Mason Hale shares how an unexpected volunteer role for his children’s swim team became SwimTopia, a global software company serving customers in 20 countries. He opens up about co-founder challenges, stretching three months of runway into six years, growing through a creative acquisition, and rejecting the traditional startup playbook to focus on what mattered most: solving real problems for customers.
Christina May: Well welcome to The Breakout Moment. I am so excited to have you here. And you have had a long, winding road trip to get here from Texas. So, why don't you tell us a little bit about SwimTopia and entertain us about this road trip you're on right now?
Mason Hale: Sure, I'm Mason Hale. I founded SwimTopia in 2011, and, we're on a road trip right now from Austin, Texas that we actually went up to Canada to pick up a travel trailer. And we've been running her way back down through the East Coast. We had to stop in Rhode Island, Massachusetts, New Jersey, Pennsylvania, and then now we're in Delaware.
CM: All right.
MH: And now Maryland.
CM: Maryland, Yep. Delaware. Maryland. Where to next?
MH: So Virginia.
CM: Okay.
MH: Few stops in Virginia and then down through North Carolina and to Georgia, down to the coast in Alabama, and then back home.
CM: Okay. So you're just running your way south all the way. So you're acclimating to the temperature all the way back home.
MH: Pretty much, we'll get used to the heat by the time I get home just in time for August. And we're we're visiting swim teams and swim meets along the way. And as a little fun fact, we brought, about 250 t-shirts and a t-shirt cannon. So we're looking forward to it. We're going to go shoot some t-shirts at a pep rally this Friday.
CM: Very fun, very fun. Okay. It feels almost like baseball thing, you know, or a sports event where you're shooting the t-shirts out.
MH: It’s definitely some something I love about swimming, especially like the summer rec swimming, market where, it's a very community driven thing. So it's sort of a thing that the community builds itself around and, just love to, like, get into that vibe. That's awesome.
CM: Yeah. That's amazing. You didn't start with SwimTopia?
MH: No, no. So I started with the problem. I was working at a consulting company at the time, traveling about 50% of the time, most of it international. And, while I was gone on a business trip, I got home and my wife said, hey, honey, I've got good news and bad news. Good news, the kids are signing up for the swim team. Bad news, I volunteered you to run the computers for the team. And I was like, what does that mean? And so then she gave me the number of the current computer person on the team, and I went to her house, and she could not hand me this old, dilapidated teen laptop fast enough. So, you know, the way that swim teams run is, surprisingly, archaic. So that software predated windows. Started as a DOS program.
CM: Oh, my gosh.
MH: It’s almost every swim team runs on or used to run on, and it just wasn't going to work with my travel schedule and things like that. So I quickly put up a site where the parents could tell me what if they're going to be at the meet and what events their kids wanted to swim. And by the way, our team had 250 kids. So it was it was a lot to keep track of.
CM: Oh, my, that's a lot. No wonder she wanted to chuck this thing at you as fast as humanly possible. That's always a sign you notice, like when you get volunteered for something and you're doing the handoff, whether it's like a board or volunteer organization or whatnot, you can always tell you're like, oh, what did I get myself into here?
MH: And the cost of making a mistake was really high because, you know, there's only so many lanes and a swimming pool
CM: Right.
MH: And so if I forgot to enter someone in the event, there might not be a lane for them. And so, you know, you have a little girl that shows up and wants to swim the breaststroke. And if she's not in, you've got a crying kid and angry parents and nobody wants that.
CM: Nobody wants that.
MH: Yeah, so I really had a problem and I was able to fix it for myself. And then by summer 2010, by that time I was the, the computer chair for the whole swim league. And we're in Austin, Texas, we're at the, University of Texas Natatorium, and I get surrounded by the other teams in the league asking how much it would cost to use this thing that they knew that I had. And it was at that point that I was like, I might have to start a business.
CM: I might have something on my hands. And you know what? A lot of people talk about that type of like genesis of a of an idea. And it's so funny. So many entrepreneurs, I feel, hunt for that idea. But in your case.
MH: It found me.
CM: It found you. And I think that's the case more often than not.
MH: Right. Yeah, yeah. There's this, great book I read called The E-myth Revisited. And it's it's about that kind of thing that the myth of an entrepreneur is that they seek out a business.
CM: Correct.
MH: And most of the time they are really chasing a dream, pursuing a passion. And they need to figure out how to make that into a business.
CM: Yes.
MH: And so I think that's a lot more common but that was, that was definitely my story as well.
CM: Yeah. No, it's similar to me in in a different way. It wasn't, the problem was more personal. It was career driven, as in, I'm stuck, I'm in this place. I'm not able to get where I want to go. You know, I had a lifestyle choice, which was, I don't want to spend 25 hours a week commuting to my 40 hour a week job. That math didn't math outright. It did make sense. At first. You're thinking, oh, this is a great salary. And then you put all the commuting in the time and, you know, the personal cost and you're like, this is terrible,
MH: Right.
CM: And between that and economics, I didn't start out with this idea of I'm going to build a company. I started out with, well, if the world isn't giving me what I need, I'm just going to go build what I need for myself. Next thing you know, you've got a company on your hands. So what was that, like moment where you're like, oh, this is real. This is. I could do something like, you got serious because I don't know about you, but for me, it was like a whole bunch of chatter in the back of my brain for really long time before it got loud enough that I acted on it.
MH: Right. So by the time I was at the pool deck and the other teams around me, well, they were actually offering me money. So they were saying, know if we gave you 5 hundred dollars or 6 hundred dollars, you know, would you do it? And so that was an interesting thing that got me thinking by that point, I'd left the consulting company, and I was a CTO at a startup that we'd raised, series around and found that path.
CM: Which is a very different path.
MH: Right. And that was around the 2008 financial crisis. We were running out of money, by 2010. And so there was just the timing of that, like I needed to find something else. And then this thing came along. And in Austin there was a new, startup incubator program called Capital Factory that had just started. So, it took me several months, but it was actually February 2011, when I sort of officially started the company. And then I got accepted to the accelerator program. So things started falling into place.
CM: Oh that's amazing. Now, I know a lot of accelerator programs focus on tech, bio, and tech. The rest of us kind of don't usually get into programs like that. What is that experience like for you? You know, what were some of the things that helped kind of propel you forward, being part of almost like an incubator startup environment, having been asked, you know, already having been part of a startup, so you already kind of knew what that look like just from a different perspective.
MH: Right. I think, in that program, there were 20 mentors that were in that initial there are more now, but it was, I had the expectation that I would spend time with every mentor and talk to them. So I got to see how they perceived my business and where we were and where we should go from a bunch of different perspectives and from people that had been, you know, had done that path in different ways. One challenge is I got a lot of different and conflicting advice. And so being able to sort through that was hard. But it was, it was good to just see the the range of those things. There were also, classes that we would go through. So like how to, how to pitch for business. We did like pitch practice, how to read term sheets, how to understand all the terms that are involved. That was very, very useful. And then just creating a peer group. So we were going through as a cohort of other people that were also running businesses. And so being able to work with them, it's really hard to start a company whether tech or not. And so just having a group that understands that, because most people have no idea, was really useful and to this day, it is extremely useful to have that network.
CM: Is there anything that was part of that experience that you felt, you know, like something that got skipped over, like now looking back because obviously you're further down the road now you've graduated out and.
MH: Right.
CM: Is there is there anything that you feel like would have been nice to have?
MH: Well, one of the pieces of conflicting advice I got was whether or not to try to go raise a series A. So in the tech world, there's this traditional path of like you go get a series A and deal with VCs. And that was most of the advice that I got was to follow that path. But I had some people that were saying, don't, you don't need to go that path. And then the whole program ended on this demo day where you're going to go pitch to a roomful of investors. So you're sort of forced to really pursue that. But I think longer term, after pitching lots of VCs, I learned that the swim market is just considered too small. And so it pushed us prematurely, I think, to try to expand to other sports. And so it took a long time, more than a decade, to really realize, like, that's not right, the right path for us. And to get off that, that train. And it was that felt like, the more uncommon way to do things or the more unorthodox way to do things. But, yeah, it took a while to figure that out. So I would say being dropped in the assumption that you're going to do series A, series B, and that that's the right fit for everyone I think if I was to roll it back, I would I would question that. And if I was to give people advice, I would ask them to like really question that. Fortunately for entrepreneurs, now, there are a lot more options than there were. There's a lot more, and things like that that are available. Plus, just especially with like AI tools.
CM: Oh, you can fail very fast, very, very fast.
MH: The cost to get something off the ground or to a prototype.
CM: It has it's significantly dropped.
MH: Yeah. At least factor of 10 if not 100. So that world is different. So it also changes the dynamics. Like you don't need as much money or as early as you used to. So I think that does give and you have more options if you do need to go raise money. And I think that puts a little more power in the hands of the entrepreneur. Versus they're feeling like this is the only thing they can do. And therefore they're beholden to the disease.
CM: And I think that's interesting because, outside of the tech world perspective, even though we're kind of tech adjacent with what we do here, at illuminate, is you know I was allergic to the idea coming away from a job where I had bosses. I was allergic to the idea of having bosses again. So when you're talking about funding. Because when you're starting, you got to have money coming from somewhere. I was allergic to raising money. Whether the family and friends round or any round it was just a personal choice. And when I went through a summer similar program with Goldman Sachs, part of that program, they put you where you are pitching to Goldman Sachs and they are a bank. And I didn't need funding. That wasn't the goal. That wasn't why I was there. And then same, same kind of thing where I kind of like felt pushed in that direction, where that was one of those things where just like what I'm looking to do doesn't require. I mean, yes, it would be nice. Who doesn't want a blank check of some kind or zeros on it, right, to implement an idea, but at the same time, it's more valuable to me to be more creative and go at this in a different way so that I don't take on that debt or leverage debt in that way right now. And I think maybe that's something that we both have experienced is just there's lots of creative ways to put together a deal. Right?
MH: Right.
CM: So, you know, I think, I think there's this myth, you're raising money, you're doing the friends and family round, you've got, you know, bootstrapping it or doing things in a unconventional way. We don't really talk about all those other different creative vehicles. And I know you've run into some of them too.
MH: Yeah, absolutely. I think I think the fundraising route also sort of masks, success. People will celebrate raising big rounds. That's not really success. And so it can it can actually put you on the wrong track. The, you know, there's a lot more options out there. I'd say the big lesson I've learned is that, if you assume that you need a lot of money to go do things, sometimes you can find another way to, to achieve the same objective without cash or with, you know, other. There's you have a lot more at your disposal as an entrepreneur than you maybe see it first. And for my case in particular in, 2017. So this is I'm like six years in, I should mention so as part of the startup incubator, the other advice I got was that I had to find a co-founder. So I was going through as a solo founder, multiple people told me I was absolutely crazy for doing that, that I had that trying to do this alone.
CM: Really interesting.
MH: I found a co-founder. There's a whole story there that I won't get into but it should’ve been perfect. But it wasn't. And so we did. We did raise a small angel round, that demo day that I mentioned, we actually won the audience choice award to have a nice plaque from that. But a little more than a year later, the, the co the co-founder relationship wasn't working, and we burned through most of the money that we raised with three months to go. I was faced with like, what do I do now? And at this point we had customers. They loved what we were doing. We weren't making that much money. We didn't have employees at that point. We had some contractors, but I had to pull the plug on that, and I stretched that three months of runway for six years up to 2017. So I basically got back into side project mode. I was doing other jobs, doing consulting gigs, not paying myself, with SwimTopia.
CM: Man, that sounds familiar to me.
MH: Yeah, yeah. And that those are the things that no one understands. But by 2017, I did have a full time employee and three part time employees, but I still wasn't on the payroll. And there I went to Atlanta and there was another competing software out there that was ad-based. So it was a free product that was completely ad-supported, but was very popular in the southeast. And I talked to the founder of that early on when I was just starting to see like, maybe we could work together. He wasn't really interested, but by March of 2017, I'd grown enough to where we had just passed him in terms of number of customers. He was at the same league meeting that I was that I was at, and so we went and grabbed a beer afterwards. And he told me that, you know, his kids had graduated and weren't going swimming anymore. And he was looking for, for a way to, to hand off his customers in some way. And, you know, at this point, I'm not even paying myself a salary. So I don't have money to go buy a company. And so my first reaction was, yeah, cool story. But what am I going to do?
CM: Yeah, Nothing I can do with this.
MH: But I kept thinking about it like, is there something we could do? So we were able to work out a structure where, he he vested stock options in my company based on the number of customers of his that converted to paying customers of mine. And that's all another risk for me, which I wasn't sure because we charged for our product. And he didn't rate the risk of how many people would switch from a free product to a paid product. And we didn't know. So that way, that structure, we shared that risk together. And it also motivated him to, sort of be a salesperson for me to encourage his existing customers to move over and that, you know, almost doubled our customer base overnight.
CM: Wow.
MH: And, also, he also had a product, both of our products mostly managed this one team. So it would do the registration to join the team and the entries for the meet and picking relays, things like that. He also had a very, very barebones product that would actually run the swim meet on the pool deck that would keep track, and do the awards and ribbons, which I didn't have. And there was another piece of software that was really dominant in doing that. And I knew that eventually we would need to take that on. But he had about 200 customers that were using his product. And so this would give us a way to start with 200 customers instead of zero. So it's sort of a a boost in two ways that helped us accelerate launching a new product and also increasing the, the customer base. And I got to start paying myself a reasonable salary.
CM: I remember when I started to do that. You're right. That's only something the founder understands. For, for me, I didn't pay myself for the first three years. Yeah. Had employees the whole thing. But I was not paying myself yet, and it was just part of what it needed to do to get things up and going and self-sustaining. And then when I did start paying myself, it was like, really?
MH: Right, right.
CM: But it does pay off later. So, you know, that's a creative deal structure. And to your point, that's not that's not what you know. Again, that's not what we're exposed to it. It turns into a moment where, you know, not only did you expand your offerings, but you expanded it with a ready to go customer base, right, with no cash on the table.
MH: Right. And it worked out beautifully.
CM: And a shared risk.
MH: We did convert 90% or more of his customers over. So that worked out and that we ended up having to build a whole new meat product from scratch. There's some legal reasons for that. But, that has been like our, our best product and, and has led to a lot more sales and growth for us.
CM: That's amazing. So that, you know, that was then fast forward to now.
MH: Yeah. I mean, now we have 16 employees. Wow. I am paying myself a reasonable, you know.
CM: A living salary.
MH: And, we have customers all over the country. Actually, we have customers in 20 countries.
CM: That's amazing.
MH: It's customers all over the country. I'd love to go visit them. Have a full engineering team and things like that. And then actually, a little over a year ago, we were acquired, so that that gave me another perspective on that, but we were acquired by another company, Camp Minder. That's the largest software to run summer camps. And, that's enabled like a whole other level. They have specialists and all kinds of things that we aren't big enough to, but like cybersecurity and marketing and things like that, that we're able to leverage and that's been a great fit because it's been a good cultural fit, like their mission around creating great, experiences for kids.
CM: Aligns with what you're doing, what you started. I mean, basically what you started with this is a crappy experience. Let me make it better.
MH: Right, right.
CM: That's amazing. So being somebody who not only has acquired a company, but has been acquired right. Did you what did you learn through that process? You've been on both sides of the table now, right?
MH: That's a good question. So I mean, I'd say from the first acquisition, it was just to challenge your assumptions. Like, I would have assumed that that wasn't even possible for me to do the acquisition that we did at that point in time. And that wasn't the only time. But there have been multiple times where you get into this sort of existential threat. You have to figure out a way to get through as an entrepreneur and you find a solution. You see a door that you can open that solves things. The thing that you realize in hindsight is that door was there the whole time. And so I try to it's like right in front of your face, you can't see it. Yeah, right. And I don't want to have to go through an existential threat to, to find those. So trying to put myself in that creative mindset of what else? What else am I missing? What other opportunities are there? What other doors could I find? Is is a challenge, but I try to try to do that a lot more because there is more out there than you would assume. And, from the acquisition standpoint, I didn't again, I didn't seek to be acquired. I was actually still on that VC path and looking to go raise a series A was really what I was trying to do. And after being turned down a lot,
CM: Again, for the niche, I bet.
MH: Right, and it was working with Camp Minder. They're saying, you know, you're just talking to the wrong people. They really felt that, trying to broaden out and focus on soccer teams and volleyball teams and things like that was just premature and a distraction.
CM: Yeah.
MH: And instead that we should just be really, really good at the thing that we're good at. And, it felt good to sort of it was validating because that's what I really felt, was true and that there's all that to just kind of, you know, aligned. I'm sorry. No, you're good. And so that's that's when it clicked. And it took a while for me to come around to that because I wasn't looking to be acquired. But when I talked to my team, I let them know, you know, without saying who. We actually had gotten multiple offers to be acquired. And I said we would never just be acquired for the money. It would have to be something that would be, a thing that was better for our employees or customers, you know, all the way around, and that this one fit those bills.
CM: That's amazing.
MH: Yeah. I think I think that's another, you know, along the lines of challenge or assumptions. The assumption is always broader, right? In marketing, we talk about positioning and we talk about horizontal versus vertical positioning. So vertical being very niche focus. You're you know you're going really narrow but you're going very deep. It's what you've done. And horizontally focused is much harder to pull off. Well because you're more of a generalist. And it is really to your point, be very good at what you do. And I find too often and and honestly, I find this a lot in software. You know, a tool was built for a reason. And then they add a whole bunch of extra junk in. They don't do very well at all. Or they quire and it doesn't mesh well into a good customer experience. And you can tell.
MH: Yeah.
CM: And it's I think we're pushed as entrepreneurs and owners too much to constantly be broadening out the offer. Instead of just dive deeper into what you do really, really well and continue to deliver that really, really well and solve for that customer. You know, your swim teams, you don't need to be soccer teams, right? There are two very different things. Even though a VC or someone on the outside might see, oh, it's the same, it's the same thing, just different sport. It's not. It's not. The logistics are completely different.
MH: And I'll say it's more gratifying to know that you're really, really good at that thing versus pretty good at a bunch of things.
CM: Yeah, I'd rather be good at really good at something than pretty good at a bunch of things.
MH: That whole path for me was another assumption that I had made that was just sort of the orthodox way that a software company was supposed to run. You're supposed to raise a VC series A, series B, and that's that's how it goes. And I had just bought into that as the default. And then it took me a while to understand that that wasn't necessarily our path. And that was a huge weight off my shoulders. Once I realized that instead of fighting that, just to fight to try and force it through to become that thing that we weren't so that we could appease what the VCs wanted us to instead be who we were and then find a different path that that valued them. And that's that's ultimately where we landed.
CM: Well, and I think, too, I think something wise that you've done is you solve for the customer. And I think too often people that get caught up in funding and rounds, to your other point, it is a false, positive, a false success narrative. I, people will hear me also say that if you're telling me how successful you are by your head, count, you're just telling me how much overhead you have. That's that's not the measure. But I think, you know, to your point, you know, as we're looking forward and, and the rounds and whatnot, there's just, again, so many different ways that you can you can look at that and especially now you're more enabled to do so but focus on your customer, your VC is not your customer.
MH: Right.
CM: You're told though the they are and you lose focus on solving for I think what you originally set out to do, which is the thing that I think most of us get excited about.
MH: Absolutely. I mean, it was it's very hard starting a company and there were lots of ups and downs, you know, co-founder break up, not paying myself for years. The thing that kept me going was our customers really liked what we were doing.
CM: Yeah.
MH: And, you know, being able to go talk to someone and then tear up because the amount that we gave them their life back, that they were able to spend time with their kids instead of staying up all night doing line ups for swim meets, that was just huge for me. And it was it was not an experience that I had before. And that's just very, very rewarding to to have that opportunity. And so I love to pull it back around to be able to do this road trip and go meet people in person and hear those stories. I love hearing how people are using and enjoying the software that we built, but also like hearing the things that we could do better in them. You know, that's how we learn and get better. But it's it's, it's great. It's also great for my wife to get to join me on this trip because, she gets to see she's seen me on the other side, just working really hard for a long time. But to be in the in these lunches and and happy hours and stuff that we're hosting and getting to talk to, everyone's been been great.
CM: Yeah. I wonder, did you ever ask her, do you like. So, you can volunteer me for for anything.
MH: She's heard me tell that story. Yeah. Many times. And then she'll tell the story now, too. But that, she has been my biggest supporter, for sure. So there was the I mentioned the t shirt cannon that we have, that actually comes from early, early on when I just had the names on SwimTopia. I had this dream that we were driving around in a tour bus and pulled up to a swim meet, and all the kids were saying, the SwimTopia is here, SwimTopia is here. And that was when I just had the first name and it just happened that that was right after we had wrapped up another road trip, and she had told me that she was kind of ready to be done with that. So there was some trepidation that I told her about that dream. And to her credit, she was like, yeah, and we could wrap it in and logos.
CM: Yeah.
MH: I found a t shirt cannon to the top.
CM: Right, right. It’s the SwimTopia tour bus.
MH: Absolutely. And so then that was very, very early on when I was going through ups and downs. Occasionally she would email me the link to the t shirt cannon web page where she could buy the t shirt cannon and say, is it time to order this? And that would be like when I was low, maybe ready to throw in the towel. That was her sign to me to keep going. That's amazing.
CM: The people, the partners we pick in our lives make or break.
MH: Yeah.
CM: Especially for an entrepreneur, our families, our partners, our spouses, they are our strongest supporters behind the scenes and put up with our flavor of crazy.
MH: Absolutely.
CM: And so kudos to her. So for encouraging you and for volunteering you. She was probably like, wow, I didn't know my whole life was going to change. So, I think that's amazing for you guys.
MH: Yeah. So it's great now to actually have the t shirt cannon that's like comfort.
CM: I can't wait to see it. So, well, thank you for being on today and sharing the story. And I really, I really do think it's a worthwhile takeaway, especially for anybody in tech, but just entrepreneurs in general, that there's always a creative way to approach, you know, expanding your company and it doesn't always or growing your company the way you want to grow it.And it doesn't always mean the traditional route.
MH: Absolutely. Thanks for having me.
CM: Absolutely. Thanks.