The Rise, Fall, And Rebirth Of A Serial Entrepreneur With Doug Hardman

Serial entrepreneur Doug Hardman went through a lot to achieve his current success. His story is all about ambition, resilience, and hard-earned humility, shaped by his determination to jump back from many failures. In this enlightening conversation, he looks back on the ups and downs of his career and life that taught him patience, commitment, and perseverance. Doug also talks about the importance of financial literacy and a proper support system in entrepreneurship, how to unlock your entrepreneurial self, and the right way to handle success when it comes your way too fast.

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The Rise, Fall, And Rebirth Of A Serial Entrepreneur With Doug Hardman

In this episode, I’m joined by Doug Hardman, a lifelong entrepreneur whose journey reveals the grit, curiosity, and self-awareness it takes to build and rebuild a venture-backed business from the ground up. Now, I should mention that I tend to avoid the venture-backed tech founder stories on this show. I’ve long felt that these stories can sometimes overshadow the more relatable stories of everyday entrepreneurs. This conversation was different.

I first met Doug nearly 20 years ago when he and his brother were just getting started with SparkBase, a fintech company they launched to disrupt the store value and gift card industry. Even then, Doug impressed me with his technical chops, relentless energy, and instinct for solving problems. In this conversation, we revisit that journey from his early days selling candy as a kid and learning to code to the intense highs and lows of startup life.

Doug opens up about what it means to learn by doing, why surrounding yourself with smart people matters, and how hubris, especially when success comes quickly, can cloud your judgment and steer you off course. This is a story about ambition, resilience, and the hard-earned humility that only comes from being knocked down and choosing to get back up. Doug’s insights are raw, real, and packed with lessons for anyone building something in uncertain terrain. Let’s get into it.

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Doug, thanks for being a guest on the show.

You are more than welcome to any of my time at any time, Gary. I met you many years ago. You came into my office back at SparkBase and we’re interviewing entrepreneurs back then, and I thought, “What is this guy doing? I’m in startup mode right now.”

“Get out of my hair,” right?

No, it was more like you were building a business around other people building businesses, and I couldn’t get my head around what you were doing, like, what’s the end game? Back then, the whole idea was you build a startup to exit. The concept of you building a startup to help other startups was like, my brother Jeff and I sat down, we’re like, “What is his angle?” Here we are, years later, you’ve written two books and helped a bazillion entrepreneurs figure out what they’re doing. You’ve always been one of those guys that’s just on my radar as this guy knows what he’s doing. If I could ever be helpful to him in his path, then I could be helpful.

What Is An Entrepreneur?

That’s awesome, Doug. I’m so grateful for your time. I’ve always assumed that people think entrepreneurs are born, and I’m probably jumping a little bit ahead, but people think entrepreneurs are born with some gifts. I’ve looked at all the literature. Psychologists trying to correlate your dispositional traits, entrepreneurial behavior, and it’s really weak. The correlation just doesn’t really hold up. It gets even messier when you start to think, how do you define entrepreneur? Is it an inventor? Is it Jeff Bezos? Is it like a small business owner? Is it a farmer? It just gets really wonky really quickly.

For me, it’s interesting. Background for readers that don’t know who I am, I spent twenty years in fintech as either a CEO or a CTO of a half dozen different companies.

As a founder?

Both, and this is what happened.

I want to make sure like you didn’t just come out of college and go get a job in fintech.

No.

How did that happen?

Let’s go way back. This is a story I love to tell. I was probably, so I was living in Kinsman, Ohio, which you will have to zoom really far into Google Maps to find. It’s super rural, literal one-stoplight town. The claim to fame of Kinsman is the birthplace of Clarence Darrow. His house is this octagon house that is like a historical whatever.

Anyway, my grandfather and father were both professional photographers. My grandfather came back from World War II and he was a photographer. He would sit up in airplanes and do spy photos of areas that they thought there was military action. He came back from the war, got married, started a photography studio. I grew up around my grandfather owning his own business. My dad worked for a steel company in Warren in Ohio. We lived in Kinsman. I remember him deciding that he wanted to get to start his own photo studio like my grandfather.

How did he get there?

That’s what I don’t know. I never asked him, and I never got the chance to ask him about that specific thing. I kick myself daily because he’s not with us anymore. He died a few years ago. I remember this very vividly. We were at our house in Kinsman, and they had thrown him a going away party from Wean United, which was this company that he worked for. One of the things that he got was a T-shirt that said, “I’m an entrepreneur,” and it had like pigs or something on it. It was really strange. It was like pigs rolling in money.

It was the strangest thing, but I remember seeing that, and I asked my mom, “What’s an entrepreneur?” I probably pronounced it incorrectly. She said, “That’s someone that decides they want to start their own business.” I said, “Is grandpa an entrepreneur?” She said, “absolutely.” From that day forward, my dad had always worked for himself.

How old were you at that time? Do you remember?

I was in fourth grade, so however old a boy is in fourth grade.

Usually, ten. I’m guessing, probably ten.

Eight or ten years old. We moved to Warren, Ohio and the house we bought, my dad built dark rooms in the basement so he could process film. Now, my grandfather’s house is still there in Warren. We just sold it when he died a few years ago. My grandfather’s house was built purposefully to also be his studio. There were six dark rooms in the basement. It had a twelve-foot ceiling in the basement. There was a room in the basement that was like 55 feet by 45 feet with a 25-foot ceiling. It was this massive studio.

I just see the correlation between the office you just showed me.

It was always ingrained in me. Growing up in Warren, Ohio, the steel days were long gone. This is 1980s, Warren. The steel industry is crushed. That was in the ‘70s, a bustling steel town. In the ‘80s, it was not. I was in middle school and only two years of high school then. All my friend’s parents worked at Packard Electric, which was owned by General Motors. That was where all the wiring harnesses for all the cars that GM made were made. I believe the Lordstown plant is where they made the Chevette, if you remember that car.

Our high school parking lot was full of Chevettes because people could buy them at a discount. That was a great starter car for kids. That was all the thing. I didn’t know that life. My life I knew was my dad was an entrepreneur, my grandfather was an entrepreneur, and they were all in the arts. They were photographers. If you look behind me, there’s a bunch of cameras back here. I’ve got my old cameras, I’ve got my grandfather’s old cameras, my dad’s old cameras.

I grew up, like my summer job when I was a kid was processing E-6 and C-41 and black and white film in my grandfather’s basement. I just knew how to work a camera. I knew the difference between different f-stops. I knew aperture. I knew shutter speed, I knew ISO of film, I knew lighting. I grew up around that. I always just thought I was going to go into the arts somehow.

Fast forward to my parents divorcing, my mom remarries a guy that lives in Cleveland. I moved from Warren, Ohio, Steeltown, USA, to Shaker Heights in Cleveland. I felt like the Beverly Hillbillies coming into this place because every car around the oval was a BMW, Saab, Volvo or Mercedes. I go from living in a place where paycheck to paycheck doesn’t quite cover it to a life of upper middle-class affluence. At that time, Shaker Heights High School was ranked like number six in the nation. They did my intake and I was so far behind, I had to take summer school before I could even start my junior year.

Getting Into The World Of Internet

That gets me to the question I’d like to ask, Doug. What were you like as a student? Were you a good student in school?

I was the worst student in the world. I was terrible. Here’s why. I still have on my phone, I’ll show you my senior year high school grade card. I graduated high school with a 1.2 GPA, like, just enough to get by. I excelled in arts, I excelled in creative writing, but in math, I was terrible because I could work it out in my head. I didn’t need to show my work to get to the answer. They weren’t teaching that way back then because you were supposed to go to college to learn this stuff, to get the job, to do the whatever.

In my head, I was going to art school. Around the first semester of my senior year, I got accepted to all the art schools that you could have wanted to go to. Art Center, Pasadena, Parsons, MIAD, RISD, all of them wanted me because I had a great portfolio and I didn’t care about school because I’d already gotten into college. I’ll get to the question that you asked. I graduate high school. I decide I want to go to either Parsons or MIAD, but I didn’t have any money for college. I decided to take a year off and work and save up money. I do, and I get an apartment in Tremont, Ohio, and it’s this really weird building called Lemko Hall.

Was it like the bohemian enclave that it is now?

It was starting to be. Let me tell you about my apartment building. My apartment building, Lemko Hall, is actually where they filmed the opening scenes of the movie The Deer Hunter. There’s a ballroom scene at the beginning of the movie that was in my apartment, and they took this ballroom and they diced it into these 4 or 5 really cool units. I think they turned them into condos eventually.

There was the editor for the Alternative Press was one neighbor that had an apartment. My neighbor on the other side was Trent Reznor from Nine Inch Nails. His studio, which was Nothing Records, was in that building. There was a guy across the hall from me named Dan. He was just like your typical computer geek, which is what we would call them back then. The internet was brand new.

What you’re saying, if I’m hearing you, Doug, you took some time off to make some money. Your path forward is pretty traditional, more or less college, etc. You wind up in this apartment building where you’re surrounded with this eclectic mix of people.

The parties were crazy because think of like soho in the ‘80s in New York. It was all like this collection of misfits that were all doing their own thing. Anyway, so Dan and I across the hall had this idea one night, or maybe it was his idea or mine.

Dan’s the computer guy, right?

He’s the computer guy. We had this idea to put computers in all the bars in the flats in Cleveland. There was an area called the Flats. It was all the bars. This is back the first time. It was cool.

It’s already interesting to me that you guys are sitting around thinking about solving problems. Where did that come from?

What eighteen-year-old does this?

That’s what I’m saying. How many kids get together and they’re just talking about nonsense and BS and drama on their phone or whatever.

We were trying to solve problems and one of the problems was, at the time, I was working for a PageNet, which sold pagers. Doctors and lawyers had pagers. Nobody else did. This was just at the cusp of that where it was cool for other people to have pagers. I’m doing that.

I remember those days. It was a badge of honor. It was like, you’re cool.

It was cool. I had like a little gold chain on mine, and I had the Motorola Advisor. I still got it right here. Look at this. Here’s my Motorola Advisor. That was my beeper.

It goes off like, you feel like super important.

I look at pictures of myself back then, and I had it on my belt proudly. It was a thing. Anyway, so we come up with this concept, like what if we put computers in bars and we let people log into them when they get to the bar that they’re at, and then their friends can look online to see what friends of theirs are at what bars, because nobody had cell phones and nobody had pagers? This was a way to check in at a bar so that before you left the house, you would see where your friends were. That was like Foursquare or Facebook way back then.

We come up with this idea. We raised a little bit of money. My grandparents gave me some money, my dad gave me some money. We made a run at it. Along the way, I learned all the tools about like, “This internet thing is coming.” We sold off whatever, made some cash. I went to work for Mac Temps.

You got out of it whole?

Entrepreneurs are builders. They enjoy the process of building and problem-solving. Share on X

I got out of it whole, I made a few bucks, but it wasn’t earth shattering. What it did was it put in me like, ‘I don’t have to work for somebody else. This is way more fun.”

Only in retrospect is it obvious, but I see this coalescing of events in your life. Grandfather, dad, the creative side, the people you’re around. Let me just add one more thing, Doug. We don’t have any way to know this because your father passed, sadly, but I just wonder if like he saw his dad be an entrepreneur, he thought he was going to take a more safe, secure route and it just got to be a beat down. We don’t know that for sure.

I know a bit of that. I’ll get into that later, so let me get back to my story for a minute because I think this will scratch the itch you’re looking at. I was really good with computers. Even when I was a kid, my first PC was an IBM PCjr. I would play games and I hooked up to a modem and I would call into the library and I would check out books by guessing their password, which was something simple like 1, 2, 3, 4 or whatever. The whole idea of computers talking to computers fascinated me.

We had sold off that startup, back before startups were a thing, like the term startup didn’t exist. I ended up working for an ad agency in Cleveland called AMG Marketing Resources at the time. It turned into AMG Advertising. I worked for a couple, Tony and Annette Fatica. At the time, I was like twenty years old. They put me in charge of their internet division and we started building websites for all of their customers.

College is off the radar now, right?

College i long gone. My mom would bug me about it here and there like, “You need to be taking classes, you need to be,” whatever. I already knew everything I wanted to do. This was where I was meant to be. I was meant to be building. I think if you take any entrepreneur ever and put it down to its core, we’re builders. We build things, whether that’s a better mouse trap or whether that’s a better system or whether that’s a better anything and we enjoy the process of building and problem solving.

Let me just touch on that for one second, Doug. Of all places, I’m not a Marxist, don’t freak out here, but I started reading Carl Marx’s theory about worker alienation. It’s pretty powerful. I think he nailed why workers are checked out. It’s pretty clear, and it still remains to this day, but one of the things Marx wrote in 1840-something is the desire to fulfill human needs through our own efforts is an essential part of what makes us human.

He called it your species essence in German, it’s gattungswesen. I think we’re alienated from that. We’re so indoctrinated into managerial thinking where someone else is going to tell you what to do, you just disconnected from it. We are builders. We are creators. It doesn’t mean you have to invent anything new necessarily, but I don’t know.

I think the desire for every human to feel like they are making an impact in something is universal, whether or not that’s something of your own creation or something that you’re doing on behalf of another company that you’re working for.

It could be just like improving a process. You’re contributing with your own faculties, with your own ingenuity. You’re improving things, you’re being recognized for it. Those are essential ingredients for human flourishing.

I think entrepreneurs take it to a different level. I’ll get to this in a bit, but when I was at AMG, I desperately wanted the rest of the world to understand what the web was going to be.

You’re an employee at AMG but they recognize you’ve got some creative abilities, so you went up high the organization young, quickly. It’s because of your entrepreneur experience.

I think that’s it. I think it’s the mindset. I’m talking to the king of entrepreneurial mindset here right now, but the mindset that I had was I need to improve this thing. Whether that’s for me or somebody else, I need to make this thing better. I build up this division, we start launching websites. Nobody knew how to sell websites. Do you sell it per page? Do you sell it per hour? Nobody knew because it was all brand new. It would take me fifteen minutes to crack out a simple page. That was something of value back then. It was the wild West, like nobody was selling any of this stuff. Nobody knew what to do.

I did my time there, built that division up, they got to be great. Left there to go work with my dad because he was doing database design for the company he was working at the time. It was another print place. We saw this opportunity for all of these ad agencies that couldn’t afford a digital department, but needed to be selling websites. We started a company together with another partner, Dan. Dan was the designer, my dad ran the business, and I ran the tech. We started designing websites and database architectures and all this stuff long before this was commonplace. We’re talking now 1998, 1999.

You were riding a wave.

I was on the wave. I was at the top of it working with local isps like APK Net, like these isps that accidentally turned into telecom companies because they sold internet access and now everybody all of a sudden wants AOL. You couldn’t open a loaf of bread without an AOL floppy disc falling on your lap during this time. I remember that was everything. You got your 500 free minutes of internet time. That was what that was. We did that for a bit.

Can I just interrupt for a second, Doug? I’m just wondering, you got me thinking about something like you come into this ad agency, and no pun intended, but you’ve got, let’s just say an above average sense of agency because of your entrepreneurial experience, not because of your dispositional traits per se. Here’s the point I’m trying to make, Doug. You said something a minute ago, like people didn’t know what to do, and you come into the scene and you’re like, “Here’s exactly what to do.”

I think this is a mindset stuff. People with an employee or what I would call a managerial mindset, we just draw from memory to navigate the future. When stuff changes, we don’t know what to do. What the entrepreneur’s doing and doesn’t know he’s doing is combining memory with imagination and those two together.

You’re getting deep on me. You’re absolutely right.

All this is happening cognitively without your awareness. That’s the key to mindset, Doug. You don’t even know it’s happening. You can’t articulate that. People look at Doug Hardman and go, “This guy is a freak of nature.”

Here’s the thing, and I hold this for everybody. Every human on the planet has something that some facet of their life that they work in where something is very obvious to them that isn’t obvious to everybody else. That’s how we all find our way and find our jobs and we find things that we’re good at. It all stems from that thing that I know intuitively that not everybody knows. That’s why some people are great at sales, and some people are great at marketing, and some people are good at operations, and some people are good at ideas. We all have our things that are obvious to us.

We don’t always honor them, just to be fair. It’s very easy to get caught up with a mortgage and a family and you’re dying, one little piece of you. I was watching these little reels where people, I think it’s funny where they’re standing in front of a microwave, pretend they’re calling in sick and they’re hitting the microwave button, so it beeps It sounds like you’re in an ER. I’m like, “Do you think this is funny? It’s pathetic. Work’s supposed to be fun. Don’t you get that?”

That’s the thing. I was having so much fun, I didn’t care what I made. I was having fun. At this point, I’m 21 years old, I don’t have any debt. I don’t have a house. I don’t have kids. I have an apartment. If my nut’s covered every month for my rent, and I get some money to go out to eat once in a while, I was happy. I would go home, plug into my computer and keep working because it was fun. I was doing something that I loved.

Getting Started In The Entrepreneurial World

Doug, I need to tell double click on that for a minute. Part of what I’ve studied for my new book is I don’t know what to call it, organic learning. I looked at like hunter gatherers like psychology, like how hunter gatherers learned. People don’t realize is that learning and work are supposed to be engaging like that. They’re supposed to be a source of fulfillment and energy and something you do. What you’re describing is intrinsic motivation. The task itself is the reward. You’re not necessarily motivated by money. I would say it’s unfair to characterize Doug Hardman as somebody who’s singularly focused on money.

Let me push back on that a little bit. I’ve gone in and out of phases of my life where I was absolutely driven by money. I think those are the times when I had my eye off the ball.

You’re making my point for me.

Let me fast forward a bit. I get through that, I get through the thing with my dad. We do whatever. It was fun, but it wasn’t profitable. I took a job for a nuclear medical supply company in Youngstown, Ohio as the CTO and built that up. That was an entrepreneur that hit a grand slam on his first at bat. Think of Ken Griffey Jr. On his first pitch, hitting a home run. That was the entrepreneur I worked for. He thought he could do no wrong because he’d never failed at anything.

I go to work for him. He starts investing in businesses left and right. Our CFO and I would sit there and scratch our heads. This was how he would do it. He would invest in a company and then send me and the CFO, Karen, in to due diligence after the fact. This was a guy that thought he was on top of everything, but it was just like about two thirds of the investments he made were not great. He just had cash.

I’ll get to a point here really quickly. One of the things that he had invested in was a gift and loyalty card company. I think they were in Twinsburg at the time. I’m working for him on just general tech stuff. I go in and I look. This was the infancy of gift card programs. There were only like 2 or 3 networks in the world that did gift and loyalty card transactions. He was buying transactions at like $0.15 and reselling them for $0.25 a transaction to the merchants. I started looking at that and this was all modem-based terminal.

You would swipe your card at the register, and it used to take like fifteen seconds before it would kick out the receipt. During that time, a 1200 BOD modem was calling from that terminal into a data center somewhere and checking your credit to see if you had enough credit. That’s how it went. That was the dawn of electronic payments. I started doing some research and I realized that a 16 second phone call doesn’t cost $0.15. It costs like six tenths of a cent. I start doing some quick hacking together, and I built up a really rudimentary gift card database.

It’s like an MVP, would you call it?

Barely an MVP. I would call it a proof of concept. I show him that I’m like, “This costs us less than a penny and I can still sell it for that $0.25.” He said, “Okay, let’s put some money into this and let’s build it.” I hire some people and I build this business. The project, it was code named SparkBase because that was something I could get the dot-com for. That sounded cool. I remember sitting in Shaker in my house doing Whois search on names that sounded like they would be fast and big, and that’s what I came up with.

I built this up and we went to a guy in Copley, Ohio that owned a credit card processor. I said, “I built this system and I can white label it for you, and I’ll sell you transactions for $5 a month per merchant and $0.10 per transaction if you’ll resell this to your merchants for me.” He said, “Great.” We white labeled it, and I had my first customer.

Fast forward like a year, I had built this incredible network and the other company, the parent company that I was hired for, was running short on cash. All these investments that he had made weren’t panning out. I was approached by the CFO and she’s like, “We have to sell this.” I said, “I’ll buy it.” Now, I have no money in the bank at this point. I’ve got a four-month-old child that I’m bouncing on my lap at the Yours Truly at Shaker Square.

I’m telling my then wife how I’m about to not have a paycheck for an unknown amount of time, but I think I can build this into a big company. They’ll give it to me on terms so I can make payments on whatever and all that. That was the time when I remember where I was and what I was doing when I was like, “I’m going to build a business.”

This was the first business that was only my idea that I came up with, that I was going to be the head of, that I was going to run, that I was going to turn into my shot at putting my name on the map somehow. That was my first idea of when I actually became a real entrepreneur. I’d been doing entrepreneurial things my whole life, whether that was a lemonade stand or selling car stereos in high school. Any of those things were just like me getting a business license and then finding out that I could buy stuff wholesale and sell it to kids in the parking lot at retail.

I look at my own journey the same way, or similarly, Doug. It’s like iterating towards the right venture, venturer fit. It’s like you’re dabbling around the edges figuring stuff out, learning. Invaluable learning is happening, but this is the thing that’s coalescing where you’re like, “This is it.”

That was my moment. I remember the booth I was in at that Yours Truly at Shaker Square. She said, “Okay.” At this time, she’s a resident. We’d done medical school and undergrad and all that. She’s a resident at Rainbow Babies and Children’s Hospital in Cleveland, I think making like $35,000 a year or something like that. We’ve got a mortgage and we’ve got all this stuff. I’m like, “I don’t know when I’m going to get a paycheck, but I’ll figure this out.”

I think I needed to bring home like $2,000 a month for us to cover the mortgage or whatever. My goal was to make $2,000 a month just to get us through. The first thing I did was I worked there, and I had four employees because these were the guys that had worked on the platform with us at the other company. I took them on and it was me and it was 3 or 4. We started building and I started picking up the phone and calling other credit card processors.

Did you have revenue at that point? You have something, didn’t you?

Barely. I want to say it was like maybe $3,000 or $4,000 a month that we were bringing in. Maybe $5,000 to $7,000. It was enough to cover the payroll of the 2 or 3 guys that worked there, and none of us were making good money. Anyway, I call my brother who had been working for an adjacent company and I said, “If I’m going to do this, I need somebody that can put me in check.”

What do you mean by that?

What I meant by that was when you’re the CEO of a startup, there is this like, “It’s my way and this is what we’re going to do.”

Sort of like a blind hubris.

Reality distortion field, whatever you want to call it. I knew for a fact that if there was anybody on the planet that could call me out, it would be my brother. I told him the thing and I said, “I’ll give you like 40% of the company if you’ll come work here and be the president, manage the books, manage all that stuff, do the stuff that I don’t know how to do, but you know what I need to do and you know how I am. You know when you can call me out.” He said yes. Now we had 4 or 5 employees and I started making calls and I started getting clients. It got to a point we had moved offices. This is when we moved into the Tyler Village office that you came to visit me at that first time.

I remember when we were doing the Cisco research, like there was a piece of plywood on two saw horses in an otherwise empty space.

We were building desks because that’s what we had to do because I couldn’t afford to go buy desks. I made desks. We went to Home Depot and bought lumber. That was just what we did.

It was scrappy. That’s what was registered in my brain. These are some scrappy guys. I feel like, Doug, also, like, I think in the beginning, that’s helpful. The lack of resources actually makes you smarter.

Startup CEOs usually stick to a single way of doing things. Share on X

That’s because there’s more at stake. One of the things that that we did early on was I was selling stock that I had, I was selling extra stuff around the house that I didn’t need to make payroll, to buy desks. We did a big Ikea run. We drove to Pittsburgh and bought five desks. I remember that being a big deal that we got five new desks and we had to pack them into my truck at Ikea. We all built them together on a Saturday.

You drove to Pittsburgh to do it, too, right?

We Had to drive to Pittsburgh. That was the closest Ikea, and all that stuff. Those days are what made me understand and appreciate the value of what it was that I was doing. We were making sales and we were getting transactions and we were doing all that stuff.

At this point, you’re funded on credit cards, second mortgages, friends, fools and family, basically.

Not even friends and fools and family, just credit cards and second mortgages. This was all me at this point.

There’s no risk capital. It’s all debt finance.

It was all debt. This is where things started to take off, but this was also the death note that I didn’t realize until much later. We started taking on investors and we raised $600,000, I think, which to me was an unfathomable amount of money.

Was it from a single investor or group of investors?

A group of investors. They put in $600,000 and they did it in three tranches. These are new terms to me. I didn’t understand what a tranche was. Participating preferred stock, I didn’t know what that was. Again, these were all things that I just was going so fast. I just needed the cash to grow the thing that I was building. I didn’t care. We’ll figure it out later because figure it out later had worked for me up until that point and I always figured it out.

What ended up happening is we took on this $600,000 and we grew and that let us hire customer service people. That let us hire another developer. That paid the rent. We started growing and then we needed more cash. We go to the local angel funds and we raised money from them on the next round. That round was like $1.7 million. That was stacked on top of this participating preferred stock that we had had on the same terms. It went on and on, and then the next round was like $2.8 million. We’re growing and we’re crushing. We had the best sales process. We had the best team. We had the best technology. I’m fast forwarding through a lot of heartbreak here, but fast forward to two things.

I remember being tangentially aware of this. You were like the golden boy of like Northeast Ohio. You were like the guy. Everyone threw money at you.

There were three of us that were buzzing around the scene at the same time. I still talk to a couple of them. A guy like Blake Squires had just had an exit, so he was the golden child.

I remember. I know Blake.

It was guys like me, Kyle Stalzer, Mark Woodka. We were all the next generation that was coming up that could do no wrong because we were all crushing our numbers. I was crushing my top line and we’re getting massive clients. There was a time in 2014 where the top of the top 250 credit card processors in the us, 220 of them were white labeling my product. Early on, if we hit 1,000 transactions a day, I was buying pizza for the whole office.

I’m fast forwarding to a time where we’re doing 1,000 transactions a minute sometimes. We were the gold standard in fintech for gift card processing and loyalty processing because of the tech that we built, the sales team that we had. That was awesome. I still talk to my sales reps almost on a weekly basis. Sometimes daily. A couple of them will still tell you that that was the best time of their life. We were everywhere. We were the golden child in this space.

Losing The Grip On The Entrepreneurial Hustle

Let me just double click for a second, Doug, on a mindset moment here, if you will. I don’t want readers to miss this, but don’t miss all the background stuff that had to happen to get you to this point. I coined this term entrepreneurial self-efficacy. Starting in high school, you’re selling stuff and it’s building and you’re not even aware of it. It’s not a conscious thing that’s happening. The point I want to talk to you about it for a minute is like to have built something with your own ingenuity that major corporations around the country are using. I don’t want that to get overlooked. That changes how you see yourself and what you’re capable of.

It does. Let me tell you something here

For the good or for the worst.

No, it was both. Here’s the thing. I don’t have regrets in life because everything that I do got me to where I am now, that gets me to the next thing. I don’t use the word regret very often. I was, at that time, out of my mind. Here’s what I mean by that. I’m a recovering alcoholic. I sit here June 16th, 2025, I’ve been sober for 35 years. I did all of this without picking up a drink. I thought that was my superpower. However, behind the scenes, I’d been going to a psychiatrist because I wasn’t able to pay attention.

They had me on Adderall and then I couldn’t sleep, so they had me on sleeping pills. They had me on mood stabilizers for the in-between. I was taking these medications to help me stay focused, but then I started getting depressed, so they put me on antidepressants, and then I got the sleeping pills and all this.

I look at that time in my life and I look at pictures of what I was doing then, and the parties that I was at, and the people I was interacting with. When you’re in fintech and you’re at the top of your game, I’m every day interacting with guys with $500 million watches on. They’re wearing $20,000 suits. They’re driving $400,000 cars. I’m playing catch up. I have to look the part. I’m buying all that stuff too.

I’m at these same parties and I’m flying to Atlanta three days a week to be at the right party with the right person. I’m flying to Seattle to meet with Amazon on Wednesday. I’m flying to San Francisco on Friday to meet with PayPal. I’m working with US Bank, I’m working with Elavon, I’m working with First Data. I’m working with these massive corporations and I’m everywhere. I did 250,000 miles in the air in 2014 and I never left the country. That was all domestic. That was me always having a bag packed, always ready to go do the thing. I was living a life that I was self-manifesting.

What do you mean by that?

I was in my own reality distortion field. I belonged with these people. I was powering the transactions that did this. I was all that stuff. I went from the entrepreneurial hustle and I lost the hustle at the midpoint, and it turned into the things. I took my eye off the ball and it turned into what stuff do I have? What watch is on my wrist? I would pack for a three-day event to go to a conference in Vegas. I would bring five watches with me. I would bring six suits. I would bring all this custom stuff, different shoes.

I’d have two suitcases because I didn’t want to be seen in the same outfit twice in the same day. My mind went somewhere else. I’ve got 80 employees at this point at SparkBase behind the scenes building all this. We’re going to be doing the next thing. We’re working on this. There are board arguments about what direction the company takes and these investors have put this much money in.

They’re calling the shots. Gary, I had 88 people on my cap table at this point. My cap table is full of rich guys that didn’t understand what we did. They didn’t understand software. I got a call from an investor once, so this is before SaaS was a term. SparkBase was a SaaS company. We were selling processing, white labeling. I had an investor call me, he was at CompUSA back when that was still a company. He said, “I can’t find your software on the shelf anywhere here. You guys need to get on that.” He didn’t understand that we were a network.

We weren’t a software company. He just thought he invested in the software company. These are the people I’m dealing with. I remember it clearly. It was 2015. At this point, I had burned my marriage down to a nub. I was never home. I’m watching my kids grow up through my wife’s Facebook posts, and I am out of my mind. I was literally out of my mind and I had to do a quarterly report for investors. My brother came over to me. At this point, we’ve got like 80 employees.

Is your brother saying anything to you like, “Doug, rein it in?”

He would in the way that he could. However, when you get an entrepreneur that has had a bunch of success and it’s unchecked, it’s really hard to argue with the hubris that they’ve built up in their own mind.

Doug, just to interrupt for one second. I wrote about this in my book. On a much smaller scale, the same thing happened to me with my sandwich shop. I started this little shitty deli on Taylor Road in Cleveland Heights, Cedar and Taylor. I worked 80 hours a week for a couple of years. It started to work. I bought myself a Mercedes. I started doing coke. I was out of my mind. I bought a bigger restaurant. It was all hubris. It was all about me anymore. It was no longer about my customer. It all crashed. Anyway, you’re just saying it’s on a much larger scale.

I’m at that point and I remember we had this spreadsheet with our cap table and I had never really dug into it. I had a moment of clarity. Now at this point, like I said, we’ve got 80-some-odd employees. We’ve got 25,000 square foot of office space that is the coolest office in Cleveland. If you go to a website called OfficeSnapshots.com, and you look up SparkBase, you’ll see two versions of our office. I’m talking about the second one. I had a room full of pinball machines and video games. We had we had a gym, we had showers, we had all the things that a San Francisco startup would have. I had it in Cleveland, Ohio.

It’s the lava lamps and the foosball tables that we all look back to.

The foosball table. All the things. At this time, we had raised a ton of capital, but we needed a Series B.

You got people all over you.

I wanted this Series B round so that I could pay off all the existing investors, reset the cap table and off we go. This was this was November of 2014, I think. We were to close the first week of December. That got pushed back. It was an $8 million round. We were going to take $2.5 million off the table.

How much had you taken in at that point, Doug, in investment? Do you know?

I think like $7 million or $8 million. We were to take off. I was going to take like $1 million off the table. Personally, that was going to get me right. This whole time, I’m doing this for my family. That’s what I told myself. The reality was I was doing it for me. I thought, “This is my chance to reset and I can be back to being a family man again. I don’t have to travel as much. I can do all this stuff. Fast forward, it is December 17th, 2014, the day we’re supposed to close on this like $8 million round.

That would’ve basically doubled the investment you had up there.

Doubled the investment, but we had a plan for how to spend it, what we were going to do, how we were going to right size the company, how we were going to do all the things. I get a call and he said, “The deal’s off.” I’m like, “Wait, we’ve done all the closing documents. I’ve already signed my half of this. What’s going on?” He said, “One of our board members talked to one of your investors and he didn’t understand well enough what you do and that spooked our investment committee. That’s causing us to not invest.”

Basically, one of these investors that was in I don’t know which one to this day knew somebody on the investment committee. They got asked what it is that we do and he didn’t know. That’s what happens when you just take money from rich people. They don’t always understand what you do. That was a big problem that I always had. I talked with other people and they all had the same issues. These people are just wealthy, made their money in being a doctor or a dentist and put money into a fund but they didn’t understand what actually these companies did. That was enough of a red flag to not push this investment forward.

At this point, it’s the middle of December. I’ve got exactly one week worth of payroll left in the bank because I’d been spending the money knowing that I had $8 million coming in. I got on a plane, I flew down to Atlanta to our biggest client, which was a company called Elavon. They’re owned by US Bank. They’re one of the largest credit card processors in the world.

I invited myself to their Christmas party. I found my counterpart there. I said to her, “I’ve got a problem and I need your help.” She takes me aside. She’s in a ball dress. She’s literally in a ball gown. They’re in the lobby of their big building in Atlanta having this Christmas party. She had known that we were raising a Series B because they needed to interview our clients. She knew what was happening and she’d been a great sport and done all the talks. I said, “I need an advance on next year’s transactions. I’ll give them to you at a discount if you can cut me a check tonight.” She said, “If you’re down here doing this right now, that means it’s a big deal. Let me go talk to somebody real quick.”

She went across the room, talked to somebody else, I don’t know who, came back to me and we went upstairs to her office and she cut me a check. It was like $600,000 or something like that. Her normal bill for the year would’ve been $1 million. She cut me a check for $600,000. I flew back down. This is the week before Christmas. I’m at the house unwrapping presents and returning them for my kids because I need all the cash I can get. My wife and I went to Goodwill and were buying toys at Goodwill to give to my kids for Christmas because we didn’t have any money.

I came back to the house. We got through that emergency and then I thought, “Let me look at how long we can last.” I made a spreadsheet with all of the investors, all the money that they had put in, what date they put it in, what their coupon was, and how long it had been since they put in. A possible exit amount, $50 million. I picked $50 million as a thing because we were raising money on I think a $40 million pre-money valuation. I plugged in $50 million.

If I sold the company tomorrow, how much would I get? Through all of that, I would’ve gotten about $45,000 because of all the preference that was stacked above us and how long those investors had been in and with their preferred status of stock. They got paid first, and then they come back in for common. It all came crashing down to where I went, “There’s nothing in this for me. I’ve done all this work. I’m doing all these things.”

You diluted yourself right out of it.

I diluted myself to nearly zero.

Part of this, Doug, just for a second, I get annoyed when I hear people say like, “Screw it. Let’s do it.” Jump off the cliff and figure it out. No, you’ve got to take some leaps of faith.

Everyone is an entrepreneur. They just do not know it yet. Share on X

What we ended up doing was I met with my brother. I showed him the cap table. I showed him the spreadsheet that I had made. We said there’s not enough room here for both of us. We need to trim a lot. We had done a round of layoffs before where we had let like twenty people go. That really sucked. I think we were down to like 60 people at this point or 50 maybe. I said, “We don’t need a president and a CEO. One of us is going to go.” At this point, my brother had just started his bagel company. That was a brand-new thing. They were just doing farmer’s markets or whatever. I made one phone call to a guy in the industry.

In the bagel industry?

No, this is in fintech. I made a call to a guy named Todd that I’d known, and he was on our advisory board. I said, “I’m thinking of leaving SparkBase.” He said, “Give me an hour.” At this point in life, my wife had left me. I was seeing my kids every week for a few days. I had a business that was way underwater. I had a preference stack that meant that if I sold the company for more than I thought I could get for it, I would still get nothing. I was just like, “Wash my hands and walk away.” I call Todd and I say, “I’m looking to make a move.” He said, “Give me an hour.” My phone rang from a company in Atlanta, Georgia that was looking for a CTO that had payments experience.

I checked all the boxes and I had a meeting with him on a Wednesday. I remember it was the day that I got divorced. I left the divorce hearing, and I drove to my house to have this interview, and I interviewed with the guy. They gave me the job on the spot. I’d already been there to see them as a client, so they knew me.

I left SparkBase and I said to the board at the time, “This is going to be a disaster. You guys put us here. This preference, you could have ended at any time. That would’ve helped. That would’ve saved us cash. All this stuff could have saved us cash. Making these moves that I wanted to make and that my COO wanted to make. My COO ended up leaving because he was just so pissed at the board at not doing the things. I had twelve people on my board, Gary. I’m a startup in Cleveland with a twelve-person board. Apple has a twelve-person board.

How do you spell unwieldy?

Also, five advisors or observers on top of that. There were seventeen people in the room every time we had a board meeting. It just got out of control. I’ll wrap up the last five years here in pretty quick succession. My COO left. He flew down to see me. I was in Florida at a conference, and my door knocks on my hotel room, and it’s my COO. I’m like, “What are you doing here?” He hands me a letter. It was his resignation. He had flown down to Florida to give me his resignation in person because he got an offer at another company. Fast forward, side quest here for a second. CoverMyMeds was that company. He went on to be the CFO of CoverMyMeds. They sold for $2 billion, $3 billion.

A friend of mine invested like in that very early.

That’s like the level of person that I had working for me that my board hated went on to be one of the most successful exits in Cleveland’s history. Anyway, I had the right people. I had great people. I had great technology. I had great everything. I had a really bad board of directors and really bad investors and I put that on me. Those were the terms I signed up for because I didn’t know any better.

Staying Sober In The Middle Of A Challenge

Let me ask you this, Doug, for a second. I get that the investors are all trying to get rich and trying to get their piece of it, maximize their return. At the same time, you talked about this guy that was buying five watches, trying to keep up. It seems like those two things together, total recipe for disaster.

What ended up happening after that point, I sat in my house and I thought, “What do I really want to do? What do I like doing?”

Did you anything about drinking and through any of that, Doug?

I didn’t. Here’s the thing. I’m going to side quest for 30 seconds on recovery. My hubris kept me sober through those times because I was failing at everything else in my life, I didn’t want to fail at that. The one thing that I would never let myself fail at was my sobriety. I was out of my mind. I wasn’t the person that I am now. I wasn’t the person that I was before then, but my ego kept me sober for that time.

I never once thought about drinking, never once thought about whatever. I had every opportunity to do all the bad things and spiraled directly out of control. It probably would’ve been the exact same outcome, but I maintained, and I would still talk to my sponsor a couple of times a week. There was no help for me outside of that. I wasn’t listening. That’s that part. Here’s the thing. I had a moment of clarity that I had lost my way as an entrepreneur.

I just want to talk to you for a second. That’s so important because so many people have failed and they just go, “It’s the board. It’s everybody else’s fault. It’s not my fault.” When you have those moments, my mindset, I’m a mindset guy. It’s like, as soon as you realize we’re the source of our misery, you’re free.

What I did was I took the job in Atlanta, worked at Payscape, became PayRock. I was there two years left there, that company exited came back to Ohio, did my own thing for a couple of years with some friends, a little startup in crypto. That went belly up, whatever. I took a job at a company in New York called SPENT and got them through to an exit. All the things that I had learned at SparkBase for doing stuff the wrong way and the right way, I learned a battle plan.

I did SPENT for two years, sold that company’s parts because it wasn’t going to be a viable business. That was March 3rd, 2020. This was a company that was all about in-person spending, and you got rewarded for credit card transactions. All that disappeared on March 13th, 2020. We sold that company in the nick of time. Got some cash then I went to work for a company called Aurora Payments, which I was the CTO of that company. That was about the third largest credit card processor in the US. I was their CTO for two years. I got them through an exit. We sold that company to private equity. I left there. It’s funny, like the things that killed me at SparkBase have become my superpower since then.

Along the way now, I mentor entrepreneurs that are in the early stages. A lot of times, I’m telling them, “Here’s what you’re in for. Look at all these scars. Do you see these? You’re going to have all of these, and here’s what’s going to happen and here’s how it’s going to happen. Here’s what you’re going to do. Are you okay with that?” Nine times out of ten, “I can’t do that,” “Then this isn’t for you.” There’s a difference between an entrepreneurial mindset of somebody that works for another company and wants to dig in and wants to make their thing better and there’s the person that can’t live without making this idea.

There’s somebody going all in.

We had the exit at Aurora. I went to work for a friend of mine who has a golf company in Chicago. I worked there for a few years and did a lot of fun stuff in and around tech. They got an investment from outside. The investors were like, “We don’t understand what this whole tech piece is.” The investors couldn’t see the big picture because they had seen a physical goods company getting into tech and didn’t want to fund it further. My time was coming to an end anyway. I’m just like, “I’ll just go do my own thing.”

I met an entrepreneur down here in Tuscaloosa, Alabama when I moved. He had an idea for a company. I took the meeting. It was my girlfriend’s friend, and I had coffee with him, and he had all the answers, and I poked all the holes in every one of his answers. He left, like most entrepreneurs do that I talk with, with his tail between his legs. Two weeks later, he texts me. He’s like, “Do you want to have coffee again?” “Sure.”

I have coffee with him again, and he plugged up a bunch of the holes. I’m like, “Here’s some other holes that you hadn’t thought of.” Two weeks later, I get another text, “Let’s have coffee.” He plugged those and he was adapting. He was doing the thing that a good entrepreneur does, where he was adapting to adversarial conditions.

He was also listening.

We did this back-and-forth dance for months where I was just getting lunch out of it. I’m down here doing my own thing, working on a little startup idea. I have some cash, so I’m not stressed for what’s my next job. It got to a point where it was like, I started to believe his dream. I took on that entrepreneurial spirit through him of, “Let’s do this. Let’s make this thing.” I told him, “This is going to take way longer than you think. It’s going to cost way more than you think. Let’s map this out, what it looks like.”

How old is the guy, Doug?

He is early 40s.

He is not a young pup out of college.

Not a young pup. Twenty years of experience in the field. He knew the ins and outs. It’s an advertising technology company. He knew Ad Tech in and out. I knew enough questions to ask, got myself up to speed on Ad Tech. Fast forward to January of 2025, or in December 2024, I said, “I want to take this journey with you.”

“However, you need to understand that this is going to take a long time, and you’ve got a wife and two kids. Let me be the CEO and run this the way it needs to run. You’re still the founder. You will always be the founder, and no offense to you but you don’t know what you’re doing with running a business that’s reliant on policies and procedures, that’s documentation on everything, that’s developed the right way so that it can scale. Setting up from day one so that scaling isn’t an issue, but the most important is this is going to take capital. I don’t want you raising money the way that I raise money.”

You’re taking all the lessons learned from the failure.

We meet weekly, and I go through yet another lesson with him, and we’ve done this whole thing. Fast forward, we started cashing checks from investors, and the terms that we got were exactly what I wanted and they don’t hurt us. Yes, it’s preferred stock, but only on downside protection. It’s not preferred stock. If we sell for a bazillion dollars, it’s preferred stock if we sell for $1 million. The money that’s coming in is from people that are aligned with understanding what it is that we do. I have said no to more investors than I’ve said yes to because they would’ve just been rich guys that would’ve been a pain in my ass.

Importance Of Financial Literacy In Entrepreneurship

Doug, I just want to stop you for a second. This is a really interesting story. I’ve never had like this a conversation. It’s like the dark side of venture backed, high growth entrepreneurship, but the lessons learned from it, it’s not all bad. The insights, if founders can just read this, how much grief can you help?

There are two things to that, Gary. There’s the first thing is I think entrepreneurs need to be more honest with themselves and not drink their own Kool-Aid.

I wrote as much in the book. I don’t know if you got that far. You need hubris. Maslow talked about this. You need to have some modicum of hubris so you’re never going to get anywhere but you got to balance it with a little bit of humility. As you have lived and breathed this, the hubris will drive you right in inside of a cliff.

Every entrepreneur I work with, you’ll see a book behind me right here, this is a book I make everybody read. It’s from Colin Campbell. It’s called Start. Scale. Exit. Repeat.. This is a guy who has built companies that we’ve all heard of, and he tells the backstory on them. It all comes down to those four steps. Start, scale, exit, repeat. That’s the entrepreneur’s journey. Now, what I would add to that is understanding the entrepreneurial mindset, which I’m currently on a show with the author of that book.

Read those two and then ask yourself serious questions. I’m going to add one other thing to that I wish somebody would’ve drilled into me way back when. This is something that I think makes being an entrepreneur much easier. A third book that has nothing to do with entrepreneurship, but helps in a way that is indescribable. Read The Total Money Makeover by Dave Ramsey and live by those principles.

Just basic financial literacy.

Financial literacy, understanding debt, understanding your finances because what happens is think of Entrepreneur A because there is a whole type of entrepreneur, Gary, and you’ve interviewed them, I’m sure, that invent a company so that they have a job. Necessity entrepreneurship. I need a job. Why do you need a job? It’s because I’ve got a bunch of debt that I’ve got to pay that off. Starting a business to pay off debt that you have is not a recipe for success because you’re always behind the eight ball.

I tell people that are getting ready to start a business or that are getting into entrepreneurship, or have an idea, “Only do it if you already have no debt,” because you can last a really long time with very little money if you don’t have any debt. I mean credit cards, cars, house, if possible. If your cost of living is only $2,000 or $3,000 a month, you can build a business tomorrow that can only make $2,000 or $3,000 a month to support you while you’re working on your bigger dream, you’ve got that. If you’ve got a mountain of credit card debt and a mortgage and all that stuff, and you go to start a business, your stress level is going to be through the roof on day one, and you’re not going to make as good a decision.

I wrote about this in the book, Doug. It’s like so many people get caught in this trap. They go to jobs they don’t really like, they aren’t really fulfilling and they try to compensate from that by buying stuff. They buy cars they can’t afford, upgrading this, upgrading that, and then they’re just further alienated from any possibility that they can escape it.

Let me tell you how I live my life now, Gary. I have no debt other than the mortgage on this house I bought. I’m going to sell my house in Ohio that I don’t have a mortgage on to pay for this house here in about eighteen months so I’m not worried about it. I’m in Alabama, which the cost of living is like free. It’s like it’s nothing down here. I love it. I shop at thrift stores for my clothes. No problem. I drive used cars. They’re all paid for. No problem. I coupon at the grocery store. I think it’s insane how much over my lifetime I overspent on groceries.

It’s like the Starbucks thing. You got to pay $4 for a cup of coffee like once a day.

I buy a really good beans and I make my own pot of coffee every day. 100%. I drink an alarming amount of LaCroix. I drink like 12, 13 cans of LaCroix a day. I only buy it when it’s buy one, get one free. I bought twenty cases because at Publix down here it was buy one, get one. That’s half off. I filled the truck with them.

The Mark Cuban thing. He talks about that.

My consumables. That’s where I got that. When toothpaste is on sale, buy twenty tubes and then you’re done buying toothpaste.

It’s better than you’re going to do in the stock market. It’s basically what he’s saying.

It’s great. I do things now that make me happy and I have zero stress going into startup life because I know I can always make it work. When you start a startup or when you’re an entrepreneur and you’ve bought yourself the luxury of time by not having debt and by not having crippling anxiety over things in your household, if you’re in a bad relationship with your wife, if you’re in a bad relationship with your girlfriend or boyfriend or your partner, if you don’t have a good relationship with your kids, being an entrepreneur is going to magnify all of those things, so you need to the right mindset.

It’s an interesting point, Doug, because your story is so powerful and it’s the full circle in so many ways, but can it be avoided? It’s like you tell a young kid, “Just make the right decisions and everything going to be okay.” I don’t know. That financial literacy piece is really important. I reminded me of a thing Naval Ravikant said, which is if you can’t be happy with a cup of coffee, you’re not going to be happy with a yacht. That seems to be like your story. You were going after the yacht.

When you are okay at a bunch of things, you are good at nothing. Share on X

I had the yacht.

It made you miserable.

Here’s the thing. I’m going to call it Doug 3.0 that I’m on right now. I got here a few years ago. I live some version of this hustle where something in my life was controlling my happiness. It wasn’t until I took control of my happiness and got happy with myself that this version of me emerged. When this version of me emerged, when I was truly happy with just myself, and this goes to you if you’re in a relationship and your spouse and you’re happy with that life, when I’m happy with my own life, light switch. All of a sudden, all the things went away.

When I was happy in my own skin by myself, when I was happy not needing this certain watch or this certain suit. Years ago, I bought 40 of the same T-shirt and I wore that exclusively for the better part of three years. You would never see me in anything other than a dark gray American Apparel T-shirt. That’s the only shirt that was in my closet. I put everything else away. I got myself down to the core. I was wearing this same pair of jeans and this same T-shirt every single day.

That almost sounds like a mind hack.

It was. I just got up in the morning. I knew what I was putting on. That was it. Done with that. That’s a Steve Jobs or a Mark Zuckerberg thing. I have my hoodie, my T-shirt and my jeans. That was the Doug outfit. That’s all you saw me on. Anyway, I digress.

How To Unlock Your Entrepreneurial Self

Doug, let me stop you right here. There are so many directions I want to take this in, Doug.

That’s why I told you to book me for two hours because if I get on a roll with something, you’re going to want to keep on it.

No, but I appreciate this. It’s almost like we’re just starting another conversation right now. It’s like the lessons learned about yourself. I said this in the book, Doug, you just reminded me of something I said in the book, which is like, I define entrepreneurship as like the pursuit of opportunity to create value for others. That’s how I describe it. It’s a broad definition because anyone can embrace it. You can work at Taco Bell still think and act that way. You don’t have to jump out. I think in the pursuit of opportunities to create value for others, we find ourselves.

For sure. To that point, and to your hypothesis that everyone is an entrepreneur, they just don’t know it.

They Have got entrepreneurial tendencies capabilities. At whatever level, it’s up to that person.

It’s up to that person. Let me give you an example. I have a friend of mine, I’ll come clean, my partner, my girlfriend, has been at her same job for ten years now. She loved her job. She loves what she does. She loves the way that she makes an impact on the client and the consumer in the role that she has at her job. She also is passionate about collecting. That’s how we met. We met literally on a golf course. The company I was working at was throwing a collector’s event. You see these head covers back here behind me for putters. She was a golfer and a head cover collector. We met at a collecting event for our top collectors.

She’s also a Harry Potter fanatic. Right around Thanksgiving of 2024, my family came down to Alabama for the first time. My brother is now uber successful with The Cleveland Bagel Company that he went on to blow up. My brother and I as entrepreneurs are always tinkering with some idea. “What if we did this? Would it be cool if that?” Jeff, my brother, we were standing in my kitchen. He goes, “You know what would be cool is if somebody invented a candle that would only last for two hours? Is there a way to time the wick?” Me being a problem solver, I’m like, “What if we did this?”

Fifteen minutes later, Jeff and I are driving to Hobby Lobby on Black Friday. They came down for Thanksgiving, and then we were going to go to the Iron Bowl on Saturday, so we have this Friday to kill. Jeff and I are at Hobby Lobby buying wax, wicks and tins. We’re going to invent a new candle. We start pouring different combinations and what if we drill and what if we use little wicks, put two of them in and their time and their different whatever. We start digging into this problem. Dana, my girlfriend, is sitting there watching all of this, and she goes, “I spent $30 last week on a candle that was a Harry Potter themed candle. Now I see how easy it is to make candles.”

I’m like, “It’s not that hard. You just do this and this.” It was like, I had figured it out just by my brain working the way that it does on how to make candles. Fast forward to February 2025, and she launched her candle brand, which is Harry Potter-inspired and themed scented candles. We’ve got a whole studio in the next room with wax melters and packaging designs and all this stuff.

She found something that she didn’t know that she wanted to do, but instantly became passionate about it because of watching something unfold in real time. Now she sold, I think, like eight candles yesterday, just as a side hustle as a thing, but the process of deciding what the restricted section smells like, what does the invisibility cloak smell like? Getting to invent these things. I think an entrepreneur, once they find their thing, has to do it. It’s not a, “I’d like to try this.” It’s a, “No, this has to exist. Someone needs to do this thing. If nobody else has done it yet, by God, I’m going to do it.”

Let me double click on that, Doug. I’ve written about this extensively. A lot of my research and understanding entrepreneurial behavior comes from social psychology. The basic premise of social psychology is that we overemphasize the importance of traits when explaining a person’s behavior. We tend to ignore the constellation of cognitive, motivational, and situational factors that are acting upon the individual in ways that essentially render your traits irrelevant. By the way, your traits are your default settings that influence your behavior in the absence of any other factor.

That’s how psychologists think about this. That in my thesis here, Doug, and Dana’s story is a good example of this, the compelling nature of the goal itself is acting on her. What’s freaky about this, Doug, is it’s like the psychology of it is absolutely freaky. It’s called prospection theory. When you’re oriented towards a positive future in your imagination. You’re able to access problem solving abilities that aren’t otherwise available to you.

Let me drill in on that. The company I’m at now is called Impact Fans. That’s what we did with Impact Fans. We literally took an idea and o this, “What about this?” and then that builds your roadmap for you on what you need to do. When you start working on those problems, yeah, you find other problems, but you also find creative solutions along the way.

You’re developing so many capabilities, like unconscious capabilities, your sense of self-efficacy, your ability to solve problems, your ability to tolerate ambiguity, which is a superpower. People don’t get that.

That’s the difference between what I’m doing right now in my life versus what I was doing before. What I was doing before started with this passion, and we’re going to create this and it’s going to be that and, “Okay, let’s get to work and let’s do it.” We’re grinding and we’re hustling and we’re doing all that stuff. At some point, I lost touch of that and it got out of control and it turned into something else.

What I do with entrepreneurs now, and all the businesses that I’ve been with is I learned to say no to things. This is the first lesson I teach with entrepreneurs I’m talking to, especially when they’re in that early stage where they’re like, “We can do this, we can do that, and we can do this.” Learn to say no. Find your core thing that you want to get really good at and put the rest of that in parking lot.

Put the rest of it in a parking lot that you’ll come to when you can’t go any further without that thing. Let’s get the baseline tech built. Let’s get policies and procedures built for all of the things that we need to do so that we can scale this when the time comes. With Impact fans, we had the opportunity to get a massive client on day one, and I told Kyle, the founder, I said, “You’ve got to say no to that. That’s going to eat you alive.” That was the University of Alabama football team. You want to talk about a marquee name in college sports? The Crimson Tide football team is about as gold standard as it comes.

We could have had that client on day one. I said, “No, I want the softball team.” I want the women’s softball team that no one’s paying attention to because if we fail at that, we can adjust and we can go back and do the baseball team, we can do the swimming team. We can fail at those things. If we fail at the football team, it’s game over because you can’t recover from that big of a thing. People are going to only know you. They’re going to know who you are, and they’re going to know that you failed at the biggest stage.

There’s another tangential thing here. I got a friend who’s a professional soccer player. He’s a goalkeeper for Columbus crew. He’s almost 40 years old, at the end of his career. He got invited to this startup, which I thought a cool idea where soccer parents will pay a couple hundred dollars to send like a sizzle reel for their kid to a pro and the pro will give them a little bit of feedback. There’s something to that effect. I might not have it described perfectly, but the thing imploded for reasons that emulate SparkBase, that lots of investors, they launched it doing soccer or football, hockey, like every sport known to man.

When you’re okay at a bunch of things, you’re really good at nothing.

Absolutely. It never really went anywhere. They should have just like stuck with one domain. Stick with soccer, figure that out, master that, and then branch out.

That’s what I tell entrepreneurs that I work with and that I mentor all the time now. Get really good at 1 or 2 things. Yes, you can do all these things down the road. I get that. We’ve done that at Impact Fans. Even Dana did that with Brilliant, but Scary, her candle company. Launch with five fragrances. We have ideas for 25, but let’s just work on these 5. We launched with that collection and sold it out a few times, and then start adding more, and then it becomes muscle memory and you know how to do the thing. It’s easy.

I’ve got to have to do an episode with Dana now. Her startup is more representative of a typical entrepreneur. It’s a side hustle.

It’s a typical side hustle.

It may never be more than that. With you on the side, it’s probably going to be more than that.

What I have done, and this was a test, Gary. Let me take you down a rabbit hole for a second. You know me. You know how tenacious I am when I get on an idea and want to build.

Dog with a bone.

This was Dana’s idea and I stayed way back here. I let her do the thing until she got stuck and then I would come in and I would say, “Do you want help fixing this?” “Yes.” “Here’s how I would fix it.”

That’s great relationship advice, by the way.

I could do a whole episode on that. It’s like, she needed a logo, she needed this. I would let her get that stuff and then I would take my design mind and just make it better but it was still her idea. Working out Shopify and building the store. I had just come from a company where we did umpteen million a year through Shopify, so I knew that system inside and out. We would do 2,000 orders a day through Shopify. However, I pointed her in the direction of Shopify, here’s some things that you can modify and then she was off to the races and figured it out. Working on candle scents.

Doug, let me just circle back to a second. That’s how hunter gatherers learn for 99% of the time we’ve roamed the earth. Figure it out, experiment, play and bring the adult into the room when asked.

That’s what I’ve done. Brilliant, but Scary is her brand. If you go to the About page, at the bottom of it, she’ll say, “With support of my partner.” You’ll see a little picture of me and the two of us at Universal Studios but this is her thing, and I always wanted it to be her thing, because I know how as important it’s for an entrepreneur to have their thing. Also, I know that it’s super helpful to have somebody that’s supportive behind you that doesn’t want to take over your dream. That’s what I’ve done with Kyle.

Is it trying to cash out in a hurry?

No. I want to be supportive. That’s what I’ve done with Kyle at Impact fans. Kyle still has the lion’s share of the stock in that company. I got called a co-founder on a meeting and I corrected them. I am not a co-founder. He is the founder. Kyle is the founder of this company. I am the CEO only because he realized that I’ve got the experience and the things that he was going to get tripped up on. In every meeting that matters, I make sure Kyle is in the meeting so that he sees how I handle a situation so that he can learn from it. At some point, he can take over as CEO and I’ll just be a guy in the background or whatever. There’s the saying, do you want to be king or do you want to be rich?

I don’t need to be king. I really don’t. There was a time in my life, Gary, and you knew me during this time where I wanted to be king. That bit me in the ass. What I am now is the happiest version of Doug Hardman I have ever been in my entire life because I am really good at saying no to things that I know are just going to be a pile of stress for me. I am more than happy to take anybody that asks me to take them to lunch or have a have a meeting with them to help them through an issue.

I ask, “Am I listening to your problems or are we problem solving? I am happy to listen to your problems and interject a little bit here and there. If you need help solving a problem, I am happy to dig in and give you my advice, if I have any,” and that’s the other thing. Knowing when I don’t have advice to give somebody is also a thing that I’ve learned in the last few years because there was a time when you could ask me a question. I may not know a thing about that, but I’ll come up with an answer because you asked me. That’s stupid. That’s hubris.

It’s like knowing when to just say, “I don’t know.” It’s not just saying no to things, but saying like, “I don’t know the thing is also.”

What I say is, “I don’t know, but let’s figure it out.” If I don’t know something, there’s somebody in my Rolodex that does. I’ll call them and I’ll get on a three-way call with the person that asks the question and we’ll chop it up together.

Impact Of Mentoring And Tech Innovation

I think there’s another point here, Doug, to be made if you will, and if we can tie it back to like recovery, we’re both recovering alcoholics. We’re both recovering based on the same framework, let’s say. The power of mentoring.

It’s way more fun.

It’s just so powerful. I work with accelerators and incubators and SBCDs and these college programs, and it’s like, well intended people that are unqualified.

I could do a whole two-hour episode on that. One of the things that I am going to do here in the next year is I’m going to start a campaign here in Tuscaloosa, Alabama, where I have lived for a year and change, and I’m going to run for school board. I’m going to run for school board not having a college education, but I’ve got 30 years of experience being an entrepreneur and using the tools that they should be teaching kids how to use.

Your wins put money in the bank. Your failures put those wins in. Share on X

My whole book is basically about that. Everybody needs these skills.

Everybody needs to understand basics of certain things.

The fundamentals of entrepreneurial thought and process. I was on a podcast, these two authors from Harvard wrote a book called Employment is Dead.

No, it’s gone.

It’s like the school system doesn’t see how they’re creating employee minded people. I gave a book talk at the Pegasus Center in Dallas, which is funded by the Hunt family who the Dallas TV show was modeled after. I was talking about these everyday entrepreneurs in this extraordinary ability of ordinary people. This guy comes up to me afterwards, he was an MD and he goes, “There’s a guy here in Dallas who’s a billionaire, and I’m pretty sure he’s functionally illiterate.” I said, “I’m not surprised. I just met a barista in the airport with a Master’s degree in $180,000 in debt.”

Even to take your story to this point, like, the game of entrepreneurship that you played is major league sports. You started in the major leagues but we don’t expect Lionel Messi to walk off a farm at 22, ready to play professional soccer. He started when he was four years old. I think that’s your point for the school board., right? If you want to create major league baseball, you need peewee league, you need a junior league, you need all the way through.

It’s part that. It’s also part using the tools that are available in real time. When we were hiring at SparkBase, so go back to 2008, 2009, 2010, I’m hiring kids right out of college that had been learning technologies that hadn’t been used in years. They were teaching them frameworks and they were teaching them how to program, at the time, I think .Net. No, you need an object-oriented language. You need an object-oriented language foundation. It doesn’t matter what the language is, you’ll learn it because you understand the fundamentals. They need to be teaching fundamentals.

My oldest is in college at Cincinnati. My youngest is a senior and he’ll go on to whatever school he wants to get into because his grades are insane. They got that from their mother, not me. The whole thing, like, we got a notice at school, as a parent, like the harms in letting your kids use ChatGPT, the harms in using and letting your kids use social media.

No, this is the future. This is when I was in 1993 in math class at Shaker Heights High School and them telling us, “You’re never going to always have a calculator in your pocket. You need to learn how to do this in real time. You’re never always going to have a whatever.” Guess what? You were way wrong because there are hundreds of millions, if not billions of calculators now in everybody’s pocket at all times. Everybody has a phone that’s connected them to all of the information that has ever existed at all times. There is a mountain of research material available on any subject at all times day or night. No, I don’t need to learn how to use the Dewey Decimal System to go to the library to learn a thing.

Doug, there’s a guy named Kevin Roose in New York Times that writes about AI. Not in a doom and gloomy way, but he came to Case. Karen and I went to hear him lecture and he did a great presentation for twenty minutes, and he sat down with like an academic guy from Case. Very quickly, the thing goes to cheating. I’m practically like standing on my chair, screaming, like, “Why do you think they’re cheating?”

They’re cheating because they’re extrinsically motivated. They don’t care about the knowledge. They care about the piece of paper. The flip side of it is to what you’re saying, if you have a bit of an entrepreneurial mindset, you know how to use AI, you can create meaningful work for five employers at the same time from anywhere in the world on your own terms.

Let me tell you what we did at Impact Fans. When I started working with the company in January 2024, right around March or April, I hired another person, my chief of staff. Her wife that used to work at SparkBase with me, who I was talking to. I’ll talk about legacy here in a second. We have four full-time employees right now. We have eight virtual employees. What I did was I worked with my chief of staff, AJ, and we created these gpts for all the things that we needed a subject matter expert in for now so that we could get by. We have built a massive company in no time. If I’ve got a question on X, Y, or Z, I know which GPT to go to, I know which AI to ask.

I’ve got AI recording all of my meetings and sending me summaries and putting to-do items on my calendar. That right there, that took care of an assistant that I would’ve normally needed. I’ve got a brand expert that knows every brand thing that we could ever think of. If I need copy written for a landing page, I go to that AI and I ask it to write a copy for this subject and this thing, and it puts it all together in 90 seconds. Copy, paste, done. It’s good. I read through it, make sure it’s on track. It sure is. It’s off. I’ve basically replaced the need for that a typical startup would have two years ago even with these experts that I pay $19 a month to have instead of $6,000 a month to have.

I’ve got this army of people now that are virtual that we will replace with real people at some point, because there’s only so much that an AI can do at this point. That’s going to change. When I’m talking to my kids about what they want to be when they grow up and what they want to do, one of them is very entrepreneurial minded. Garrett will probably start a business here at some point soon. He is already tinkering on it. I’ve got him working for me as an intern. I told him, “Before you start your first company, I want you to work for a really bad entrepreneur and I want you to work for a really good entrepreneur. Right now, you’re working for me. It’s up to you to tell me if I was the good one or the bad one.”

It’s hard to be objective when it’s your dad.

That’s why I have him working with other people. I don’t interact with him at all. He’s working on a different team on a different thing. All I do is once a month, I get a ping from my chief of staff and I’m like, “How’s Garrett doing?” She’s like, “He’s crushing. He’s fine. Don’t worry about him.” I know that, and I run payroll and he gets paid. Just as a summer job. The point is it’s going to be different for him than it was for me. The difference in understanding where to go to get information is something that entrepreneurs now have that they didn’t have 5, 10, 15, 20 years ago where there is a million hours of content about any subject that they want to learn that they can go to and get for free now.

The fundamental difference, Doug, mindset, it’s, again, unconscious is the underlying assumption that it’s up to me to figure out how to make myself useful to other humans. A barista with a Master’s degree has an unconscious assumption that somebody else needs to tell me what to learn and do in order to be successful. That’s a deeply held value, let’s say, or assumption of which we’re not even aware that the impact on our lives, monumental.

It’s gotten worse in the last several years.

The letter from the school, “Your kid is crushing it in school,” and they’re sending home letters telling them to avoid like AI. That’s just criminal.

My son is still in high school in Orange up in Pepper Pike. They’re not allowed to have their phones on their bodies during the day. They have to stay in their lockers. The kids have all gotten smart and they get Apple watches so they can see their notifications and all that. That’s so stupid to me. If you want a kid to learn, let them learn the way they want to learn. Some kids need to learn by reading books. That’s not me. If that’s them, then let them do that thing. Let kids learn the way they want to learn and they will consume the knowledge at an alarming rate much faster than you can teach them.

You’re talking about intrinsic versus that restrictive motivation, fundamentally. Doug, just to wind it down. I want to start with a quick story. I was in Johannesburg training a couple hundred career in technical education teachers how to cultivate entrepreneurial thinking in their classroom. We’re now training 10,000 teachers, but there’s 225 career and technical education teachers amassed from all across South Africa.

The youth unemployment rate in South Africa is 60%. The age is 16 to 25. They’re all racked with anxiety about what are we telling our students? There’s no jobs. We were in this huge luxury resort. At the end of the day, they asked me to, they would bring in local entrepreneurs. They asked me to interview, and we created this little makeshift studio in another corner of this compound. I would go off the end of every day after training all day, and they brought four entrepreneurs. I spent about an hour and 45 minutes with each one. These were entrepreneurs who were starting companies with $50, $100.

It struck me because to a person, Doug, they all said like, “If this doesn’t work out, there’s opportunity everywhere.” I was struck by the difference in the mindset and still to this day, what haunts me, is something is called the Pygmalion effect. The teacher’s unconscious assumption has an enormous impact on a learner, good or bad.

It’s always been that way, Gary.

It’s always been that way but the teachers don’t realize how they’re indoctrinating young people into an employee mindset that’s leaving them increasingly vulnerable.

The only two teachers that I remember from my entirety of high school and grade school, there are three. Mrs. Lacey in fifth grade.

What was her claim to fame in your world?

Let me tell you back then, I’m sorry. Mrs. Lacey was great. I remember a teacher when I was in third grade. The Atari 2600 was the big thing. They would all break. I figured out why they were breaking and which circuit needed replaced. I would go to Radio Shack and buy that circuit. I was fixing Atari stations. I was an eleven-year-old boy and I’m fixing Ataris with a soldering iron. If I finished my work on time, she would let me fix Ataris in the back of the room. I had a soldering iron, an old station, and I would fix Ataris. That was somebody that saw something in me and let me do thing at my own pace.

Mr. Johnson, my senior year of high school in creative writing, let me write the way I wanted to write. I was one of only two kids that year that he gave an A to. Mr. Hoffman, my art teacher who let me do art the way I wanted to do art, and didn’t hold me back and didn’t give me weird assignments, “Let’s do a drawing this week and let’s do it this week.” He would give the problem and let me come up with what my solution to that was.

Those were the teachers that mattered. My government teacher, my math teacher, my criminology teacher, my everybody else teacher, if I didn’t do something the way that they expected it, I got a bad grade. That’s why I graduated high school with a 1.2 GPA, because I had two As, and the rest of them were d’s. They got me through to graduation because they didn’t know what to do with me. That was why I graduated high school. They didn’t know what to do with me.

Same. Let me try to land this point, Doug. I think I’ve interviewed 700-plus entrepreneurs all over the world, and very often, there are people that are being overlooked, rejected in the academic domain. These are people that are C students. I think there are other dimensions of intelligence beyond GPA. I think that this obsession with GPA is just overlooking this huge swath of talent. You’ve heard the joke, I’m sure, like the A students wind up teaching B students how to work for the C students. That’s how it goes.

Being Happy With Yourself

Doug, just to wind down here, we’ve been going for nearly 2 hours but it seems like about 15 minutes. It’s like, there’s so much to unpack here. I feel like there’s still more, we needed a 2.0 here, but you’ve learned some important lessons about yourself. I’m so grateful for your willingness to be transparent, vulnerable, and talk about your failures.

My failures are more important than my wins. My wins put money in the bank. My failures are what put the wins in.

I also love that you are using that to help aspiring entrepreneurs and to coach entrepreneurs and be there for people. That’s such an important part of the equation. I think that’s an overlooked resource that’s in every community we don’t really tap into.

It doesn’t exist in a lot of communities too. That’s the thing.

I think you can create it.

You can create it, but you need a spark. You need somebody that in that community that’s willing to roll up their sleeves and get dirty with somebody else’s dream.

This nineteen-year-old kid, he’s a freshman in college, he reached out to me, he goes, “I created a podcast just to create my own learning journey. Would you be on my podcast?” Yes, I will. That kid, nineteen years old. He got that guy, that FBI hostage negotiator guy. He got him in his podcast. You can create this learning network, but again, what it comes down to, Doug, it’s not the know how.

It’s like psychologists talk about this hope circuit. Is the hope circuit in your brain open? Are you looking for answers or you just trying to distract yourself? That’s what it comes down to. What have you learned about yourself in this journey, Doug, that you think can help aspiring entrepreneurs at whatever stage they are, whether they’re Dana side hustlers, or the hardcore all-in tech entrepreneurs?

I can’t speak for everybody individually because literally, everybody is different. What makes them tick is all different. By and large, the best piece of advice that I can give to anyone is to be happy with themselves above all else because when you’re chasing a dream, it’s really easy to say, “I’ll be happy when I get X or I’ll be happy when I achieve Y or when this comes in, then I’ll be happy.” That’s backwards. Get happy first. It doesn’t matter when that other stuff comes in because all you’re setting yourself up for is disappointment and resentment.

You’re also setting yourself up to be just a stimulus response bunny.

That’s not the right way to be. The right way to be is if you’re happy from the jump, it’s all upside. I’m telling this to my kids right now, “I don’t care if you are a basket weaver for a living, as long as you are really happy weaving baskets.” As a father, nothing is going to make me happy than my boys being happy with who they are and what they do.

It doesn’t matter the degree, it doesn’t matter the education, it doesn’t matter the pay. If you can cover your bills and you’re happy with what you’re doing, that’s the goal. That’s game over. When you are doing something that you love, it’s not a job. If you’re making enough money to keep your life okay, then it’s not a job. You have all the options in the world to do whatever you want to do. That’s the best.

That’s beautiful. Doug, I put a quote in my book, I forgot to name the Greek playwright. Steam just went out of my head, but essentially, he said like 2,500 years ago, it’s the duty of a man to make himself useful to other humans. By doing so, he advances the welfare of mankind.

That goes back to the service part of the AA triangle.

Absolutely. It’s all twelve-step stuff, Doug.

It’s all twelve steps at the end of the day.

I love it. Doug, let’s leave it there. Thank you so much for sharing your story. Thank you for your honesty, your heart, your brains, all of it, bringing your story. Thank you for sharing it with the world, Doug. I really appreciate it.

Of course. Anytime.

Important Links

• Doug Hardman on LinkedIn
• Office Snapshots
• Start. Scale. Exit. Repeat.
• The Total Money Makeover
• Employment is Dead