Killing It: An Entrepreneur’s Odyssey

0:00Thank you. a pitch competition, and discussing whether it's time to give up over 40s in Catfish when your first potential customer ghosts you after you traveled multiple states for the meeting. Ultimately, WorkHound found a home, but not without its ups and downs. Max lived the entire arc, building something that almost died repeatedly, watching it get absorbed into something bigger, staying inside as an employee, and then choosing to walk away from the identity as the founder entirely. That's not just a success story. It's an honest one. So, Max, when I first met you, I remember thinking you'd just, you know, finished doing business development for Douala, you know, part of this little empire of payments that exists in Iowa that I don't think everyone fully appreciates.

1:15Like, you know, with the Bano crew and the Douala crew stuff. And, you know, I guess that's what someone who studies sociology at Grinnell does, right? You either end up with a sociology degree working at McDonald's or you end up in some kind of business development degree, right? You know, there aren't a lot of folks that took the for-profit route that graduated from Grinnell and majored in sociology. It was certainly a rare thing. But, you know, I'm fortunate both of my parents are entrepreneurs. So I had seen that firsthand. And I think sociology gave a good lens into being a startup founder just simply because you wind up being really good at customer discovery by default because sociology is all about getting in the field, connecting with people and understanding people.

2:01When we met, I think you just gave me the through line. You started talking to me about trucking. And normally I like scare people off with esoteric conversation. Alex, especially, like his ability to go deep on some like esoteric, you know, financial service or fintech topic. But you started talking about one of the most overlooked labor markets in America, the trucking market. So like, why trucking? Like, how did you find that as a place to plant the flag? Yeah. So with with Dwalla, you know, I was so like there was so much passion and purpose in the work we were doing. We were disrupting the financial industry, and I was excited about the work I do.

2:41We were in Des Moines at the time, and I would walk around downtown, sometimes in the skywalk when it was cold, and see these people that work at these insurance companies that are just miserable at their jobs, walking in twos and threes, grumbling. I was like, why aren't they excited like me? Why can't they have this passion for their work? So I quit to launch a corporate innovation consulting firm focused on how do you create entrepreneurs inside companies? But I realized I was selling a vitamin and I really wanted to solve a painkiller problem. And so I talked to a mentor and said, OK, well, which industry is hurting?

3:14He's like, well, do you know what's going on in trucking? I was like, who cares about trucking? Like it's an old, dirty industry. And he's like, no, seriously, like look at the driver turnover rate. It's 95 percent year over year. Look at the shortage. There's 50 ,000 driver shortage and the average age of a driver is 50 years old and increasing. It's like that's a fascinating set of problems. What was driving the turnover? I mean, that's absolutely insane to think the industry could even sustain itself with that level of turnover. I mean, there's a lot of things. Like, it is a really hard job.

3:49And so, unfortunately, trucking has become this job of last resort. Because you can't become a professional driver and drive across state lines until you're 21, they miss out on a lot of the people like choosing that as a career out of high school. And so then they wind up capturing a lot of people in their 20s, 30s, 40s, 50s, that it becomes their second, third, fourth career and say, oh, I want to give trucking a choice. So you take those two factors and many others. It's it's it's a hard job. It's it's just it's tough. Why weren't other people building this? I mean, it sounds like you kind of stumbled into it a little bit by accident.

4:32Is it just like, I notice a lot of times the disconnect between people who have sort of a lens on entrepreneurship, particularly when it's sort of tech oriented versus entire sections of the economy where solutions from tech entrepreneurs would be incredibly useful, but it's just completely outside their lived experience. Was it that? Like, what was the gap that other people weren't seeing? Well, I think the thing I've learned is that anytime you have an idea, there's already five people working on it somewhere. And that held true. I remember keeping a running list of companies that did employee engagement stuff, period, in frontline workspaces and even in trucking.

5:14And there were like eight companies over the course of our journey that existed in some form or fashion. And we would win out either because we were tech focused versus services focused. We just had a simple offering to the market versus just something that was overly complicated. And then there were some people that had like a good idea. They just didn't know how to go get customers. and we were able to go do that because getting our first five customers was so brutally hard in that industry. It took like 18 months and a lot of people would have quit then. So it was like this combination of just sheer stubbornness and just keeping it very focused that I think led to us standing out a bit more from the noise.

6:01So you stumbled upon a problem, but it's an industry you didn't come from. And I love this part of your journey. And talk to us about, and I think Alex is going to love this story, how you really got to know the inside of the cab and develop the empathy, what it means to be a truck driver. Yeah. You know, in true sociology fashion, it's like go get in the field in customer discovery. Go talk to the people. So I sat with executives and interviewed them. I just shadowed dispatchers at trucking companies. But I did a ride along. I rode with a truck driver from Iowa to Los Angeles. I slept in the truck, ate in the truck, showered at truck stops, and saw the beauty and the ugly of the road.

6:47This was at a time when, I don't know if you're familiar with paper logs versus electronic logs, but in the past, prior to 2020, a lot of drivers would find ways to shortcut the system by using paper logs so they could drive longer. And so we would be driving sometimes like 16, 18 hours in a day going from Iowa to Wyoming through the Rocky Mountains, the desert, and then getting into California. It was a wild ride. But what was crazy about it is that this driver, when he's not driving, he's a DJ. And he calls himself the turntable trucker. And so we back up to this dock in South L.A. and again we've been going for 48 hours straight barely any sleep and he pulls out turntables from underneath the bed of his truck plugs into the speaker system and he starts jamming out and if you know anything about trucking like there's detention time we were there for seven hours waiting for the truck to get unloaded and so you have nothing to do but kill time so he's DJing practicing for his next nightclub gig in Iowa and at a certain point I was like hey Charles you got a microphone.

7:56He's like, what do you want a microphone for? And I was like, I want to rap. And at that point he knew that I was a rapper. I've shared the stage with GZA from Wu-Tang. I've shared the stage with Too Short. And so there's a video out there somewhere of me and the turntable trucker jamming out. I'm freestyle rapping. He's DJing. We're just in the middle, in the back of a Peterbilt at like nine in the morning in South LA. Just like, what else are you going to do? And so the part of what made me fall in love in pursuing this problem was just the stories and the people and that, you know, in spite of this, the trucks and the equipment and the supply chain, and it's all about moving loads, like it's a people business.

8:35And that being a guiding point for us was really critical to just making this thing exist. I do love that story. And now I want to go out and try to hunt down that video. Before we get to kind of the focus, I guess, of this episode in this series, which is the killing it part, tell us a little more about what you sort of landed on as the product evolved in terms of what the solution was, how you solved the problem, how you sort of stood out. Like, what was the thing? Well, the biggest thing we saw was that all these companies were focused on solving a recruiting problem. They said, we just need to hire more people.

9:15That will solve the problem. but there was a leaky bucket. Like you got to go patch the holes at the bottom of the bucket instead of putting more water in, cause that's not going to solve the problem. And there were some of these companies that had five to$8 million a year recruiting budgets just to keep their trucks full because of how high the turnover rate was. And what we realized is just something pretty basic is like, if you listen to your people, act on what they say and tell them what you did, good things happen. So let's build a feedback loop. And so what we wound up building with WorkHound was a real-time feedback loop.

9:47Workers share feedback anonymously. Companies get insights into trends, patterns, issues, where are things happening across the business. And then we gave them tools and analytics to follow up with the workers that had issues and then close the feedback loop so they could say, hey, we're listening, we're working to get better, and your voice matters. And so that was the whole thing. It's like, listen to your people, act on what they say, tell them what you did, good things happen. And that's what we just kept improving on year over year to the point where WorkHound started to get baked into the culture of a lot of the key partners that we had, where these companies were operating with a culture of curiosity and really just changed the way they thought about their people, their business.

10:30And that was probably the most rewarding thing. It was just people, companies started to give a damn when they historically hadn't. How hard is that to get started? Like changing a culture of the business you own and operate in is hard enough, let alone changing the culture for someone who's hiring you. That's the job to be done. And now you're talking about a distributed culture on top of it. And I remember some parts of this story, like to get that flywheel going before you can get that satisfaction, you have to convince someone to take the leap with you. So start, you know, taking us through the entrepreneurial journey, like the highs and the lows of the early days of getting started.

11:15Yeah, well, we first off, like you had to, I think part of the thing that we recognized is that you had to lead with the economic pain. Because if you said, hey, make your people enjoy work, they're like, we don't care. But if you say, like, it's costing you$8 ,000 every time somebody walks out your door, and you weren't proactive, then they care a little bit more. It's like, hey, what if you can pay a couple thousand dollars a month and save tens or hundreds of thousands a month? Is that interesting to you? We had three first customers. And I remember, I know you're probably curious about moments where it's like we were like throwing the towel.

11:55But one of our first times, we drove from Iowa down to Arkansas and we had our first pilot customer. They had agreed to the install workhound. And we said it was important to be in person to go do this. And an operations manager objected to rolling this thing out to them. And they were like, we're not going to do it. So again, drove 10 hours, first customer. And 20 minutes later, Andrew, my co-founder and I were sitting at this catfish restaurant in Arkansas, just drinking 40s. They sold 40s. We're like, this calls for 40. And we're just looking at ourselves I was like, what are we doing? We drove 10 hours for nothing.

12:32We don't have another immediate customer. We got to go. Do we throw in the towel? Do we pivot? And fortunately, we just kept chipping away and were able to score our first customers through a few creative strategies, which I could go into if you're interested. I mean, let's get the build. I think people need, before we get into the killing it portions of it, people need to understand like the, uh, the, you know, opportunities and what you had built towards here. Yeah. Well, I mean, some of it was just like, keep showing up. Like there was a, one of the oddest of like pitch competition events that, that I'd ever done.

13:13It was called truck tank. So this, uh, this group put on the shark tank ask show for entrepreneurs doing something around the trucking industry. And it was at this big truck show trucks all around and they filmed it. And, and we went, WorkHound wound up winning truck tank. I think it was the only time it ever ran. So like historically only winners of truck tank in life. And, uh, and, and so we got this huge check, this$5 ,000 check. Uh, we got press written about our, our big win, which led to our first customer. Um, but probably, you know, one of the most awkward things was taking this big check and, and walking out, uh, out of this convention center, because nobody prepares you for a big check.

13:53Like you can't take it to the bank. So I remember taking it to the car and somebody asking for money. And I was like, I can't tear off a piece of this check and give it to you. And so it's just surreal moments like that. But fortunately that event led to press that led to our first customer and then they led to our next one. And there's a ripple effect from there. I'm curious for the first customer, the initial hypothesis around closing the feedback loop, you know, in that work, there have to be greater details below, like the actual tactics of closing the feedback loop. What was the original hypothesis and did it actually work out of the gate?

14:36Yeah, well, one of the hypotheses was, again, create that feedback loop, be proactive instead of reactive. Don't do an exit interview and wait for an autopsy, but make it where people can share feedback anonymously and you can have a way to to request to connect with that person so our whole thing was anonymity you can do something about because often anonymity gets thrown into the void what we were able to do is say reach out to this person and ultimately became two-way anonymous messaging over time where workers could share an issue the company could say oh we can fix this and they could go in and have a chat with this person to work through an issue and just have more at-bats to address issues or grievances and then figure out what does it take to improve our business at the micro level with the individuals, but then the macro level.

15:24And there were all these strategic changes that wound up coming out of the data to see, oh, we have low satisfaction in this area of our business or this location. We got to fire this manager or coach him up. So these companies often operated with operational data and financial data. we gave them the third leg of the stool, which was people data. How much is actionable, though? Like, it feels like endemic to one of the challenges. I remember you and I talked about after the cross-country trip, just how, like, strenuous the time and the loneliness attached to that. Like, how do you solve that problem that feels like something that is ingrained in the business itself?

16:07Well, if you've ever called a truck driver, it's really hard to get them off the phone because they want to connect. We're giving them an avenue to connect with their company because often these executives, I'd say, well, how do you tackle turnover? They'd say, well, we have an open-door policy. I'd say, cool, but your people are getting paid to be 1 ,000 miles away from your office and your open door, so how are you going to connect with them? And we have a mechanism where you can do that, where they can essentially be connected to that open door and share what's on their mind without the fear of retaliation.

16:40And they're like, well, yeah, drivers do love to complain. It's like, would you rather them complain to you or would you rather them complain to Google Reviews and Facebook and Glassdoor? It's more important for the company to control the message. So it's your call. And then ultimately it's their call. Are they going to use the tool to take action or are they just going to justify, explain and defend why they're not going to change? I mean, that reminds me, TAB Bank, which stands for Transportation Alliance Bank, that we've known for many years. Their highest rated customer service representatives in the call center were the ones that were chattiest.

17:17I think they would end up with truck drivers calling in to deal with an issue, but would also just have a long chat. What they realized is the metric that they needed to optimize around wasn't how short was the time to resolution. Satisfaction came from they had a relationship with someone in the car. All right. So before we go to the break, so you got the first customers. And is it now a clear runway and you're beginning to take off? It was always like a, you know, like this along the way. And then, you know, maybe a little down, like there's nothing's ever a straight line. If they are, I would love to work in that business.

17:56But the, you know, it was, it would be, we built up enough momentum, then it'd go raise more capital to put some gas on the fire. And oddly enough, anytime we would raise, we would struggle again, just because I would focus on fundraising versus top of funnel. And a lot of workhounds motion was founder led sales. But it was, yeah, it was ebbs and flows. Like, there'd be moments where we felt like we had everything figured out. And then there were moments where it was like everything is about to break and this is a dumpster fire. Like, that's just the roller coaster we signed up for.

18:33Well, with that, after the break, we're going to take a quick one here to hear from our sponsors. We're going to come back and talk about the roller coaster, some of the near-death experiences, how close she came, and then the eventual exit and what happened to work count. I'll leave with Paul Mader at Highland Capital once said to us in the Perk Street journey, said to Dan and I said, right before every breakout, every great company has a near-death experience. And Dan looked him in the eye and said, you know what, Paul? Every company right before it dies also has a near-death experience.

19:11All right, with that, after the break, we'll talk about War Cound and its near-death experiences. So, as promised, we wanted to make sure we talked about near-death experiences. I think from all the stories we've heard over the course of this series, you know, things always appear different from the outside than they are experienced from the inside. and whether something ultimately ends up as a success or not, everyone seems to have a collection of near-death, like, oh my gosh, I don't know if we're going to make it, stories along the way. Which ones jump out to you, Max, as like things you still think about or maybe in sort of a like having back-to-school dreams in the fall, like maybe have nightmares about at times?

19:57You know, I think there's a few that stand out. Like I told you all about getting the first customers And that was one of those ones like, should we even keep going? Yeah. Another one was during COVID at the very beginning, because historically, if you look at the U.S. economy, trucking is one of the first indicators of a recession or the first to get hit. And as we all saw, like COVID very quickly entered this recession. We were like, damn, recession equals trucking bad. All of our revenue was in trucking. We hadn't diversified it at that point. And so I remember talking to our board and our team, like, do we start to diversify industry?

20:36How do we buckle down to weather the storm? And I remember basically being at a point in the early days of that, like trying to just give our product away, just to get into more places to hope down the road that these companies will pay us more. Like it felt that desperate. But what was interesting in COVID, like that fear wound up being an advantage because trucking was even more needed. And it led to this great boom in transportation because everybody wanted new refrigerators and new four wheelers and new patio furniture. And so truckers became heroes. And WorkHound started to become a bit of a thought leader in the space of like, what are drivers saying during this very tumultuous time?

21:21So we were really fortunate that we were able to turn this moment where we were like, man, this is not good. I remember having some concerning board meetings to saying, hey, I know we thought about pivoting to other industries. We're doubling down here because the iron is hot. So that one, we were very fortunate it turned around. I would say another one was in late 2023, I remember we were struggling on revenue simply because trucking was in this freight recession. So COVID, you had the spike and then all of a sudden everything started to balance out where people didn't need to buy patio furniture anymore.

21:59They had our botanet and there was just this great resetting of the industry and it went through its longest freight recession ever. And so we're in the middle of this slog and we'd raised a series, a growth equity expecting to burn a bunch of money to grow. And we weren't growing at the rate that we wanted to. I remember looking at our board and I think we had like four months of runway the way we were burning money and to put together some plans for how do we go fundraise. And in short, the board, we didn't come to an agreement on how do we capitalize the business. And I remember a board member saying, you need to run off the cash you have.

22:36And and, you know, they they were looking pretty bleak of like, how are you going to turn this around? Because you only have four months of runway. but you know fortunately for for us it's like the company's dna is built on running lean and scrappy and and i remember putting together a plan of like this is how we're going to go get profitable and break even and control our own destiny and it led to like just brutally hard calls of how do we structure the business differently so that we we don't have to worry about additional financing and and because we were looking at do we wipe out the cap table in order to to do a financing or do we go back to scrappy us?

23:13And I remember calling some investors saying like, hey, here's some of our options right now. And they're like, we'll back scrappy you, like go make it happen. And we did, we got the business profitable and that put us in position to go get the exit. But it wasn't without that like just brutal moment of realizing like, we have four months to right this ship or else. what were some of the toughest parts of making that call like did you ever come to a point where you're like is this even worth it for sure it's uh you know because there's always the i'm i'm as an entrepreneur you're a betting person and and you know when when things aren't going to plan like one of the things you look at is how do you like how do you cut burn and uh and and reset things and you know that I'm looking at people's jobs and, and especially people that I really value that took a bet on me.

24:08And so there's, there's a way of disappointment. I think one of the things that was really helpful in, in, in talking with mentors, it's that like you, you will have to make a hard call or, or the business will die. Like that is, that is the, the, the, the fact. And you have to decide, do you make a hard call sooner to, to protect more people and give more certainty to the team going forward versus keeping a bunch of people in panic. And like, it's just a perpetual series of trade-offs. And I think one of the lessons I learned is that often people think that as a founder, you're making decisions of right and wrong, good and bad, best and worst.

24:49Like sometimes you're just picking between the least worst option. And that polarity management was really clarifying for me is that like there are two turd sandwiches in front of you. Which one do you want to go take a bite of? Because you have to take a bite of one of them. Sometimes that's the kind of choice you're making. And you just have to say that one looks like it has a little less turd in it. So I'm gonna go that one. It is interesting, because, like, to your point, you have to do some, you have to do something, right? So you can't not act like not acting is a choice. And it just perpetuates whatever problem you're sort of finding yourself in, right?

25:25So you have to act, but you have to act and the choices in front of you, none of them are good choices. The other thing that occurs to me about a lot of the examples you shared is a lot of them are just like luck, timing, circumstance, right? Things where it's like, there is no real way that anyone could have foreseen how this was going to play out. And I sometimes find when I talk to founders that they're sometimes a little bit surprised the first time going through it where they're like, yeah, I assumed that my board, which is made up of these investors who've had all these experiences and work with all these other companies, would know the answer or would have some secret knowledge or ability to parse these things that I didn't have.

26:08And once you go through it, you sort of realize no one knows. And these are all calls you're making with very limited information. Yeah, it's so true. And I think the other thing I've realized, I was like, now I'm an LP in some venture funds. And so I see the other side of it. And that was really enlightening for me to realize that all this blood, sweat, and tears that we're doing to try to figure things out, we're just a line item on a spreadsheet in somebody's computer in New York. And every month or every quarter, they're marking that position up, down, or the same. And so once I put it in perspective of all these really hard things are just so that that number can change a little bit on that spreadsheet, you really start to think about like, this isn't everything.

26:57There is a life outside of this. And you have to put the whole picture in perspective versus work being life because you will go crazy in the negative moments if work is your everything. And that was also really helpful for me and learn getting better at compartmentalizing. I wasn't great, but I got better at it over time because you had to so you could show up at home and just be a human. So that's a great segue to you get to an exit. How did that come about? Were you at the point that you were ready to sell and you were shopping? You were approached by a larger player who just raised money the year before.

27:38Take us through now the decision to exit. You've gotten the business up and you're profitable. You control your destiny. One of my mentors, My first startup told me revenue covers a lot of sins. Profitability covers all of them, right? So you've gotten to the profitability. The world is your oyster, maybe not the most flavorful oyster, but you control destiny. How'd you come to the decision it was time to exit? Oh, I mean, there's a few different things. Like there's like one of them is just recognizing the business had four stakeholders. It had the employees, it had the investors, it had the founders, and it had the customers.

28:18And anytime I'm making a decision, it's what is the best decision for this set of stakeholders? Or in some cases, what is the least worst? And so I was able to just assess in the moment where we're at. So we got the business profitable and taken a whole bunch of risk off the table. I think one of the things I had to learn is that as a founder, if you're not having fun in the business and you don't feel like you have oxygen, then nobody else has it. And so that was something that profitability gave oxygen. So that was really helpful. But I think it was a couple of things. It was that we were gridlocked on getting additional capital into the business.

28:59And some of the bets, especially with AI rapidly increasing, would have required R &D. that we just didn't have access to tap into. And then just looking at the faces of some of the team and even reflecting on myself that like we're not operating at 100%. You know, it's like an old iPhone that you're maybe at like 80, 85 % because you're just, you've been grinding so hard. And then I thought like, what is the best thing for customers? And when we looked at various potential partners, it was being able to see, like we have an opportunity to give them a much more robust offering than what they currently have.

29:38We can give employees additional career opportunities. We can give investors some return. So again, it was thinking about like, what leads to the ideal outcome given the set of constraints and trade-offs that exist in front of us? One thing I'm curious about, you mentioned a bunch of different stakeholders who kind of thinking of as a part of that decision. How did you sort of, and this might not have been a conscious thing, It might have just been sort of unconsciously where you landed. But how did you sort of like weigh the interests of different stakeholders, right? Because probably not everyone is going to have exactly the same view on if like now is the right time to exit and like what the best thing is.

30:16And there's like co-founder, there's employees, even among employees, there's like early employees, later employees. Same thing with investors. There's obviously customers. Like, how how did you experience the thinking about what the right outcome or ending was balanced across all those different groups? Yeah. So we were fortunate that we we had multiple term sheets when went at the at the finish line. And that's all I wanted was to be able to have optionality. Like, I think any time you run an exit process, like you will just want choices versus being being forced. And again, it was just really looking through each of them and just assessing, like, here's the worldview of if we go with company A versus company B versus company C.

31:05And then, like, selfishly, it was as the founders, it's like, which one is more exciting for me too? Because, like, you know, one of the ugly things about starting a business is that, like, yes, you want to achieve some sort of additional wealth for you and your family. but more often than not, it usually ends with indentured servitude of some period of time. And like you go into this to be your own boss, but in order to achieve the fruits of that labor, you have to go work for someone else for some period of time. It's like the most bizarre, maddening thing that I don't think it's talked about enough.

31:38But so, yeah, I was weighing all those factors and then just saying, okay, this is a place where I know my, like the reason we partnered with Workstep, I know our customers will be taken care of here. This is a net positive for them. Our team has, you know, not everyone from the team went over, but for that team, like we, we can, we can take care of them in a pretty good way, uh, for investors, again, path to, to, um, to liquidity for, for them. And, uh, and then for founders, like it was interesting work and, and a new opportunity to go learn from, from another company and, and, and just soak that in.

32:14So let's talk about your year of indentured servanthood, right? And it worked out to be almost a year, right? Just shy, if I remember. I was there full-time for six months and then stayed around as an advisor until the exit. But I wasn't as involved at that point. There's been a lot written about this more recently that actually post-exit feels a lot like grief. like the, and they describe, and it's interesting because it almost overlaps perfectly with you. They describe this six months of euphoria, right? Like you've crested the mountain, but then they're call it the Valley of Shadows afterwards.

32:57I'm curious if like that timeline goes with you, right? Because, you know, you said you started it to be your own boss. You end up in the indentured servanthood, but then also you come out the other side and this thing that you had built is no longer yours. It belongs to somebody else. Well, like on that front, fortunately, like Dynamo was one of our investors out of Chattanooga and some of their founders, they exited their company. I remember them saying like the moment that we handed the keys over to the building, that business was no longer ours. And they made all these promises of nothing's going to change.

33:29And ultimately everything changed, but that wasn't their call anymore. So it was a very helpful reminder that when you do that handshake or sign that piece of paper, it's not your call and you just have to be at peace with that. And so fortunately, like I wasn't like hoping that there was going to be some substantial change or thing. It was just more of like, this is the choice that we made. Let's go forward. And I'm going to go treat this like an MBA and go learn and learn how another leader leads. How does another company operate? How they communicate? What are the tactics and strategy that maybe I was missing out on that I can be better?

34:04How can I treat this as a course for me leveling up for my future endeavors versus being pouty and bitter that they're not doing it the way I would have done it. Because I could have done that. I know plenty of other founders that have done that. It's just not helpful or healthy. That's a very good mindset to take. And I don't think I've heard that exact express that way before. Although I always like to think of every chapter of my career as like getting paid to learn something new. So that's a great way of putting it. What was one thing that you learned when you had that mindset watching during that six months in particular when you were really engaged?

34:40Yeah, I was very impressed with how that that company was just meticulous and process oriented. Like for for me, I'm a gray area person. I got I can it doesn't always have to be black and white or systematic. Like I could go in the flow. I could wing a sales call like no other, but you can't create a system on just winging it. And so while I may have that ability. If you're trying to coach sales reps, you can't just say, go wing it on a call. And to see the meticulousness that went into everything they did, I would argue it was almost too much, but it worked for them. And so it's like game, respect, game that they set it up that way.

35:22So that was really helpful to see that if you want to get out of founder-led sales, if you want to make things repeatable, you've got to create more robust systems. And yeah, that was simple, but enlightening. You talked about the compartmentalizing piece. What advice would you give for founders? Because it's really hard to compartmentalize because startup life, that first part, getting to the first customers is all consuming. I mean, for the love of God, you rode in a cab of a truck across the country, you know, not sleeping for 48 hours. It's not really compartmentalized. So how do you and when do you make that transition?

36:05As a founder post-exit? No, like along the journey. Or do you have to wait to exit? We're going to get into your post-exit rediscovery and how you're thinking about life now. But along the way, how do you protect your own mental health. Yeah. Um, you know, it's, it's really, again, always reminding yourself that this isn't everything, you know, that I've got my wife and a, and a son at home that, you know, to show up well for them is important that, you know, to, to make, take time to go do guys trips and, and go hang out with my, my college buddies. Like I went to the world cup in 2022 when I was really debating, do I skip it?

36:44Because, um, you know, because things were, were hard in the business. Like, no, this is important for the mental reset to show up well. And so like, you don't need to go keep enduring the suffering because things aren't going well in a business. Like you've got to go find ways to, to find, be your true self, whether that's working out, taking trips, walking through the woods, like whatever it takes to go get oxygen. So you can show up well for your team. Because again, if you as the founder aren't having fun, the people can feel it and they're not having fun either. And that's just like this vicious cycle.

37:18So what is next? You're exited, you took some time off, a sabbatical. Do you miss being the work hound, like the hound being part of the identity? How have you rebuilt that part of your identity? I'm very much at peace with it. That was a great journey. And that was part of my whole endeavor was like, I want to jump into an industry where I know nothing, understand the framework of how do you go do that and know that I have that, that skillset in my, my arsenal to go take wherever. And, uh, and so, you know, I, maybe I'm in the valley of shadows now of starting to realize like anything is possible.

38:03Like I can go start something else. I can do entrepreneurship through acquisition. Maybe it's a boring business. Maybe it's working somewhere. Like there's, there's a lot of different possibilities. You know, I think one of the things I think a lot about is like in pursuit of mastery, you have to learn, do and teach. And so right now, like one of the things I'm interested in is like entrepreneurs in residence. Can you go teach other entrepreneurs and other founders and portfolio companies? How do you skip some steps based on some of these lessons learned? But then like for myself, like I'm having to learn how do you go build a startup in 2026?

38:38Because the playbook from 2015 is is dusty. so you know the game's changed out there uh but i'm uh i'm in a good place all in all so maybe one last question um i mean speaking of giving advice and maybe helping teach others or helping people learn from your experiences what is one piece of advice uh that you would want to leave uh folks listening to this with about that journey and you know something you took away just from the experience of, as we've discussed, the ups, the downs, the near misses, the lucky breaks, like just boiling that all up. What's one piece of advice you'd want to leave folks with?

39:19One thing that was really enlightening for me was I'm in a peer circle in a group called Hampton. And so in my peer group with some other entrepreneurs, I was sharing my challenges. They'd heard them months on end and they were like, why go through this pain? Why do this to yourself, like your investors, your line item on your, on their spreadsheet, like your, your net worth isn't going to materially change here. So like, why, why do this? And I think that's a really helpful reminder that like, you think you owe people something when, when you're pursuing it. And your job is, as the founders, like, can you go find the light in a dark room?

39:59Like if you can take a sledgehammer to it, but if it's just a really dark room and there's no light, like if you can't find a way, the team can't find a way. And so that's when you need to just go fight either for financials or fight for a narrative. Those are the two things. And sometimes you may need to just go fight for a narrative and go land the plane and say, hey, I got an exit. If there's a path to financials, great. Go get that. But you got to have that light. Otherwise, why go through the pain? Max, thanks for sharing the workhound journey. And I think everyone is going to enjoy going and watching you freestyle rap next.

40:37And I think one of the takeaways for me in this is I don't know that enough founders, particularly in fintech and financial services, it's very easy to build products around their own experiences. Alex and I talk about this quite a bit with some of our other fintech nerds, right? They build around the problem they know, but it's not a real problem. And I love that one of your competitive advantages was not coming from trucking. You weren't solving a problem you had. So you had to go do the sociology aspect of it and go ride in the truck. And I think that's important for everyone in what they're building to go get into the customer's shoes.

41:20And that's a great takeaway for me. And thanks for sharing that. And really appreciate your vulnerability and talking about the near death. And even as you walked out with a big truck and going to drink 40s, you know, thinking you might need to walk away. Sometimes you just need some catfish and 40s to reset. Yeah, that's a great place to leave it. That is going to be the title of the episode. Thank you. That's it for another week of the world's number one fintech podcast and radio show, Breaking Banks. This episode was produced by a US-based production team, including producer Elizabeth Severins, audio engineer Kevin Hersham.

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