Tyson Nargassans | Jurassic Capital

Tyson Nargassans | Jurassic Capital

[00:00:00] Welcome to the Amplified CEO with VC and serial entrepreneur, Richard Stroupe. With today's guest, Tyson Nargassans. He's an operating advisor at Jurassic Capital and the founder and former CEO of Saylent, a FinTech company he led to a successful exit. Tyson is a seasoned board member, founder and CEO, who has scaled multiple B2B software companies, empowering teams, and using data to drive results across FinTech, healthcare and enterprise software. 

Tyson, welcome. Thank you. Good to be here. Absolutely. You recently spoke at a Jim Roberts event a couple weeks ago at UNC Wilmington and, and I was in attendance and, and I was very impressed to hear your background and your skillset and everything that you've accomplished. So of course I had to ask you to come to this podcast, so thank you for, for coming and indulging us.

Well, you gotta get to talk about all the things that we did. It's some of the fun times. So thank you. Absolutely. [00:01:00] So going off your involvement with Jim Roberts and others, how active are you kind of giving back to the community and sharing your story and, and the kind of an advisor role in, in just helping organizations like gems?

I think there's a lot of people who've helped me over the time of my career and, and one of the things, when you find a, found a company, there's just a lot of. Big efforts, small efforts, just people along the way. Mm-hmm. And so I have always wanted to, to give back. It's one of the things I think that fills my cup.

I wish I could do it more. Mm-hmm. I try to do it as much as I can, and right now I'm, I'm fortunate enough to be able to, to do that. I try and tell people all the time. There's tons of things I've done well, I think, and then there's a lot more probably that I, I didn't do well. Mm-hmm. Both offer value, I think, to people who are going through it the first time or just one another perspective.

Right. Founding a business, running it, being a CEO is a lonely job sometimes. Mm-hmm. Especially if you are, well, even if you have [00:02:00] co-founders, it's still lonely. It's, it's, it's often, you know, you don't know who to talk to and what you should share and how you should do that. So I try to be a resource as much as I can to everybody else and, and help it out.

And, and I've really enjoyed it getting involved with cd Jim Roberts. Um, just local ecosystem, the founders. It's been a, a, a tremendous joy for me. That's great. Now, do you sit on boards, a lot of boards now. How active are you? Um, I don't sit on any boards currently. I sat on rubric. Um, I do like the board perspective.

I think I've learned a lot having, having done it, both sitting on a board and, and working with a board. I, I think I know where your value should be. I would like to sit on more boards. I think it's, it's a really interesting perspective. It's one of the things I have not been a big proponent of CEO coaching and, you know, I'm sure they offer a lot of value mm-hmm.

To, to different people. From my perspective, I liked hearing somebody else's problem and being able to relate it to, to what I've experienced. And, and I think when you see it from a different perspective, I'm, I'm [00:03:00] human like everybody else, you'll get too close to it in the old forest, through the trees, right?

Mm-hmm. And so. Trying to see it from a different perspective is something that I've, I think is really valuable at, at all levels. And I would encourage every founder to stay out, talk to people, see it from a different lens. Mm-hmm. And try and then apply that problem to your business. 'cause one of the thing you recognize is the patterns are pretty similar.

Right. So, pivoting off that, what, what are, what's your views on today's world? I know your background is in B2B software and FinTech, um, or, or data science, I guess. Mm-hmm. Like what, what is your views on today's economy and what, what everything is going on right now around the world? It's a really interesting time for B2B SaaS.

There's, uh, you know, there's the, um, gloom and doom message around AI is gonna overtake everything and vertical SaaS isn't gonna be relevant. And then there's. The other side of that coin, I suppose, where AI is gonna cause everybody to just be more productive and more effective and mm-hmm. [00:04:00] And more focused on, on the problems at hand and the less on the, the, the menial tasks.

And I think I ride somewhere in the middle of those. I, I, I've seen enough trends. I think where, you know, we started sailing no six back in that time. It was big data. Mm-hmm. The oop, data lakes, data warehouses. Mm-hmm. Uh, it moved and morphed to visualizations and analytics insights and then it morphed into machine learning.

Then it morphed into ai and now it's LLM and you know, whatever will be next. Um, so I think like anything, technology advances mm-hmm. You need to be flexible enough to advance with that and see how you're going to take that new landscape and apply it to your business. Mm-hmm. There are still problems to be solved.

Computers aren't gonna be able to solve 'em all. Um, right. And so, but it does require a shift, I think. You know, that's the technology side of it. I think the business side and the sort of macroeconomic environments also changed a [00:05:00] lot. Where, you know, there was growth at all costs for a period of time.

Go back to the dot com when, when I was there and, you know, it was all about just raise money and grow. Today everybody cares about profitable growth or, or, you know, cash efficient growth or The, like, they're not, they're not interested in this, you know, uh, grow at all costs mentality. And so I just encourage founders.

I was talking to one on the ride down today and I just said the most important thing you can do for your business is to show people, um, or prove that people want it want it. Um, and that can come in a lot of forms, but the proverbial traction show, traction show that people are interested in what you're doing.

And I think be, be wary of. Building what you want Versus what people are telling you they're interested in. And there's a fine line between holding your vision [00:06:00] and being stubborn with it. Right. So, yeah. Have you been experimenting with any AI tools and just for research purposes or, or commenting to other founders about how to adopt AI to I have.

That's been my big, um, effort. This, this sort of transition period that I'm in right now was trying to really use AI to my own advantage. Mm-hmm. And to learn about that and where can it be used and how smart is it? And sometimes how dumb is it? Mm-hmm. And, and, you know, where is, where can it be applied to make me more productive?

So as I've started to learn these AI tools, the, the thing that has been really valuable has been. Learning new markets, understanding new competitive trends, where is the, the, the size and, and market moving, and then taking those learnings and putting your own lens over it. 'cause it's not always gonna be right.

But it is incredibly valuable in trying to come up to speed on how effective or, uh, your product is in the market. Mm-hmm. Uh, where the, where the market [00:07:00] is moving. Um, I, I find that incredibly valuable. When we exited Salan, one of the things I was really conscious about in, in, as I came back from my recharge was I didn't wanna be label the FinTech guy.

Mm-hmm. And if I went back into FinTech immediately, I was gonna be the FinTech guy. Mm-hmm. It, it's important for me in my own personal growth that I wanted to see new industry, see new markets, see new problems, not just continue to solve the same problem over and over in the same industry. Right. With the same players.

Mm-hmm. And so I, I made a conscious effort with procurement, uh, and with everything that we're doing now, just to try and make sure that I broaden my own perspective and that allows me. Now to see it and see all the patterns that, that exist across that. Mm-hmm. The problem sets tend to be very similar.

Mm-hmm. Um, the solutions may be different, the market may have nuances, but the problems are all the same. Mm-hmm. And so, um, and I think AI has been really valuable in that and just helping me understand and, and get up to speed instead of what used to do if, you know mm-hmm. Read a ton of [00:08:00] books and, you know, Google search your way through, through all the learnings and talk to everybody you possibly can.

You still have to do some of those things. Mm-hmm. But it can synthesize data pretty well. Absolutely. So tell me about your early days at Skidmore. I understand you were a basketball player. I was, how did that shape you being a college athlete? How did that shape your leadership style and working with others and building some resilience and grit?

Uh, I think basketball's a core part of who I am, and it's always been I, I try to, to remain active, remain playing I coach and, and I really enjoy, uh, staying connected to that. I'm I think what you learn. And I, I, I'm a big believer that athletics and being an athlete and competing, uh, on your own and with teams is, is just a, a really valuable skill set and something that, that really helps you in business.

So from that perspective, it has always been part of me. I think you learn, you learn what your role is, you learn how to work with others. You learn how to lead, you learn how to [00:09:00] follow. Mm-hmm. Um, and I, you know, just at Skidmore, you know, I was everything from a, you know, bench player and a reserve player to a key reserve player, to a leading scorer to a captain.

And so, through my four years, my role changed year over year. And what I was asked to do changed. But, you know, I think understanding where you are, what your role is in that organization, how you make them successful, how you work with others, how you motivate others. Um, how you build culture and build, uh, on what.

What you're trying to accomplish and, and, and doing it together. Uh, some of my best moments were not always on the court. I, I probably remember, tell my teams this all the time. I probably remember three to five games in my career. Mm-hmm. Um, but I, I have countless memories of my teammates. The bus rides, the dinners, the right, um, the interaction, the camaraderie.

Yes. And, and that's part of building a [00:10:00] business, right. There isn't, not everybody can be the leading scorer Not everybody can. Mm-hmm. You know, there are roles that you all play. And, and, and I think that taught me a lot about competing, overcoming adversity, working with different, you know, characters and personalities and trying to accomplish a singular goal mm-hmm.

Uh, with a team that's been, you know, really valuable to my business career. Absolutely. Yeah. I, I share your experience. I played, uh, football in college and I've pushed sports early on. All my kids. I have three kids and. My oldest daughter plays volleyball, um, in college and she's entering her senior year and she, she thought about giving it up 'cause she's an ROTC as well.

And for a time commitment, like, ah, I'm entering my senior year and, you know, I try to stress, I'm like, no, you have to see this through. Like, it's consistency. I know you may want to believe you would save time from practice to devote it in other areas. [00:11:00] I said, but looking back, you're gonna regret not finishing out your senior year.

So I'm glad she's decided to, to finish her senior year sports, you know, for most of us sports is a, is a wonderful experience. It can be incredibly humbling and you have a, a lot of adversity. I remember in my sophomore year, I, I, like I said, I didn't play a ton my freshman year, but in my sophomore year, I, uh, we went overseas.

I thought I played pretty well and I thought I was gonna come back and have a really impactful sophomore year. And I, I. I probably did in hindsight, but in the moment it felt like, oh geez, I should be getting more, I should be having more time, more shots, whatever it might be. And so I remember after my sophomore year, I walked into my, uh, my coach's office, um, coach Q, it's good Morning's Great.

And I walked in, I said, you know, I'm thinking about transferring. This is well before NIO transfer portals. And anyway, oh, that's a mess, isn't it? Yes. Yeah. Um, and he is like, okay, you know, and he's like, I think you should stick it out, but you know, I'm not gonna, I'm not gonna beg you to stay and mm-hmm.

And so, you know, overcoming that [00:12:00] adversity. And then the next year, I think I had a really good year. We bonded. There were three of us that was sort of leading the team. And, um, I think one of the challenges in today's society, not to get on my soapbox, is that it's too easy to quit and move to someplace else rather than fight through that adversity.

Mm-hmm. Um, I'm all for people getting paid and doing, doing what they need to do, but sometimes you gotta fight through it. Mm-hmm. And you know, there's a lot of business parallels to that. We can go through a lot of Saylent discussion about that. Founding a company and, and going through the journey is by no means a linear event.

There's tons of hills and tons of valleys that you will go through. Mm-hmm. And if you're not used to fighting through that adversity and overcoming the obstacles in front of you, you will not be successful. Mm-hmm. It's never pure, it's never simple. Right. And so, I, I think sports teaches you a lot about that.

Yeah. Does your, your kids play sports? They do, both of 'em do. Uh, my older one was a three sport athlete, uh, probably more of a track in cross country than a basketball player, though she did play [00:13:00] basketball. Mm-hmm. Uh, my youngest is really focused on basketball, has no interest in playing at the college level, which sometimes pains me, but as a parent you just, you just accept that and I'm just happy that they find their own course back.

One of the greatest times I was an assistant coach with, um, the school I coach with right now mm-hmm. Where my oldest daughter was a starter and a senior, and my youngest daughter was an eighth grade and a, and a starter as well. And so I got to, mm-hmm. I have a unique experience as a parent where you got to coach 'em in the sport that you love and, and all them have success in it.

And I'll cherish that one. That's, that's a great memory that I'll have for forever, so. Right. Yeah. Were you recruited by other colleges other than Skidmore? Love to tell you. Yes, I was. I mean, you know, I was, I hurt my knee not to make excuses. I hurt my knee junior year, 10 games in, did not blow out the ACL, but, uh, that ruined my junior season.

A lot of the recruiting. This was high high school. Yeah. This was high school. Yeah. Um, and then, so when I was a senior, uh, I had some D three offers and mm-hmm. And looks around and [00:14:00] Skidmore was the right fit with me. There were a couple other schools that I could have gone to and played. Mm-hmm. Um, one of the things I prided myself on that I think is, is important and something I carry through today with, with my family and, and my friends.

I just think it's important. Mm-hmm. One of, one of the most. Valuable things I think I brought to the table is I think I've constantly improved. Mm-hmm. Um, through my athletic career, through my business career. I, that's the only thing that drives me. I want to continue to learn. I want to continue to get better.

I wanna learn from the mistakes that I have. Mm-hmm. And I never wanna be complacent with where I'm at. Mm-hmm. And so I think seeing some of those things and, and, you know, I was, I was proud of how I came on with not being a, a heavy recruiter to end as, you know, the proverbial thousand point score. Mm-hmm.

I, I got that milestone in college, which was a lot of fun. Would you say it kind of put a chip on your shoulder a little bit to prove people wrong? Like, Hey, I am a better player and let me show you not as much as I think you'd think. Mm-hmm. Um, I was more [00:15:00] focused on trying to be the best version of me.

Mm-hmm. Um, I was trying to check the ego at the door as best I can, although I certainly have one. Um, and, and really enjoy the moment I. I just wanted to continue to get better and I wanted to beat whoever we were playing. I had a, a, a real competitive spirit and a drive, and a, and a need to, to win. Mm. Um, and do everything I can to accomplish that goal.

I, I was not too, I look back on it now and think to myself, boy, I, I probably could have done some other things if I really wanted to, or maybe pushed my athletic career to a, to a D two or a, probably a low D one. Mm-hmm. Skidmore was a great fit for me. I really enjoyed the experience and like I said, I think it shaped who I am today.

That's wonderful. Now, you grew up in the Boston area? I did. And you, you moved back to the Boston area after college? Yes. Yeah. I, I've been, uh, Boston. Really born and bred for the most part. Lived there all of my life with [00:16:00] my wife. I. I did have a short story, a short stint after college in New York City.

Mm-hmm. But have worked and lived in Boston pretty much my whole time until we moved down to Raleigh in, in Covid time. Mm-hmm. Yeah. Boston's such a wonderful city. Yes. It almost feels like a, a big neighborhood anywhere you go. The back Bay or Cambridge or, you know, down by the, the, the water. I mean, it's like, and people are generally warm and welcoming.

Yep. Um, you know, the Italian district, I, I don't know, the North End. It's great food. There's a lot of food there. Yeah. It, I, I love Boston. I appreciate the weather down here. More than I appreciate the weather up there. I've, I've gotten in my old age, uh, I have no purpose for, for winter sports. I don't, I don't, uh, I don't ski, I don't, I don't play Hockey are brutal.

Yes. Yeah. I mean, I could live in Boston except not in the wintertime, you know, I just, I don't think I could, I. I I wouldn't like that. I mean, I was, uh, if, if we could design something, I'm okay with [00:17:00] January and February being cold. It's cold down here. It's not as cold, but Right. I, I'm okay with January and February.

What I realized when I moved down here was I was pretty depressed in March, April, and early May. Mm-hmm. And the reason I associate that, uh, to, to Boston is I think there's always a 60 degree day, sometime in late February, early March where you think spring's upon you and the world is gonna change and you can go golfing and boating or whatever you wanna do outside.

Mm-hmm. And then it's gonna continue to snow on you for the next two months. Right. And so March and April, I was like, aren't we done with this? Yeah. Let's, let's go. Um, and then down here, you know, March one, it's spring and, you know, you might have a cold day every now and again, but Right. It's gonna be spring pretty consistent.

Yes. Yeah. My daughter attends, uh, WPI. Worcester Polytech. Sure. So we go up there a lot and see her. She plays volleyball there and the great school. Great, great. Um, yeah, there's a lot in that area. Yeah. Surprisingly, Worcester's got like really good restaurants. Yes. You know, there's, there's a [00:18:00] seafood place that, that she always wants to go when we go visit her.

And it's like, they, it's just awesome. It, it, oddly enough, I really do like Boston, like Massachusetts, since we've moved down here, I don't think I've been back yet. Um, oddly enough, but How long has that been? Five years. Okay. Well, you probably do. Yes. Well, we don't have, we, we have friends up there, but our family's, uh, my family's not there.

My wife's family's up there. We have not mm-hmm. Traveled back. She's gone back for some, um, some events that she had to go to, but we have not made it back there. And I think that's. 'cause we're happy in Raleigh, not because we were sad to, you know? Right. Yeah. Yeah. We obviously miss our friends there and miss our family, but we really enjoy where we're at.

Yeah. So you're a big Red Sox fan being a Boston native? Uh, I would say I'm a, a bigger Celtics fan. I'm a little disappointed about, uh, the last night's outcome with the Knicks, but Right. Um, uh, in order, I would say I'm Celtics Patriots, probably Bruins and then Red Sox. Okay. Um, but everybody asks, well, who, you know, who, what [00:19:00] college do you root for?

Or whatever. You know, it's more of a pro town than it's a college town, so, right. Yeah. Uh, I have not, um, I, my Allegiance is now, or to Carolina, 'cause that's where my oldest daughter goes. Okay. And, uh, we'll see where the youngest goes. We will add that to the, the flag and go from there. Yeah. Yeah. Going to Fenway is an experience.

Yes. It's, I mean, it's, I, I took some classes, well, this, uh, executive ed program at Harvard where it was in the fall, which fall time in Boston. Phenomenal. Like, you know, the, the boat race on the Charles River and. You know, it's just, it's iconic. You can, you can't really describe it any, any better, but, um, the cohort and I, there was a lot of guys that wouldn't like to go to the, the baseball games.

We would always take the, uh, cab ride, metro, whatever, down to the Fenway and watch a baseball game. And every time we went to Fenway, we always sat next to someone who was super interesting and they had a story to tell. One night we were sitting with a bunch of rowdy guys from Southie, you know, [00:20:00] 'cause Sure, you know, they, they have their own unique Yes, they do.

Personality. And, you know, wool Wool was one of the comments I was talking about. So we were sitting there chitchatting with the guys and they were buying us beers. We bought them beers and it was good. So, of course, like, you know, where are you guys from? What are you, what are you doing in Boston? And we said, oh, we're taking an HBS, you know, course we're here for three weeks.

He's like, oh yeah, I go to, I go to Harvard every, every night. I deliver newspapers there. Ha ha. You know, it's a dry sense of humor. But there was one time we went and I was sitting next to a family and, um, it's guys very nice. Everybody starts talking, Hey, who are you? What, what's your name? Where are you from?

You know, just wanna know your background. And this guy starts talking about his kids, you know, and, and he's talked about his daughter, you know, oh, my daughter's fantastic. She's in, she's at John Hopkins, she's, she's gonna be a surgeon and she's in med school and blah, blah, blah, blah, blah. And he just goes [00:21:00] on and on and on and on and on about his daughter.

And I'm like, oh, what about your son? He goes, oh, that a-hole. He's sitting right over here, you know, and then this kid like peeks around the side with his, his hat sideways and you know, he starts shaking his head 'cause his dad's sitting there just railing him. He's sitting right next to him. There is no shortage of characters in Boston, that's for sure.

And while I say I don't follow the socks much, there is a, a, a definitive experience to go to Fenway. Right. Um, it is tremendous. If you haven't had the opportunity to go, I would encourage you to sit up on the wall seats. Those are phenomenal. Mm-hmm. Um, there isn't, I mean, there's maybe a bad seat 'cause you'll be behind a pole or turn the other way sometimes.

Mm-hmm. But, uh, it is an experience and, and so I always would go to one or two games a year just for that experience. We had the opportunity living in Fenway for a period of time and that was great. Uh, we were walking distance to the stadium one of the [00:22:00] years they won the championship. They celebrated outside our apartment window at the time.

And it was, it's just a, it, it's a very interesting community itself. Mm-hmm. Just generally. Um, and the, the characters, the people are, are always fun. So Have you been to a Dropkick Murphy's concert there? I have not. I've been to a number of concerts in the Fenway area. Mm-hmm. There's a couple of venues there and, uh, they, the Drop Kit Murphy's are, are certainly popular with, with the, uh, the Irish group though.

The Irish community. Yeah. They came to DC earlier this year. I, I, I went with a buddy. Oh really? For that concert. It was, it was wild. They get after it. Yeah, they do. Yeah. Very high energy. Yes. Upbeat. I told my daughter, I said, you should go to Fenway to the, you know, St. Patrick's Day concert. And she did. And her and some friends win.

I'm like, oh, you know, it was like, that's awesome. Yes. Yeah, there's some great stories there. I understand. Every year, CNBC always puts out this best, best state to work in for business. And North Carolina [00:23:00] always ranks high on the list, if not one in the top five. Uh, did that have any insight or impact into your decision?

I mean, why, why did North Carolina, I would say you took into account that it was a good state for business. Mm-hmm. We were already doing business, so that was less of a factor, I would say, in the choice of why we moved here. I, I would say it was a little bit more lifestyle. There were a couple of, uh, requirements for us.

We needed to be close to Boston, easy to return to the, to the business. When we did come back, whenever that might be from Covid, um, we needed some technology in case there were engineers or, or people comfortable with. Mm-hmm. You know, B2B SaaS and just the ecosystem that, that both we could connect with and potentially hire from.

Mm-hmm. Um, financial services was important. So East Corridor, uh, the eastern corridor was important to us. The weather in North Carolina was a nice selection. We looked at, we didn't want anything to do with San Fran at the time. You know, Austin, Texas was, was discussed. Atlanta was discussed. Mm-hmm. But ultimately it [00:24:00] came down to North Carolina and then looking at the.

The various cities we could live here. Mm-hmm. And Raleigh just offered a different, um, experience. I think for us. I think Charlotte would've been, while not Boston, maybe closer to Boston. Mm-hmm. And Raleigh offered just a nice community for us to settle into. Mm-hmm. There were a lot of, uh, hopes and dreams about what it might be.

You never know. 'cause it was covid. So we didn't have a great opportunity to experience what it was like until a couple of years after. I would say we, we moved where everything really started to settle down and back to normal, I would say. Mm-hmm. But we really enjoyed the experience. It's been, it's been a great thing for our family.

So you mentioned starting sailing in 2006. So what was, what was, what was the item that pushed you? What was the, the aha moment that made you wanna start your business? Classic entrepreneurial story. Um, I was at a conference in Vegas and we [00:25:00] had an opportunity, I thought I. From all of my discussions, we were in, in the ATM field at the time, and we were selling to, originally to ISOs, which were independent employers of ATM machines mm-hmm.

Managing their business. And we converted and moved, uh, to expand our market to banks. Um, and when we did that, we saw a very different mentality with the banks on, on our solution and what we could do. Um, they viewed ATMs as cost centers and while they were touch points with their customers, they were really trying to make it a, uh, a low touch, very efficient, um, uh, distribution opportunity or channel for them.

But they did have a revenue opportunity in cards and, and their debit and credit cards in particular. And so, um, people had told us that for a long time. And so the aha moment was just a series of listening to what the market kept asking us for. We couldn't deliver that. Mm-hmm. And so there [00:26:00] was a gap. And when you started searching, there was a very apparent gap in, in analytics around card behavior.

Mm-hmm. And so I drew on a napkin in a bar after a conference to one of the customers that I had sold to saying, I think this is what you need. Does this align with that? They were very positive about it. Talked to another customer, they were positive about it. And so I flew home and woke my wife up out of, out of a sleep, you know, come home in Vegas time, it's 11 o'clock if you leave early in the morning.

Mm-hmm. Woke her up, said, I think we got an idea for something. What do you think? And she asked me to talk about in the morning. We did. And, and at the end of the day led to, uh, led Tost. And so I had always wanted to start a business. I'd always wanted to, to go through this experience. Um, I didn't know what it was, and I promise you when I thought about it, it was never gonna be, I was gonna develop a banking, you know, FinTech solution, but.

I think if you listen to the market enough, the market tells you [00:27:00] what they're looking for. Mm-hmm. Where you'll see the gaps that are, that are present. And they, they're not all home run ideas. They're not all, you know, billion dollar unicorn companies. Mm-hmm. There's a lot of solutions that businesses need.

And if you listen hard enough and you are, I think, bold enough to try and take the, the adventure on, right. Um, that's, that's how Stanley got started from that experience. And the idea, how did that transition into a prototype? So you had, you had a customer, you gave them a vision, and they're like, yeah, I'd love to use something like that.

Um, did you develop this yourself? Did you hire a developer? How, what, from a technology point of view, how did you create. This analytic engine. Sure. That, that's probably the naiveness that I had of, of starting a business. I, I thought to myself, well, I'll just design what it should be. Mm-hmm. And then I'll hire somebody to help me build it and off we go.

Um, looking back on it, that's [00:28:00] maybe somewhat foolish. Um, but there was a lot of learnings. 'cause you're going into a highly regulated market in banking. Right. They don't love risk. Um, so you have all of these factors that are driving against being an entrepreneur in banking. But the idea, I think, was strong enough to what we're doing.

So, um, this is one of the things I talked to a lot of of founders about. Mm. You have to take your idea and then operationalize it. Mm-hmm. And, and that requires a set of rigor and discipline that not everybody has. It's pretty easy to talk about an idea. Mm-hmm. And. I've, you know, challenged. I, I think you learn a ton by putting business plans together and, and projections, right or wrong, the, the, uh, the exercise to put it down on paper.

Here's what we're gonna build, here's what we're gonna go do, here's how the business model's gonna work here, the projections that come behind that, here's what we're gonna need to accomplish that. Mm-hmm. [00:29:00] That rigor flushes out a lot of, um, information and makes you make decisions along the way. And so, back to your point, I went to work on writing a business plan, and I went to work on the product spec and I said, this is what I think the market needs.

I validated it with the customers that I had talked about and people I knew in the industry. Mm-hmm. You know, I, I went through the whole, uh, you know, I incorporated right. Started the business, got the legal fees done, and, you know, some of those things are now a little easier than they were in the past, but mm-hmm.

I, I think we tried to set it up right from the beginning. We tried to go after it and then we, we validated that I actually was fortunate enough to get two customers to buy into it mm-hmm. Before we ever coded anything. And I promised him, I said, we'll build this. I would love your input. Uh, I'm a big believer in customer driven, uh, and market driven development.

That is not to say you make custom software, but it, it does mean [00:30:00] to allow some input from the people who are gonna use this, that, that they're the ones that have the problem that you're trying to solve. Mm-hmm. And so we had them sign, I hired a developer and we went off and, and running. So I would say we, we incorporated in January or February oh six, we probably had our first deal, um, March or April mm-hmm.

Of oh six. I think I hired the developer in, in March of oh six, I would say. Mm-hmm. And we bootstrapped it for 15 months. We paid the developer. Um, we got to market later that year with our first sort of prototype. Mm-hmm. MVP. They liked it, they enjoyed it. Um, they were super helpful in, in allowing us to build the business.

The, I'll never forget, uh, the two customers that came in early, they were incredibly impactful. They stayed with us right to the end. Mm-hmm. Which was great. Um, and, and it was an incredible journey. Your experience is very difficult to replicate and it's easy [00:31:00] 'cause like when we talk to kids at colleges, you know, 'cause entrepreneurship and starting a business is, is huge.

It's like a, the up and coming trend. Everyone must take an entrepreneurship class and they have majors now of entrepreneurship. Like, how can you major in entrepreneurship? Like it's a, it's a tool to process and methodology, but it's like, it's not a major you need to focus on. Core engineering or accounting or business or medical or biology or chemistry, you know, just something core.

And I always tell kids, go get experience. Go learn how businesses run and how customers interact and what, what works, what doesn't work. And then seek out validation. Find a business need that's unmet. You know, a lot of, a lot of kids come up with ideas and start pitching just off a PowerPoint, oh, this is a good idea.

Well, have you done the market analysis? Have you done the validation? Is there an unmet need? What's the competitive landscape look like? You know, [00:32:00] so it's a good idea, but somebody already solved that, you know, so you have to do that type of research. And it sounds like you were very fortunate to be at the right place at the right time, and you uncovered a business need, uh, that was unserved.

And in addition, you signed customers before you even had expenses. As, as in today, a lot of lot of companies, you know, have expenses before they have customers. They don't mind the burn and they get in trouble and now they have to look for capital. And you're speaking to a point that I talk about a lot, which is, you can't dance, you can't, you can't do this part-time, you can't, I mean, we jumped in, maybe you could argue, you know, without a parachute, maybe that wasn't the smartest thing either, but you, we fully committed into what was about to happen.

Mm-hmm. And there wasn't, it was either gonna be successful or it was gonna fail, but it was gonna do those two things on its own merits. Not because I didn't put the time in appropriately. Mm-hmm. Uh, or I didn't, [00:33:00] I didn't go after it fully. Mm-hmm. Um, and I think there's a lot of, um, desire to, to not risk, to be an entrepreneur without the risk, which is not what entrepreneur.

Mm-hmm. I mean, you have to. Be willing to Right. Fall and fail. Absolutely. And, and so I think that's a really important thing. I think it is. Again, I think you can do things on the side. I think, no, not everybody is, is fortunate enough to be able to just quit and not have income and do that. I get all that.

Mm-hmm. But, and, and you can start the mechanics of, of a business on the side, you just can't run it. Mm-hmm. Um, you know, it has to be from there to a proof point. Right. And then that proof point has to lead to another proof point. Mm-hmm. Um, and at some point in time you're gonna have to jump before anybody else is gonna believe in it.

Did you keep your full-time job and work on this on the side or did you I did not. You quit your full-time job. Mm-hmm. And you went all in. Mm-hmm. Did, did your [00:34:00] wife continue to work her job? Did you have income? She did not. We were, uh, so this was January of, no, December of 2005. Okay. We, we had the idea. So I think we can do this and, um.

In January, we started putting the mechanics of the business plan together and the, the product spec and the PowerPoints and, you know, all that kind of stuff. We did, um, we're fortunate enough to do a little bit of friends and family, put a little bit of money in just seed stuff to, to allow us to hire a developer.

Mm-hmm. We put our own skin in the game, both monetarily and not being paid, right? Mm-hmm. So we got to a point where we could find somebody to build it. I'm not a technical resource. I, I think I understand how to build product. I think I understand how to, how to build, you know, code. I, I couldn't do it myself, but I don't understand what is a good I.

Software product and what isn't. Mm-hmm. Um, I wish I had those skills to be fair. 'cause that would be easier. Well, you have a little time now, right? I know. I, I I should, I should go after it. Go back and get your doctorate. [00:35:00] Yeah. But it, it was, we, we fully committed, um, we, we were about to have our first child, um, that following May, uh, sorry, July, uh, we built a house that was delivered in May.

So, okay. That's a huge risk. So you stop work, you went all in on a business plan, your wife's pregnant and you're about to have a kid and you built a house. Yes. There's a lot in six months. Like, let's add a little more stress to your, that's part of it. And, and you know, I would say a little bit, part of that is good.

Uh, I used to have a, a mentor of mine. He was, uh, the CEO of the ATM company that, that ultimately got sold. Mm-hmm. To, uh, Jack Henry. And he would always tell me, you know. You have to go and, and do it. Mm-hmm. And you just have to be willing to put it out there. And, um, so we, we were really fortunate to be able to, to sort of make the decision to, to do it and [00:36:00] then to just be all in.

Mm-hmm. Um, whether, whether, you know, you do that again today or you know, what the different, uh, macro environment looks like. Mm-hmm. You know, or micro for you, what, what is your current financial situation? But to me it was about, there's an opportunity here. We're either gonna make it work or not. Mm-hmm.

Um, but it's not gonna be for a lack of effort. What was your backup plan if this didn't work? Since you, neither one of you had income coming in, you had some expenses and some outlays coming ahead. Um, did you have a backup plan? Did you have a, a period of time like, we're gonna give this a run? But if we don't see traction or income by this date, I'm gonna go back to work.

Or what would it look like? We did not have any of that. It's interesting because it's one of the things I tell founders now, uh, about how they should start their own business, especially if they're gonna bootstrap it and self-fund it for a period of time. Mm-hmm. Um, our backup plan was, it would fail and I would go find a job that's part of maybe the, the [00:37:00] ego slash confidence slash mm-hmm.

Cockiness, whatever, whatever's appropriate, um, to felt like I could have found a job again. Yeah. 'cause you, you worked in a very highly desirable sector that was growing Yep. And needed people like yourself. So you, you felt, you felt confident enough that if it didn't work out, I can enter back into the workforce pretty easily.

Yes. And I was fortunate enough, and I mentioned that I, I tell founders this today, it's pretty easy to, to die from a thousand cuts if you just mm-hmm. If you don't watch and, and. Really validate, are you getting traction on your story? Are you getting the proof points along the way that suggest you should continue?

I think we had always had that, so I never had to step back and question, is this right? Do people want it? Mm-hmm. The market was showing us they wanted it, I think because it was rooted in feedback from the market at its nascency, right? [00:38:00] Mm-hmm. We knew that the market had this problem, we just had to build it faster than anybody else.

Mm-hmm. And so we continue to have proof points along the way, but if you're coming up with an idea that hasn't been vetted or hasn't had that same feedback from the market, founders are incredibly scared sometimes to be vulnerable with their idea to the people they're trying to sell to. Mm-hmm. I'm sure for, for all the same thing.

Nobody wants to be told they're, they're, they're. Their idea's no good. Mm-hmm. Or they're not gonna buy it or somebody else did that. Those are, those are difficult things to hear, and it's hard not to be defensive when somebody says that to you. Mm-hmm. You know, so, but it's really important. Mm-hmm. You have to be able to, to, to be the leader of the business and realize that maybe what you're leading isn't what people want.

Mm-hmm. And so, in a founder situation, I now tell a lot of founders, if you're funding this [00:39:00] on your own and you're doing this, I would advise you to treat yourself as a VC or an investor into your business. Come up with a dollar amount, whatever it is, include your salary that you're not gonna be making what you would normally make in a market.

Mm-hmm. Um, and, and put that in. Said, I'm going to invest 50, 100 200,000, whatever the right number is. If you take loans and things like that, those are important elements for you to have a discussion with. You know, your friends, who, your co-founders, your, your spouse, partner, whatever it might be, because it will then tell you when you run out of money mm-hmm.

Which inevitably you probably will, then you can validate, have I made enough proof to where I would invest again? Mm-hmm. And if you have, invest more, and if you haven't, then maybe it's not the right idea. Right. And that's okay. Right. One of the things, I, I heard this at a conference, I wanna say last year, it might've been the Grandpa Palooza conference, [00:40:00] or it might even have been, um, Ed's Venture Connect.

I can't remember which one it was. But there was a VC that had talked about Covid actually hurt a lot of founding businesses, um, because it, there was so much money around and maybe rational or irrational excuses to why you need money. Mm-hmm. Because the world shut down and everything changed that it, it.

Limited business failures in a normal business cycle. Mm-hmm. And so you didn't have the normal run of people starting businesses, some being successful, some raising money, and some failing. There were a lot of businesses that sort of were, were zombie businesses that, that stayed around and probably shouldn't have.

Mm-hmm. And because there was money to just keep investing into the problem. And I think we're out of that now, but that, that still has a little bit of a drag on, I, I think the, the normal startup ecosystem of mm-hmm. [00:41:00] Find an idea, try and get it funded, try and build it, be successful, or fail and move on.

Mm-hmm. Um, every success and every failure causes you to have to re reevaluate your, your question earlier about my, what's my plan B Oh. But plan B could have been another idea. Mm-hmm. But if I feel like this idea's still hanging on, I'm more willing to put time into that. Mm-hmm. And so, um, I think it's just important.

Because you will invest more than you think. It will take longer than you think. Mm-hmm. It will be slower than you think. Nine times out of 10. Mm-hmm. And, um, that's okay. That's part of the process. Mm-hmm. But boy, it can, it can really, you can look back and say, I invested a ton of money in this and it never really worked.

Right. If you're not constantly evaluating and am I getting enough traction? Mm-hmm. Am I that it's a, it's a, it's a big word for me. Right. You gotta just, you gotta prove that people want what you're doing. And that's [00:42:00] the goal. So how long did it take for you to get some solid traction? I know you had two customers and then you started to actually develop the application.

I assume you used Hadoop Technologies Did not. We built it in sql. We built in T Net. Okay. Um, that was what the technology I was comfortable with in the prior, that was where the developer came from. Okay. That was his comfort. Um. Open source was just starting and in banking banking's five or 10 years behind a normal curve just because of the regulatory environment.

So open source was not gonna get widely accepted. Right. Um, we did not do Hadoop, but we were, we were in sql. We built it to, to answer your question, we had a 15 month bootstrap sort of mentality. So from January of oh six to March of oh seven mm-hmm. We were in funded on friends and family and our own money.

Mm-hmm. Uh, in our own time we had the two customers. We went to a conference that, later that year, um, in November, got [00:43:00] some real good success and interest from, uh, customers. I, I talked to Jack Henry was a big customer of ours, the, the company that acquired the, the prior company. Mm-hmm. I maintained all those relationships that I had, but we had continued to see traction through our life enough that we could go to the investment community.

Or the investor community and the VCs and say, we think we have an idea. Here's what we're gonna go try and build. Um, we were fortunate enough to find a great investor that, uh, backed the, the early round. Our first safes weren't big then. Convertible notes were, but safes weren't really popular. Right. It was you were gonna do a seed or a Series A.

Mm-hmm. We did a series a, a million and a half, um, led by, uh, a great investor in, in the north with half the check. And that's the most important thing. You've gotta find the first person mm-hmm. Who's gonna put their name down and said, I'll invest this if you can get to this number mm-hmm. And be the anchor for the round.

So that you said a million and a half. A million and a half, [00:44:00] what valuation did they give you at the time? Oh, that's a great question. I can't even remember it. It was low. Like sub low single digits. Yeah. I mean five, five to seven kind of thing. Yeah, that sounds about right. You know, especially if, if you pre-revenue.

Yeah. Or, or barely breaking revenue. Yep. Yeah. We had some good opportunities and partnerships ahead of us. We had, we had revenue coming and, and so, uh, that was the model we were gonna go direct to banks. That was how we started. Mm-hmm. Um, we had proven it out, um, at least in the early stages, again, with people saying they're willing to buy it, they're willing to contribute to it, they see the value.

Um, and, and so we had always had traction throughout. Mm-hmm. Um, but the, the first capital raised really allowed us to think about the business more holistically. And, and with greater intent for the future, we, now we can start talking about how do you build a development team? How do you think about a sales engine?

Right. How do you, [00:45:00] this is where, coming back to basketball, this is where just working with people and motivating and, and you know, you're selling mm-hmm. In everything you're doing, you're selling. Mm-hmm. You, you're, you're selling a product, you're selling business, you're selling, you're yourself, you're selling mm-hmm.

The vision. Um, and so to get people to come on board and, and join the. The vision was, was, um, mm-hmm. A lot of fun. Uh, there were a lot of yeses and no's mm-hmm. And both were helpful. Mm-hmm. Um, but I, I couldn't have been happier with the team that we had built. So was a dotnet architecture. Mm-hmm. Ms. SQL server in the backend.

Mm-hmm. Did you have to acquire your own servers? Like where, where did the data reside in the application to begin with? Yes. Yeah. Because again, this was a little before cloud started to be adopted, so I think we had found somebody who were selling servers on the side. And so we bought these rack servers And you set this up in your basement?

Set it up at the time, set it up in like, the closet of an office. Okay. I mean, it's classic, it wasn't our garage, but it was, it felt like it at times. Yeah. [00:46:00] Um, it was in a bank building and uh, we just had a whole bunch of servers lying on the tables, no rack. 'cause we couldn't afford the rack, so. Right. Um, we started building it on that, and the model when we first started was we would deploy it in their environment.

Mm-hmm. Um. And it was fine. They, they adopted it. But in 2007, October, 2007 happened, when Lehman went down, you saw the financial crash coming, I remember mm-hmm. The recession, everybody remembered that there was no money in the banking system. Mm-hmm. And so, as a startup, we had just taken money, which was the only reason we survived.

'cause we could pivot a little bit. And we started to say to ourselves, we're not gonna be able to get, you know, 50, a hundred thousand dollars checks, whatever it might be from banks. They had no ability to sign off on that. Mm-hmm. And so we looked at the market and we were getting some interest from, uh, what I would just loosely call payment processors.

People who mm-hmm. Run and [00:47:00] approve the transactions on behalf of the individual banks and cardholders. And so there's a handful of them in the market. There are probably 40 or 50 at the time that's since consolidated. I. And we were getting some traction there. And so we said to ourselves, okay, we we have to scale this thing up, make it multi-tenant, make it a SaaS delivery model.

Um, and so our model was, we made a pivot from, instead of being a a assailant driven product, we were gonna create loosely distribution channel arrangements mm-hmm. Where we would pre integrate with the payment process, which was the source of data we needed. Mm-hmm. Uh, in order to be beneficial for the individual banks and go through a white label powered by Lant model.

Mm-hmm. And that happened really from October, 2007 to, I would say early mid 2008. Mm-hmm. We had made the shift, we had two payment processors on board, and that became our business model. Mm-hmm. It was not the way I wanted to go [00:48:00] to market with it. It wasn't, I. It wasn't how it was supposed to go, if you will, from the business plan, the product was the same, but the revenue cycle, delivery management sales cycle, we were essentially offloaded all first line sales and support mm-hmm.

To these partnership arrangements. And we were second line sales support, second line tech support. Um, but we got to get out of individual bank by bank selling that would've asked for 15 to $25,000 in an implementation fee. Mm-hmm. X amount in an annual license and uh, uh, an ongoing maintenance to a, you can have it for a thousand bucks a month or whatever the right number was.

Mm-hmm. And to use that, it just opened up the gates because there's revenue in managing their cardholder behavior for them. And there's a need to understand customer behavior from a banking perspective. They just couldn't afford the price tag. Mm-hmm. And [00:49:00] so it was a question of how do you shift your go to market to adapt to what was at that time a new world with a lot of uncertainty into it.

Mm-hmm. And so we kept growing through the recession, which is, uh, which was great. Mm-hmm. Um, allowed us to really accelerate in that model. We sold a number of other processors, um, large, large companies that, that wanted to deliver this to their customers. And so it was, it was a, an interesting evolution of the business.

Were you only selling the product or the software as an annual license, or did you have services attached to it where they were paying you by the hour to when we started it was all license and, and software costs. Um, and when we moved to the SaaS model, it was a, a, a very simple. You know, per user. Mm-hmm.

Um, subscription fee. Mm-hmm. Um, later in our time we had actually, we started in the payment analytics. We had since, uh, we had, by the end of it had [00:50:00] built two other products and we had three products in the market. One that was very payment analytics centric, that we started with. One that was more, uh, rewards checking or a relationship rewards sort of model.

We could lever the relationship in certain ways. And the third was maybe a combination of the boast and more of a customer engagement platform. Mm-hmm. Um, and when we started to get to the latter years, we did start to offer marketing services that we would, uh, improve upon the information that they had.

We would, we would prepackage these programs for them and let them sign in so that they could check a box that they were moving the needle. Mm-hmm. From a customer perspective. And tho those were just learnings that we had never thought about when we first started, but mm-hmm. But again, the market kept saying, Hey, why, why don't we run a, uh, a joint program across multiple regions and mm-hmm.

Multiple banks and just swap logos and images and the like. Mm-hmm. And we had all the data with which to do so. Mm-hmm. [00:51:00] There's an interesting balance when you do that because now you're moving a little bit from a pure software company with great gross margins and all that good stuff to a, a little bit of a services business.

And there's a really interesting balance as you think about valuations and how you go to market. Mm-hmm. Not getting too weighted in that mm-hmm. Uh, was an important characteristic or concern of ours as we were built in the business. But, uh, ultimately it worked out and there was a lot of learnings in that, um, that I think we'll get into maybe a little later, but really moving from a software provider to being the expert on what they should do.

And, and that evolution's a pretty interesting one. How large was your team? I think at our peak we got up to about a little shy of 50 people. We were pretty capital efficient. We only ever raised about six and a half million bucks. Mm-hmm. Um, we got it at exit to around 10 million in a RR and about a million, million and a half in ebitda, somewhere in that range.

Mm-hmm. Um, I would say we were optimally sized [00:52:00] around 30. Okay. That's where we probably should have been. Mm-hmm. Um, that's one of the challenges when you start taking money and you think about growth plans, is there is a, a tendency to over hire or be more aggressive than maybe you should and mm-hmm. And what the fundamentals of the business would suggest.

Mm-hmm. Were most of these customer support engineers or like help desk? I would say we, we did a pretty good job. The system had a lot of of functionality into it that we didn't have to spend a tremendous amount of time in the, the support and training side of the house that we certainly had customer success.

I would say the, the two groups that we had, we had a. Obviously a pretty heavy engineering team. We built it all here. We didn't offshore any of it. And so our engineers built a lot of it. Um, and we had sales, uh, and relationship managers. Because we were managing through those channels, we were able to be more efficient with our resources.

So we didn't have to support a thousand financial institutions. We had to support 5, 6, 7 processors at the time. Mm-hmm. [00:53:00] And help them and their sales team be effective to their customers. I know you talked about bringing some venture capitalists into your business, uh, raising some money. How integrated were they and helping you with customer acquisition and helping you with the day-to-day business operations?

A loaded question. They, um, they were tremendous supporters of the business. Um, they did, I think everything they could to make connections, but, um, they were financial investors, most of them. Um, and I would say they allowed us to be operators. Mm-hmm. Um. So they were impactful in creating relationships and helping us think through the problem.

They probably didn't make as many connections as we would anybody would like. Mm-hmm. To, to just continue to penetrate and, and, and gain, uh, adoption in the market. Um, but I couldn't have done it without them. We had a great board. We had a great group of investors. Mm-hmm. They allowed me to make mistakes and helped me guide through the, the challenges of, of being a [00:54:00] first time entrepreneur.

Mm-hmm. And going through multiple cycles. It, you know, what takes you from zero to one, one to five, five to 10 is are, they're just very different needs. And I wasn't perfect in any of that, but, um, I had a great team. We had brought on a great group of people and it was, I think they were very supportive in trying to, I.

Teach, impart their wisdom to me on what they've seen be successful mm-hmm. In other industries. Then it was sort of on us and the team, how could we take that information into our industry, into this market and these products and, and not make that mistake. Mm-hmm. And it's not always the same solution.

Mm-hmm. But the problem set that you see is, is um, was very helpful to get that information ahead of time. Who were your VCs, if you can name them? Our VCs, the lead venture capital group to start was Venture Capital Fund of New England. Mm-hmm. Um, [00:55:00] we had then had another early stage, it was called Seed Ventures.

They were a Southeast Massachusetts development organization that was actually funded by a lot of banks. Mm-hmm. Um, but had a very Massachusetts centric, um, growth mm-hmm. Model when they invested us and, and economic development model. So they were in it, um, outcome capital, uh, uh. Five Elms, um, Brett Rome and that group mm-hmm.

Uh, came outta Capital One Venture Arm. Those were the primary, uh, VCs that were in it. There were five or so. Did they influence your decision to sell the business? Like walk me through the process of when you decided, Hey, now's the time.

We need to think about exiting at a board level. After about year eight, it was probably a pretty constant drum at the board level of what should we do, wins our exit horizon. We were actually pretty close to taking it out in 2014. Mm-hmm. Um, hiring a banker. We had, uh, actually interviewed a number of, of different bankers to take us to [00:56:00] market.

We had selected it, we were preparing the sim, getting ready to go to market, had the plan. Mm-hmm. And we had two pretty impactful customer. Uh, attritions that we had to deal with, and they were partner attritions more than customer attritions. And so, so churn basically. Yes. That, that created a, um, that created a real obstacle in the business.

How much, how much revenue did that impact you? Probably a million and a half to 2 million of our over over 10. So you're talking about 15%? Yes. Okay. Um, and at the time it was probably even more impactful. It was probably closer to 20% of the businesses total. What was the reasons for the customer churn?

One was an expected one that I think we could have done. Um, they just didn't renew. They were on an older model where it was a license and maintenance. They were in a maintenance mode. Mm-hmm. They, their business model had shifted, so they were gonna go into maintenance only. Okay. And it, we could have survived that one.

Mm-hmm. The other one was a evolution of [00:57:00] the, our customer. Um, they, they had hired a. Multiple people to fill the same role. And so the person who had hired, uh, who had purchased the, the, or signed the relationship with us mm-hmm. Was now no longer there. We had a new person come in with different ideas, different thoughts about where they wanted to put their money.

Um, and so they, they decided to, um, break their contract. They did, they probably didn't have rights to, but mm-hmm. Unfortunately, you know, to go after them, the money associated with that, the time associated was likely not gonna happen. And so we let them break the contract, but that had a, a material impact on the business.

Mm-hmm. And so we had to really think about, okay, what is our next evolution with the time We had two products and that was a real, you know, come to Jesus moment, what are you gonna do? Um, that is the valley. Right. And there was a lot of low points in that, especially as you thought about what was going to be a pretty good high.

We were on a good growth trajectory. Mm-hmm. You could see. [00:58:00] At the time, I, like I said, I think we were seven or 8 million. You could see 10 coming. Mm-hmm. Um, just in normal course. And so it felt like the right time to take it to market, and we knew we couldn't. And so now it's like, okay, well not only that, now we're 6 million or whatever the number was instead of eight.

Mm-hmm. What are we gonna do? Um, at the time the business was in a suburb of Boston, Franklin, Massachusetts at the time. Mm-hmm. And we said, we really gotta retool this business a little bit if we're gonna get back on the right growth trajectory. And so we spent a lot of time thinking about what that was.

We decided ultimately that we needed to sort of do a little bit of a, a a, of an overhaul of the business. We needed to think about it differently. We needed to act differently. We moved from Franklin to downtown Boston. Mm-hmm. We had some employee churn. As a result of that. We hired some new employees coming in.

There were a lot of great people who stayed with us. We got to reinvigorate [00:59:00] our culture. We got to reinvigorate the, the vision of what we're gonna try and do. Mm-hmm. And we started crafting our next product, which was the combination of the two. We had, we felt like through the business there was a focus on providing tools mm-hmm.

To bankers to do their job. Mm-hmm. What we started to learn at the end of it was that we had seen more than everybody else had seen. So instead of one bank's view of what it was, we saw a thousand banks view of what should happen. And we had done it enough. And so we said to ourselves, let's stop asking and providing tool sets with the idea that they're gonna take it forward.

Let's start being more prescriptive into what they should do. Mm-hmm. And so we developed, um, a third product that took all the same data streams that we had, took a lot of the same tools that we had, but we packaged it in a way that told the bank. Here's what you should do. Mm-hmm. If you're interested in [01:00:00] driving auto loans, here are a thousand customers who, based on their behavior profiles, likely need a car loan.

Mm-hmm. Here are people who just moved now at a risk or leaving you, and you should probably reach out to them about your, you know, branchless environment. Mm-hmm. Um, whatever it might be. We were very prescriptive, including the return models, the marketing campaigns, and so we were trying to identify, need, risk, or opportunity from the data that we had.

Mm-hmm. And then recommend the behavior change, the change of behavior campaigns. Mm-hmm. That would allow for a return and a lift in the performance. And we got to see, because we had all the data, all the ancillary impacts to those campaigns, we allowed to, to very easily sort of correlate the impact of that.

And that. That put us on another growth trajectory that ultimately led to, to the exit. Mm-hmm. Um, and [01:01:00] so when, when Covid came, there was a lot of everybody trying to figure out, you know, the two weeks to slow the spread and what that really meant. Mm-hmm. And allowed us to say, what's this world gonna be like?

And unlike the recession became very, um, advantageous to the banking community, there was just a ton of money in the market. Mm-hmm. And so now it was talking about in a, in a completely sort of, um, distant world at the time, how do you stay connected to your customers? Mm-hmm. That was a core, um, uh, sort of point that we were sort of picking at.

And so we started to continue to see more and more traction outta that. That was around the same time we decided to move down. And so when we decided to move down to, uh, Raleigh. I was driving our, our, our cars down and I got a call in from a, uh, a PE back strategic saying, Hey, we, we think we should combine the businesses.

Mm-hmm. Are you interested? [01:02:00] And so we danced with them for a little while and there's a whole nother story that comes from that. But, um, that's, that's how it all started. So it had been a constant drum since I would say year seven, year eight. Okay. Then there was a recognition that it wasn't gonna happen.

Mm-hmm. And then the question was, okay, how do we get back to that? Um, the, the investors again, were very supportive. We had enough cash to operate. We were operating within our own means at that point in time anyway. Mm-hmm. It wouldn't suggest we were wildly profitable, but we weren't burning cash either.

Right. And so the question became, okay, well how are we gonna change? How are we gonna adapt to what is the new world? Mm-hmm. Um, and, and so we put it on a different trajectory. So you didn't hire a banker per se. You did at one point and you thought about chop it, and then you had a little bit of a setback.

Yep. And then, then you decided, you know what, we're not selling, we're gonna double down, reinvent the culture, move offices, and kind of like we're here for the long haul. And you're, [01:03:00] so somebody reached out to you several years later, you said private equity? Yes. A p back strategic, uh, west coast. They wanted the business.

They, and I thought the thesis made sense. Mm-hmm. Um, and you know, we were in the business at that time, 14 ish years. Mm-hmm. You know, the investors while patient don't have unlimited patients. Right. And so we knew we had to get to a liquidity event. And so we danced, uh, I would say with that particular firm.

Um, and what's interesting, and there's a lot of learnings from this, when you're in a process to sell a. Whether it's, uh, an inbound bid or you're running a process with a banker mm-hmm. There's just natural momentum that builds mm-hmm. Internally in yourself. Um, for those that are in the know, but certainly at the board level, there's this momentum.

Mm-hmm. Um, and it's very hard to stop. Mm-hmm. And so, you know, I, I do think there are firms that, you know, [01:04:00] legitimately retrade for the right reasons. Then there are firms that I would say legitimately don't retrade for the right reasons. Mm-hmm. Um, I would say we were in a spot where I didn't feel like we had any reason to retrade we were a better company when they started.

Everything we had told them was true. Mm-hmm. And so I went to the board and said, I do not think we should accept this retrade of the offer. I think what we should do is reject the offer, hire a banker, and go to market. And so the board, I. Supported that. Mm-hmm. Um, so this is now, we moved down July of 2020.

This is now probably September. Mm-hmm. September I reached out to, uh, banker firms that I had known, uh, previously. Mm-hmm. Uh, found a great banker, uh, in Leones and partners in New York. Mm-hmm. Um, that took us to market and we ran a picture. Perfect. Sort of as they draw it up for you, uh, process, was it an auction or strategic?

We were running two [01:05:00] sides of it. Mm-hmm. We ran a dual process. We were predominantly asking for an exit. Mm-hmm. We also indicated we'd be okay with a growth investment as long as they allowed some secondary to go out. Mm-hmm. And so we, we had, you know, did a, a preview of it, uh, in the late December timeframe, getting ready for Q1.

The goal was to try and get a couple of strategics really interested early. We did that. Um, a another PE-backed strategic came in, um, in toma back strategic called Meridian Link came in later and we signed an IOI or an LOI in in late February. Okay. And the deal was closed April of 21, or March 31st of 21.

So it took almost a year mm-hmm. For due diligence to go through that process. No, no. I would say the whole process when I moved down July of 2020, being in an exit mode or mentality, right, mm-hmm. Was probably nine months. [01:06:00] Okay. The actual process mm-hmm. Took three months. Okay. And I would say we were 45 days, which is pretty fast.

We were 45 days from IOI to close. I'm sorry, I thought you signed the LOI in 2020 and closed the deal in 21. Nope. No, no. We signed, we signed LOI February of 21, and we closed it March 31st of 21. That, that is impressive. I've never heard anybody closing a deal that fast. It was, it was quick. And I give a lot of credit to our CFO, uh, bill Rooney.

Um, our, our, I think the way we built the organization mm-hmm. We didn't have a lot of skeletons in the closet. We were pretty solid, fundamental business that had our, I think our ducks in order. Right. Um, the due diligence process is not for the faint of heart. Right. There's a lot in it. Mm-hmm. You have to be ready for it.

Mm-hmm. It, it is, um, for any founder starting something, it's good to start early with the right mechanics, the right mm-hmm. Documentation, the right, the, the right model. Mm-hmm. Because it's gonna come back at you. I tell [01:07:00] any founder who's. Any interested in m and a, either on the buy or sell side, is to get an advisor either on the board or, uh, your, your board of advisors, whatever.

Yep. And that's had experience in m and a because that's a whole part in itself. Yeah, it is. Yeah. And like you said, there's, there's a lot in it, right? Mm-hmm. There's both momentum and interest from everybody else to get to an exit that it means a lot to the funds. It means a lot to the founders. It means a lot to employees.

It means a lot to the acquiring company usually. Mm-hmm. Um, and you go through those things. It is a, is a process. It takes a lot out of you. You will be very distracted. It will take a lot of time, no matter how prepared you are. Mm-hmm. But we always took, I mean, when we took money, we knew what the plan was.

Mm-hmm. I mean, the whole thesis of the business was we were going to build it up and sell it. Mm-hmm. So that mindset already existed. Mm-hmm. And so we tried to put everything in place. Where [01:08:00] we could reach that. Mm-hmm. Um, and I think, you know, we were fortunate enough to go through that, uh, successfully.

And, and one of the things I think I'm proudest about just assailant in particular was most transactions don't have a, a win on all sides. Usually somebody's losing. Mm-hmm. You obviously want everybody to win, but the likelihood is there's, there's somebody who's not gonna be happy. Mm-hmm. I feel like we tried to, um, I feel like we accomplished it where the acquirer got the product and the team that they wanted.

Mm-hmm. The team got both, some liquidity as well as, you know, a future. Mm-hmm. At the new company, the investors all received, you know, good returns. The founders received good returns. Mm-hmm. And we all felt good about it. The product's still in market today. Mm-hmm. The team is still active at the, you know, that doesn't happen a lot.

Well, that's a great and success story. 'cause you're, I think the statistic is 85% of all deals fail post. Transaction. Just, you know, just transitioning into a new [01:09:00] culture, new brand, new direction, new leadership, new management. It just, sometimes it doesn't take, so it's, it's a testament to your own leadership and your ability to transition your company with the strategic buyer and, and still keep the band together.

'cause there's many that fail at that. That's good. Yeah, and I wish I could take a lot of credit for it. I think I got better over the Hy Assailant mm-hmm. Of recognizing that it was going to be the team that was going to be successful. And the group that we brought in, Russ Predator, our sales Bill Rooney, Joe Mer, Chris Fahe, uh, uh, you know, Lawrence Snow, a bunch of people there that were just very valuable to the process.

And it, it is. Ingrained in me now. Mm-hmm. That, you know, you need to find those people who are going to see what you're trying to do and help you do it. Mm-hmm. And, um, you know, there were new people along the way. Some of our more recent hires, Laura Costello, she's now [01:10:00] over there in a marketing role, just constantly improving what happens.

Mm-hmm. Um, and trying to be the best that the company can be. Mm-hmm. Because there's no chance you're doing this on your own. It just doesn't happen. Right. Was the process of selling emotional for you? Was most founders go through a bit of heartbreak 'cause so sort of like selling your child? Yeah. My, the, the, my baby founder, um, I was never one of those.

Okay. To be fair. Yeah. Um, I've seen it. I, I always felt like, and, and this comes to maybe another learning from, from basketball or coaching or whatever. Mm-hmm. My view of success has changed over time. Mm-hmm. I, I used to think success was you just, you just go win. Mm-hmm. Or whatever that, that might work out to be.

I think success at the moment is about maximizing the opportunity in front of you. Mm-hmm. And if you can maximize everything in front of you, you've done your job in that [01:11:00] success. Mm-hmm. Because not every team's gonna win a championship. Not every company's gonna be Google or Uber or whatever other company in Nvidia, right?

Mm-hmm. Some of them, the, the model isn't there for that. But that doesn't mean you can't be extremely successful in your own right. Mm-hmm. And so you have to be able to look at the people you have, the market you're serving, what is the best this company can be. Mm-hmm. And if you can approach that or exceed that, I think that is success.

Mm-hmm. Um, try not to get, try not to get too focused on, am I unicorn or am I, you know, am I on the tweener fund? And I think the tweener fund's great. Mm-hmm. But like. Just build a great company. Mm-hmm. Build a great company that people wanna be a part of, that people want to buy, and, and make sure you're as successful as you can be with that.

Mm-hmm. Because I otherwise you just set yourself up for disappointment mm-hmm. In, in everything. Right. And so what procurement was gonna be, what Rubrik was gonna be, what the next [01:12:00] company will be, they're all individual in nature. Mm-hmm. And so you have to be able to look at what is, where are we and what does success from this point right.

Look like. Mm-hmm. Um, and I think that allows you to, to carry great focus mm-hmm. On what your job is and what teams you're gonna put in and how big you're gonna get and how much money you need and Right. All those things play in. How long did you stay on with Salan after the transaction? Zero days, oddly enough.

Zero days. Um, it was actually quite jarring to be fair. Um, they were about to go public. Mm-hmm. They needed our product. I don't need, they, they wanted our product. It was good for their story. It was a good revenue add for them. Um, but they needed to meet a certain mm-hmm. You know, performer into the market.

Right. Um, they had already had a founder who was sort of in the chief strategy officer kind of role. Mm-hmm. Um, so they didn't need me and I frankly [01:13:00] was, was okay with going and recharging a bit. Okay. Um, so there are only three people that left the company myself, the CFO and, uh, our hr. Mm-hmm. And to be fair, in every company the CFO and HR are pretty normally part of, uh, an exit and moving, not moving on doesn't always happen, but those are pretty common.

Mm-hmm. And everybody else remained. Um, and so I remember we, we closed it, I think, like I said, we think we signed it on April 1st. Mm-hmm. Um. That was a Thursday if memory served me right. And Friday I went up to check my email and I couldn't get into my email. Wow. It was pretty quick. Yes, it was. It is very jarring.

'cause as a founder, your whole life is in your work. Yeah. All your personal contacts, all of your mm-hmm. Emails, they just, you know, nobody used my Gmail account they just used. Right. And so not having access to that, I, I remember I walked up, I couldn't get in. I walked out. I said, I guess that, I guess that's it.

And so I, [01:14:00] I don't know what I did at that point in time, but I looked at my wife and said, I have no idea what I'm gonna do right now, but Right. I, I know I'm not gonna work 'cause they don't want me to work, so. Mm-hmm. Um, that was the, the beginning of the next phase of, of life, of trying to figure out what to do.

Mm-hmm. Because I had been in a market now for nine months that I had really very little connectivity into. Mm-hmm. I knew I wasn't ready to be connected or to help anybody yet I needed my own downtime. Mm-hmm. Um, and so. That was part of, okay, well what do we do now? Right? So what are you doing now? Well, so that lasted probably a year and change.

So you took, you took some time off, like you were just completely unplugged? Yeah. I, uh, I golfed, I, I tried to, um, we didn't do as many vacations. We sell the kids in school, you know, we, we ended up, um, spending some time at Lake Gaston, you know mm-hmm. Touring the area, all that kinda stuff. But I would say I came back about 12 to 15 months [01:15:00] later.

Okay. And said, I really want to get connected into this ecosystem. I don't know anybody here, nobody knows me. Mm-hmm. Um, let's spend some time meeting people. Mm-hmm. And so I was, try to be pretty methodical of who I went, I talked to, to, to just the ceds of the world. Mm-hmm. Uh, NCID, um, the local VCs, the local lawyers, the, you know, the different pockets of people.

Mm-hmm. Just, Hey, let's grab a cup of coffee. Oddly enough there, everybody was raising funds, so they were very happy to talk to me about a number of things. Mm-hmm. Um, I didn't probably appreciate that when I first started doing it, but now I do. Mm-hmm. Um, and so started mentoring some companies. C does a great grow program for those that are interested.

They do a 12 week kind of incubator ish style group. There's a lot of studios that do some things. Mm-hmm. But I just started getting back to having cups of coffee and mm-hmm. And meeting different, um, entrepreneurs and, and people [01:16:00] along the journey, including the schools and mm-hmm. And their, their entrepreneurship groups.

And I think through that, um, as much as I enjoyed it from the, the, the fill your cup model and the, the, the pay it forward model mm-hmm. I did start to get the itch to operate again and wanted to be back into it. I, I, I tell people, I, I, I know what it takes now, so I. I ha I don't, I didn't have an idea that I said to myself, oh, that's an idea I'm super passionate about.

Let's go do that. Mm-hmm. And go through all the pain that I'm well aware of about to happen, but I do want to get back in. Mm-hmm. And I do wanna figure out ways to help companies, whether it be as an operator or a board member or whatever. Mm-hmm. And ju or just a friend that they can, you know, bounce stuff off of.

Mm-hmm. And so I tried to do all of that for a period of time. Um, and then that led me to procurement. And, and I, I think at the time I had met, uh, one of the investors in the business at the same time, the founder, um, and the [01:17:00] founders, both great guys were, were starting to evaluate what their next cycle was and how do they grow the business.

And I think there was some realization, or at least some openness to saying maybe I could be more valuable in different pots parts of the business. Mm-hmm. And, uh, so the, the investor connected me with the founders and, and ultimately led to me joining procurement on a pretty specific mission, I would say.

Mm-hmm. Um, to try and help them along in, in that path. And so that was now, call it September of 23. Mm-hmm. I joined them. And you're still active there? I'm not, we were, the goal was pretty simple. We had to, um, we had to refocus what the business was gonna do. Mm-hmm. Uh, we needed to set it on a growth trajectory, and we needed to try and raise capital or exit.

Mm-hmm. One of those two was, had to happen. Mm-hmm. And so we put together a story. We had a great investor community in the business already. We had leaned on them and said, we, we, we need some operating [01:18:00] capital to, to execute our vision. Um, I think we did a really good job. Um, the two founders, uh, Brandon McCarty and Chris Rge, uh, Brandon was the, uh, CEO, Chris was the technical lead.

Mm-hmm. And CTO. Both brilliant guys. They moved, um, Brandon moved into the more of the product centric role. Mm-hmm. And we just started crafting our vision to try and take them from a procurement company to a procure to pay company where we started both seeing the purchases and the payables and invoicing side of the house and mm-hmm.

Um, we served dental organizations, um, what are called DSOs, but the rollups of all these mom and pop kind of dentists or the, the, the retail fronts. And they had a lot of problems trying to control the spend. There's a lot of spend in, in dentistry and what you have to do for all of the, the production that that comes.

And so we were sort of the backend office for that. And so we, we put that together. We saw some really good traction. We moved the, the customer mix and the [01:19:00] revenue mix from a procurement only play when we started was probably 15% of our, our mix. Um, from a procure to play side to a 60, 65% mix at the end, we had good momentum behind us.

And so we reached about the middle of the year of 24. Mm-hmm. Um, said, this is the time we've gotta go to market and see if we can either get capital to finish the story mm-hmm. This journey of it, or find somebody who, who would be a good partner in a good home for it going forward. Mm-hmm. I think we would've been super successful if we had raised capital.

Um, I think one of the learnings there was a mismatch in what our scale was versus what investment dollar amount we had taken in. Mm-hmm. And so it was a little in between rounds and so there was some difficulty in getting people on board with that. And, and, and so we ultimately found a, a home for it, um, and sold it to what was our largest competitor.

Mm-hmm. [01:20:00] Uh, and closed that transaction in February of 25. Mm-hmm. So a couple months ago. Um, they're still in the transition part of it. Mm-hmm. Um, moving the business over and converting the customers, I think it's going really well. Mm-hmm. But, uh, that was a different process. We didn't hire a banker, it couldn't support it.

I ran really the banking side of it. Um, we talked to a lot of people, but this was the right place for the business to, to end up. Mm-hmm. Now, are you, have you ventured into being an angel investor? Have you invested in any startups? I have not yet. Okay. Um, my wife and I have talked about it a lot. We've talked about it with a number of funds.

Mm-hmm. The way I look at it right now is I'm still in my operator mode. Right. Um, I think I'd be a, I don't know if I'd be a great investor yet. Mm-hmm. Um, and so I'm pretty interested in, in continuing the operator cycle for a little while. I do think there'll be a time it moves to being, uh, more of an investor, whether it be an angel or fund specific, I'm not sure [01:21:00] yet.

Mm-hmm. Um. But I, I really enjoy operating at the moment. Well, I will tell you, um, an operator, investor, they're highly desired because most founders I talk to that have taken capital from VCs, their biggest complaint is that the VC doesn't really understand their business model, or they don't understand what it takes to run a business.

They have no experience sitting in the driver's seat of the day-to-day ops. So, being an operator that can pivot into being an investor, you can jump into those companies and really give them some good down to earth experience and, and advice that, Hey, you know what, I've run payroll. I know what it takes to, you know, lean your house and mm-hmm.

Do this. And, you know, I mean, it, it, it's, it's a different experience than running from a, an Excel spreadsheet. So. So [01:22:00] I think you would be a great investor with a lot of great experience, not from operations, but from m and a. Well, I appreciate that. I, I enjoy it. I enjoy being involved in it. I think that was one of the things I really liked about the Rubrik experience is I did get a chance to sit on the board there and was an independent, uh, when they took in some capital from Jurassic Capital.

Mm-hmm. And I, I worked really, really hard at being the type of board member that I wanted as part of my board. Mm-hmm. I wanted to make sure I knew the product, knew the challenges, knew the team, um, that I, I, I, I dug in enough to the market to know about it. Mm-hmm. Um, I didn't get in the weeds and, and try and get myself into being an operator for them.

Mm-hmm. But to start helping them out with, Hey, this is the next thing you're gonna see. Mm-hmm. This is the, I've seen this problem before and what it sounds like is. You know, maybe it's a, a, a people problem or a talent problem [01:23:00] or a, you know, just a, a, a customer problem, whatever it might be. Mm-hmm. And just trying to be the board member I wanted from my board.

Right. And, uh, you know mm-hmm. I'm sure I times I did that well and then I'm sure times I didn't, but I, I tried to be that person. Sure. Um, it is interesting when you see these things from different perspectives now, different industries, right. I was an early stage employee. I founded a company with my wife.

I, we, you know, I joined a company that was already founded and come in as a, you know, sort of an external CEO been a board member. The problems and the patterns you see are pretty similar. Um, the solution may not be identical, but pattern recognition about what's going on is, is real. Um, and I think that's an important, um, that's a value.

I think that that is inherent and just having gone through it, I remember I was talking about this with, um, the rubric, CEO, Nate. Um, and we were just sort of talking about how much we didn't know when we started [01:24:00] and what now seems sort of natural. Um, you wake up and you're like, well, okay, this is what that means.

This is, boy, that was a bad decision. I dunno why I made that decision in year three, right? That now I would never made that decision, but you have to go through it to experience it, right? There's a lot there, which again goes back to, you know, I'll make coffee for anybody as much as I can, because I just think there's so much there that, that you learn over time that is valuable to somebody trying to start their business.

Absolutely. So now that you had time to reflect on your journey from early times, working, starting your own business, going through the scaling, pivoting through struggles, seeing your market basically get devoured, having to reinvent yourself, and then successfully exiting. Um, what, what are a few things that you [01:25:00] wish you could do that you didn't do?

Like, looking back, it could have been better or maybe I made a mistake. Like what, what are some things that you, if you had that chance to go back in time, you would unwind some of these decisions? I would say there's probably not enough time in this podcast to hit on, but just a couple. Uh, there's a couple of, of really sort of meaningful ones.

I suppose. The first was, I'm a believer, like I've never bootstrapped a business from nothing to wherever. Right. I've, I've bootstrapped it for a period of time, but never made it without money. Um, so a lot of my experiences come from that and I view capital to be incredibly valuable. And the old adage that everybody says you should take as much money as you can when you don't need it versus when you do that is a true statement.

There's a lot in that though, because. We took fewer than we should have from, uh, one of our, we closed a series C at one point in time, a small series C [01:26:00] um, later in our life. This was probably 20 13, 20 14. And we had gotten some bites externally, which can be the worst thing for an investor, for a founder to hear, and an investor for that matter.

And so we got a little enamored that something might happen. Anyway, we were raising a $4 million round. We decided to take two. And that decision definitely impacted our ability to be successful on the thesis that we were raising money on. If we had more money, we would've been able to last the, and, and finish the vision of what we're trying to do.

And, uh, I just, that, that is in my mind pretty consistently. I think this market tends to underfund businesses. I know there's a theory at the moment around just fund to, to certain stages and fund to the next growth curve. And I agree with all that. But there is a point in time where when you are taking capital, founders get a little too sensitive on dilution.

You know, 20% of zero is still [01:27:00] zero, right? 40% of zero is still zero. And so, you know, take what you need to be successful and if you are successful, the extra capital or the extra dilution that you took will make itself okay. You will be comfortable with that at, at some point in time. If you take less and fail, you will regret that for a long time.

Mm-hmm. Um, so I, I would say properly funding the business on what the business needs instead of a really optimistic view of like the least amount you could raise is, is, is maybe a learning. Okay. The other one that was there was just trying to navigate the team dynamics over time and recognizing when somebody is a great.

Person for the zero to two journey, but maybe not the perfect person from the five to 10 journey is a really hard thing. 'cause you create relationships with people and, but it's the same reason in the NBA, if we go [01:28:00] back to, to, to basketball, that, you know, you'll trade, you know, an up and coming superstar in a draft pick for somebody who's done it before.

Like, there are reasons that, that those people are there. Mm-hmm. And, and seeing it and having done it is a, is a valuable experience. I think that, that's another one. Um, trying not to, trying to find out when you should delegate and when you should be beginning to let the reins go and empower the team behind you and, and doing it yourself.

And I've made a ton of mistakes in that, about. My team every now and again would used to call me the fireman, right? Like I'd go around a fire over fire and I thought I was doing a great job, but just solving all these problems. But I, I didn't mm-hmm. Do a great job. I was actually a tornado coming in. And so learning when I need to have guidance and oversight and leadership versus doing is, is a real challenge [01:29:00] for, I think a lot of founders.

Um, you need a great team behind you and you need to trust that team that you build. And there are things that need your attention. What I'll, I never forget a comment from one of my investors. They said, I don't think a founder or CEO should ever delegate the vision. Mm-hmm. Where you're trying to go can be influenced by people, but like, it needs to be what you believe in.

Right? And so that, that those missteps through the course of time are just, they're not things that hurt you. Mm-hmm. Um, individual. Items they won't, but a series of them will build up and become impactful. Um, and so learning how to dance on that and learning when you should be involved and when you shouldn't, is, is a challenge.

And you can do it wrong at both levels. Right. You can be too involved and too less, too involved, too late, or too involved, too early. I mean, it's just, they're all, they're all problems. Right. Well, [01:30:00] sounds like you have some really great experience and, and I hope that you find some success getting on boards and being a mentor to a lot of the startups here in Wilmington and Raleigh and other places.

Um, if there's anything I can do to help even with, uh, kind of touching into the venture capital side, you know, I've learned a lot doing that. So if there's anything I can do to help kind of navigate you, I think you'd be an awesome investor. Thank you. That's a, it's a whole different world. It's a, it's an interesting, uh, evolution, but I.

This market is a great market. I think they've got a lot of really, we got a lot of really smart people and, and I think some driven entrepreneurs that sometimes they just need a little bit of help and, and sometimes they just need a voice to bounce things off of. And so I really do enjoy it. I'm not that, this is not for the podcast, this, I, I enjoy hearing the different challenges and at least gimme a perspective.

And you know what? My perspective may be wrong sometimes. Mm-hmm. And that's okay. It's just a perspective for you to take. And I, I really do like that. So, do you [01:31:00] know a gentleman by the name of Leland Winstead? He's outta Raleigh. He commutes between Raleigh and Wrightsville Beach. I don't, he runs Wolf Pack Ventures, which is the alumni group that, that seeds, you know, startups out of NC State.

I'll put you in touch with him because he has an energy background. And with your FinTech background, I'm interesting. There's, there's gotta be like a Masterminds group that can meet in Raleigh. And just pull from folks like yourself. 'cause he's also a cash out entrepreneur, tons of experience. Um, it would be worth our while to kind of create a little club or group just to kind of say, Hey, this is my experience.

I'm available for boards. And that way, you know, as a, as a team, we can kind of pivot and look at some of these startups and offer expertise. In all fairness, I I would welcome that I, that, that's one of the areas I have not done a great job is, is penetrating can win, uh, Duke's Duke venture arm. Not [01:32:00] to say that that, but the university, I have not mm-hmm.

Had great success finding, uh, ways to help. Yeah. They, they're very siloed, you know, they, they have their own architectures and organizations and incentives. Yep. Yeah. Yep. I really appreciate you coming today. This has been a fantastic discussion, and I hope you come back on the podcast and we can talk about whatever you're working on is your next, your next phase into your transition, uh, whether it be investments or boards, or any other activities that you have in the area.

Well, I'd love to, I, I, I really enjoy it. Thanks for having me. I appreciate all the time. Yes, sir. Thank you. Thank you.

Amplified CEO is produced by Topsail Insider, edited by Jim Mendes-Pouget, and sponsored by Cape Fear Ventures. For more information about Amplified CEO, Richard Stroupe, or Cape Fear Ventures, please contact Christa at (910) [01:33:00] 800-0111, or christa@topsailinsider.com.