He bootstrapped to a $90M exit, no investors | Silas Deane

Mark Cleveland

I'm your host, Mark Cleveland. And today I've got a powerhouse guest, someone who knows exactly what it means to bootstrap, scale and exit, and then do it all over again. Silas Deane is the kind of entrepreneur who proves that persistence, grit, and a little bit of crazy can make you go a long way. Back in 2021, he sold VendEngine, the fintech company he founded serving public safety markets.

He sold it to Tyler Technologies in what the Nashville Business Journal called the largest technology transaction in Nashville's history at the time. It was a $90 million deal. And here's the kicker. No investors, no debt, and more than a decade of pure hustle was his superpower in scaling that business. Along the way, he acquired two other companies, growth by acquisition, and he landed on KPMG's list of the fastest growing companies in America.

But Silas is no stranger to the roller coaster of entrepreneurship. Before VendEngine he started, sold, and even failed at multiple ventures. His first taste of the startup world would come in 1999, right in the heart of the dot-com boom, when he built the only surviving company to emerge from the high-profile Nashville internet incubator,

Econception. Now, after three years at the top of Tyler Technologies, Silas is in what he calls his reconnect and reenergize phase. And knowing him, that probably means he's already plotting his next move. Silas, welcome to the show.

Silas Deane

Thank you, Mark. I'm looking forward to it. This'll be fun.

Mark Cleveland

Well, here we are. I was fascinated by this creation story and your big your big move with Tyler Technologies and VendEngine. Tell us how VendEngine got into your mind and out into the universe and to reality.

Silas Deane

Well, VendEngine was about my fifth or sixth startup, as you said, maybe 10th startup. can't recall. you know, It's one of those things where the universe just sort of speaks to you. And I was listening to a story with national public radio and I was hearing this story about people and the challenges that they face, especially incarceration or when they're having to deal with the government in some ways. And I thought, well, I know cloud technology, I think I can solve this problem. So not knowing anything about the industry or anything about the problem, I started just interviewing people, talking to people. And before I knew it, I was sucked into the rabbit hole of, of just trying to solve this complex challenge. And, before you know it, we, got some beta projects done. We started some down the path and, lo and behold, we had uncovered a need that had been sitting there all along. The challenge grew larger and larger and so the solutions grew deeper and deeper and it was a lot of fun just solving problems and helping people along the way. We changed the entire industry and it was a lot of fun.

Mark Cleveland

So changing an entire industry is not understatement in this case. You had customers bringing five dollar bills to a jail in order to put that on the commissary account of one of their loved ones or friends inside the jail. And it just strikes me like cash in a jail is a bad thing. How did you approach this marketplace? What you know, what what solution were you trying to bring and how was it received?

Silas Deane

That's a great question because the thing that we did was again, I started this, I knew absolutely nothing about this industry. So it literally was, you know, boots on the street, walking into the local county uh, jail facility and saying, Hey, tell me about this challenge. And I'm getting it from the woman sitting at the front desk perspective. I'm getting it from the sheriff's perspective. I was getting it from the inmates' family's perspective and the inmates themselves. And so what we did was we met with each one of those constituencies and said, just tell me your journey here. How do you put money on an inmate's account so they can make phone calls, so they can buy commissary, so they can do things? And the journey was perilous. I mean, people were taking city buses to the jail. They were walking to the jail. They were doing all kinds of things and handing cash to someone behind a desk.

And good, good, or ill intent, either one cash inside of jail, as you said, is not a good thing. And so, what we did was we, we set up a payment system, basically a Venmo is Venmo before Venmo and allowed people to bring cash, to a kiosk machine that we put in a reverse ATM machine. We took money not to not to give it. And we allowed them to have that transaction safe and effective, get a receipt for their transaction. And we knew that the, that the money was going where it was intended to go. And the reception across the law enforcement agencies was they wanted this and they were like, thank you for showing up and doing this. So, it was, it was something that was just sitting there. It should have been done a long time ago. We just stumbled on it and we got lucky and, turned out to be a great result. And we helped a lot of people along the way. And before you know it, we transitioned all that to the cloud. We transitioned that to an app. We transitioned that to electronic means. So there was no longer this journey that people had to take to do this anymore. It was all convenient and easy. The nice thing is we started, how we made, we only worked with county governments. We didn't work with these large for-profit facilities and things like that. We only worked with county governments. We tried to help counties solve the problems that they were having. And so it was a great journey.

Mark Cleveland

So that's the county jail versus the state prison and federal prison system. They probably have the same problem though, right?

Silas Deane

Right.

So they do have the same problem. And so we solved it at the county level first. And I'm talking, Mark, we worked in places like Sequatchee County, Tennessee, and Bledsoe County, Tennessee. These are small rural places. And we tested this thing and it worked fantastic. So at the end of the journey, we've now closed a number of state Department of Corrections now as well using the same system. It is, it's a journey. It's a need across the board.

Mark Cleveland

So Silas, when did you start this business?

Silas Deane

The official start was 2011. The mind thing was 2009. If you're talking about parallel entrepreneurs, it was 2009 is when the journey sort of started. It took us two years to bake the concept and really sort of, know, "okay, this is a thing" and so the official launch was 2011.

Mark Cleveland

You're doing product market validation. You're researching. You're trying to figure out, hey, it's 2011. It's 2010. How is it possible that we don't have automatic cash tracking systems? It's an opportunity sitting right in front of the entire world. And you just recognize that it was there.

Silas Deane

It was there. And, and not only that, the more we began to talk about it with people, the more the light bulbs are going off, not just for us, but for them. And, and when you have that kind of synergy going, you know, you're onto something.

Mark Cleveland

I've had an opportunity to go into Tennessee's jail system and enter and deliver entrepreneur training. You know, these are some of the most creative people in the world. And they've had the wrong product, but they're great salespeople. Right. And there's a lot of tragedy in in in those stories as well. And people just working really hard trying to get back out, get on their feet. And so inside that jail system is an economy.

And there's things that they buy and sell and they have to live and, you know, describe the day and a life of a, of somebody interfacing with the VendEngine. And how did you, how did you make their life easier while they're in some form of a restoration?

Silas Deane

Yeah. So the challenging part about our business model was you're working with people who are at their absolute lowest point in their life. They've been incarcerated and some of those may have been incarcerated multiple times. Some of those that's their first time, but regardless, it is a challenging part of their life. So when you, when you enter that world, you do begin to see this economy that's happening inside of a jail correctional facility. And the economy could be anything related to paying fines and fees, to be paying bondsmen, to be paying for commissary or to pay health care. There's health care challenges inside these facilities. There's all kinds of things that need to be paid for.

And so what we realized real quick was we could get money into the system, but then we had a double challenge. We needed to help them be able to facilitate, to be able to spend that money or to be able to move that money to where it needed to go, be it for healthcare or be it for mental care or be it for commissary goods or whatever it might be. So it presented the second challenge to us, which we didn't anticipate, which was a point of order system or a sales system of some sort. So now all of a sudden we were building a Point Of Sale system. And then we started having to build an accounting system to match the point of sale system. So before you knew it, we were chasing a lot of different things inside these economies. But there's a lot of money that flows through these, legal fees and all kinds of things, that flow through these facilities.

So our burden was to make that a seamless, easy transaction and keep it, you know, auditable and accountable and clean. Before we showed up, I mean, you had a cell boss and that was the guy that ran the place. And, you know, we put that guy out of business, hopefully.

Mark Cleveland

That's fantastic! I mean, this now this business grew one jail at a time, one state at a time, one county at a time. And eventually you got to over 400 facilities.

Silas Deane

Yeah, when I exited Tyler last month, we were at 425 facilities.

Mark Cleveland

Wow.

You know, I've known you since before you joined Tyler. And as you are a Parallel Entrepreneur, we're going to get to that, but then you became part of a big company and I share that experience. We sold one company that I was division president of and became a leader of that company inside a publicly traded company. So I have my Fortune 500 experience. Tell me what your Fortune 500 experience looks like. How did you go from entrepreneur, blowing and going, into corporate America. And what was that transition like for you?

Silas Deane

Yeah. As an entrepreneur, you know, you're, you just hit the gas pedal and you go, and that's what you do. And, I, I loved the Tyler bought our company. was the perfect acquisition and exit for our company. I don't think I could have planned it any better.

And so going into Tyler Technologies I enjoyed the experience. I loved every minute of it. Great people, great team, enthusiasm about what we did. They were they hands off, us do our thing. But you know, I sort of akin it to when you go to your investor, you go to put your investor portfolio, your 401k together.

They ask you, are you a conservative, a moderate or an aggressive investor? And I always ask the question, uh, do they have a hyper aggressive investor? Cause that's me and hyper. So, um, you know, uh, having a hyper growth person inside of an S&P 500 company just sorta, it gums it up. It slows it down just a little bit. And that was a good muscle for me to learn and slow down and, and do things

Mark Cleveland

hypergrowth.

Silas Deane

a little bit more methodically, because entrepreneurs take a lot of risks. There were some conversations where it needed to slow the roll just a little bit sometimes.

There was one occasion where a large Department of Corrections availability came out and I said that I wanted to chase this one. And I think some of the people at Tyler felt that it was a little too big to chase and we probably weren't ready for that just yet. And I went ahead and did it anyway. And we ended up winning.

Mark Cleveland

You won the business.

Silas Deane

And we end up winning the contract. And now Tyler's quite proud of that contract. But at the time it was like, shoot, what did he do? So why did you do that? So, but it worked out.

Mark Cleveland

It's a hill to climb. And besides that, it was a great growth spurt for you and you you handle it well, right?

Silas Deane

We did. It was a challenge. I mean, we definitely had to staff up. We had to ramp up. We had to do some things to service that. But it worked out great for everyone. So good results.

Mark Cleveland

And this would be an example of where, you know, were you by yourself in, in, in VendEngine, you probably would have imploded trying to go after an account that big. So you were inside a much larger organization that helped you with scale.

Silas Deane

It was sort of like, if I had done it under the VendEngine days, be like sort of the dog chasing the bus, right? Well, in this case, the dog caught the bus and thank goodness we had Tyler behind us at that time, like you said, because Tyler had the ability to scale like that. We could have never have done it had we been the smaller company, the startup, you know, in our in our cashflow phase.

Mark Cleveland

Did you do acquisitions while you were at the helm of VendEngine inside Tyler? Was that an acquisitive growth strategy as well as organic growth strategy?

Silas Deane

So the answer is yes, we actually did do a couple of acquisitions that we folded in with VendEngine. There was a very similar path acquisition going on on a payments company called NIC that Tyler bought right at the same time they bought our company. And it became very obvious to everybody real quick that there was a lot of synergies between our two companies. And so that was a nice parallel opportunity that we sort of jumped into. But along the way, I made some suggestions to Tyler on some acquisitions and they actually acquired one or two of them. And so, and we were able to kind of put those into the fold to create a much better package. As a matter of fact, that large contract that we ended up getting was a result of having all those companies together, made us eligible to win that contract. So.

Mark Cleveland

So finding creative synergies to flow between diverse and oftentimes unrelated functions or activities. I call that - "paralleling" - you know, you found different organizations, different companies to acquire, to merge even within your parent company and then found ways to make those synergies into a superpower. When was the moment that you realized, hey, wait a minute. I got this.

Silas Deane

Well, the beautiful part about Tyler, when Tyler reached out to us to acquire us, I didn't know who Tyler was. And so the more I learned, the more excited I got because Tyler Technology's specialty was county and municipal governments. That's what they did. And that's all they do. They're bigger than Microsoft when it comes to what they serve as the government. So what I entered into was a world of just lots and lots and lots of possibilities and lots of technologies I'd never heard of. Before I knew it, one of the acquisitions that we made was a hardware division. Well, that hardware division happened to work perfectly with Tyler's parks and recreation division, right? So who knew that there would be a synergy between what I did and say state parks and county and local parks needs. But the synergies were incredible and it was a lot of fun.

Mark Cleveland

And another impact you've had on Tennessee that people don't appreciate, you know, because it's a story that's not told very often, but there's manufacturing facilities in Tennessee making hardened kiosks now, right? Talk to us about that.

Silas Deane

Correct. So, along our journey, you know, I mentioned that we had to create an accounting system. We had to create a point of sale system. Well, at some point you can't just hand inmates a cell phone and say, "Hey, go use this.." Uh, because there's all kinds of security challenges. They, you know, there's some bad guys in there. So you have to really watch this. So we ended up having to deliver a, a hardened, you know, something that could take a punch, a kiosk machine of some sort so the inmates could access that so they could access their bank account, they could access their things that they needed to do. And so along that way, we realized, you know, nobody makes these. We had to design it ourselves, make it. And so eventually, working with a metal fabrication shop here in Nashville, we actually ended up buying that company along the way in a cash deal. And now we could, because we were growing so fast,

We couldn't get our metal fab shop to just focus on us. So we needed that focus. And so by doing that, we bought the company, we continued to grow it. Then Tyler came along and says, okay, what's this software thing? Why do you have this hardware division? Tell us this story. And the more they got excited about it and learned about it and realized that they could help their state parks and rec division or their school bus division or whatever it might be.

They actually invested in building a large facility here in Kingston Springs, 21,000 square foot facility where that's all we do is manufacture hardened kiosks to serve local and county governments.

Mark Cleveland

So in the introduction, Silas, we talk a little bit about the many companies that you've had. You've started in the dot com days when everything was nuts and you continued with different types of businesses at different times. Are there any mistakes you made early on that shaped the way that you run business today? Give us a crazy moment, some early lesson that shaped how you approach business today.

Silas Deane

You know, I, I don't think we have time on this podcast to talk about all the crazy things that happened or mistakes I made along the way. but, you know, a lot of mistakes were made. You know, I think as an entrepreneur in general is a series of coming up with great ideas, challenges, and then making a lot of mistakes, refining those mistakes along the way.

But I think the important thing for any, any entrepreneur is when you do make a mistake is try not to make the same mistake twice. Just take that as a learning experience to continue to grow and be better than you were last time.

Mark Cleveland

Well, we'll just we'll call that everybody's equal opportunity crazy because we've all done it. We've all got those kinds of things. When you look back and you say, I can't believe I survived that. Time management is one of the questions that I get most often from our listeners. It's like, how do you do this thing where you've got so many different companies and so many different marketplaces that you're attending to. What sort of time management hacks did Silas Deane deploy to get things done?

Silas Deane

So everybody that works with me knows never to have a meeting before 9 a.m. with me. And that was my number one rule was I generally took my kids to school at 7 a.m., 7:30 and then I headed straight to a coffee shop and between 7:30 and 9 was my time. It was my time to get organized. It was my time to get everything together. And then meetings could start at 9:15.

I needed that time every morning to sort of get organized to think about it. But I think an entrepreneur never shuts down. I mean, even at night, you're thinking, you're dreaming about this stuff. I don't know that entrepreneurs ever stop, but, at least the time hack for me was that time that hour and a half time every day, when I had that time to myself.

Then I could take on the challenges of the day. And I was really lucky in my journey, Mark, in most of my journeys, I had a number of the same employees, the same exact people that stayed with me through almost all of these different journeys. So a lot of times they were wearing multiple hats. It wasn't just the entrepreneur doing parallel things. I had employees doing parallel things with me because they believed and they enjoyed doing that as well. So, the type of people I hired were people like me. And that's what I loved about it.

Mark Cleveland

So you are also generous with your time and your leadership skills. You were recently named to the Kentucky Business School Hall of Fame. This is where Silas serves as chairman of the board for the UK Entrepreneur Center. And you worked previously with Senator and then Vice President Al Gore and U.S. Representative Clement. Talk to me about how leadership in the organizations that are commercial that you've started and built, and leadership in government and leadership in service to the people - how are they similar? How are they different? And what were some of the lessons you pulled out?

Silas Deane

The journey for me, particularly with people like Al Gore or Bob Clement or even other Congressmen, I've worked with a number of people in Congress or in leadership positions across the government and even Bill Clinton. When you look at those people, they believe in what they're doing and they get others to believe in what they're doing. And so that, that's infectious.

And I always tell people, my employees especially, you are the expert. When we walk into the room, you're the expert on the subject. Even if you don't think you are, you are. And the client looks at you as that expert. And I think that's what a number of these government leaders do is you believe in what they're saying, you believe in what they're doing.

And so as a leader in my team, I try to be as confident as possible. Even when I don't know the right answers, I tell people I don't know the right answers and that's okay. But together we're going to solve this problem and we're going to work at it. But if the people don't believe that you can lead them, then I think it's going to be a challenge for any leader. So you have to believe it even when you don't sometimes.

Mark Cleveland

As you mentor young entrepreneurs in the UK system and people down here in Tennessee that have access to your time, what is the most important skill or trait that you think someone should develop as an entrepreneur?

Silas Deane

The most important thing they need to think about is being able to pivot. can you pivot and are you amenable enough to believe in what you're doing, but yet also be willing to be wrong and the abilities, to be able to be wrong and to pivot toward right doesn't mean you have to change everything, but it means you need to be, malleable enough to, to, listen to your customers and be wrong. And I, and I encourage people all the time to, you know, when they come to me with a business idea and they're hardcore set on this is the way it's going to be done. I'm always like, well, has the market told you that because you need to go out and talk to the market on that and listen to what the market tells you. And it may be a little different than what you're thinking and you need to hear that and be able to pivot toward what you're hearing, not just what you're saying. And so now the entrepreneur has that weird balance, right? You have to believe in what they're doing. And so that's the weirdness of it. You got to believe and you got to be convicted, but you also have to listen. And so that's, it's a weird balance and it's a hard balance. And that's why I think a lot of entrepreneurs fail because they get very dogmatic about one thing or another and that could kill a business, in my opinion.

Mark Cleveland

Yeah, you talked to me about this experience where you wandered all around Nashville trying to find financing and trying to find somebody to invest in VendEngine and couldn't get it done. So let's what happens when you can't get it done? How did you hustle this thing to a 90 million dollar valuation? I suppose that's got to be the question.

Silas Deane

But, yes. Uh, Mark, I think I had mentioned to you in 2021, uh, during COVID 2020 and 2021, I'm that guy that answered every spam email that you get that says, Hey, we can run your business better than you, or we would like to get into your business and we would like to know more about your business.

And so I'm the guy that returned the email and all during COVID, what I did was I sat on calls like this and I just listened to people's pitch. I heard their stories. I listened to everything. Because - I will back up - when I started this business, I went to every venture capital group, every finance group in the Southeast that would even listen to me telling them about this great thing I had uncovered and I couldn't get a single investor to listen to my story. No one would, no one would do it, it was too risky. I was working with inmates. I was working with financial payments. My business model wasn't the right business model. But my customers and clients kept telling me I was doing the right thing. So there's that weird part about being the entrepreneur, the pivot. I'm hearing this and I'm hearing that two different approaches. So I had to listen to the clients and the customers that did. So eventually in 2021, now after we'd proven the model, every company was wanting to give us money! And so we had no shortage of people that wanted to do it because we'd proven the model could work. So we listened to all their pitches and we put out a book, the book for the investment book. And we had dozens of interested venture capital groups that wanted to put money into our company. And so that was our journey on the finance side.

Mark Cleveland

Yeah, so sold several companies of your own previous to getting into VendEngine. Let's explore what did you learn in those early moments?

Silas Deane

Well, let's not forget that I failed several times too, during that journey. The lack of selling things probably taught me more lessons than the ability to sell things. But, you know, when you're an entrepreneur, especially a Parallel Entrepreneur, you chase a lot of rabbits. And so sometimes you just lose interest in something that you had been doing or, maybe you realize you're in a dying industry and, you just need to get out. So finding people that will help you get out is a great thing. I was very lucky in the sense that in two of my ventures, I was able to find people that would sort of take it on. Now I will give you an extreme example though, Mark, of a time when I needed to get out and it wasn't so pleasant. I had a retail business, the Baden Bath and Supply Company you mentioned earlier. I had a retail a store out in Cool Springs, Tennessee. And, I had gotten way behind on the rent and, I was getting pretty worried. And so, we scooped in in the middle of the night and got everything out of that store that we could before the owner locked the doors on us. We took it to our warehouse, put it in the parking lot and and hired an auction company to come auction it all off.

So we could pay the bills. So that was an exit also, if you think about it.

Mark Cleveland

How did that moment shape you? Did you have sort of entrepreneurial PTSD afterwards or did, did you say, Hey, this is the lesson I learned and I'm taking that forward.

Silas Deane

All of those things. The first was being scared. Am I going to make enough money to pay this guy off, you know, for my rent? Fortunately we did. And the PTSD and then having to listen, to those who told me that I was doing it all wrong, you know? And so I had to learn those lessons, take my lumps and, just move on from that experience. But yes, it definitely informed me.

As I moved into my VendEngine business, it helped me not to make some very similar mistakes along the way.

Mark Cleveland

So what do you find fun about being a Parallel Entrepreneur? Where does the heart get involved and what is making this fun?

Silas Deane

I have to say, I think I've probably always been a Parallel Entrepreneur, and I mean, even going back to being a kid, right? My very first business was actually Junior Achievement. I was the president of my company and the head of the head of the, Junior Achievement came to me one day and pulled me out of school and said, you've run up the largest debt in Junior Achievement history, in our, in our area, like you're going to have to sell. And so, so he pulled me out of school with my principal's permission and I had to hit the road and sell. And, along that way, I started selling other things as well, like, cause I was getting all this traction.

And I ended up being the number one salesperson in the country for Junior Achievement that year and got a scholarship to go to University of Kentucky, changed my life as a result. Cause I grew up in a farm community. But I think it was just one of those things where once you start doing that, you start to see that success, you just can't stop. And so starting multiple things, it's like an ADD problem, I think. I'm not saying it's for everybody, but it was for me.

Mark Cleveland

Yeah. Well, you know, in my journey, I've heard so many entrepreneurs, particularly parallel entrepreneurs say, well, it's an ADD thing. And I've heard other people look at us and go, well, they must have ADD. And I think, you know, step aside from the lack of capacity to make a clinical diagnosis like that. Let's lean into that, because I think, track with me. Tell me if you think this makes sense. I think that it is a superpower to be able to pay attention to a problem that someone brings you - the relationship, the dynamics, that conversation, and it's in finance. And then six seconds later, you're paying attention to another situation that is a customer complex relationship, and you got three people involved, and you got to get the product team involved. And then the next morning, you're talking about technology and you have to pay attention. And I don't think it's about an attention deficit.

I think it's about an attention superpower and you just are so flexible, you can move your attention and pay quality attention and solve problems. Roll with me on that. How does that sound?

Silas Deane

I was actually listening to one of your earlier podcasts and I heard this conversation and it started making me think. Um, I agree with you. I think the flexibility part is super important, but, um, also as, as an entrepreneur, you know, you start a business and you do everything you do, the finances, you do the phone calls, you do the customer service, you do sales, you do it all. And as you begin to bring in people who are experts - you bring in a sales expert, you bring in a finance person. All of a sudden you don't have to do those things as much as you used to have to do. Not that I was great at finance, but I now don't, I now I have an expert in the room. So now my attention span can, can move to other things. So as I continued to grow, I found myself with the ability to think about other things.

I think you're right. I mean, the ability to be flexible, but also the ability for your mind to just look elsewhere when it's not having to worry about survival.

Mark Cleveland

So you were in a PR business. You were in several different consultative businesses as well. How did those experiences shape you?

Silas Deane

Well, being in the public relations business, I got a PhD, I think, in watching people make bad mistakes and watching people, be untethered or, or maybe not stay true to their mission or maybe chase other things. So it helped me a lot to watch others and see the mistakes they were making - some of them very predictable mistakes and some of them hit out of left field. So it taught me a lot to watch as sort of the marketing arm of what they were trying to achieve, um, and seeing them run up large debts or whatever it might be. So it was, it was good experience.

Mark Cleveland

I heard you say earlier that you entered VendEngine in that space in the corrections and jail systems technology business, not knowing anything about that industry. And I think I have found for my own reflection that I've gone from sock manufacturing to short sea shipping to mobility, incentive management to large fleet data systems.

And I didn't know anything about some of these businesses that I entered. And I think that fresh slate, clean slate approach to problem solving might be another superpower for us Parallel Entrepreneurs that need to go discover and learn something else in order to keep this motor running. How did you feel with this clean slate approach to VendEngine? What was that like?

Silas Deane

Well, first of all, it was super freeing, right? I mean, it's just like a blank canvas and you can just attack the canvas with what you see in your head and what you're hearing from other people. I loved it actually not knowing anything about it because I came in with no preconceived notion of what I could do. Now, as I listened, I began to hear and think of things and began to formulate that. But with a blank canvas, it was wonderful. And I can imagine being an artist starting with a blank canvas just staring at it going, OK, how do I make this look like a mountain? you know, and that's that was that's fun. It's a lot of fun,

Mark Cleveland

I'm thinking about the things that feed us creatively. What do you do as an entrepreneur? What do you do to feed your creative drive?

Silas Deane

Well, you and I have talked about it. I love history. And so I love to dive into history and sort of understand history because I think history somewhat informs us today so much, you know, things not to do things, things that work, things that didn't.

Mark Cleveland

Well, for our listeners, we're sitting with Silas Deane, the what, fifth?

Silas Deane

I think I'm the 16th in the line of Silas Deanes, yeah.

Mark Cleveland

16th. So if you're a history buff and you know that General Lafayette was 17 year old Marquee in France who was very upset with the British because the British were responsible for the death of his father when he was four years old in a battle that I can't recall off the top of my head. But I do know that this is an orphaned young wealthy man with military training and the capacity to field a Navy. And he he was on the sidelines in France and Silas Deane was authorized by Congress to go and discuss his participation in the American Revolution. One Mason to another Mason with Benjamin Franklin circling around this storyline. And so it's not fair to say you just like history. You're a part of it.

Silas Deane

Yeah.

Well, yeah, I inherited that. But I love history. It's weird. I love stories like Magellan and stories of these sea captains that would go try to conquer the Antarctic or something against these incredibly difficult odds and do these things. And so I love stories like that about history. I don't know, I love to sail myself. So one of my goals after I left Tyler - I want to sail the Antarctic. We'll see if that happens. That's a humongous challenge. One of the most challenging places to sail in the world.

Mark Cleveland

What are the books you're reading today, Silas?

Silas Deane

So ironically, after having a great exit with my company, I just read The Power of Broke, which is done by, one of the Shark Tank guys. And he talks a lot about the power of being broke and how that really drives entrepreneurial spirit when you really have no choice but to be successful.

Besides that, I'm reading right now currently a book on Battle of 1812 down in New Orleans. I really did not know that part of history with Andrew Jackson and some of the players in that, Alexander Hamilton, some others.

I had no idea the political, you know, scandals that were happening at the time and all the politics involved with that particular battle, but it's fascinating.

Mark Cleveland

So there's there's a pattern in parallel entrepreneurship that seems to me to be each time you do it and as you do it in another industry, as you explore what you don't know, then there are common patterns that I think reassemble in your mind and these are the structures that you're going to check the box no matter what industry you're going into. So, some people might call it mission, vision, values, and some people might call it an operating system. And some people might just say just gut instincts and rapid, rapid decision-making. What do you think is a superpower that you have developed that's going to help make you more successful? And where did you find that nugget in your previous experience?

Silas Deane

I think one of the things that doesn't change, no matter what industry you tackle or where you go, business basics are business basics. It's important to have a good accounting system. It's important to have a good revenue stream. It's important to have a good expense, uh, moderation. Uh, these are business basics I think can apply obviously to anything. That's why they teach them in business school.

But it's how you apply it. And I think as you go through your journey and now, you know, six, seven, eight companies in, you begin to see the patterns of success as you go through those. So by helping other entrepreneurs, I try to help as many as I can, I speak to them all the time. And I really talk about the business basics, how important it is to understand just, just read a balance sheet, understand what a balance sheet's telling you.

If you can read a balance sheet and let that balance sheet inform you, you can pretty much conquer almost any industry, I think, by those business basics. But then there's gut, there's intuition, there's other things that fall into that. And I think part of that's just learned experiences. It's failing and learning those experiences and moving from them.

A lot of people give up when they fail and I think they're just getting started when they fail. And I think they need to suck it up and go one more time.

Mark Cleveland

Right, right. Did you have somebody in your life that you were able to mentor in that area and you could see them take that advice and recover and be successful? Tell me a story about that.

Silas Deane

I got a chance to work with a young man, George Bell, and he actually had a fitness app that he wanted to get going. At first, I was like, everybody's got a fitness app. Well, he gamified this thing and turned it into something ended up going on shark tank and, he got funded. And so super proud of George.

He's got Mark Cuban on his side and some other things and it's fun to watch him take off.

Mark Cleveland

There's there's a nugget right there, right? Getting the right people on your team. I'd love to have Mark Cuban on my team. Yeah. And yet I think in my teams, in my different companies at different times, I've had a Mark Cuban, you know, somebody that just had that kind of brilliance and that kind of ability to really work with people and work with customers and and in their own swim lane, they were the Mark Cuban of that part of my business. You know, just really, really special.

Silas Deane

Yeah, you wouldn't.

Mark Cleveland

How did you discover talent when you were in these companies and what was the secret for observing and surfacing talent?

Silas Deane

You know, I think the main thing I mentioned before was when I was looking for people to work with me, I look for people like me, who were flexible, didn't like to be chained to a desk. Cause, I hate being chained to a desk. I always tell my employees you're 10 times more effective outside the walls of our offices than inside them. I look for people like that, people who were just, able to go out and kill it, weren't too worried about how they looked or, if they failed, it was okay. I tried to build a culture that it's okay to fail, but the fact that you tried is the feature that we want as a part of our company. And I think that gets infectious because I think other people see that and they start trying. Confidence was another feature that we really wanted and in all of our businesses, even down to the person answering the phones in the office, do you have the confidence that you are the expert on the subject matter? And that's something we look for.

Mark Cleveland

So when you make a mistake, first you have to recognize it's a mistake. It's a mistake compared to what? You know, the outcome was less optimal than we thought it would be. What is a mistake? Right? And when you've made one, how do you pull it apart? Is there a process that you have implemented where people are studying what happened, what went wrong, what was the lesson? How do you turn mistakes into a competitive advantage?

Silas Deane

Yeah. Yeah, so the one thing we really spent a lot of time with as a team was when we analyzed them, when we make mistakes, we celebrated it to a certain degree. You know, okay, what did we learn? Let's talk about what we learned. What could we have done that would have possibly changed this? And sometimes, you know what? Sometimes you're just going to fail just because the customer doesn't want what you have. You know, that's okay. That's an answer.

And so let's don't look for customers like that anymore. Let's not waste our time with that. So there's a lesson there. Let's not waste time. But also sometimes I think an unsuccessful entrepreneur might listen to their clients maybe too much sometimes and be doing things that help their client or help their customer achieve something and that may not be necessarily mission, missional to you and helping you drive your business further. So I think one of the things that we explore a lot was, that, is that something that's helping us or is that something that's helping them? Or does it help us both and stay true to that.

Mark Cleveland

And particularly with software, it's easy to chase rabbits in software. Customers tell you that they want your software to do a certain thing, and it's not designed or architected to do that. But in order to win the business, you've gotta do that thing. And now you've got a one off. Most of the time I've had experiences like that, the customer was just flat wrong. They did not need that thing to do the thing that they wanted it to do in the particular way.

Silas Deane

That's right.

Mark Cleveland

They needed to adjust their process to what might quite often be a superior process. But you're having this combat with customization or standardization. I don't know, man, I think business is business is business. Why does every business think it needs to have some unique custom appearance of software?

That's an expensive thing to do. Let's all lean into processes that make sense and can be standardized. How do you feel about that?

Silas Deane

I agree with you a hundred percent. And it's a spiral effect because you know, it's one thing to fix your problem today. Okay. I'll fix your problem today. But now I've got to support that long-term because the next guy that comes in, he wants it - well, I want it green instead of blue or whatever. Now I have to support that. Now I'm making a bigger investment in my client and, I have found anyway that eventually you know, two generations later, they're not happy with it anymore because they wish it did this. And so now you're having to fix whatever it did the first time. Or like you said, the process changes or the technology changes.

Mark Cleveland

We're living in a technology change moment right now with AI. How do you view that as either your next opportunity or, gosh, I'm glad I got out when I did, or how is AI sort of running through your mind and the landscape of opportunity?

Silas Deane

You know, I'm seeing so many parallels to the dot-com boom. Everybody was chasing dot-com, everybody wanted it. And I realized AI is a different beast altogether. But the enthusiasm, the, the dollars, all of those things are flowing just like they did in the dot-com days. So you have to think that the market's got to sort this out at some point.

It's called the power of six, I believe is what it's called. You eventually come down to six major providers at some point. You start out with hundreds and you get to six and then eventually you'll get to three. These things happen. I'm seeing those parallels from the dot-com days for sure.

Mark Cleveland

So when you are looking into the future, what gives you hope about where we are economically, politically, where this country is? What do you hold on to that gives you hope?

Silas Deane

I believe in the spirit of America, in the spirit of who we are as Americans, et cetera. And I try not to get caught too much up in the flavor of the day. I think you really have to look at the long-term. I think it's hard to do. Our social media and our media drives us toward caring about the latest thing somebody tweeted or whatever it could be.

I honestly turn all that off. As a matter of fact, I've never had a Twitter account ever. You'd be surprised to hear that as a tech executive. You know, our government is brilliant - the three tiered system being the judiciary, the legislative and the executive is good. I think right now there's some challenges to that and that's okay. I think you need to ask those questions every now and then. But hopefully our democracy is strong enough to stand through all that.

Mark Cleveland

That's wonderful. You can look through history and find an ancestor that helped to create America.

What advice would you give to your younger self?

Silas Deane

You know, I'd love to look back at my younger self and say, you're okay. Go relax, have fun. And so, I'd like to have that conversation with him, about that because I was a super focused kid that was really just trying to make it in this world. And it was, it was stressful. It was very stressful. You know, I didn't grow up with a lot of money. So, there were times when I couldn't even afford the bus fare. So I'd love to go back and tell that guy, know, Hey, you did it. You're good. Just, just, just go relax. Have fun. Drink a beer. Yeah.

Mark Cleveland

Just chill. Just chill. That's fantastic!

Well, Silas, I appreciate everything about your journey. As we start working together to help define and surface the superpowers of an entrepreneur who is a Parallel Entrepreneur, what do you think your superpowers are?

Silas Deane

I think there's a couple of things that's critical for any entrepreneur, but mine particularly is integrity. You have to be an honest person so that people, know who they're working with. So, honesty, integrity. And I think I told you, Mark, I was a rugby player in college and rugby players are fearless. So, being fearless to a certain degree. Now, that's not always a good thing. Rugby players aren't always known as your smartest guys, but you know, fearless and the ability to just, tackle something that a guy that's twice your size and coming and running at you, you just gotta be able to do that. And so I think my superpower is being fearless and not being afraid to take a chance and not being afraid to risk things.

Mark Cleveland

I'm a risk taker, I'm not a gambler. And I've mentally separated that in my mind as two different things. How do you view risk? What is an acceptable risk? Why are we addicted to risk?

Silas Deane

My wife asks me that every day. Why are you risking that? I I'm not a gambler either, but I'm highly akin to taking a large risk. I think it's the adrenaline we get from it, being right. The reward that comes with the risk, I think, is great. And like I said, if you're okay with failure, if you're okay with not winning all the time, or being wrong even, I think there's a lot that can be learned in that. So the risk is always worth it to me.

Mark Cleveland

I wonder if the part about taking risks in business that is addictive to me is that my team is with me and together we're attacking something and Even within the team, they're saying this is crazy. we're out ahead of our skis here but you're taking the risk as a team,

Silas Deane

Yeah.

Mark Cleveland

ultimately as a company. And then all of a sudden, when you have that success, it's like everybody gets to experience the bonus of being a part of a risk taking activity. And then there's rewards that come from that that can be economic, that could be intellectual, that could be spiritual. They all, I think, express themselves as growth. How does that sit with you? Does it? Are you are you seeing the team that was with you on that risk? And how did you how did the team benefit when they were in your wake?

Silas Deane

You're exactly right. When it's a team win, it's a wonderful feeling. I've had scenarios with say, VendEngine when we're in startup phase where we could win this contract, but we're going to have to invest a lot of money.

And my finance team is saying, I don't think that's a good idea. I don't know if we should do this. You finally have to like, so to say, we're going to do it. And the wheels start turning and it just happens and people are bought in and you're doing it. And now everybody's, you know, trying to make this a success. And so in this case, it was a wild success. So everybody's celebrating, everybody's enjoying it.

Mark Cleveland

When you exited, there was a, what 400 facilities in your portfolio. How many more facilities are there to get?

Silas Deane

So we had about, I think the analysis said we had about 18% market share. So long way to go.

Mark Cleveland

Yeah, so that's the value of a large addressable market, right?

Silas Deane

Yeah. The TAM was incredible. And not only that, not only just the number of facilities, but the number of other technologies that could be brought in was incredible. I mean, it's a very large TAM. I can't remember the top number, but it's enormous. That's what attracted Tyler to it.

Mark Cleveland

Right, right. And they're just walking by on a trade show and they say, hey, we're interested in you.

Silas Deane

Yeah. So we had the book out. We were looking for venture capital. We were ready to sign with a venture capital group out of Richmond, Virginia. And one of my sales executives said, "Hey, this company stopped by, here's their card. They want you to call them." And so I called the lady on the card and I didn't, like I said, I had no idea who they were. And I thought they just wanted to partner with us or something. And they're like, "Hey, we've seen your book. We'd like to just buy the whole thing." And I said, "okay, let's talk" and they made me an offer I couldn't refuse.

Mark Cleveland

Well, there you go, ladies and gentlemen, you heard the beginning and the end. Come back to the Parallel Entrepreneur when it's time for you to tell this next story, Silas, because I have a pretty strong idea that after you tackle the Arctic, you will you will be back for another challenge.

Silas Deane

Yeah.

Mark Cleveland

Thanks for your time, Silas.

Silas Deane

Yeah. Thanks a lot, Mark, appreciate it.