specific way that actually works? That’s what started this whole series of building content for M&A based off of those interviews, but then creating dedicated resources to build more structured content like the courses and things of that sort.

This is the beauty of your approach is that you continue in the true Agile fashion, right? As we look for what’s the next thing? The OG sort of Waterfall approach of stuff. We’ve seen it fail in every possible angle of both business and technology. It’s been successful despite itself, I think, there’s really the truth of that early project management world. But nowadays, it’s really fantastic that you can see it come into play. We talk about Gene Kim as sort of one of the greatest voices around early movements with DevOps.

But he says I took everything from Deming and from Goldratt. I just took manufacturing stuff and then brought in here Eric Ries. Of course, Lean Startup is about based on lean manufacturing. Their human behaviors, that when you unlock the science behind it, you realize that you can have opinionated approaches to things and you see it play out in the M&A space. There are sector specific things that have to be fairly opinionated for regulatory reasons and such. But generally, like I said, there’s a playbook.

There are things that are in there, and then you can find the wiggle room around that we as humans, we almost don’t want that to be that simple. I guess it’s kind of a funny. It’s a dichotomy of the human system is that we’re like, it can’t be this easy. There’s no way.

Yeah, there’s some real truth to that. Well, humans tend to complicate everything beyond. There’s a lot of stuff out there. When you look at best practices and look at Agile, all these techniques, there’s too much out there. I think that’s what makes it challenging is there are so many things you can look at and whatever vertical, whatever industry or function you’re in. But ultimately, one common element that really drives success is a culture of continuous improvement. We mentioned Lean. I think that was my favorite part of Lean.

They used a Japanese term Kaizen, which is a word that translates to good change. But in reference to lean management, it’s continuous improvement. My youngest son actually named Kaizen because my wife had a dispute with giving my name. So somehow the compromise was Kaizen. So I was reading a book on lean management at the time. But if it’s one thing I could drive in any organization to create value is continuous improvement as a culture becoming change-oriented. Too many companies get stagnant. It just happens. It can happen in startups in various ways.

But the more you can continuously drive, to continuously influence continuous improvement, you really get something good there. That’s where we keep adding new products. We’re identifying new problems, creating new solutions, pushing ourselves to improve on all fronts. But I think that’s the one common thing that really drives a successful organization is that culture. Or if you’re in that situation, and you work in a larger entity. There is a lot of stagnant pieces that need to be awoken and revitalized with that kind of approach. And you reformat the culture and still that change-oriented values.

When it comes to doing something like this that has a financial impact, sometimes with it, is there additional responsibility that you feel in the rigor that you have to apply to the software development process and the way you run your teams because it’s dealing with sensitive financial transactions in the end, and especially when it comes to stuff like firm room where you’re dealing with really true regulatory public information. This is one that often separates people. The moment they say, like the more we have to touch money, stop developing your software because it’s a dangerous game.

Yeah, it is. There’s a lot. If you don’t know what you’re doing, you could waste a lot of money, which I learned the hard way. You can waste a lot of money quickly and have nothing to show. That’s why I’m a big believer in taking the light rapid prototyping in the beginning, to really validate what you have and then have this clear expectation you’re going to rebuild what you stood up in order to have it ready for scale. That part is definitely one component of it.

I think thinking back the biggest challenge was balancing that with the security nature. Like you mentioned today, it’s a never ending thing. Every year, we’re dumping more and more money into security, dealing with adding more certifications. It’s all the SOC 2 Pen-Test, whatever other certifications more we grow as a company, we just reinvest into that front, I think especially it makes it easier now being all virtual. Then you just reallocate office expenses into your digital infrastructure, which includes security. Early years was extremely difficult. It takes about three years to really get security nailed down.

Looking back out of it, there are some deals we’ve done on the platform that we should not have been doing. We just did not have things set up the way they should have. It really takes. There’s two parts. There’s infrastructure and how you have that set up, and then there’s your actual application. What are you doing for us? Because the nature was managing highly sensitive information. We had to learn. What are the key things that help with that automating watermark so if a document does get out, you can trace it back to who leaked it out and making sure you have a really rigorous audit trail, which isn’t common in software, that every single click or interaction is tracked and logged and auditable and tamper proof at that.

There’s a lot of little things, and then you have to learn how to build that stuff. It just was a challenge of its own to really create those kind of functionality that, it’s truly secure. Like I said, you start getting things, but security is a roadmap like that thing, it’s a never ending roadmap.

For sure.

And you got to keep updating it and prioritizing it. Work with external teams to help you find out where you should be prioritizing.

You can’t treat security like a juice cleanse. This is not a thing that you just throw developers and a couple of weekends, like you said, it’s an evolving thing, especially as we see new compliance frameworks that come in new regulatory things that we got to be prepared for. But it’s funny when you say the early days, there were stuff where the systems may not necessarily today stand up where you were four years ago on this stuff. But the funny thing is, it was being done with paper being passed across tables in the past.

The irony is the rigor that we’re held to in systems technology is far greater than the failed human to human interactions of literally people talking in open hotel lobbies about a potential deal. And meanwhile, you’ve got people from some hedge fund just sending all their interns to walk around the base of every Shangri-La to see if they can find out what’s going on in the world.

Yeah, that’s so true.

Now the next piece is the idea of giving good information away and guiding through the community. And the result, whether even planned or unplanned, often of like, actually eventually leads to bringing business. And I think this is a beautiful thing. I love that you’ve got such a great education opportunity in what you’re doing, and you’re doing it through blogs and you’re doing it through your Academy. And then you probably will find by bringing this real good education to the world that those people will be like, hey, we’re about to go through a deal.

I think I know where I want to go. The folks that taught me how to do this. It’s an interesting move in business that you can educate first, and then business often comes as a result. How has that played out in how you’ve done work with the Academy?

Eric, if you’re going to build a startup today, that’s software focus, a part of your strategy should be building a media company within your company. It’s becoming a must because that’s allowed us to really position ourselves as a credible resource, trust our brand and allowed us to dominate over competitors. We have competitors bigger than us, and we’re out ranking them in Global Alexa ranking. We’re getting better speakers at our events at our podcast. We’re more in-tune with the community, and that’s the biggest driver of it is the fact that we’re running a media company within our organization.

We’re 30 people in the business now, and our marketing function is ten, in full stack. We got everything in house editors, podcast editors, video editors. We got multiple writers, full time designer just for marketing.

It is such a perfect phrase. I’m going to steal that totally from you. I love this idea that the media really is such an important part and we miss it because like I said, number one, it gets your voice out there. It allows you to create this beautiful narrative through storytelling. And that’s why the way that you write is beautiful because it’s like reading a conversation. And it’s not quite often, especially in technical companies. They treat it like technical writing, not like technical marketing, and their different things than new ones.

But technical writing is like manual creation, very distinct flow, very machine- like in the idea that simplified to the point, no fluff. But then technical marketing is show something technically, show something that’s detailed and in this case, the M&A, is the tech, the function behind it, but make people care about what they’re reading so that they stay through to the end. And like I said, I’m a fan of your content because the style of the writers that you’ve got has shown that I want to get to the last paragraph every time.

That’s great. I’m glad. I definitely got a great marketing team that drives a lot of that.

Now in going to the M&A side and your background when it goes right, it’s easy to recreate history on how it went right when it goes wrong. It’s really tough for us to visit that, but when it does go right and go wrong, how do you use your retrospective view to go to the Agile format to look back on a deal? Wherever it went and really bring that and try and find data and signal amongst what happened to then influence the way you would approach it the next time.

For us, we’re not hands on. We’re not in there engaging with the actual employees of the company that’s getting acquired. But we do spend a lot of time with the companies we work with, really understanding how their deals are going. Where do they see value getting leaked and what are the outcomes then going backwards and understanding what were some of the causes around that? I’ll tell you, this is the fun part to get into this. When we see M&A go wrong, it’s because of the people.

It is not financial or somebody screwed up the model. People having problems, communication problems, accountability problems. That’s the reason why you’ll see billion dollar deals get screwed up. We see deals where they did it for 5 billion a year later, they’re writing it down to 1 billion. A lot of value lost. Probably a lot of people left that company. I hate tattling on some of it because I don’t want to throw our own clients out of the bus. But we’ve seen it where they’ve bought a business unit for $3 billion and had a lot of aspiration on new products that they were going to introduce.

A year later, the whole executive team left frustrated with the way the integration was handled, and they end up writing down that business a year later for 1.3 billion. And five years later, there’s no innovation coming out of there.

Yeah.

What would have been probably a company that was on it’s up-and-up could have been a 510 billion dollars company today or greater, but it’s gone. It’s just going to be a small little thing that’s in a stagnant state and will probably stay there. So such a critical thing as the people experience.

And I would say the lesson learned from doing 100 of these M&A focused podcast is all about the people, align it from the very beginning. No surprises. What you have planned and what you’re going to do with that company you’re acquiring. Put that front and center. Put it to the point where there’s clarity and crystallization on what the final state is going to look like when both companies come and merge together and bring down the front. So both executives, the buying executive and the selling executives, CEOs, are aligned around it.

That’s one. That’s what that division is going to look like. From there, they can start developing a go-to-market outline and understand what that’s going to look like. I think the other thing is for those two CEOs to understand values. A lot of the problems when we talk about people conflicts and frustration are because of culture clash. We’ve seen a lot of examples of that. If you can align around that early, the way to really root it is by getting clarity on each organization’s values, then getting a sense of, hey, How’s this going to work?

Your organization has a very rigid, top down management approach. We’re a flat, believe in Agile empowerment and have our folks running their own show. How is this going to work together? And we may not want to fully integrate, maybe we can still work together but keep some of that level of independence and be open and clear about it, that it is a different culture and it’s not going to just integrate together. That stuff gets lost out the window. And I think of you grooting it by values allows you to really align.

When you do build a story and have the communication publicly to the employees, the customers, the vendors on this big event that’s going to happen. That’s going to create a lot of change and why it’s happening and then also, like, validating it. In addition to that story, we also see why we’re going to get along and can really articulate it well. And that’s an important thing. Thinking about the events that happen after you close a lot of change management, the largest amount of change management organization is going to go through.

There’s a nice narrative and everybody’s aligned around the rationale for the deal. And there’s a good story on, hey, this is actually exciting, and I want to be part of this like, heck, yeah, there’s opportunity for growth out of this. If this comes together and the organizations create the value that they see by combining these entities and creating a better solution for customers to be happier and acquire more customers. This is a great thing. And now I see what they’re doing, I want to be part of it. When you’re left in the dark and all you’re dealing with your own fear and uncertainty because you’re just like, oh, this acquisition is happening.

I know what that means. They’re going to want to cut costs.

Right.

And I know there’s not room for two lead PMS in this team or whatnot, so that fear, uncertainty, doubt sinks in and I’m going to start looking for another job. I haven’t even heard the news yet, but I’m already out there. It all comes back to the people. If you can manage the people experience from the very beginning, make it engaging. The other thing I think often doesn’t get done in M&A is a reverse diligence.

You’re doing diligence to understand if the company is worth paying for and the risk of it. But at the same time, you should be encouraging them to do diligence on your organization so they understand how it’s going to fit in as you complete the acquisition and be able to ask some of those questions, be able to get clarity, make them part of that understanding earlier. I think that empathy at the end of the day, if you can look across and we talk about curious earlier, but really spend the time to understand people are frustrated and you can see in their face.

You can always start when you interact or meet somebody and I’m doing a lot of this on video, but you could tell if they’re happy, having a good day, you’re having a bad day, something’s up, you have something you want to talk about, you can see it. And if you lean in with that, people tend to open up and really sends them out. Like, get a good understanding and some things you got to put out there and just put yourself in their view and get a sense of what are they thinking. Saying, hey, you’re probably dealing with a lot of change and a lot of extra work right now and then they’ll tell you like, yes, I am.

No, I’m not. Just by listening. That’s like, the most important thing. I think M&A, we get so much caught up in a plan and driving top down management, pushing to change. But at the end of the day, people are dumb. They know what they’re doing. You just got to level up with them. If you can take or flip the 80 20 ratio around and spend that time just to listen and understand, you’ll get a sense, you’ll know, you’ll know what they’re concerned about, you’ll know where their heads at, if they’re motivated, if they have a clear understanding about what’s going on, if they’re committed or not, until you have that, there’s no point in talking at people.

It’s really wild, and that carries into every part of our interaction with people. Right? Even when I’m in front of analysts all the time and in customer situations. And there’s a great book called The Coaching Habit, which is one of my favorite ones. I use it a lot for leadership, and it starts with the simplest things. The first thing you ask is what’s on your mind and give them the chance to immediately convey. And then the favorite thing is the second question is called the awe question, A-W-E, and what else?

Because they’ll always have a canned response and then you say, and what else? So I’ll do this even in situations where they ask about your technology, like, how are you better than or different than X or whatever? And I’m like, well, what’s the thing that really excites you about that platform that you’re talking about? And they go through? And I don’t even have to ask the ‘and what else’ question sometimes because as they’re talking up this thing to be like, you know what I really wish it would do.

And it’s like being in the therapy session. It’s so fantastic versus if I had gone in and like you said, just treated it like a diligence exercise of like, you’ve asked me these questions, I will show you the technical comparisons. If I throw data at it, I can give it all the context I want, but in the end, just be humans to each other. Like, it’s so amazing the impact it has. And at the end of that experience, especially when you’re dealing with M&A like, the amount of uncertainty, it can have a profound effect, not just on the direct human impact, but the actual value of the organization that they’re buying in the end.

Because like you said, if you have a lot of uncertainty, it creates certainty. People who are certain that they’re going to get out before they find out what’s happening. They’d rather control the outcome. He said, I don’t know the outcome yet, but I’m pretty sure it’s going to end this way. So I’m leaving. I see it happen all the time, especially as startups get sort of consumed. When I was at SunLife, it was a 5000 person organization that was buying a 5000 person organization. They were on the buy side of the transaction.

They were the end name and the brand would be attached to it. But it was literally mashing two ships together, and the leadership exchange was very interesting because then you would have all these people underneath. They’re trying to work out the org chart, and it wasn’t obvious who was going to do it in the end. And it’s a really weird experience, because by all matters of science, it should just, it works. Right. We know we’ve got the org chart here, the org chart here. Perfect.

Grow the business. Do this. Follow the details. Profit. Us humans get in the way of that.

I had an interview with one of the HR leaders who’s in a Global HR role at the time, Sallie Cunningham. And she said it best, where a happy workforce generates more income.

But to go to what you and the team are doing both through being able to educate on here’s the process that you’re involved in, right? Here’s how you can take best practice and bring it in there. And then it gives you the confidence that the platforms that you’ve created are built on these foundations of, like, these people know what they’re doing. So it gives us real credence. You’ve got skin in the game. You’ve lived the life before you came to start the company. It’s this beautiful flow.

And like you said, the truth is, I’ve heard you say it before. It’s like Excel is probably the number one software tool in the world for everything under the sun. And it doesn’t need to be that way. So when you show people that there’s a better way to do this, it creates that happiness that Sallie talked about, it creates the comfort that, hey, we’re using a system that’s built by people that understand what we’re going through, and it lets them focus on the matter at hand, which is retaining their culture through a merger.

And there’s very few schools on that, unfortunately.

No, there isn’t. And it’s interesting because they’re talking about changes amongst us behavior and the way we work together and think about which really stems to a lot of core leadership skills. And then the other piece, we talked about the technological solutions. A lot of people are fast to adopt, slow to adopt. That’s a whole area we didn’t really talk much about when we talked about the startup cycle, where there’s a lot of ideation going to market, getting the market fit and all these things you have to do to really prepare to have a product you can take to market.

But the distribution model, that’s actually the hardest thing to get. Right. You’ve seen it. We’ve seen it so many times where it’s the best product, but they didn’t have the best distribution model. And we’ve seen it where the lagging product actually ends up being the winner because they had a better distribution model.

Look, I’ll say this. This is my opinion and my opinion, alone, right? Microsoft has a lot of bad products, right? But yet they’re out there all over the place. I say this as running a lot of Microsoft organizations over based organizations over time. It was hilarious that we used to joke in the early days of like, well, they don’t have better products, they have better marketing. But it really was, they had better distribution. They had ways in which and it didn’t even make sense if you looked at it by the data. Right?

If you were selling Microsoft software, you made, like, one point on the deal. There was no margins, there was no way to discount it. You were literally just a pass through to write down the contract. You were papering the deal, and then you would try to hopefully wrap services around it. So by all measures of how it should go, it shouldn’t have worked. And yet they became dominant because they solved a specific problem. And then they marketed it so beautifully and created a distribution channel to make it easy to consume and get.

And that was truly it. And now, with the ability to digitally adopt most products, distribution is really different. Right? So on that basis, Kison, what’s the distribution solution? What’s the thing that you saw as your way to differentiate in distributing a platform today?

That’s the whole thing to figure out. We talked about validating your idea, validating the solution. When you’re validating your solution, you should be validating your go-to market. Really understand how is this customer, how their channels to learn about new products, get information? Who do they actually trust and understand where you should spend the time to find their influence? I think that comes in shapes as an ongoing partly, I think there’s other drivers with the startup where you start off with one view on what you’re solving.

And as you explore the market, you’ll find different areas you want to focus on. For us, we started with smaller M&A deals in the beginning, and as we now work on with the larger companies, we’re working and know that, hey, if it’s a larger company, they’re going to have bigger problems. And it’s interesting to solve bigger problems. And inherently, you get compensated better for solving bigger problems. So you sort of shift the model and start going upstream. And we went dramatically. We went from $100 a month self service solution to now. We’re selling enterprise anywhere from $30 to $150,000 annual subscriptions, so vastly different.

But I think that’s one big part is understanding that. What problem are you solving for? What market and what’s the value of it? A lot of people are familiar with that. You typically tend to go lower than you actually should. We learn that, too? We’ve been bumping our prices up every year since we started the company, and it’s always been the best where everything is always net positive results. We end up getting more clients and selling more.

There’s just so much truth to that perception of how you price your solution. You price it higher, they value it more. They’re more likely to use it, make sure they get value out of it. Or if you give it away, nobody cares. They’ll just throw it away and never use it. There’s the pricing model part. But then there’s a huge part around the language, how you talk about the product, how you position it. There’s so much that goes into it. I got to give a lot of credit to the marketing folks out there.

That’s not easy. There’s a lot of in-depth psychology to learn, and it’s a never ending learning thing. How do you pull that language you learn when talking to people about their problems and solutions? Pull it up front and really make it part of your website content, the things that people interact, the way their part of your brand. And there’s a lot to really think about. And then it all ties back together. I think your values tied back to there in your organization, because when you think about distributing your product, a lot falls to the customer experience and your values drive parts of that.

And they’re the pillars of the customer experience that you’re putting out there. So how is your team aligned around what they’re committed to on values that then transposes over to customer experience, and that turn lends into your distribution model. And one thing, where one of core key first value is responsiveness. We manage confidentiality and we could be working on a billion dollar deal and not even know it. So we just treat everything like a high sensitive billion dollar transaction, and they’re extremely responsive throughout the company.

That’s one thing. But now that goes over to the customer experience that goes into our distribution model. When you reach out to any of our sales team, interact with them. That’s the one thing I want you to be very, immediately understand, that they’re responsive. When we’re done at the meeting, you should get a nice summary follow up, and they should be prompt. They’re not going to wait around where these guys go. That’s a big thing. That’s part of our values that then comes out when it comes to customer experience that affects your distribution.

That very much is how people interacting with you, what perception they’re getting, especially if they’re going through competitive process and evaluating benchmarking against competitors.

So this brings a good question of how did you scale your culture through the changes in your go to market?

I don’t know if it’s scaling culture. The culture shifts quite a bit when you think about a company and you start with just two people and you’re like, okay, I’m going to think and design. You’re going to build and you influence each other right there, just like you see it when you have a partnership and then you add people and it’s so critical in the beginning. And I really wish I put a lot more thought and emphasis on the culture when making early hiring decisions and made that the primary driver.

Then followed by the capabilities. Sometimes if there’s a trade off, you’re going to work with somebody in a unique role and they’re going to be, maybe, quirky, and that’s just what it is. And that’s fine. But are we aligned on values? Are we committed to this? The responsiveness of him. Picking on an example, when we go through an interview process today, that’s what we’re looking for. We’re looking for, how long does it take for them to follow up this interview and how well of a follow up did they do?

Attention to detail is another value in our company. So we want to see how well they wrote the follow up. Do they say, thank you. Nice meeting you. Or did they really summarize the key things we talked about? And we have one candidate, knew the values we talked about because we review them in the interview process and articulated why they would fit and be aligned with those values. It’s like done. Perfect. So when it comes to scaling it, I didn’t think of the one thing I didn’t understand, I thought it was a soft, fluffy thing.

You just put on your about page to get some warm, fuzzy feeling for some website visitor. But no, they’re really real. When you think about envision, your success and where you want to go and you reverse engineer that, it should boil down to those core values. And then you build off of those core values. When you hire people, you make sure they’re 100% aligned and let that be your leading driver to make your hiring decisions. And that’s probably how you scale your culture out.

It’s doing it like, think about the envision. Where do you want to be? How do you imagine the company operating and reverse it? Get commitment from other current team members. You have work with them as a workshop and say, hey, I really want to do this right. I want to have these core values that we all can stand for, and we make this part and we do it. First interview, you’re going to hear the core values. Second interview, you’re going to hear about core values. Final interview, you hear about core values. And it’s just constantly there, but it’s just reinforcing it saying, hey, this is what our expectations are.

I don’t want you to go through this process and find out there’s culture fit. We want you interview multiple people and get a sense of the culture. But this is what we align. We’re committed to these core values, and we want to make sure that reflects and that you’re a fit for it. If you’re not the person that’s ultra responsive in attention to detail, then maybe this isn’t going to be the right fit. Let’s talk about that. You can be missing. I don’t have attention to detail.

Maybe you have one of the values, you may be a little behind and that’s fine. Let’s see where you’re at with the rest of the organization.

Yes, it’s not just the message that’s written behind the reception desk. Culture is how they behave when you’re not looking, right? And if you’re not willing to go right to that, right? And like I said, approach it early and nearly higher. And it’s funny I used the phrase scaling culture, and I like that you sort of said, it’s not really scaling. It is an adaptive process. And I love that you’ve been able to be curious on that. In that you’ve accepted that, yes, some stuff happened.

It’s like we figured it out, but just the fact that you’ve assessed it that way. You’ve never said, like, well, here’s the original values we had, and some people deviated like, no, we’ve adapted as a company as we change. This is what builds successful culture is the willingness to listen as much as to send them a link to the corporate values page on the website.

If I were to go back and do it again, I would have introduced core values earlier much earlier and would have evolved them, too. I think as a company, all those things will evolve. Those things. The way you talk about yourself, those things will evolve. I think one key thing is try to get your positioning down early. That’s the most critical thing. We went and positioned ourselves to sell directly against the legacy competitors that were data rooms, and that pinned us down and probably stunted a lot of our ability to have this detailed positioning that we are different from them.

We’re a lifecycle management solutions, what we really evolved and shaped it to. I think if we had that positioning earlier, it would have helped the market understand where we actually sit that’s different than what they’re used to.

Right.

But I think I’ve seen that where companies, because even within, you’re in a big category, you can still carve out a niche and saying, all right, whatever, we’ve done all the organic stuff now, it’s like diapers, but organic diapers. We do custom printed diapers. That’s kind of our thing is like, the customized baby.

I don’t know, but you know what I mean?

It’s artisanally crafted. Whatever. There’s some other moniker you attach it to.

You can get that early also. I feel like it took us a little while. We were kind of battling with data room, data room plus project management jumping around with different positioning. So some of those things. Marketing team is critical again here, but get the heads together, kind of put together all the learnings and really come up with something that there’s a good commitment behind.

Yeah. And I love again the curiosity of the process and the willingness to go back and look at what went right and what could have been done differently and then letting that influence your future decisions and accepting that, yeah. It’s funny we made these mistakes early on versus most people are like, no, we’re here because we’re here and it’s very easy in that human behavior to just say, we’ve been right, the market’s been wrong.

We talk about continuous improvement, that’s the thing that’s creating that culture. I think one key thing is encouraging people to face those things is the criticism. Yes, we want positive criticism, but sometimes I don’t have time for that shit. I don’t have time to sit there and tell you the good and make you feel all warm and fuzzy.

The good sandwich. We’re like, I really appreciate how this is going. And you’re like, oh, no, here it comes.

Let me just go straight to it. But I think one key thing is brief. Occasionally, you have to brief the team. Like, look, I want to give you direct feedback, because objectively, if I can help you get better, the team gets better. And I think that’s one part, is you got to preface it. You got to mention it here and there. Remind people because they do take that communication of personal business and fuse it together. You need to remind them to consciously split that up. Put personal out to the side and take the business context I’m providing to you.

I’d say that’s one piece of it. There’s another, losing my thought on this one. We had the..

What’s it? Go ahead.

But this, Ray Dalio, really kind of became prominent in this idea of, like, the radical transparency and radical candor. And it’s funny, I’ve actually interviewed a few people that have worked there and they’re like, yeah, it’s radical. Candor is not a good thing because some people just think it’s a license to be an asshole. But there’s a way in which people have taken that fundamental and been able to say, like, you can still be empathetic but give truth and transparency. And it is about don’t dance around it. I could sit here and I could tell you, you’re doing great in your job.

You’ve had a great few months. All you’re doing is just setting them up to wait for this hammer moment versus you say, one thing we want to sort of solve right now, there’s a problem that’s been happening. And so I want to find out what’s the right way we can work together and we can get this fixed because, like, things are going well, we’ve got lots of great stuff. What can we do to fix this particular thing? Just make that the focus. Don’t try and hide it amongst a compliment sandwich.

Yeah. I think making sure there’s a ‘why’ attached is another big thing, that’s very much in conjunction with this. You get the criticism, but there’s got to be clarity on why. Like, hey, we’re doing this to specifically improve this. Other thing, anything you put in there, you should have a why to it. I teach my kids early when they start learning how to say thank you and sorry. It’s like, don’t just say thank you and sorry, because they’re very transactional words that have no meaning to it. I need you to add some meaning to it.

Tell me why. Thank you. Why? For what? And they think about it. And I remember we always go to restaurants, and it was, thank you for the great service. And thank you for the recommendations. My daughter would go to the grocery store check out. Thank you for being so quick. Thank you for the conversation. Add some context to it. Sorry for what? Sorry for bumping into you. Sorry I lost your umbrella. And same thing in the workplace. You’re going to ask somebody to do something. Add a why to it.

Make sure there’s some clarity on why. And a lot of times, people, nobody wants to be told what to do. So can you look at something and frame it as a problem and invite them into the conversation, has appeared to solve the problem? Hey, the bathroom is super dirty. Go clean it. It’s like, how can we keep this bathroom clean? Well, maybe I’ll put this reminder to myself and I’ll make sure it gets done. Okay, great. You don’t have to tell people what to do. I think if you identify it, frame it as a problem, invite them in through a question, then it creates this nice lateral positioning that you both work together to solve it.

And more likely, they’ll know what they need to step up. And they’ll own it, too, because they presented the idea, right?

Yeah, it’s the involvement of it. Boy, oh boy. I can say the folks that work with you and for you, Kison are a lucky bunch. But I really respect your approach, the platform and the education you bring. So we’ll definitely make sure we point folks to.

Let’s talk about how easy it is to be a hypocrite too. Because that’s a whole thing of its own. Everybody’s on a soapbox with some great things to preach. But the reality is it’s extremely difficult not to be a hypocrite.

It’s hard. Yeah, that’s it. There’s a real difficulty in taking the tenets and making them practices. It’s very easy for us to point to the wall. Look at the culture statements. Culture statement says we do this and you’re like. But transparency with confidentiality is an interesting line, too, because you want to be transparent. But be careful. There are certain things we absolutely cannot cross a line of transparency on. And it’s a human challenge to make sure we build a separation. I get asked all the time. Even if you go into analyst or specific customer situations and you say, look, we sign nondisclosures walking into this room.

Of course we did. But if you say you mentioned a customer name that you’re not supposed to mention outside of this room, they’re humans. They’re going to go to the next person and say, yeah, these guys are selling to X. There’s a point of making sure that you can understand that human behavior. And like you said, creating accountability and eliminating hypocrisy. It’s a challenge because we’re always forced to split the line. And as a leader, unfortunately, as the founder, as the head of the company, you sometimes have to make very difficult decisions that may seem at the moment to be hypocritical or antithetical to the values.

But there are legitimate, immediate things that need to be solved that require hard decisions. I can tell that you would approach it in a way, saying like, there’s the why I don’t like what we have to do right now, but here’s why we have to do it.

It’s creating a framework. It’s creating a communication framework that evolves into decision making framework and having your team aligned around it so that if you’re not around, things will carry on. They’ll know that there’s a flow for the way they communicate, the way they bring up the problems, the way they make decisions on how to solve them.

We need a framework for life. So I’ll look for that. That’ll be the next book, Kison’s framework for family success. My two year old daughter. She is so funny. She’ll run into something. She’ll just be running around and she smash into my legs. She goes, Sorry, Daddy. She doesn’t even almost know why she does it. But she knows, like, I bumped into you. I should say, sorry. So cute. And then, like I said, when they get older, you want them to add the context to it.

I think about four or five years old, get them to start doing it then. And you’ll be surprised. I remember going to a fine dining restaurant. My daughter, she was only seven years old, and when we’re checking out, she told the server, Andy, thank you so much for the great service and the recommendations you made. And the woman at the table next to ours just, like, cracked her head, whiplash, like, oh, my God. And she’s just like, how do I get my son to do that?

It’s funny. And it’s something that’s just good because then they can build off of it. A lot of the Ray Dalio principles are great. I actually read Ray Dalio’s principles to my daughter when she was seven. Obviously was way above the reading level. I’m done with Harry Potter. I actually want to read this. It actually does the job. It gets you right to sleep. This will be great, but it led to a lot of good conversations. When we talk about open minded versus closed minded, how do you establish these goals and build milestones to it?

And I started doing it with her ever since then. Just say, let’s talk about these goals. What are you trying to do? Well, if you’re trying to do that, what do you need to do? How much time do you need to spend towards those goals to make sure you go in that path? Let’s start thinking about what are we doing? Between once your taking up your time between proactively using and reactively using your brain and these little nuance things. It’s fun. It’s really good. That’s what actually led to the personal podcast.

We didn’t talk about that at all, but I started this year. It’s called BossMove, where I interview influencers about what are their top three principles for success and leadership.

Nice.

We can collaborate on that, but we do a little workshop, so imagine the audience are high school kids because you can’t come out and do the Gary V, be empathetic, be vulnerable.

Yeah.

Like, no. What does that mean to a high school kid? You got to really break it down into some practical how tos. And it’s a fun, challenging interview, because when you start thinking about it, you’re getting into a lot of details about what is the mindset component there.

How do you take that thinking and build it into a real behavioral pattern that becomes a part of you. It’s a fun interview.

That is wild. Yeah. I’ll definitely have to pour over that one. And that’s when I’ll recommend. I’ll make sure I get links as well as part of the show notes. There you go, there’s Ray Dalio and his authoring team. They need principles for teens. Principles for. It would be great to have principles for the five year old range. There’s definitely the ability to take that almost like parables and like, Aeop’s Fables sort of took this idea of stories and made them accessible. But they really were truly telling these big, bold, almost biblical type of things.

But then they just made it about bunnies and turtles.

I’m hoping because we have the model in M&A science where we’ll extract what we learn and write up plays. And there the step by step how tos. And we started drafting it pretty early in moves for this BossMove podcast, you learn this life lesson and do a write up. How do you turn into a practical how to? And one day, I’d love to see it evolving into something like Khan Academy, where here’s the free public school that teaches you the life lessons that you don’t learn in school.

There you go. I’m holding you to it. We’ll be back in a year with Kison to announce the moves.

The Boss Academy.

That’s it. I love it. Excellent. Well, Kison, thank you very much. And for folks that did want to get connected with you, what’s kind of the best way that they can do that?

If you want to learn M&A. We have over 350 published pieces of content. You name it. We got it. It’s on mascience.com. If you like to connect with myself, I’m always on LinkedIn. Just Kison, K-I-S-O-N, Patel.

That’s it. I love it. Well, thank you very much. And yeah, I definitely recommend people get in there and take in this content. It’s fantastic. We’ll have links to the podcast as well. And yeah, now listen to BossMoves. Go do it right now. Go click that button.

My principle is discipline. You have to have discipline to be committed. So if you’re interested in M&A, you want to learn. Check it out. I love your style. I think you did a great job interviewing. I enjoyed this conversation, Eric.

Great. Thank you very much.

Looking forward to following you and seeing who’s up next in your podcast.

Maybe I’ll be lucky and I’ll be able to get on the Moves podcast. That will be my new goal. Is be valuable enough to make it on the BossMoves.

Yeah, let me know. You can start thinking, what are your top three principles? I think that’s a good one. We talk about what lends to values. You got organizational values. But do you have values personally? And are there certain principles that shape those values? And then is that something common you have with your partner? I don’t know, but I’d love to hear your thoughts on your principles pretty soon.

All right. Mark the calendar kids, will be on that one. Great. Thank you very much.

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Craig Goodwin is the Co-Founder and Chief Platform and Strategy Officer at Cyvatar, a technology-enabled cybersecurity as a service (CSaaS) provider.

He has over 15 years of experience leading security across both the public and private sectors, building holistic security functions that combine the range of security disciplines under a single effective function.

We talk about the method of delivering Cybersecurity-as-a-Service, the reason it’s more critical than ever, and also the approach of building leave-behind process and platforms to deliver the best customer experience. 

Check out Cyvatar.ai here:  https://cyvatar.ai 

Watch the Full Show Here

Transcript powered by Happy Scribe

Welcome, everybody. It’s Wednesday. Or at least it is if you’re catching this when it comes out fresh because this is the DiscoPosse podcast, your weekly leading technology startup podcast, and you’re about to get exposed to a fantastic conversation with Craig Goodwin, who’s of Cyvatar.ai. Now Craig is really fantastic. He’s co founder and he’s somebody who I really enjoyed because as a chief platform and chief strategy officer, he had this beautiful mix of having lived the life of doing the things around security and now brings them to how to deliver these as a platform, as a true cybersecurity, as a service.

Really great stuff. His methods, approach, just a very enjoyable discussion as well. Somebody I would love to spend a bunch of time chatting with. And speaking of spending a bunch of time chatting with. I got to tell you that the reason I get to spend a lot of time chatting with these amazing people is because of the amazing folks that actually make this podcast happen and supporting it. So I want to implore you to please do me a favor. Number one, go check it out because everything you need for your data protection need. You can get from our good friends at Veeam Software.

I’m a longtime friend, fan, and they are really cool and that they’re supporting the podcast and making sure that as they look to bring their own message to the market. I’m pretty pleased that I’ve been able to be a part of that featuring some of the great folks at Veeam as well. So go to vee.am/DiscoPosse. They just came off of AWS re:Invent. They got a really cool campaign. It’s a comic book download, so really cool. So go there. It’s actually the landing page. If you go to vee.am/DiscoPosse, you can get your very own AWS superhero comic book.

Please do that. Very cool. I absolutely recommend it. And also, of course, speaking of protecting, the one thing you want to make sure is not just protecting your data wherever it is by protecting it inflight. Protecting your network, protecting your identity. You can do this by using ExpressVPN. I’m a longtime user of ExpressVPN because I travel a bunch and as part of it, I want to make sure that I’ve got consistency of experience and safety while I’m traveling around and using other WiFi and other networks.

So please do try that. Go to tryexpressvpn.com/DiscoPosse. It really is just that easy. Oh, that’s right. And also, have a coffee company. I hope that you enjoy it. I do. And if you want to go check it out, it’s diabolicalcoffee.com. Not much more to say about that. Really, really good coffee. Go check it out.

Hi. My name is Craig Goodwin. I’m the co-founder of Cyvatar, and you’re listening to the DiscoPosse podcast.

So thank you, Craig, for joining. I’m definitely in excited mode in what we have a chance to talk about, because when I saw Cyvatar come up on the list. You’re actually on my companies to watch. And it’s a rare treat when we can dive into, I’ll say it’s funny. It’s like this burgeoning area around cybersecurity and offering it as a service and injecting ourselves earlier in the development and operational workflow. It’s new to the world, which is terrifying because it shouldn’t be. But this is why the opportunity is huge.

So I think the best thing we can do for folks that are new to you. Craig, if you want to give a quick bio and we’ll talk about Cyvatar and the challenges that you’re solving.

Absolutely. Pleasure to be here, Eric. And thanks for adding Cyvatar to that list. I’m sure it’s a long one given what you do, but I’m privileged to be a part of that. Sure. My name is Craig Goodwin. My background. I’ve been on the end user side of cybersecurity for about 18 years before that. I was in the intelligence services with the UK government and fell out of that when chief security officer was just becoming a thing, really. And then spent 18 years building, operating, running large scale cybersecurity businesses as an end user.

So companies like Monster Worldwide, Ferguson plc, CDK Global, which is a big automotive tech firm out in Chicago and then Fujitsu before finally co founding Cyvatar with my co founder, Corey White, who is based in Orange County in California. He’s also got a long history in cybersecurity, but from the other side of the house. So he’s been building and running cybersecurity vendors for 25 years, and I come from the end user side. So the first pitch of cyberattack is always that we’ve got both ends of the spectrum.

We’ve been there and done it from an end user perspective and also a vendor’s perspective. So we know what’s broken and we know what we need to fix to deliver better outcomes for customers and businesses globally.

I think this is really why I loved your sort of mix in the founding team. It’s a fundamental problem that we have in so many startups is that we attack it purely from the intellectual like this is sort of the scientific method, and we come at things and there are points when you have to have a very opinionated resolution to things. It’s often how we succeed, is you can’t just sort of do incremental change. You have to come in and say, this is the way that it’s going to work.

We have to remap some of the processes. But because you’ve come from the experiential side, the buying side. I used to do the customer deal as well for a couple of decades, and it allows me to approach technology in a way that I know well in a pure intellectual approach. Fantastic. But will this actually get adopted and used in the way that we would hope. Really, the thing that I want to focus on, Craig, is this idea that you’ve seen it in flight. You’ve seen it in play.

You’ve actually implemented solutions, and you know that it’s much more a human problem sometimes than a technology problem, especially in the area of security and cybersecurity. So how did that two sided approach influence your choice to start the company?

Yeah. When I met Corey a couple of years ago, at the kind of founding of Cyvatar, I was in that place where the industry is going crazy right now, particularly from the VC point of view, there are, I don’t know. It changes every day, four and a half thousand plus products out there or something crazy. So I was having a lot of VC friends. A lot of founder friends say to me, you should found a business. You should do something now that you’ll be able to get the funding.

You should take that knowledge that you’ve got as an end user and create something. And I’ve been thinking about it for 6, 12, 18 months, but I wanted to find the right, and it sounds like a bit of a cliche, right? But I wanted to find the right thing, the thing that actually solve the problem as an end user. I’d fought with it for 18 years, and the kind of problems that I found were that I bought pretty much every product that existed. You could say the Noah’s Ark of Cybersecurity, but two of everything.

And that was true. You’d go out and you’d convince yourself as a CSO that your number one objective was to convince the executive team or the board to give you more budget, and you do that. And I do that really well. And then with that budget, I go and buy some more products, but still wouldn’t get to secure. I still wouldn’t get to the actual outcome that I wanted as a chief security officer. No matter how many products I bought, I still found that I needed large internal teams or my own platforms that I built myself internally to actually do the hard part.

And the hard part was actually the fixing. Actually getting into the outcome of secure. And I found that 90% of the products on the market would point out my problems for me, but simply add to that list of things I had to do. Add to the problems that I had to fix and not actually fix or solve any of those problems. When me and Corey met, he told me about his idea for Cyvatar and as a service solution, I said, Well, look, I’ve done that internally, three or four times over.

I’ve built the platform that we need to build to allow that to be successful. I’ve been the end user side consuming that. So let’s join forces. Let’s bring those two components together. He’s been running services businesses for 18 to 25 years, so he knew that one-off services just didn’t cut it anymore. I’ve been running the end user side and knew that products didn’t do it. So then things combined just led to what Cyvatar has ultimately become, which is the ability to pull to your point people, process, and technology altogether into easy to consume subscriptions that mean you’re getting to an actual outcome rather than just finding more and more problems.

Well, I remember, the thing was ADT security or something. It was like something like a physical home security company that had a great set of commercials. And it was the whole thing of there’s monitoring. And then there’s us, right? And this whole thing of like a guy, a bank is getting robbed. And someone just looks at the guard says, “Aren’t you going to do something?” And he says, “hey, he’s robbing the bank”. This is monitoring. Obviously the first layer is always discovery doing that monitoring that observability, which is sort of the new catchphrase in the industry.

But then from that point, is being able to action on it, is the gap, rather than just basically saying, hey, there’s something going on. And now it’s your fault. Your just handing it off to an operator or developer. And this is a complex ecosystem in the organization. The CSO doesn’t have effective control over IT in the same way, because they generally report up, like directly to the CEO. They report up, if anything, possibly adjacent to a CIO, possibly through legal and procurement. More so than just operational IT.

And there’s really a lot of stuff that falls under that bucket. So while they could say, there’s my aspiration to achieve a secure workplace, a secure environment, this now has to cross into seven different divisions of IT and many, many other things.

Yeah, 100%. And I could talk about that for days. I think to unpick that a little bit. You’re absolutely right. I think the trend and it’s going to continue to be a trend is decentralization of the security function. I used to joke or half joke as I was building security functions, that my ultimate goal should be to not need a budget as a chief security officer, right? Because I shouldn’t need to protect the organization. It should be so ingrained into everything we do as a business to your point, the different departments that actually, they understand it.

And I build such a strong culture of security that they pay for out of their own budget. Craig doesn’t need a separate security budget. I’ve tried to do that at the businesses that I’ve always been at, which is to put the power in the hands of the developers, for example, right? Where they have the tools, the power to be secure by design as they build their products, as opposed to what doesn’t work, which is Craig’s team coming along and acting like the police, right?

Which is definite cliche in the industry. But it’s hurt us for many, many years as that kind of outsider type approach to security. And then the other thing you touched on, which is just incredibly important and a lot of people forget is the politics associated with it. Like, how do you drive behavioral change that first day shouldn’t be about looking at technology. It should be about going to buy a Starbucks card, so you can take all the executives that you’ve got to influence out for coffee and build those relationships. Right?

Because that is 100% the most important thing. And one of the things that we’ve done from Cyvatar is enable that. The platform that we’re building or the platform that we’ve built really enables that decentralization. It enables those workflows to be created across organizational bounds and put the power in the hands of the people that actually need to fix it, as opposed to just firing a load of vulnerabilities and alerts at the security team and expecting them to do the hard work in chasing up and getting things fixed and influencing people.

It becomes the challenge. I was at an organization, and this was in the 90s through the 2000s and the CSO didn’t exist. That function wasn’t there. It was at least rare in sort of the Canadian world, particularly, we’re such a friendly bunch. We didn’t need one. Right. And all of a sudden, we see a CSO show up. And this is right around the time that Sarbanes-Oxley also was implemented. So you had, first of all, a functional change in the organization that they were separating out this role of information security officer, and also everybody that had the CXO title was signing their name on a contract that put them personally liable for the outcomes of their organization.

And it really changed things. So immediately, the first thing that happened, as we do with security organizations is they hired a bunch of VPs of security, and then they hired a bunch of directors, which are basically sort of their very high titled interns. And they began crafting policy, crafting policy. Quick. We must craft policies. And it was almost like a Monty Python ask level of, quick a proclamation. And they would come and they would post it on the board, and they would email it out and send. And immediately you’d say, “Well, we can’t do this”.

And they’re like, oh, no worries. Then file for an exception. And then they built a system to file for exceptions. And they had created the sort of process spaghetti. And I was torn, right? Because with what’s going on, I recognize what you needed to do is we need to actually look as an organization. How are we going to attack this problem? How do we recognize the problem within a medium, this is like putting a government into a functional organization and where they don’t see the outcome, they don’t see the negative side effects.

They just simply have to come in and say, policy checkbox. And then as it made it further on the organization, we would just find ways to get through the audit safely. And that was the first phase. But then from there like we’ve seen it in action. We’ve seen real. No one wants their company name to show up in the news. And it’s like when somebody has their name show up in the news and the word embattled is in front of it, there’s certain things you never want to have.

And I’ve got good friends who are solar winds, and that was a tough one to watch them go through where the reputation attached to being exposed to a vulnerability carries for a long time and has a real commercial effect on them just as an example, right?

That was one thing where they’re in the news. So at first it was like, in 2009, it was probably happening all over the place, but it wasn’t in the news. Now there’s a really significant risk that it’s prevalent that this is active in the industry, like DarkSide did it. They created ransomware as a service. This is fantastic. But how do we attack the problem and make sure that we don’t end up in the news? But most importantly, that we aren’t vulnerable. That’s the real thing. Obviously, the news is bad, but let’s actually fix the problem.

So if the ransomware has a service, then what do we do to counteract that?

Yeah. And I think you hit the nail on the head and we could talk for hours about the compliance versus security debate. But I think actually, in a number of cases, compliance is damaged, what we would call real security. Because if you think about, you mentioned the top down approach. One of the things that all those compliance standards first say is, go and get the board approval, like, get your executive buy-in all that stuff, which makes it that very policy focused, like top down approach where we create mandates and then we try and force it into the organization and actually back to that decentralization conversation.

The most effective way I build security is from the ground up. That doesn’t mean negating the executive buy, and you need the budget. You need people to understand what your objectives are, but being very clear with your sponsorship, your leadership, about what is the objective. Do we actually want to be secure, or are we just ticking a box for compliance purposes? If your answer is we actually want to be secure, that’s a very different journey than creating a ton of policies. And that’s one of the fundamental principles when we started Cyvatar, was that there’s a ton of really quick and easy ways to go and get SOC 2 compliance, for example, like, I say, 27001 compliance and will help with the operational aspects of that.

But the majority of the small to medium sized businesses and other companies that we’re serving wants is to be actually protected from ransomware, is to be actually secure. And to your point, like solar winds prevent their name from being in the media because they’ve lost data or been hacked or been interrupted or whatever it might be. They actually want to be secure, and that then differentiates them from their competitors because they’re more secure. So what we’ve done with Cyvatar is build real security in and security that actually gets you secure, which is a big step change from a policy, creating something and telling everyone that they’ve got to do it.

This is real world. How do I prevent that from actually happening and moving to that prevention? Moving to that remediation is the key step that the majority of vendors in the market just don’t appreciate or don’t help customers to achieve right now. .

When it comes to differentiation, it’s funny, I lead them. I’m not going to compare you to anybody. I’m going to compare you against the industry at large, in that you’ve chosen to price by human rather than object. And this is interesting because quite often when we think about security services, developer services, all of these services, they’re effectively marked per application per object per cloud target, per whatever. There’s always some technical target. So let’s talk about that, Craig. The idea that you’re basically working at the human layer with technology and thus you price, I’ll say differently than most folks would expect.

Yeah. 100%. And that’s another indication of number one, kind of that really customer centric approach, making the experience for the customer a lot more streamlined. One of the things me and Corey are constantly looking at the industry or taking our experience and changing the way that things should be done and making it simpler when we thought about the customer consuming it for anyone that’s ever commissioned a penetration test, for example, that horrible booklet of, like, 20 pages you get from the provider that says, and it used to take me even with a security team, four weeks to fill in the technical data to have to gather this technical data, to even get the scoping document back for a penetration test. Right?

And that just can’t be the way it is. So what we wanted to do is number one, make it customer centric, number two, make it really easy to consume. So therefore, what we do is we use the number of employees in the organization as an indicative factor for the size and scale of the organization itself. Right. And that then allows us to build those subscriptions, build those solutions based on the size of the business and scale it effectively. For example, we’ve got customers who have 500.

They’re in the entertainment industry. They have 500 employees that never touch a computer, for example. Right? And we’ll work with our customers to figure out how that subscription works and how best to address it and make it more palatable for that customer themselves. We have other customers where some of their employees have got three or four different laptops. And in the old model, that means four or five different licenses, right? We want to deliver security, true security for the customer. So we’ve build all that complexity.

And we just say, let’s base it on head count. Let’s base it on head count of the organization. As you grow, we grow, and we’ll partner with you to deliver security, whatever that means for the size and scale of your organization.

When it comes to the mapping to importance of the business, it really is a human tally, right? Because the scale of the workforce is effectively a marker of the network effect of risk, because the more people you have, like you said, they’re specific. Some employees, they’ve got seven devices hanging off them. They’re much more active, their field work, so they may be sort of more exposed than others. But then back office folks, they log into the computer only to get their morning email. And then the rest of the stuff they’re doing is they’re scanning paper into systems.

It actually makes complete sense. And you start to think like, ‘Why hasn’t someone done this before?’

That’s my favorite thing. Like, my head gets a little bit bigger because I love it when we sit down with customers. And hopefully that’s an indicator of a good idea, because we sit down with a ton of customers and customers go, doesn’t that exist already? And they’re like, actually, no, no one’s done it like this before. No one’s done it the way that we’re doing now. The reason that we built what we built is because the business model exists elsewhere. The likes of Netflix and the B2C space, the likes of Trinette and others within the B2B space for HR.

Why would you not have that model for security? And that’s what we’ve built with Cyvatar. We always use the example of why would I bother building a HR function at this point and even our revolution? I wouldn’t. I’ll go and outsource it to Trinette because they’re better at it. It makes sense. It works for the scale of business and how we operate. I don’t want to be a HR professional, just like a lot of these businesses don’t want to be security professionals, right? They want someone who can do it for them and actually get to the outcomes of secure.

So that’s why we built the business model that we did for sure.

When you looked at, obviously, the first thing we have is we have team, the three T’s. Right? Team, TAM, technology, as they call it. Right? You’ve got your co founder. You have to address on the technology side, you both come at it from each angle and see if you got a good sense of where you in the technology stack will be able to attack a problem. When assigning TAM, this is really about choosing your first market. What is the ideal customer that you wanted to begin with? Because it literally could be anywhere from SMB up to global enterprise.

There’s a lot of potential. And if you’re a VC, of course, there are like trillions of TAMs. They want this Gartner Esker type of up and to the right quadrants everywhere. They want to see a lot of that stuff. But you, as a founder, you have to be pragmatic about your first market.

Yeah, 100%. And you’re right. There’s a ton of opportunity in terms of even larger enterprise organizations. I’ll talk about that in a second. But if you think about the absolute target market, it’s those Greenfield organizations that haven’t built a security function yet. And what that normally means is probably 500 employees or less in the technology space where the ROI, the return on investment, associated with the model that we’ve created is quite frankly, a no brainer. When you talk to customers and you spell out what it takes to build a security program these days, with the cost of talent, with the complexity of tools, with just everything that’s out there.

And back to that original point about the CTO, and the startup really wants to be focused on making their products great, not doing the cybersecurity stuff. You come in and you take that pain away. And the model from a Greenfield perspective, just makes absolute perfect sense. And even a lot of our customers have got a single contributor, the first CSO hired, like you mentioned before, or the first security person hired into the organization. Even then, what they’re not going to be able to do on day one is justify another ten resources.

And that’s relatively lucky, right? So to have a solution that enables them to be successful and deliver those outcomes as well in a cost effective way, that’s number one target. Right. And also to your point, from the vendor perspective, it’s just a massively underserved market. We talk to a lot of our partners who say anyone under two and a half thousand employees. Our VCs are telling us not to touch because the economics don’t make sense when you get to a certain scale and we throw the term democratization around.

But it’s true. We’re taking these best-of breed technologies that perhaps wouldn’t be accessible to that smaller end of the market and making them accessible, making them consumable because you don’t need those internal resources or expertise to get them in and operational quickly, which is what we’re able to do.

Yeah. It’s kind of funny. Like I’m in the tech space and I meet with large organizations all the time, and they have more developers at most North American banks than the vendors they buy from. So it’s really difficult to go in there and sort of say, all right, we’re going to do a ground up development of this service approach because they’re just like, well, we’re going to use you for six months, and then we’re going to take a team and make them shadow you and then build the thing you do.

So it’s actually often a dangerous thing, especially for a start up to go in with a great fundamental challenge solver because they’re just going to go in. Tech companies are the same way. Right? Large social networks are famous for this one, right? Where they’ll buy a company, buy a product for a year and then not renew. And you’re, like some people on the sales teams are like, I don’t understand, why didn’t they renew? Because they are filled with amazing technologists. And they just watched what you did for a year. That’s all they needed, they needed to be close enough.

I think one of the real differentiators that we’ve got is that we started as a platform player. Right?

So we’re not a product led company. We are true platform. And you see it, we all see it. There are many businesses out there that claim to be platform based organizations. The problem that you’ve got is particularly with the larger businesses. They’re tied to their own products as well. So if you’ve got a shitty antivirus product and then you go and build a platform, well, guess what, which antivirus products are going to be the one you use in that platform. Right? And that’s the problem. What you’ve started from is a very blank canvas that we’ve started from a point where we’re building the platform first.

And therefore, if you want to integrate with us, we will be picking the best-of breed technologies. We’ll have a selection. We’ve got three or four different partners in each of our solution areas, and our member services team is constantly assessing what’s the best out there, what’s going to get the best value for our customers? What’s the best solution? And the customers are subscribing to a flexible subscription, which means if one day AV number one is the best one on the market, we’ll install that. If next day AV number two completely outdoes them and gets to a better state of prevention than number one, we’ll change it out for them.

And that’s all part of that subscription. So it’s focused on the subscription outcome as opposed to the particular product or technology that you’re driving.

Yeah. One of my favorite platform stories. And like, I’m in product marketing, I know, it’s always like, you’re not a tool. You’re a platform. It seems like better marketing. But Dave McJanett, who’s the CEO of HashiCorp, and I said, I described to him and I said, it’s great because you effectively got all these layers and it ultimately makes a platform. And he goes, well, we describe as it, if you squint hard enough, it’s a platform. But it really is a separated set of tools that integrate very easily.

And it was funny that even he was unwilling to use the word platform for fear that it would have this connotation of something that is easy. It’ll be automatic, you have to buy one thing, and then you have to buy the other four things. Their goal was ultimately interoperability, which is, again, this is why I wanted to pick on this point with you, Craig, by being able to know that you’re looking for the best of capabilities, the best-of breed. And you are handling the integration since the interchange.

It means that I don’t, as a customer, have to get locked into going to antivirus A and looking for the best deal, because, effectively, they’re going to tell me why I need them, and then they’re going to suddenly become the one that wants everybody else to integrate with them. I want to have a platform approach where that I can think of it as a framework that I fit things into. And then it gives me the comfort that I can negotiate with those vendors now, because before, especially an antivirus vendor, it’s the easiest thing in the world.

We have 3000 endpoints. How exactly do you think you’re going to change that over? It’s one step away from, it would be a real shame if something were to happen to your car, now, wouldn’t it? Like that’s almost a Mafia-esque type of way. But I’ve worked in organizations where we’re like, I actually had 22,000 endpoints and yeah, we got it done because we threw humans at it. But it was a huge expense. It was a huge lift. It was a huge risk. So if I can offload that risk and that assessment of the right current set of platforms to you, that’s a huge win in my eyes of why I would say Cyvatar is like, all right, this is a true platform play.

Yeah. And you got two things, I think. Number one, you’re absolutely right. A lot of those businesses, like I said before, four and a half thousand products out there, like, what startup wants to come wade through all of that.

The periodic table of things.

All Eric’s product marketing. Who wants to go wade through that to find the one problem. Sorry, the one tool that’s actually going to fix your problem, right? No one can. No one does. Right? So, yeah, that’s number one. My own member services team are experts in the field, have been doing it for 100 plus years, whatever the combined number is, and they will pick the best-of breed, right? Agnostically and build them into the partner framework, build them into the platform. And like I say, we’re not afraid, right?

When partners aren’t performing or it’s not the best tool anymore. We have the capability and the wherewithal to change that out. Because we’re so customer focused, we want it to be about the customer and delivering the right outcome for the customer. The other big deal here, I think, is really important. We went on this evolution, I think you mentioned it earlier for inSecurity from technology, and then we’re definitely focusing on the people right now. But the process bit for me, is probably even more important than the people, right?

Because you can have the best cybersecurity experts in the world. You can have the best tools in the world. If you haven’t got the process that makes those things successful, you’re still ultimately going to fail. And what we’ve built with the platform that we call the operating system for cybersecurity is the process of security, what we call, we’ve got proprietary methodology that we call ICARM, which is installation, configuration, assessment, remediation and maintenance. So you go from all the way from installation of the tools, all the way from maintaining a full security program.

But essentially all it means is the process of security. Like, how do you get from a point where you have nothing or a very immature security function to the point where you’ve got something that’s functional operational and you’re maintaining the organization in a clean maintained state and the tools can be interchangeable. The people can be interchangeable. But that process remains constant. And that’s what we built in the platform. And that’s why I think we are so successful in such a short space of time in terms of getting those outcomes for our customers.

We’ve got that experience, we’ve got that knowledge. We built those processes into the fabric of what we do. And that’s why we’re driving this speed and easiness of security that just amazes people to the point where they don’t believe us sometimes, to the point where people go, how do you do that? And it’s because you’re taking that fundamental approach and you’re building the processes right.

And I don’t want to talk about people leaving the platform, but the subscription model opens the door to a sense of freedom in that they’re not locked in to you, which is a strong thing, right? It’s sort of illegal and functional lock in is difficult, and people don’t want to take on a new thing because there’s sort of a risk there. What’s the thing that, what they say to you, Okay, Craig, I like what you’re doing, but let’s just say for whatever reason, we have to change gears in six months, and I stopped my subscription.

What does that mean for my organization?

Yeah. So we built ‘cancel anytime’ into all of our solutions, just like any other subscription but don’t like using it so much. But back to the Netflix example. For as long as you’re getting value out of Netflix, you’ll continue to pay your subscription. And me and Corey, and the whole of Cyvatar, is not afraid of that model. We truly believe that with those process components, with the people components, with the way that we’re driving value for our customers, it challenges us to continue to continuously drive value across that lifecycle and that lifetime value of that customer.

And we’re not afraid of that challenge, right? We haven’t had anyone canceled yet, and I’m hoping we’re not going to in the future because we are driving that consistent value. We all know my favorite quote ever. I don’t know who said it, so I might just claim it as my own. Security is a condition to be managed. It’s not a problem to be fixed. And that is absolutely true. It’s not a one-off engagement. This is about growing with the customer, partnering with the customer, and being that continuous source of security for the business.

So the short answer is, Eric, as long as we continue to deliver value and the customers see value from it, we’re not scared of it, but we’ve built-in’ cancel anytime’ so that customers, if they really don’t see the value, can make that break.

And I love this idea that you talk about something to be continuously managed. This is not like a juice cleanse to suddenly make you healthy. Security is something you just sort of throw a tool at it, and then by magic, it’s fixed. It really and truly is an operation, because even if the choice is right today, it’s not to say that that particular product or some process that you’ve got won’t be suddenly vulnerable just because of a change in the ecosystem or change in process in a month or two months or six months.

So that’s why it does need to be the subscription and the service model really makes sense to me, because this is something that I want to make sure is maintained. And we think about maintenance as SNS on a contract, right? Like, oh, I can phone 1800. I’ve got a problem with something, but that’s really not what maintenance is about. Maintenance is about maintaining the health of the ecosystem, right?

Yeah. I love the hygiene and health analogies. I think they’re really helpful when you’re thinking about cyber hygiene and cyber security. It’s that continuous process. Corey always gives the example of, I don’t know whether this is true or not, but always gives the example of doing the dishes, right? Doing the washing up, you leave it for three or four days and you’ve got a massive pile and it’s a hell of a workload to get through. Whereas if you do little bits on a daily basis and you could do the same analogy a million times over, whether it’s automotive maintenance or whatever, it might be doing those little things and keeping up with it means that actually over time you’re continuously maintaining that state of hygiene.

You’re continuously maintaining that in a clean state, which makes your job much easier over time, means it doesn’t cost you as much. We talk about another good example is always the developers building code. And if you wait until a vulnerability or whatever is out in the wild, it costs you 50, 60 X, the cost that it would be to fix it while it’s in the development lifecycle. The same is true for general security across the board. Fix it while it’s being happened, build it in, make it a maintenance. Again, back to process.

Make the process continuous, and you’re in that position where you’re getting much more value out of your security program. Pentest is another great example of that. How many organizations just do a one -off pen test every year? How many times have I done a one-off pen test next year. They come back the year after and say, why is it the same as it was last year? Yeah, of course it is. And that pentest somehow makes you secure. But no one does anything about it. It shouldn’t be one-off, it should be continuous.

And in our threat and vulnerability management program, that’s what we’ve done. Yes, you get a pen test every year, but also you’re continuously scanned all year round because you might do your pentest on the coming Monday. But who’s to say six months before that, you didn’t have a vulnerability that’s been hanging around for the last six months. So, yeah, I can’t say enough about the ability to be continuous in that program. And that’s what subscription brings.

This is the funny thing, right? Like you said, compliance and security, while seeming to go in the same. There’s an ampersand between them, like it’s attached to most people’s resume in that way. But it truly is separated functions because compliance is the annual or the quarterly checkbox to make sure that you’ve passed a test. Security is an ongoing operational process to make sure that that’s happening. You said pentest is one that’s interesting because as we develop more active testing, it teaches us to make antifragile systems as well, much more than defensive.

But truly, I’m going to build a system so that it can withstand continuous penetration testing. Actually, at this one place I was at, we used a product and they would do, like, regular scans. So every night, it would go and scan all this stuff and it would wipe out half of our homegrown applications because it would just basically batter them like a denial of service. And then you’d have to restart all these services. And I was like, they said, well, can you stop scanning the system?

I’m like, no, can we start developing to be prepared for it? Like, it was funny that integrating, the tooling changed the practice of development.

Yeah, one of the things that I always liked. And I was talking to someone about it the other day. I was used to just talk about, security is another facet of quality, right? Developers, a lot of development organizations understand the concept of quality. They’re constantly scanning the code for quality. They want to create quality products and quality code. But security is somehow some kind of outlier from that. And when we started to take, and one of the tips I always gave to kind of CSO as they were going into large product based or application based organizations was borrow from what’s already there.

Like take the quality scoring mechanisms and just add security in as a facet of that, because they’re building quality code. They wouldn’t, for the life of them, send out bad quality code. So security is just another facet of that. You can’t build a quality application or product if it’s not also secure. So borrow from that language of the existing business instead of trying to be a special snowflake on the side.

Yeah. Now let’s talk about the Forbes Technology Council. So this is a rare opportunity to be invited in to be a part of this. You’re involved, which it’s a testament to, obviously, your history and your skills and your involvement in affecting the industry, not just purely from your product perspective. What do you feel is a real strong opportunity with something like what the Forbes Technology Council is able to do?

Well, like you said, the name Forbes is one of those things you grow up with, I think, isn’t it? You go through school and you think about Forbes and who do I want to talk to and what’s the goals for me? So, yes, incredibly privileged. I think it’s a great group of people. There’s a great online platform where we share ideas. And to your point, Cyvatar has always been for me, about fundamentally changing the way the industry operates, not just about creating a product, not just about solving a spot problem.

Like a lot of the current solutions do. It’s about fundamentally changing the way we consume. So I think both ways, number one, giving to the Forbes Technology Council, sharing my 18 years worth of CSO experience with other members, helping them to understand how you build security programs, how you do security effectively, what you should be focusing your investment on, but then backwards as well. We get a ton of feedback from those council members about what they want to see, because ultimately, one of the things that we built with Cyvatar is we wanted it to be a business tool as much as a technical security tool, right?

Our audience in startups, particularly is CFO sometimes, it’s CEOs, it’s cofounders, who are not necessarily the most technical savvy people. They want a business outcome, not a technical outcome. So taking feedback and you see a lot of security vendors will take feedback from the technical security communities, which is great and valid. And we do that as well. But also, there’s a massive advantage to taking feedback from senior technology leaders, senior business people who can say, you know what, Craig? I don’t want to see a cross-site scripting vulnerability in an application.

Quite frankly, I couldn’t care less. Tell me how and when it’s going to be fixed. Tell me what it really means to buy business. Tell me how much it’s going to cost me to sort it out. Tell me how I can solve it in the future. Those kind of things, those ROI business based conversations is what we want to solve as a business. And therefore, hearing that feedback, having the opportunity to share that with Forbes Technology Council. Senior technology leaders really benefits Cyvatar and really benefits the way we’re building the platform and the business.

So, yeah, it’s a fantastic opportunity. And I’m proud to be a part of it.

When you’re a certified CSO, which is quite often, the CSO, sadly, is a role that they’re like, it’s like the CIO, which at one point when I was in first getting into tech, CIO used to stand for career is over, right? It was just somebody from the business unit. They were just like, you’re the CIO now. And they’ve served their two years to ride off into the sunset as they headed to retirement. Now it’s an active function and then CSO sort of fell into the same thing, like somebody has to be a CSO.

You, you’re the CSO, right? Make sure no one picks up USB sticks and push them in their laptop. And there was a sudden, you’ve heard a wide eyed thing of like, how do I be an effective CSO? And it’s because it’s a burgeoning role. Certification is something that I think had been vastly missed. So what is the path to certification and what are ways that professionals can look at working towards that?

Yeah. Well, I think that particular qualification is interesting. I think more widely the question around kind of experience as a CSO, to your point being thrust into a role where you’re told to stop USBs being put in computers, for example, I think ultimately comes back to it. And a lot of the responsibility falls on the individual. I did a talk a number of years ago about challenging CSOs as to whether they really are CSOs or not. And what does it really mean to be a CSO? And quite frankly, I don’t have the answer.

I don’t think anyone does. The answer no one likes is it depends. But what that means is when you start that job, you need to fundamentally understand why the role was created and what the executive and the business expects you to do and make sure that’s compatible with what your skill set is. And that’s what needs to happen more in the industry. It’s the same with, I always say, ton of CSOs will join a role and won’t have had a budget conversation for the first twelve months.

They just plow on, on the understanding they’re going to be allowed unlimited products and tools, right? Getting those things upfront, what is my role to our conversation about compliance versus security? All right, you’re hiring me as a CSO, but does that mean you just want us to get top two compliance if it does. And you’re happy to take that you approach that in a very different way than a role that says, actually, I want you to be the technical knowhow, I want you to work with the development teams to embed security into the development lifecycle.

Or I want you to be the strategic leader that is the figurehead for security across our business and drive sales cycles by being better at cybersecurity. All those roles are roles of the CSO, but in different organizations of different maturities and different expectations, and you’re ultimately setting yourself up for failure. If you don’t have that conversation up front with the executive team, with the business. It’s a long way of saying it depends. But as long as you’re clear up front what your role actually means, that’s the only way you’re going to be successful.

Yeah. And I think that’s the ideal thing, even like the CISSP, if you look at the foundations that it tests, it’s very wide range. And it’s everything from physical security to low level programming, understanding all the way up to much more high through technical cloud and networking. It shows you what it takes to really be a security leader in an organization or CSO. It is much more than just one aspect of it. And quite often it’s counter to what we’d expect if we make things more difficult.

If we make things technically challenging, that’s not always securing the environment, it could influence poor practices, because if you make everything super complex and people are just going to write it down, they’re going to write down their passwords. They’re going to do things that will then move against the policy setting, and it becomes, you’re effectively working against yourself by coming with this top down of you will not pass approach.

Well, the advice I’ve always given to anyone kind of early in their career or moving through their career that wants to ultimately become CSO in the end, is wider rather than deeper. It’s becoming more and more a business role. It’s becoming more and more about strategic leadership, about business leadership. There’s been a trend in many large organizations where CSOs aren’t coming from technical backgrounds anymore. You’ve seen people come from the risk function or the project management function or the program management function into CSO roles. And for me personally, I think that’s a really positive thing, bringing people in with that wider business experience.

That wider kind of programmatic experience and strategic leadership, I think, is really important because you get that separated agnostic view like boys and their toys tend to get excited about security technology and AI and all that kind of stuff, whereas someone that takes a business centric approach and says, what’s most important for the business, what is it we’re trying to protect? What is my job here? Like, all of those things contribute to being much more successful than diving in and going, oh, I need to buy this product.

So I think that’s really important. Back to SIT phase, it’s incredibly wise. I think it’s a great certification that you have, out of all the ones that exist to get you that kind of width in terms of understanding when you’re ready to do that. But I think as your career progresses, you want to know a little about a lot of different things. I’m no technical expert. I have technical people who do that for me. You can’t do everything. And it’s about having a little of a lot. I think as you grow up as a CSO.

In the world of tech, especially community is incredibly important, and the ability for people to find a peer group. We’ve talked about the Forbes Tech Council, which I primarily is savant at the C-suite. There’s a lot of folks that are there that they can really look at the leadership level. There’s others that go further down in New York. But then you’ve got the bottom up, sort of the SANS and even the BSides and those types of conference opportunities. What is if you’re saying, as a Cyvatar founder, what’s your community of practice that you feel is effective in helping your team both empower as well as to stay close to what’s really going on out in the world?

Yeah. I think it massively differs depending on the team. Right. So for me and Corey as co-founders, it’s entrepreneurial organizations. It’s learning from other founders, people that have been there and done it. And actually, one of the things that I’m really passionate about is not in cybersecurity. I’ve got some great friends who are founders in cybersecurity, which is fantastic. But you’ll see from the way that we’ve built the business, we haven’t learned from cyber, we’ve learned from other business models, and we brought that into the immature space that is cybersecurity.

So therefore, when we’re learning from other businesses, subscription based businesses like ourselves or SAAS businesses or whatever. So me and Corey have been very conscious to take those learnings from other areas. And the other thing to remember is we read a lot of books. We listen to a lot of audiobooks, get ideas from those things, but don’t prescribe to one single thing. There’s millions of different ideas from different theories and different books all come together to create a strong business model. So I would say, for me and Corey, that’s important.

But then, obviously, like our member services team, they’re heavily embedded in the ethical world of security. It’s their job to know what the best products are on behalf of our customers. So they’re absolutely interacting in the black hats of the world, the cybersecurity conferences of the world where they can hear have their ear to the ground so that ultimately our customers don’t need to do that themselves. And we’re taking that burden away from them. And then we encourage everyone. One of the things that we have all done in the business is go through a course called Scaling Up, which is a methodology for building businesses.

And we’ve been really open with the whole team from the beginning. It would be easy just to have me and Corey do that because we’re building the business. But actually, we wanted everyone to understand that methodology. The Rockefeller methodology for building a business. We wanted everyone to know what that meant, how it operated, so that as we grow, we can be completely transparent with the whole team. And everyone understands that they play a part in it. Everyone understands that they’re a part of the growth of the business. We do KPI stand up calls every day where everyone sees what the business is doing.

Are we failing in certain areas? How do we change that? And we have those open conversations with the team where everyone shares the learning and we build the business together. And me and Corey think that that visibility is incredibly key. So to your point, there’s definitely external communities, but there’s also internal communities where we bring all of that together and we grow as one team.

And I think this is also a testament to your approach in that when I choose a vendor, why we say the three T’s begins with team, I have to depend that the company that I’m buying from has viability, and it’s really difficult, right? If you’re like, they look around and know that, I’ve got twelve series A technology companies that look exciting and you know that they are close enough in their messaging and in the end, in four years or six years, there will be three series D company. But I have to lay that bet.

And your approach is beautiful, right? It’s differentiated because this means that trust that you will grow with me as an organization, as a customer versus like, yeah, we got a widget problem, I get to solve your widget problem. That’s fantastic. There are pure specific problems to solve, but being consultative and not just looking at like, all right, I’m just looking to get the CRC and get bought by Accenture like, whatever the thing is, not that that couldn’t happen, but you’re looking at growth. You’re looking at building a foundation on which you can grow with customers.

And again, like I said, the weird thing is I called on the pricing and the subscription model early because it’s such a rare treat that, you know, that the sense of freedom gives you the ability to be free to adopt. It’s such a funny thing, but it’s a welcome change, especially in the world right now, where we have to be able to adapt. We don’t know what four months from now is going to look like, and just that sense that you could buy as you need grow in a consultative approach, learn from experts who are, their economy of scale is knowledge scale.

I can’t possibly, with an 800 person organization or 4000 person organization, trust that I can hire 25 people that I’m going to send to conferences every week and make sure they’re on top of things and that they’re doing their bloody job. That’s why I love the approach.

100%. And I think that’s why it’s so important for us. If you look at me and Corey, you look at many VC funded businesses, ostensibly, you have a very technical founding team. You have a team that is focused on product building the widget, whatever it is. And that is what the team is really highly focused on. They’re very good at doing that. And then you get a ton of sales people who go out and push that with you and push that product, right? Our business is fundamentally built on the experience of the customer, where we add value is in that people and process space, it’s not necessarily what we’ve got some solid technology in the platform.

It’s not product led, and therefore it’s really important to us that the customer and the customer’s experience is at the heart of everything that we do. And that means that we approach it slightly differently. That means that all of our team members are highly skilled in what they do, highly skilled in making the customer experience incredible. And second to none, not necessarily highly experienced in selling a widget. Right?

Which is not what we’ve built the business to do. And to your point about cancel anytime we fail, we fail as a business. If the customers aren’t seeing the value and the fundamental value proposition that we deliver, so that’s where our heart is at. That’s where we focus. The business is all about that experience.

Yeah, because there’s nothing worse when you buy a product and you just look concerned. It’s always the matrix is the same and look like I said, I’m in product marketing. I know the dance we do. You’re going to have a three column thing and most people will land in the middle. You want to edge them towards the far right. You want to put them in the enterprise plus, or we call it platinum or unobtainium. We call it some exciting new thing, and it’s always like basic bronze, iron, cobalt, whatever. We try and make it like no one buys that thing.

But the fact that you’ve got a freemium entry point all the way up through effectively scaling on consultative additions to what you’re doing. You’re using a human based counter on the engagement level. Like I said, it’s a refreshing change. And I was excited by the approach, and I’ll be excited to have you on when we announced your series D as well. So mark your calendars, kids. You’ve got a lot of really good stuff coming ahead. I’m sure.

Yeah, we’re super excited as well. Thanks for having me on, Eric. Yeah, I think you mentioned it there. We want to take that consultative approach. We’re not afraid to say customers, don’t buy this. It’s too advanced for you right now. Don’t go buy APT protection against AI threats when you’ve got, you haven’t done your basics of building a threat and vulnerability management program yet. You don’t know what assets you’ve got. So we take customers through that journey. We don’t sell them something they don’t need, and we really help them to build a program that’s strong enough for where they are in their maturity in their growth phase.

But then, from a Cyvatar perspective, we grant super quick. Really excited to be on this journey. I say to the whole team, we want to enjoy the ride as much as the destination, if not more. So we’re having a great time doing it. Team is incredible. Customers are incredible. And yeah, looking forward to updating you on series B, C, and D, hopefully.

Definitely a lot of good stuff. And as far as the building approach, too, this is something we can actually, I’d love to have you back on, and we can dive into the founding team relationship of a technical founder and a nontechnical, is always such a, it sounds almost like a pejorative, but in that you’re not purely technical as a founder. It’s such an interesting mix and finding that match, it’s kind of hilarious. I’m sure when we look back on it, it’s always like chapter one of every book where you’re like, here is Craig.

And then he was sitting in a coffee shop in San Francisco.

It was a pub in San Francisco instead. I said, it super fast. The story of Cyvatar is just, the founding story is an incredible one because there were so many factors that might not have led to it happening. I lost my father a month before RSA in San Francisco. I nearly didn’t go. I was very tired at the end of a long week, and I nearly didn’t grab a beer with Corey. All those things just capitulated. And I eventually did. And the rest is history. Corey would say it was the universe.

I’m English, so I’d say it was luck, but whichever one it was worked out in the end, and like I say, the rest is history. But yeah, there’s a good story for a book there one day.

Yeah. And it’s hilarious that when you look back on it, you realize how many of those opportune moments that really, truly like I said, it’s luck of occurrence and somebody else as well. I literally just went into an Apple event and I happened to be sitting next to somebody. And next thing, they were backing my start up that I had never thought I was going to build four months later. It’s like just by the happenstance of sitting in a seat, never know what can occur. But it’s much more than the luck of the moments.

It’s the gumption and the choice of the team to put the time and work into it. So it’s pretty amazing see it come together. Good stuff. So, Craig, if people want to reach out to you and get connected, what’s the best way to do that?

I love the social media. I’m all over it, Eric. So hit me up on LinkedIn. I’m on Twitter or obviously Cyvatar.ai for Cyvatar stuff, but I’m pretty easy to find online, so feel free to reach out.

Excellent. Well, thank you very much, Craig. It’s been a real pleasure. And there you go, folks. The links will be down in the show notes and such. And yeah, this was great. And sure enough, just like I said, history always tells you that if I say I’m going to have technical problems, we had technical problems. But we got through it. And this was a really great conversation. Thank you very much.