Practical Founders Podcast

#33: Bootstrapped a CRM for Auto Dealers that Sold for $150 million – Matt Watson

Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in 2006. VinSolutions started by helping auto dealers upload photos of their cars to sell in the popular Autotrader catalog and website. Matt was the first developer and product visionary who lead a team that build their popular CRM and lead management system to help those dealers manage internet leads and sell cars faster.

Their revenue doubled every year as they grew to eventually serve thousands of auto dealers with their pioneering web-based software. VinSolutions didn’t raise any venture capital or private equity investment as they grew to over 300 employees. In 2011, VinSolutions was acquired by itself for a reported $150 million. 

Matt started Stackify in 2012 as the CEO funding the startup with his own money. Stackify is a tool for software developers using cloud platforms to manage and optimize application performance, a problem Matt had experienced at VinSolutions. Stackify grew slowly and struggled at first before they grew steadily. Stackify was acquired by Netreo in 2021. 

Best quote from Matt:

“The most important thing is just asking people for help. Finding mentors and advisors is by far the most important thing other entrepreneurs can do.

“Being an entrepreneur is a lonely place. There are not a lot of people who you can relate to. The key is finding people that have done similar things as you in your industry.

“Just finding advisors and mentors who are willing to give you 30 minutes of their time could be a game changer for your business.”

Edited transcript of the Practical Founders Podcast interview with Matt Watson founder of VinSolutions, Stackify, and Full Stack in Kansas City.

Greg Head: And we’re live with Matt Watson, the co-founder and former CTO of VinSolutions, a success story in Kansas City, and a few more companies. Hey, Matt. Welcome to the Practical Founders Podcast.

Matt Watson: How’s it going, man? Thanks for having me today.

Greg: Busy day for you today, Matt, in Kansas City?

Matt: You know, I work remote, so you know, it’s just jumping from one video conference to another.

Greg: Who knew what we’d end up with here after all this advancement in our lifestyles and technologies here? So, you have two exits under your belt and several companies. You’ve been doing this for 20 years. You started young and created a software company for the auto dealer industry here in the U.S. that grew quite big. And we’d love to hear the story of VinSolutions. So, why don’t we start with the end there? Like, when you sold it there in 2011, What was VinSolutions when you sold it? How big was it? What was the focus?

Matt: The company started out doing inventory management for car dealers, and I can tell you that story later if you want to hear the details of how it started. But the way it really ended was we were doing CRM for car dealers, specific to them. Really what made us unique is how we handled internet leads. So if you think about going to or something like that and you submit a lead, those leads would electronically get routed to the dealerships. And then, we provided the software they used to track all those leads and follow up with the customers and create all the tasks for the salespeople and all this different kind of stuff. And then we did a bunch of other things; we managed their inventory, we provided websites for them. There was a bunch of just sales and marketing kind of stuff that was very industry specific.

Matt: When we sold the company, we were doing like $35 million a year in revenue. The company had been bootstrapped. We had 250 employees, something like that. It was profitable; it was only profitable probably the last year of that eight year journey. Lot of stories there. And to this day, it is still the number one CRM solution for car dealers in the whole industry, which is really cool. They have thousands of customers. And probably my favorite part is my dad just retired there at the end of 2022, the end of December 2022. And that’s my favorite. My dad worked there for over 16 years. And that’s probably my favorite part of the story.

Greg: Wow, that’s exciting. And you sold that company to AutoTrader, part of the Cox Network for a successful exit. Reported to be about $150 million, and maybe we can get into some details there. You know, during the 2003-2011, that was the pre-cloud era. You got on the wave of AutoTrader and selling cars on the Internet and helping dealers do that, right?

Matt: Well, that’s why I should tell you the original part of this story, because it’s fascinating. So, the way this started in 2003 is there was another gentleman who was my co founder and his name was Eric. He, ironically enough, worked for And he was going around to car dealers and trying to get the car dealers to buy listings on Back then, the dealers spent more of their money advertising in AutoTrader magazine that you would get at the grocery stores and stuff like that. A lot of people don’t remember that, but that was really huge. And of course, newspapers and other traditional media. So anyways, he would go to these dealers and the dealers would all be like, “Hey, we don’t take pictures of our cars. We can’t upload them to Like, that’s not a thing. If you will take the pictures for us, we will buy” So that was the light bulb moment for Eric. Eric’s like, “Okay, fine. I will go take pictures of these things so I can sell some stuff and meet my quota.”

Greg: Like a sales guy who did some of the work to make the deals happen.

Matt: Yeah, exactly. Now, it’s important to remember this was 20 years ago. So back then, the iPhone didn’t exist. It didn’t come out until 2006 and it was terrible in 2006, right? And even then, digital cameras were still not very common. They were definitely a luxury item and most people didn’t have them. So it was kind of in the early stages of all that. And so, I met Eric through one of these dealers that he talked to. Eric was going around to these dealers and saying, “Hey, do you know somebody who understands software stuff that can help me do this thing?” And I literally met Eric at Applebee’s and Eric told me what he was trying to do, and I’m like, “Sure, I can build a little database. We can FTP the photos or whatever we need to do and we’ll figure out how to do it. I’ll help you do it.”

Greg: You were the coder kid to help build something.

Matt: I was. I was 22 years old. I had no idea what I was doing, but I was just opportunistic. I’m like, “You know, I like to do cool stuff and whatever. And sure, whatever, I’ll do this thing.” And that’s how it started. Eric had like 10 or 20 different customers in the Kansas City area he was going around doing this for, and that’s how it started. And then ironically enough, Eric got fired from, I believe, for doing this, even though he did it to sell AutoTrader listings. So then it’s ironic that eight years later that’s who actually acquired the company. But what was interesting is, back then, was free because AutoTrader magazine was the big thing. And then of course, as time went on, AutoTrader magazine died and became like a billion dollar a year business. And so for them, it was sort of planned obsolescence, I guess. And I think that’s also the reason they acquired… Most people don’t realize this. They acquired my company, but they also acquired, which most people have heard of. Kelley Blue Book, they acquired that, and then like 10 other companies in the industry. And they were trying to, I think, diversify away from just being in the advertising space and they didn’t know what was going to happen with Craigslist and eBay. And everybody else is trying to create the next; it’s like a never ending thing. So I think they were just trying to diversify in the industry, and now they own, I think it’s like 17 businesses or something.

Greg: Holy cow. Well, this wasn’t like we see a big opportunity. We’re going to be software entrepreneurs, that like the modern people think about the dreams of unicorn and funding and all of this. You were there in the transition from the advertising in catalogs to the Internet in an industry that kind of moved slow and everything was moving like this, and you guys just found an opportunity. Did you think it was a business at first or did you just think this was a little “producty” toy or did you quit your job or go full time? How long did it take before you guys realized you had something?

Matt: Yeah, so it was definitely a side project. And at the time, I was working at a medical laboratory. I was basically like the lead developer, architect, of a laboratory system. And so I was doing this on the side, and we eventually started to sell the software on its own. So it wasn’t just the service of him taking the photos. So we were starting to sell it to a few people. It was more of a SaaS product.

Greg: It started as a service.

Matt: Exactly, yeah. And then eventually we started doing both. To answer your question, after a few months went by, I started getting busier and busier with this. We’re making a few dollars with it, but not a lot of money, you know, like $10,000 a month or something like that. It wasn’t a lot of money. But eventually, I worked part time at my job. I convinced my boss, I’m like, “Hey, I’ll come in at six in the morning and I’ll work until noon every day. I’ll take a little bit of a pay cut. It’s okay, but I’ll work like 30 hours a week and keep my benefits.” And then I worked basically all afternoon and all evening and every weekend doing this business. And that’s actually where my dad came into the story, too. Eventually, we became so busy, I needed help. And my dad was the first person we hired and he did the customer service. He was dealing with the car dealerships on how to use the product and all that stuff, and I was focusing on writing the code.

Matt: Yeah, so think about it like inventory management or syndication. I mean, so basically we had a little database that they would put all their vehicles in and all their pricing and descriptions of the cars, all that kind of stuff. And then we would broadcast that, syndicate that to different places. And then you could also print window stickers in our system, like you go to a car dealer and you see stickers that are on the side of the car that say what it is and the price and stuff. So it was a pretty simple thing. And then we did websites for dealers too, but they were not very good websites, but we did websites. And then later on, the product totally morphed and changed as the years went on.

Greg: When was it like a real business? Quit your job, a few employees, you guys looking at each other like, “I think we’re on to something.”

Matt: I think it definitely took a couple of years. It definitely took a couple of years. And the crazy part of this is about 6 to 12 months in, we were looking to get some data about the cars and I found another company and another couple of guys that were in Massachusetts that had all this data about the cars, and they also had some key relationships. And we created a partnership with them to do some stuff. The key to the story there was they helped us get a partnership with somebody that we thought was going to resell the product. It was one of the largest companies in the industry. We thought we were all going to be like billionaires or something because we got this partnership. We spent several months trying to get this partnership to work where they were going to resell our product. I told you about the window sticker part of it. This company basically made the paper and they wanted to sell these stickers. The salespeople that sold the paper were going to resell our software. That’s the angle they saw, right? And long story short, we spent forever trying to make that partnership work, and it never worked. That’s one of the problems as an early-stage company is you try these different go-to-market strategies and traction channels or whatever. And if we would have put all of our eggs in that basket, we would have died. For a while we did. We were counting on that to be some big thing. But the good news is, in the background, I kept just improving the software even though we were trying to hope that would work. And then eventually, we had some other success selling what we were doing and growing and just continuing to grow alone. And we were a little SaaS company, and I didn’t even know what a SaaS company was. I didn’t even know what a startup was. I didn’t know what any of that stuff was. I was just a guy writing some code and having some fun.

Greg: And you were the only coder at the time too? Like, “Hey Matt, write this.”

Matt: It was me, yep. It was all me.

Greg: So when you say a SaaS business, was it recurring revenue from the beginning to dealers? You guys kind of got everybody on the “pay us monthly” drug. That was pretty early for that. That was not how most software was sold back then.

Matt: We were doing a little bit of the service where we would take photos, but we also had a subscription for people that wanted to take their own photos, and they would pay us a couple of hundred dollars a month.

Greg: Right. And a lot of companies that started at that time were still on premise. Windows software and servers that worked on PCs, but that was already cloud-based stuff.

Matt: I don’t even know where we were hosting it early on. Eventually, we were hosting it… We were hosting it in Kansas City, eventually. But yeah, that’s a whole different world that kids these days can’t appreciate, man. I mean, back then, you might have to spend tens of thousands of dollars or like a really high monthly fee to be like, “Hey, I need five servers and a whole bunch of storage space and all this stuff with…” Of course, then you’re renting network equipment and switches and all this stuff. It was expensive to do all that and get VMware and a SAN. That stuff sucks. Everything about all that sucks. And that’s why with my next company, I refused any of it. I’m like, “We are 100% in the cloud, you know.” And people don’t think about that, but back then it’s like, “Hey, we need to get new servers and add capacity for VMware and we need to get the SAN and whatever.” And it’d be like $50,000, $100,000. We didn’t have money for that. Ain’t nobody got money for that. We were a bootstrapped company. It’s so much easier these days in the cloud to be able to spend an extra $1,000, $2,000 a month, to be able to scale up and do that right instead of having the big capital expenditures.

Greg: So let’s talk about how you got the revenues to do that. It wasn’t the partnership with the sticker paper company. Did you just hire a sales guy or, your Eric, your co-founder started calling dealers and started to get orders and cash would come in and this kind of grew?

Matt: It was slow and steady. Yeah, it was slow and steady for the first three or four years. We eventually got out of the services business and exited that. In the entire history of the company, I think we only took in, say, I think it was $200,000 in capital total from some of the owners.

Greg: I don’t even think you could call that capital. I think you’d call that a little bit of cash, maybe, because you need to make payroll that month.

Matt: Yeah, it was. There were a couple of times it kind of… I don’t want to say bailed us out, but it was a big need when we needed it. And for the most part, it was all financed on Visa and MasterCard, and frankly, just not paying our bills. I mean, that’s another way of finance that people don’t think about. You just don’t pay your bills, and then whoever screams the loudest, you pay, and then you just don’t pay the other one.

Greg: So how did you start growing revenues? Was it one on one selling to dealers or did you have some other marketing?

Matt: Yeah, it was. It was all direct sales. And the great thing about our business is it was easy to get our customers on the phone. You can call the car dealership up and be like, “Hey, I want to buy a car,” and they would transfer you to, back then, the person who was called the internet manager because selling cars online was like this weird thing and there was like a weird guy who handled the internet leads, right? And so you could easily get that person on the phone and be like, “Hey, I’ve got technology that can help you. Can we set up a demo? Worst case scenario, you’ll learn some best practices,” whatever, you know, blah, blah, blah. And yeah, we just did lots of demos and sold the product. And even back then, when we started doing more of the CRM side of it, a lot of our competitors had salespeople that they paid $200,000 a year to drive and fly all over the country, and they were selling an on-premise system and old server-based, client-server kind of apps and stuff. And so we were some of the first people to do a true SaaS-based CRM system. And it was all cloud-based and only inside sales, we only did inside sales. It was different; a lot of people weren’t doing it then.

Matt: And one of the other things we did that was dramatically different is we didn’t even have contracts. We’d be like, “Hey, it’s $500 a month, $1,000 a month, whatever, to sign up for our software. And if you don’t like it, just cancel next month. We don’t care. It’s cool.” And that was a totally radical thing then that nobody did. And the reason we didn’t worry about it is we knew we had a good product, but we also know, and I’m sure you know this too, nobody likes to change CRM systems. It’s like changing accounting systems or phone systems. Screw that. Like, nobody wants to do that, right? So we know once they buy our product and they start using it, the odds of them changing are not very high. Like, they just don’t want to go through the pain of doing that again. And so that in itself was its own contract was the point. Because even though we had a month-to-month contract, the switching costs were so painful that they don’t want to change anyways.

Greg: So you went from this kind of simple solution either about the AutoTrader photos and then a few other things, printing stickers, and you kept like sneaking over to the core application which is getting your leads and selling more cars and sell more cars and the core system that they would log into every day. So the good news about CRM systems is once you get them working, you don’t want to change them as you say. But the bad news is, it’s tough to get them up and running. You’ve got to get all their data up and going and then you have to train everybody into the habit and everything. And I’ve been there. Data is hard, especially if they have old, crappy, old systems. How did you guys solve that?

Matt: I have battle scars from that. And to expand on that story, everybody always talks about like, “I want to have more customers than I know what to do with.” Like they want that problem. No, you don’t want that problem, because we had that problem. We were signing up like 50 to 100 car dealerships a month. That may not seem like a lot to some people. If you’re selling like a $10 a month widget, you know, some little product online, like, yeah, maybe you can sign up a lot more customers. But for an enterprise kind of sale, that was a lot of customers. As you mentioned, importing the data from their old system. And then we also had to import data from their… In the industry, what is called the DMS system? Just think about an accounting system they use, basically. And so we had to import data from these different places, and yeah, do data hygiene and matching and all this stuff. And that was painful. And then we also had to build websites for them. And so, really nothing about setting up a new client was turnkey, is kind of the point.

Matt: Back to my point earlier about you don’t want to have that problem of having more customers than you know what to do with because now all the people you just sold to in the last 30 or 60 days are mad. They’re upset already. They’re calling the sales team all day and complaining about why they’re not installed yet. So now instead of my sales team selling something, they’re taking angry phone calls and they can’t even go sell anything anyways because we can’t even install it. Like, I’ve got a bunch of salespeople that can’t even do anything because we can’t install the software fast enough. It was not a good place to be.

Greg: You didn’t raise $10 million to go hire 50 people to get ahead of that or something like that.

Matt: No, this was 2008 and 2009. If nobody remembers, that’s when General Motors and Chrysler went bankrupt and we were in a major recession.

Greg: Yeah, so you couldn’t get funding back then. The doors were closed. So, like people are saying this is a tech recession right now, there are layoffs and the rest. It’s nothing like 2000 or 2009. The doors were closed for funding, effectively for startups. It’s like, “No, thank you.”

Matt: I’ll never forget, I was actually at a trade show, I think it was in Las Vegas, and we were standing on the trade show floor. I’m with my other couple of business partners, and executives in the company, and we get the news that General Motors and Chrysler are going bankrupt. We just all kind of look at each other and we’re like, “Wonder what is going to happen. Are we going to have like 10% of our clients that are going to cancel? Like, what is going on?” And Ford had closed some stores and stuff, too. They didn’t go bankrupt, though. And, we didn’t really know. Honestly, for the next several weeks, our phones just started ringing off the hook and it was because we could save them money.

Matt: So, most car dealers were spending tens of thousands of dollars a month on advertising in AutoTrader the magazine, newspapers, radio, TV, and all that stuff. And everybody was trying to figure out how do we save money, but how do we still sell cars? And selling cars online, like doing all the digital marketing, was where the movement was. And so again, we had a low-cost solution. It was SaaS-based, it was monthly, it was month to month, and you could cancel. And so we were just in the right place at the right time. And I definitely believe for any other kind of founder that’s listening to this, there’s a certain element of timing that is always critical to the success of any business.

Greg: Yeah, you had the pain of being early, right? And the frustrations of this early technology and you had an up-and-running solution. You filled out your solution and built this CRM stuff and lead management stuff at the moment.

Matt: We were ready to go.

Greg: Yeah, at the moment. It’s kind of like the COVID moment for Zoom, right? And all of a sudden, the spotlight came on you. And it doesn’t always happen in a vertical SaaS business, or software business. Sometimes the spotlight goes away. So what was it like? This was bootstrapped and you weren’t profitable, you weren’t taking money out and all that. You didn’t pay yourself a lot. But all of a sudden, was this like $1 million, $2 million, $4 million, $8 million, $16 million? Like, did you just double, double, double for these years?

Matt: Yeah. It was roughly kind of double every year. And definitely from that like, 2008, 2009, 2010… 2011 is when we sold, early in 2011. Yeah, we were doubling basically every year, and that was painful. I mean, going from 50 employees to 100 to 200 to get on the elevator with somebody and they ask, “Sir, what floor are you going to?” And you’re like, “Dude, you work for me. You don’t even know who I am.” Right? Like, those are weird moments. From when it started, it’s like me and my dad in my basement, literally working in my basement to that. It’s very different, that startup journey of all that. But it’s fun. It was a wild ride.

Greg: Yeah, it’s exciting to double like that, but it also, you’re like a different company every year inside. How you did things last year, you can’t do them the same way, and there are different structures and different people and everything, so there are inflection points there. What was the hardest part about that exciting double-doubling growth journey, internally? Was it you going from the one-man coder to now you’ve got 25 people on the team and being a leader, executive leader, or what else? What was the hardest part for you personally in that?

Matt: Well, the hardest part for the company was definitely the support side. Like, we didn’t have enough people to support the product and keep up with the growth. And the product was complicated and it did a lot of things. It got to a point where there was nobody in the company, including myself, that understood how it all worked. There were too many bells and whistles and features and things and whatever. I mean, there was just too much to it. The hardest part for me, I think it was definitely an evolution for me of being… I was super young. I was in my 20s, although I still probably look like I was 15 the day we sold the company. I always looked really young. And you know, just going through that evolution for me was definitely eye-opening from just being a business owner. I was always a product guy, so to me, I was always the developer and the head of product, basically. And so the combination of those two is why we were successful. When we sold the company, we didn’t have a QA team, we didn’t have a product team, and we didn’t have unit testing. We didn’t have a bunch of things that most people think are critical requirements today. We didn’t have any.

Greg: And why was that? You just didn’t do it, or it would slow you down so you avoided it?

Matt: Or those just weren’t common things 12 years ago, right? Like, we didn’t have the cloud, CI/CD wasn’t a thing.

Greg: So it sounds like you didn’t have a problem building product, you didn’t have a problem selling it. It was just keeping up with the hard things. So, that’s an exciting thing. Not all software companies, as everybody knows, kind of get in a chute and get pulled up like that despite warts and the weakness and not having a lot of funding and being in Kansas City.

Matt: We were very fortunate because I was very good at my job and what I did, but on the other side of the executive team we had a couple of individuals who were truly gifted at sales. And so, we had both sides, plus we had the timing that helped us. And actually being in Kansas City was a major advantage to us because of travel, because of travel. So, we had over 50 people that traveled on a weekly basis to do installs and onsite training and all of that. So being in Kansas City is a 2 to 3-hour flight to anywhere you want to go.

Greg: Middle of the country. Was there any ecosystem or anybody who did it before in Kansas City in software?

Matt: Nobody knew who we were. I myself really never had any… I never really had any mentors besides just like my business partners or whatever. You know, there are some big companies in Kansas City like Garmin and Cerner and stuff like that. But if you actually considered us a startup, we were definitely one of the first large exits in Kansas City, you know, over a $100 million dollar exit. There’s been a few since then, but we were definitely one of the early ones. Actually, because of our company being in Kansas City, there are actually a lot of other automotive companies now in Kansas City. Just like in other cities, if it’s health care or pharmaceutical stuff or whatever, you know, different cities are known for different things, right? Well, automotive became a big one for us because there was a lot of talent here. So, if you wanted to do something in automotive software, you knew you could go hire people that used to work at VinSolutions or whatever, right? So there’s actually a lot of other automotive tech stuff here now.

Greg: That’s interesting. You actually helped create an ecosystem like that. You couldn’t really leverage it. I don’t know if the word “bootstrapped” was even a word that you guys used. I mean, did you ever think about raising funding? I’m sure you got offers as you grew.

Matt: We did.

Greg: Okay. So why did you stay off the funding drugs? Was it you were wise about what came with all of that or you weren’t that cool and you were this small vertical solution that was kind of early?

Matt: I think in 2008, 2009, and 2010, like in that era, we were in a recession, but we hired a CFO who came in and his job was to help with a lot of these things and raise capital. And we came close once to striking a deal for some mezzanine debt. And we ultimately killed kill the deal because not only did we have to pay like 12 or 14% interest or something for the mezzanine debt, then we also had to give up a bunch of equity in the company. So we’re like, “Screw that. We’re not paying twice for this thing.” So we ended up killing the deal. And then we basically kind of started the process over. And I think that’s ultimately when we sold the company. When we went to sell, we weren’t really trying to sell, we were trying to raise money. We’re like, “Hey, let’s go raise some capital. We’ll take some money off the table. We’ll take a little secondary capital, take some money off the table, but we’ll swing for the fences and go grow this thing.” But we didn’t really know what the company was worth.

Matt: I mean, the other thing is SaaS investments were not super common back then. Like, it was super new. One of my favorite things about the whole journey is there was a process for probably like 90 days that then stretched on to probably six months of doing that dog and pony show, like going around, going to Silicon Valley and San Diego and all these different places and meeting with VCs and private equity kind of people. And it was crazy because it’s like, “Oh, somebody offered us $80 million for the company,” and then next week it’s $85 million, and the next week it’s $90 million, and the next week it’s $95 million. And then there are three people at $100 million. That was like the craziest time of my life, right? We literally had this expression, it was called “every day” because it was like every day there was a better offer. And it was… It was a fun time.

Greg: That’s pretty fun, especially when you dig this thing out of the dirt and you get this business going and it starts to take off. You don’t know what it’s worth and nobody’s telling you all the time and giving you big dreams out there in the middle of the Midwest, early SaaS. And then, you go out, you’ve built this company headed towards $30 million and people are telling you you’re cool and it’s worth a lot, like big numbers. That’s pretty amazing.

Matt: It was. And one of my favorite things that happened that was crazy is with one of my business partners who was a CEO. We went out to one of the companies and went back to them in California, and he’s like, “Hey, the only reason we’re going to go out there is we’re going to get the valuation up.” And we literally go there and the whole pretense of us going there is like we told them, “We don’t understand why your offer was so low. It was the lowest offer we received from all the other people.” And little did they know that their offer was actually the best. But my business partner had this crazy idea of going out there to tell them like, “Hey, why did you guys offer so low? Your offer was crazy. Everybody else is offering more.” It was just like a crazy, wild experience. And ultimately, we almost ended up selling the company to a different strategic. The guy that owned it was a billionaire. He’s one of the most infamous, big players in automotive. He came to Kansas City, we met with them, shook hands on the deal. I literally hugged the billionaire and said, “Okay, yeah, we’ll do the deal. We’ll sell the business.” I literally hugged the dude. He’s like this 70-year-old guy. And so then that night we called and said, “Hey, we know you’ve been busy acquiring these other things and you didn’t have time for us and whatever. Sorry you missed out. We’re going to sell the company to so-and-so.” And they said, “Nope. No, you’re not. We will be there in two days.” And the rest was history. They came in and they offered us substantially more. But to this day, we still convinced them their offer wasn’t the best either.

Greg: Yeah, that’s awesome. And they got it for cheap. I hear they got it for cheap, Matt. It was a deal. Deal of the century.

Matt: It was. It was a steal. The deal of the century.

Greg: So how did you go from “we could raise a little bit more money, grow, get some secondary, put something in our coffers for the founders,” how did you go from that to acquisition offers? Did the conversation just turn or different people showed up to the meetings and said, “We want to buy you outright,” and you guys said, “Maybe we should sell,” because that’s different to say, “Gosh, we’re going to sign up for another 10 years of fast growth. No, let’s get out now.” Like, how did that turn?

Matt: So that’s an interesting conversation. And here’s the hard part as a founder. You’re thinking, “Man, my company’s worth $100 million dollars, $150 million dollars,” whatever the number is. You’re like, “Man, we’re doubling every year. If I don’t sell a year from now, it’ll be worth $200 million, and then in another year it’ll be worth $400 million, and then it’ll be worth $800 million,” or whatever, right? And that is what goes through your head. You’re like, “Why would I sell? Why don’t I just keep going?” But the reality is, at some point in time, it’s so much money, you just take the money and you run. You just take the money and run. And that’s where it came down to us. And actually one of our shareholders, Dad, actually, said that. That’s what he told us. He’s like, “You idiots, just take the damn money.”

Greg: A bird in the hand.

Matt: “At what point is enough money? It’s enough. Like, it’s a crazy amount of money. It’s like generational wealth for you people. Just take the damn money.” So we, we did, we took the money and ran. It was a fun ride.

Greg: Well, Matt, you had a co-founder in this. And then you had some other team members and the rest. Was this mostly owned by two guys or an executive team or were there the normal partner equity gyrations that most startups have?

Matt: Well, we had some business partners that came and went. So, my original business partner that we had at one point in time, we had like bought out because of some stuff that had happened. And you know, in the end of it, there were three of us that owned the vast majority of the company. And then there were a couple of others that owned little bitty minority shares. And probably the best part was I think we had about 10 employees or so that had some stock options kind of deal. And that was probably one of my favorite things. Like the day we sold the company, there were like 10 people that were millionaires or something that day, right? And so, that was a really cool feeling. We had several a few employees that had a nice win as well.

Greg: So, you were one of the co-founders and presumably one of the largest shareholders and you must have been about 30 about this time, something like that. Not an old guy. And all of a sudden, the big prize and the clapping and the recognition. How did that feel to go through that process and say the bank account looks different and the next 10 years look a little different and, I don’t know, people look at me differently now? Did that feel good, or?

Matt: It’s interesting and there’s a lot of weird stuff that happens from all of that, and everybody handles it differently. I was 29 years old. It kind of feels like after you sell, though, it’s like you get off the roller coaster. Like, the fun part of it was the journey of building the company and do all of it. And honestly, I have to say, the actual selling of the company was sort of anti-climactic. It’s like, okay, my bank account has a big number. But other than that, what do I do now? What do I do now? What am I going to do with the rest of my life? Like, I put my entire life, the last eight years into this thing, and now what do I do?

Greg: Well, that’s usually a stunning realization, which is I’ve been 110% over here, and now it’s at zero or something less. You’re resting, investing inside the big company now, it’s a totally different game. And, it’s, “Surprise! Everything you had fun with, you don’t get to do anymore, and you haven’t planned for this kind of thing.” Some founders say, “It was the best day of my life when it hit the bank account and the worst day of my life the next day when I realized my identity and everything else had changed.” But, what kind of transition was it for you? I mean, did you take a vacation, buy a big house and have fun with AutoTrader for a year? Or what did you do? How did that go?

Matt: I bought a house and bought a couple of other toys later. But for the most part, life was pretty much the same. I stayed at AutoTrader for a few months and we had an earnout through the end of the year. I had started getting an idea for going and doing something new. And that was right before I decided to go and start Stackify. And I actually went to our CEO, my main business partner one day and I said, “Hey, our earnout’s up at the end of the year. How long do we have to stay here? Like, I don’t even know. Like, they’re giving us a bunch of money, I’m just going to do whatever they want me to do. If I got to stay here for two years, what am I going to do?” And he’s like, he told me, he’s like, “Matt, they abolished slavery a long time ago. If you don’t want to be here, you don’t have to be here. They can’t make you be here. They don’t want you to walk around like a zombie all day. So if you don’t want to be here, you can go.” So like, “True. I’m out of here. I’m out of here.”

Greg: That’s amazing.

Matt: So, yeah, it was like 30 or 60 days later, I was out. That was it.

Greg: Just so people could hear this, you were the crazy entrepreneur, the builder-doer, right? You’re an entrepreneurial CTO tech leader, right? You’re not just a coder and leave the business to everybody else. You’ve got a lot of startup ideas. What was it like to be inside AutoTrader? Was it like a totally different game and you said, “This is no fun anymore and it’s corporate meetings and all of that,” and, “I’m not responsible anymore. The buck doesn’t stop with you.” How’d that feel?

Matt: So honestly, not a lot changed right away because we had an earnout. So for those who aren’t familiar with an earnout, we had, as part of the contract, we had revenue targets and stuff like that to hit by the end of the year. And that affected how much money we received from the sale. And so we told them, “Hey, don’t distract us with anything. We got our own goals. We’ll talk on January 1st.”

Greg: Okay. They left you alone.

Matt: We put up the walls. Now, they did come in and we had some meetings and what have you. The number one thing that we needed help with was actually our data center stuff, as I mentioned earlier. Servers, equipment and redundancy, and all this stuff. Like, we needed help. Now, they didn’t do any of that. It took them two or three years before they finally did that. We were pretty isolated because of the earnout situation. I will say, though, one of the coolest things I’ve ever done in my life was going to the board meeting for AutoTrader after the sale. You know, it was a well-run business that did a billion dollars in revenue a year or whatever. And going to that board meeting was probably one of the coolest things I ever did because I like presented to the board about the company and what we did and whatever and blah, blah, blah, and got to meet the owners of the company. So Cox Automotive is actually owned by… It’s privately held; it’s not a publicly traded company. And so, it was my understanding there were a couple of ladies that owned it and then one of their nephews was like one of the key people. I never thought I’d know somebody who was a millionaire. I almost sold a company to a billionaire, sold a company to a different billionaire, and then I bought a house and lived next door to a billionaire. You know, it’s just weird things about life, you know? But going to that board meeting was just super cool. I don’t know why; it was just kind of a neat thing for me.

Greg: It’s almost like going pro, right? You know, it was all this scrappy company and all of a sudden you’re real and it looks good. And people and serious professionals are saying, “That’s awesome,” you know, and worth a lot.

Matt: Yeah. I almost felt like I showed up to Wall Street or something and like, this is how the big boys do it. So, it was just a cool moment for me.

Greg: Yeah, that’s awesome. So that was a big win. In Kansas City, is that known as one of the big wins? Are you a big man about town, Matt? Do people know who you are?

Matt: It is. I mean, I think there are definitely people in the tech community and startup community who know who I am. I mean, I’m an F-list celebrity at best, probably. I mean, in the Kansas City automotive industry, I guess I’m an A-list celebrity. But in the rest of them, no, nobody knows who I am.

Greg: Yeah, that’s right. Cool kid in that room. So you started another company called Stackify, and this wasn’t a vertical software company, and it wasn’t just U.S.-based, and you started that. I don’t know if you had co-founders. Tell us about Stackify and how you got that started.

Matt: You know, one of my frustrations at VinSolutions was when I left there, we had like 40 software developers and none of them had access to production. None of them knew how to like, troubleshoot things and know if anything worked. And we always had all sorts of fire drills all day long about the server doesn’t work, the app doesn’t work, whatever. And so the idea was like, “Man, we really need some software to help monitor all this.” And at that point in time, the most cutting-edge thing we had was Nagios. I don’t know if you remember that. That was a giant piece of crap. There was no doubt some other expensive enterprise things existed, but we didn’t have any of them. So I had this crazy idea…

Greg: It says your server’s down or performance issues or some kind of hiccup in the big web system.

Matt: That was the idea is I was going to go create something designed for software developers to help them troubleshoot and monitor their applications. I was the only founder of that. That was very different for me from basically being the CTO to being the CEO of a tech company, and it was all me. You know, hired a few people and started to do that. And that changed over time because originally we thought we were going to do monitoring and remote access. And then as the market changed and the cloud and everything, we eventually built what is today known as an APM solution or application performance management or monitoring solution. And we honestly kind of getting sideswiped by New Relic and Datadog and companies like that. They didn’t exist when we started, or if they existed nobody knew who they were either. They started around the same time. They raised hundreds of millions of dollars and went public and whatever. It became very difficult to compete with them, ultimately. And it was a brutal fight.

Greg: Well, that’s the flip side of the bootstrap story. If you find yourself in a hot space and the race is on, if you’re not taking the rocket fuel to race faster, then sometimes you can’t keep up. Is that a story? I mean, did that happen?

Matt: Yeah, yeah. I mean, that is the story, right? It’s like, you get off the airplane in Las Vegas and there’s a giant billboard in the airport for one of our competitors. Like, I don’t even know why they have billboards at the airport, but they do. You know, they’re spending tens of millions of dollars a year on sales and marketing and stuff. It’s just hard to compete. So we tried to focus on SMB or different programming languages and things like that, trying to find our niche. But it was just brutal competition in those spaces. It was hard, very hard.

Greg: Yeah. So you built a product, you kind of pivoted and found a focus. How did you go to market with that? I mean, you got that up and running with revenues, right? How did you go to market? It wasn’t sales guys calling out like on your dealers with VinSolutions.

Matt: No.

Greg: Was it product-led growth, promoting to developers, and they could try and use it and see? How’d you get your first customers?

Matt: You’re not going to believe this, but software developers don’t answer the phone, and they don’t like advertisements. They don’t like spam. They don’t like any of those things. And so, yeah, learning to market to software developers was brutal, brutal. And they are by far the hardest people to sell to because they can also build it themselves, or they think there’s some open-source solution or whatever. And so yeah, it’s a tough market, but we eventually figured it out. The one that worked really well for us that we had seen some success with, that we doubled down on was content marketing. So to this day, I still believe there’s a universal truth. If you have a problem and you want to know how to solve it, if you’re smart, you just go to Google and search for it. So we focused very heavily on creating high-quality content for that. I personally wrote hundreds of blog posts myself. We crushed it. Our website would get 10 million website visitors a year. More than our competitors that were spending millions of dollars on sales and marketing, trying to do enterprise sales. We were doing SMB sales, right? And we crushed it doing content marketing. We did very well. And we also created a free product that was like a free tool, like a different tool.

Greg: I see, right?

Matt: And that worked well for product-led growth like you mentioned. And so those two traction channels worked well for us. But to be honest, it was still brutal competition. You know, we’re trying to do SMB sales, trying to take the SMB market. I mean, the only good news for us is our competitors like New Relic and AppDynamics, they didn’t want our customers. Our customers were paying a couple of hundred dollars a month, $500 a month, whatever. They didn’t even want those customers. They wanted the ones that were spending thousands of dollars a month. So that was the only thing that was in our favor, is we were trying to pick up the scraps from the big guys. And that’s a really, really hard place to be. I’m going to be totally honest.

Greg: Yeah. And unlike VinSolutions, you came in with some new technology, cheaper, faster, and easier, and you were landing punches against the old legacy competitors that people use. Like, you guys were way better than the previous solutions. And this one, you had some big competitors that product and marketing and reputation and customer base were way ahead.

Matt: And some of what we did was ahead. You know, today the term observability is a big thing, right? I’m sure you’ve heard that term and anybody who’s a CTO or whatever knows what observability is probably at this point. Well, we were doing that before anybody else was, but nobody knew what it was. Even though we were doing it, people weren’t buying it. We were talking to SMB and SMB companies definitely didn’t know what it was.

Greg: They don’t do buzzwords.

Matt: No. So I mean, that’s the hard thing about it, and to some degree, we were trying to create a market that wasn’t there yet and trying to sell to developers. But developers weren’t really looking for our product. It was just tough; it was hard. It was very hard.

Greg: In the end, you sold that and it sounds like it wasn’t a huge win. So that was 2012. How long did Stackify go?

Matt: So we started in 2013 and sold it in 2021 to a strategic company called Netrio. They were private equity backed, and so we were basically part of a roll-up there. And they were still on infrastructure monitoring and so they saw our application monitoring as something that was a nice add-on to what they were doing. And the craziest thing about that is we sold the company during COVID. I literally never met any of the executives at the company or the investors, the PE, none of them. Literally, never met a single one of them in person. And we sold the company, wire hits the bank, and we got the money, never met them. And I offered many times, like, “Oh, I’ll come to California and meet you and whatever.” No, they were scared of COVID and all of it. And that was the weirdest thing ever. Like, sold a company and never met the people.

Greg: Isn’t it interesting compared to the old days of software? You had 50 people flying all over the country every week.

Matt: Oh, yeah.

Greg: What lessons did you learn from VinSolutions? There were lessons learned along that. But you know, you get a lot of credit for the things that went well and the growth and the exit. But, I don’t know, what lessons did you take away from Stackify either about how to approach a market, or, next time I’m going to have a co-founder or getting traction first before you quit your day job?

Matt: I mean, I think it’s all of it. You just learn so many things. I mean, that’s the thing is we don’t know what we don’t know. Just because you’re successful and, okay, I founded VinSolutions and it was a good exit and all that, that doesn’t mean you go do something again and it’s successful. Like, there are no guarantees of any of this. This stuff is hard every single time.

Matt: Now, if I would have stayed in automotive, I probably would have had like a thousand times better chance of being successful because I knew the industry and all that. I went to a totally different industry trying to build a product and not knowing how to sell it, the go-to-market strategy, and the problem we were trying to solve, and all of that. One of the traps that I fell into that I see other entrepreneurs fall into is they’re like, “Oh, I have this problem, I’m going to go solve it.” It’s like you’re trying to scratch your own itch, but that doesn’t mean that anybody else cares. Just because you think it’s cool doesn’t mean anybody else thinks it’s cool. And I think that’s part of what I fell into is like, “Oh, I could really use this Stackify thing. I’m going to go build this.” And then realized it’s like, “Man, actually selling this to other people is going to be way harder than I thought it was going to be.”

Greg: But you also bootstrapped this. Did you ever think about getting funding? Because sometimes funding follows around the successful founders who exited. Did you ever think about funding or did you choose to stay off the drugs? Did you raise a little funding?

Matt: I just invested my own money into it, which is its own dangerous thing because it’s so much easier to invest your own money than it is to go beg other people for money. You’re like, “Man, I don’t want to spend the next six months going to try and raise money. I’m just going to fund it.” And that’s another dangerous thing because you can just keep funding it. Even if everything you’re doing is absolutely terrible, you just keep funding it. There’s no market there to kind of validate whether or not somebody would invest in this thing. You could just keep writing the checks. And so that’s also interesting. Eventually, we did raise some money from some local angel investors, just individuals, private individuals. And then we eventually did venture debt. So we took on some venture debt. We were a perfect candidate for that. That worked well for us to kind of bridge us to when we exited the company. I say all this was hard, but we were still an Inc. 500 company. We were still growing 40 to 60% every year, and it was a good business and all of that. But it was just hard. It was really, really hard. Just to be honest, it was hard.

Greg: Yeah. You were pushing the rocket. Sounds like with VinSolutions, you guys kind of struck the cord and got pulled up, right, and were like, “Slow down, slow down.” And this one, you kind of had to fight hard, push hard. There’s the coder having to write his 75th-long blog post about a particular topic, and that can grind it.

Matt: And then a byproduct of Stackify ended up being my company Full Scale, which does offshore software development. That was an accidental business because I needed to hire software developers. Like most people, I get spammed by companies in India and all these places every day. But I don’t know who any of these people are and I don’t trust any of them. And so a friend of mine had developers in the Philippines and I said, “Hey, you know what? If this works for you, let’s try this and I’ll hire ten people, and let’s try this thing.” And it was like, “Hey, you run the thing. You go find the people. You go do all the work. I got my own company to run, but we’ll partner on this thing and do it.” And so we did. And it turned into an accidental business. I told a few people that I knew that I was doing it, and then we hired like 100 people over the next six months after we started it. And now the company has like 300 employees. So it was like a weird byproduct of Stackify that was never, you know, not really not part of the business, but it was like a weird byproduct that happened.

Greg: So you actually use Philippine offshore developers for Stackify, partly?

Matt: We did. It was a mix, yeah. I mean, that’s the thing. We didn’t have a lot of funding or anything, right? So it was hard, and I’m trying to compete against these giant companies. And the only way I could compete was by leveraging offshore because it cost 60, 70% less. And I had to go to my developers here in Kansas City and be like, “Hey, man, the only reason I can afford to pay you $150,000… Like you’re awesome at your job, you’re fantastic, I could hire nobody better than you. But the only way I can afford you is to dollar cost average you down. You’ve got to work with these other three people that are offshore.” And that model worked really well for us and we had a lot of success with it. And no doubt it played a key success in Stackify in the end of being able to build the technology we built. It worked well for us.

Greg: So tell us about Full Scale. There are a lot of offshore development solutions, marketplaces that match, and so forth, but it sounds like these are employees. And so an entrepreneur says, “I need to add 10 developers to my team to do this dollar cost averaging and reduce, get more done with the less average cost per developer.” Are they your team members, your employees, but they’re reporting to the client, tech leaders? So how does that work?

Matt: Yeah. So there are a couple of different ways that people do this. You know, people refer to it as outsourcing or offshore. And outsourcing to me means more like “I have this big project to do and I’m going to have this other company do the project. They’re going to run the project and at the end, I’ll get the result of that when it’s done. I get the deliverables.” And so that model does not work very well, and it does not work very well especially if you’re a SaaS company that’s trying to innovate and build your own thing. Adding other layers, or like, “Oh, I talked to some project manager and then he manages some team or whatever.” That quick iteration does not work that way. The other alternative is doing staff augmentation, which you know, there are some offshore companies that do that. And that’s what we ultimately decided to do. It’s like, “Look, we want to do staff augmentation. We don’t want to do project-based work and involve that because we don’t feel like it works very well.” And what we see all the time is there’ll be companies that you just deal with that project manager, and then heck, the development team may not even speak English or you don’t know who they are or they’re not that great developers. And it’s just kind of a black box of like, who’s writing the code and doing the work? When you’re doing staff aug, for us it’s like, “Hey, you need three developers? We give you three people. They basically work for you now. They’re like your employees. If they’re doing a bad job, you’re going to know. If they’re doing a good job, you’re going to know. They work directly for you. They assimilate to your business however you want to do business, and you know, we just provide the labor.” And that works really, really good. I mean, if you hire really good, quality talent, that model works really, really well.

Greg: And so you’re not selling to startups that need one or two developers. You’re selling to companies that have 20, 30 or more, that build SaaS products that say, “I need 10 people at a time.” What’s a typical company?

Matt: A lot of our customers just need a couple of developers. We actually do a lot of that. Now, I know another guy that owns a similar company to us and he has 2,000 employees that do this same sort of business. But yeah, his customers come to him and they’re like, “I need 100 people,” or, “I need 20 people.” We talked earlier about SMB versus enterprise. Like, he only deals with the enterprise. He doesn’t want the one or two-seat accounts. He doesn’t want to deal with those. He makes like $25 million a year from T-Mobile. We have focused on primarily startups. We have a lot of customers in Kansas City but in other places. And yeah, they’ll be smaller teams. I think our largest team is say, 20 people.

Greg: This isn’t like “I’ve got an idea. Do you have some developers who can build something?” This is, what you’re augmenting, adding to an existing small development team. Or, what’s typical there?

Matt: Generally speaking, I would say that I would agree. You know, if somebody comes to us and says, “I have this crazy idea. I want to build some software. Can you guys build it for me?” We usually will say no, because if they don’t know how to lead the project, they don’t know how to build software, their expectations for all of it are unrealistic and it just doesn’t work very well. We have done that a few times only with people that we knew or who were experienced or whatever. But yeah, that doesn’t work very well. We typically always want to see some sort of product owner or tech lead to work with, absolutely. And then it works fine.

Greg: So now you’re in the services business and maybe there’s a little technology that you guys have, but it’s a services business. Is that fun for you?

Matt: It’s totally different. And all the credit goes to the team. You know, we have 300 employees that do all the work. I don’t do any of the work. They do all the work. You know, our job is just helping run the business and finding them more work to do and creating more jobs for more people. You know, I think in 2023, we may hire 100, maybe 200 people. And you know, that’s fun. But it’s a totally different business than a SaaS business, right? And I would definitely recommend to people to consider some form of service-based business because it’s so much easier to do, to get off the ground. My first couple of SaaS companies, you spend a couple of years just even trying to make meaningful revenue and then you may spend a couple more years before it ever becomes profitable if it ever does become profitable. Where service companies can be profitable almost right away.

Greg: So, Matt, let me ask you, the VinSolutions, you grew it fast, right? And fast-growing companies that are starved for people, you’re not taking other money out of the business. You’re living lean, growing this thing. So you’re bootstrapped, but thinking big, going fast and going for the exit. You got your exit, right? Put the money in the bank and you have this other company and put some money in. But you got an exit there and this thing is profitable. What does somebody who makes a pile of money do with all this money? This is kind of the big win question. And I’m a Midwesterner, you’re a Midwesterner. Like, maybe if you’re in L.A., you buy the biggest house at the top of the hill or something like that, and that’s how you keep score. But what does it mean to have successful businesses and to just not worry? And you can buy whatever you want at The Olive Garden now.

Matt: Yes. And I can go to Chuck E. Cheese anytime I want.

Greg: But what does it mean? Is it worth the sacrifices, or?

Matt: I think ultimately the best thing is being able to have time to do whatever you want to do. I retired when I was 29 for a few months. I retired when I was 39 or 40 for a few months. And that’s boring. I need something to do. And I love working. I love startups and I do some different advisory work and different things. And I’m thinking about starting another SaaS company, as crazy as that is. I enjoy that part of it. During the few months that I took off, I honestly mostly figured out a lot of every way possible to lose money at crypto for those few months. You laugh. You’ve done that too, huh?

Greg: Yeah. It’s funny how like, you’re counting pennies for all these years and then you get out and things loosen up and it’s like, “That went pretty fast, you know?” That’s right. Angel investing does that to you.

Matt: Yes. Yeah, I’ve done several angel investment deals. And, you know, recently I started working basically as a fractional CTO for a company. And I had a lot of fun with that. I love being back in the game of helping them and doing that is just rewarding. I enjoy working. I can’t imagine being retired. And I live in a neighborhood that’s on a golf course, and every once while in the middle of summer, I’ll be driving through the neighborhood and I’ll see some guy out there golfing and it’s like 100 degrees outside, he’s by himself. And I’m like, “What in the world? Why would you do this? It’s 100 degrees outside.” The only thing I can think is like, “Man, this guy must hate his family or something.” I’m like, “Why are you out here?” Like, I couldn’t do that. I enjoy working. I’m definitely not going to go golf every day, that’s for sure.

Greg: Yeah. Well, it’s a common story on the Practical Founders Podcast. What did you do? And then it’s either three months or six months, I hit my limit and I got back into the game. So very exciting. And I know you have a successful podcast. You have over 1,000 episodes of the Startup Hustle. Talking about all the nitty gritty here. So you’re another contributing to the ecosystem and helping out and helping founders. Matt, congratulations on all your success and the brutal learnings and excitement and thrills of all of this. We didn’t get into the near-death moments and the tears or whatever dark moments that were there too much, but what do you think founders need to hear that they’re not hearing? You’re talking to a lot of folks at the ecosystem and founders who want your services, and people come on the podcast, you’re interviewing founders. What is it that they need to hear that they’re not hearing from the media and the funding industrial complex and the ecosystems?

Matt: I mean, I think the most important thing is just asking people for help. Finding mentors and advisors and all that kind of stuff is by far the most important thing other entrepreneurs can do. I mean, being an entrepreneur is a lonely place. There are not a lot of people that you can relate to. The key is finding people that have done similar things to you in your industry and whatever.

Matt: Some guy reached out to me today and he’s like, “Hey, I’m thinking about starting a company like Full Scale. Can I ask you a question?” I’m like, “Sure, whatever.” And I got on a video conference with him for 15 minutes and I’m like, “Here are all the things I’ve learned in the last five years that you need to know.” And I think the guy was probably the most grateful person in the world for 20 minutes of my time. And I’m like, “I don’t really care, man. Good luck.” For him, that was super invaluable. Just finding advisors and finding mentors that are willing to give you that 30 minutes of time that could be a game changer for your business is, I think, a really big key thing that people need.

Greg: And it’s a challenge for bootstrappers because they’re not selling pieces of their company for help to investors or to the ecosystem or to the accelerator incubator that all wants a little piece of it. But if you’re not doing that, your head’s down, day and night, not getting out much, and nobody knows you, even in your own ecosystem. They tend not to get as much advice, especially if the advice coming from the ecosystem is mostly about getting funding. There are a lot of mentorships… You know, the first answer is, “Well, get on the funding truck.” Accelerators are notorious for this, right? They have the normal thing about customers and products and growth and everything. And then it’s the pitch game, right? And then you end up in the room with everybody pitching. It’s like a gateway drug to the funding truck.

Matt: It is. And usually, that personality of people is more like CEO, sales type kind of people as well, right? And I’m more of a tech, product guy, so I’m kind of a different personality as well which is an even lonelier place to be, I think. I’ve met a lot of great people on LinkedIn and I know a lot of people in Kansas City. But, you know, it’s just all about finding your group there and finding people that you can network with and relate to and bounce ideas off of. And anybody who’s listening, if you want to reach out to me, you can find me on LinkedIn, and always glad to chat.

Greg: I appreciate that, Matt. And I could recommend the Startup Hustle Podcast. It’s really interesting. It’s founder stories and other advice that you’re giving out over there. And Full Scale sounds interesting too. I’m sure you’re helping a lot of crazy founders out there.

Matt: We are, yeah.

Matt: Matt, congrats again on your success, your practical founder’s success, Midwest style, and I appreciate your sharing your insights and making yourself available to founders if they want to reach out.

Matt: Any time. Thank you so much for having me on the show today.

Greg: Thanks, Matt.

Greg: Thanks for listening to the Practical Founders Podcast. I hope you found this interview interesting, and well, practical and useful. Please subscribe to the Practical Founders Podcast in your favorite podcast app and stay tuned to hear amazing stories from successful founders who are winning their big prizes and doing it their way, without big funding. You can visit to join the community and get my weekly email with deeper insights for practical software founders all over the world. And you can reach out to me directly on LinkedIn. Let me know what you think of this podcast or connect. Love to meet you. Goodbye.

In this episode, Matt explains:

  • How they started by taking photos of cars for auto dealers to sell those cars online, then bootstrapped a CRM software product to help dealers manage internet leads
  • What it was like to be the CTO of a pioneer in web-based software with a recurring revenue business model back in 2008 when the auto industry was in a massive recession
  • The benefits and drawbacks of growing a large vertical software company in Kansas City
  • Why they tried to raise capital but started the process to sell the company instead
  • Why Matt started a new company called Stackify as the CEO with a different customer focus, technology stack, and different sales model than his previous company
  • Why did he self-funded Stackify and then raised venture debt as they grew, but didn’t raise big VC funding
  • What it is like to be a two-time founder of software companies with successful exits before he was 40 years old

VinSolutions Company Facts

  • Founded: 2006
  • Description: CRM and lead management software for auto dealers in North America
  • Number of Employees: 300 employees
  • Funding: Bootstrapped with credit cards, revenues, and a tiny angel investment, but didn’t raise big outside debt or investment 
  • Acquisition: VinSolutions was acquired in 2011 for a reported $150 million by, now a division of Cox Automotive
  • HQ Location:  Kansas City, Missouri

Stackify Company Facts

  • Founded: 2012
  • Description: Stackify develops Application Performance Management (APM) solutions to show how and why cloud-based software applications underperform
  • Number of Employees: 20 employees before the acquisition
  • Funding: Self-funded by Matt, then revenue funding and venture debt funding 
  • Acquisition: Acquired by Netreo in 2021
  • HQ Location: Started in New Jersey, but not they are a remote global company



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Greg Head recorded this on episode on February 17, 2023 for the Practical Founders Podcast see all of the episodes.

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