$169M Founder Reveals the Cost of Ignoring Your Limit (Aaron Houghton)

I had an unlimited to-do list at all times. I felt a lot of guilt any time I said, all right, I'm going to leave the to-do list right there for today. I'm going to pick it up tomorrow.

When I think about this problem, there are two fixes typically: an emotional fix, like what's the underlying psychology behind this? But then also the mechanical fix of how can I just look at the data and decide like what makes a good life for me? How do you think about that problem?

Yeah, I think about us as like each having both a player and a coach inside of us. The player is just the core resource, figuring out like, you know, what, what to do to fill the time to produce the output. And then the coach has kind of got like the gas pedal and the brakes and trying to figure out like, how much can I utilize this resource before I blow it up? A lot of trade-offs that are related to should I be working on this or should I delegate it are more of like coach-type decision, how I optimize my, my time on this earth a little bit with those two hats of, of that player role and the coach role. Aaron Houghton is a serial entrepreneur who started his first business at age 17. He founded and scaled multiple tech startups, including one that he grew from just an idea to 350 employees and $50 million in annual subscription revenue and sold for $169 million before he even turned 30. Today, Aaron helps hard-charging founders and executives Live and work at their maximum capacity without burning out, and is currently leading research studies on how business leaders perform under pressure. When we sold the business, I found myself feeling like lonely was kind of the word. I was still continuing to experience anxiety, full-on, like crippling anxiety. I was so ashamed of having panic attacks as an entrepreneur. A foreign maid of mine said, "When was the last time you were really, really happy?" The answer to that question was in high school. Actually, 3 people came up to me. One of them had lost a sibling to suicide, and that sibling had been an entrepreneur. There's something really serious on the line here. Like, if I can share more of this message with more people, maybe I can help high-pressure, high-achievers try and figure out where their red line is.

If you could go back and tell that guy something, 10, 15 years ago, what would it be? Welcome to Money Stories, where we have conversations with founders about money, meaning, and what makes a truly rich life. Today I am joined by Aaron Houghton, who is a serial entrepreneur, built and sold multiple companies, including one in the 9 figures.

Mm-hmm.

And now he helps founders live at the optimal pace. I am super excited to dive in. I think we have a lot of overlapping life philosophy here.

Yeah, I think we do. Thanks for having me, Mike.

So as always, I just like to start from the beginning. Tell me how you grew up with money and how that drove you to become successful.

Both of my parents are teachers and my kind of long line in my family before my parents is kind of is on the legal side. So they're like, we have a lot of like federal circuit court judges in southern Indiana going back to like 200 years ago. And so these were people that were kind of leaders and trusted people in their communities. And my dad took a kind of different path in our family and wanted to be an educator and became a professor. And so my earliest memories in my childhood were living in what I kind of fondly called like family and married family housing on the side of University of Wisconsin-Madison in Wisconsin. As my dad was getting his PhD. And so he was still actually a student technically when I was young. And so that's, that's where it all started, living in a small 2-bedroom apartment with my 2 brothers and myself. So 3 kids and 2 parents in this very international community in Madison, Wisconsin. We were, you know, one of the only families that lived there that was native English speaking. These were families from all around the world. So a lot of, a lot of Arab families, a lot of Asian families. And so I grew up in this like real melting pot of students and culture and academia in the central part of the United States. I think a lot of people maybe forget that, you know, there's a lot of people from— there are a lot of people from the whole rest of the world right there in the middle of the country, in the Midwest, in Wisconsin.

Yeah, it's so interesting. I'd love to double-click on that, how that shaped your worldview and particularly, you You know, I imagine with your, with your dad as a student, money wasn't particularly abundant at that time in your life. When did you become aware of money and how did that shape you to become an entrepreneur?

My parents never talked about money. That was kind of a family value, was that they kind of trusted us or sort of asked us as kids to trust in them, that kind of they, they're working on it, they got it. And so it wasn't we were not a family where we worried about having the next meal on the table or, you know, there was real like financial challenges that were brought to, at least brought to our attention as kids. Um, but on the opposite side, we could also see that we were not like other families that, in fact, when I was very young, I didn't know these other families existed that maybe went on huge vacations because my entire, uh, community and circle was grad students that had pretty much picked up from where they lived on the other side of the world and come to the United States. And so, um, I wasn't wanting anything as a kid. Um, I felt like I had everything. I had friends and food on the table and a, and a tight-knit family. And, and so I, I felt like I had everything. Um, it was probably, uh, my dad's first job as a professor was in Fayetteville, Arkansas. He got 3 offers and I, I always think about how differently my life would've gone. So it was Jacksonville, Florida, Fayetteville, Arkansas, and Juneau, Alaska. Wow. 3 offers. So like, how, how much would my life have been different had we gone and lived in Alaska when I was 8 years old? Or even, even Florida, I think would've been really different than Arkansas. Arkansas felt a little bit still like the Midwest, kind of like Wisconsin. We just drew a line straight down and, and off we went. And in that community and, and in middle school, I think I started to see the difference. And I remember the first time I got invited to a friend's house and I didn't know what it was about this house, but I walked in and everything smelled really good and there was fresh carpet on the floor. And I, and I remember realizing like, oh, this is a new house. Like people build new houses and live in them. I didn't know that was a thing. Like we had lived in apartments. We'd lived in old houses that we rented. I actually got a really interesting opportunity this spring to go back to Arkansas. I went there to go mountain biking in Bentonville and I drove down to Fayetteville because I couldn't resist. I haven't been back once since we left. We left there and moved to North Carolina when I was 13. So I got to go back and see the house that we lived in. It was the first house I ever lived in when my parents moved us from Wisconsin to Arkansas. So out of this small apartment into a 3 or 4 bedroom house. And, um, it's a dump. I didn't realize it when I was a kid and it has been 30 years, so maybe it was a little nicer then, but taking a look at this place and I went and knocked on the neighbor's door and my parents, I was talking to my parents on the phone. This is back in April. They said, you know, the neighbors across from us had similar age kids. They were about our age. Like they might still be there, maybe the same people. So I walked across the street. I parked my $150,000 car in front of the house and walked across the street and knocked on the door and said, hey, you know, I grew up across the street. Are you guys still the same folks that were here, you know, in 1992 when we left? And they said, yeah, absolutely. And they said that house that you guys lived in is owned still to this day by this guy who's kind of a bit of a slumlord and he's got a couple of crummy houses and he's actually lived in this house for a couple years and after my family left, it was rented to a bunch of frat boys that basically threw parties and got the cops called all the time. And they said, yeah, um, you know, a couple years ago when the owner was back in the house, he was, it had a flat roof. This is in the like, uh, Frank Lloyd Wright kind of zone where there's a lot of houses with like cool architecture there. So kind of cool architecture, flat roof. And the neighbor said, yeah, the owner of it was up there trying to tar the roof himself and lit the whole roof on fire. And we had to go over and save him because the part of the roof that was on fire was between him and the one ladder that he put to get up there. And so I'm starting to just draw this connection and this picture of who I was and who my family was in the early '90s and the late '80s. I was born in '81. And, uh, kind of where our socioeconomic position was in the world at that time. And, you know, we lived in a house that was then rented to frat boys that later the owner caught the roof on fire. And it's just like, what is this place? And where did I come from? It brought up some really interesting questions about that.

Yeah. And so how does that start to unfold into entrepreneurship for you? Where did your drive come from?

In Arkansas, when we lived in that house, that's the first memory I have of this. And I consider like maybe there's lots of different types of entrepreneurs, but like the core driving thing for me is being a tinkerer and just wanting to like tear stuff apart and put it back together and understand it and being curious about it. And I started tinkering in that house. So there was a, um, there was a carport added to the house off the end of what was then a finished garage. So there was a, there was a, you know, a space that had been a garage before with a really nice flat floor and then just like kind of filled in with windows that I broke a few times as a kid. And so it made like a kind of a cool shop space basically that was enclosed in the house. And so I started working on my own bicycles because I was able to, you know, get kind of like a salvaged bike from a neighbor. Actually, the neighbors down the street who are doctors had a fair bit of money, had run over a Trek road bike that they had accidentally. Somebody backed over it in their driveway and, um, and so they didn't know what to do with it and the frame was bent. And so they gave it to my family. And so that was my first bike. It was probably like a, a $500 bike back then, which would've been a lot of money. But then the back triangles on it were bent to the side. And so one of the first things I did was try to figure out how to put this bike back together. I saw this as an opportunity. It was like, wow. If I can figure out how to make this thing work, then I'm going to get a really sweet bike that I don't care if it's damaged. Like, it's better than, better than no bike. And, um, so I started working on it, had to replace some of the components and fix the derailleur and went to, my parents took me to the local bike shop and got to figure out what parts I needed. And so I fixed that thing up and made it serviceable. And that's when, I don't know if the idea occurred to me or maybe my parents sort of planted the seed, but I had this thought of, wow, I can, I can go find salvaged bicycles and make them decent and usable. And I started selling them to the neighbors, uh, parents in the neighborhood so that my friends could all have bikes too. And so I did this 5, 6, 7 times over the next couple of years. I remember selling them for, you know, $200 and I'd probably, I would, I was getting them from the junkyard for nothing, I think. And then putting, you know, maybe $50 worth of components on them. And so I was in there like hands in the grease, you know, fixing parts, taking them apart, figuring out how to put them back together. And when I messed up, taking it to the bike shop, going like, hey, can I, can you guys just tell me, like, does this bolt go here?

Here.

Like, I don't have money to pay you, but I bought the derailleur from you. Maybe you can help me figure out how to do it. And so I remember making, making that money. And then in that, at that time too, I actually remember being in, um, probably it was Cub Scouts at the time at that age and going door to door and selling popcorn. Do you remember that?

I do. I might have sold a few bags.

All right. Yeah. Yeah. That, that was a thing. And actually they still do it today. I found out. Boy Scouts and Cub Scouts still sell popcorn. So I remember knocking, going door to door in the neighborhood. That was kind of my first experience with sales maybe. And then having, you know, that experience of like people not wanting to be interrupted or sold to and having to try and figure out how to be friendly and approachable and not look like a weirdo that's just interrupted them in the middle of the day in their slippers in their house. And I remember getting some of those checks for popcorn and just thinking like, wow, that person just spent like $65 on popcorn. Like, that's a ton of money for me. Like, I could fix up 2 bikes for that. And I wasn't getting all that, but I was maybe getting some sort of perks from that. So I remember that, that feeling of like, ooh, that's a, that's a check. That's cool. And ooh, someone just paid $200 for that bike. I can now go fix up 5 more bikes. There was sort of this like exponential feeling to it of like, I fixed up 1, but now I can fix up 5. And then if I fixed up 5, maybe I could fix up 25. What does that mean? Do I want to fix up 25 bikes? Do I have the time?

So early on, there's, there's this sort of distinct, like, realizing that other people might have more than you. Yeah. And you can be in charge of your own destiny and improve your lot. I mean, is that what I'm hearing?

Yeah. Starting to feel like I can, I can move that dial and then starting to kind of see my path as different than my family. You know, I'm still probably, what, 10, 12, 14 years old in this time frame. And so I think the, you know, if you had asked me at that age, like, how will my path unfold as a, as a person in the world and what value will I create? I probably would have thought, you know, maybe I'll be a teacher like my parents someday or something, or certainly will go to college and then go to grad school and then go to lots more school after that. And that was just the path I'd seen in front of me. Also, actually, my grandfather was a retired newspaper editor. And started a pottery studio in his house in central Wisconsin. And so I had that example too of it was, it was sort of a retirement hobby project. But when I would visit their house, we would walk into the, the like basement walk-in on one side and it was his entire pottery studio. So the walls were just lined with like beautiful stonework everywhere with price tags on everything. So that was another path I had seen of like how you can make things with your hand and sell it for a buck or something. And, and that's a, that's a way to make money. And I would see people pull off the rural road in central Wisconsin and drive up their driveway and come in and look around at pottery and leave with a big stack of things and, and spend money on it. So yeah, I think those were the, the only paths that I knew existed in the world. And so I'm starting to kind of find my own in like, wow, if I set aside time And I really focus on this thing and I use this just one skill that I've developed for figuring out how to fix up old salvage bikes that are, that have completely fallen apart or that other people have given up on. I can create something that somebody else sees value in. And that felt powerful. I actually learned a lesson a couple years after that. So then we moved to, to North Carolina, to the Asheville area when I was right around 13, 14. And I learned a lesson around that time that still haunts me to this day, even though the economic value on it, I think, was like $20. And it was an interaction between myself and a friend and then myself and my parents. And so I still remember this. This is, you know, 30 years later. So without biking around the neighborhood, this is my skill again, is like fixing bikes. And I was with a friend, a good friend from the neighborhood and school friend. And we're maybe a mile away from home and his chain comes off of his bike. And he says, I don't know how to fix this. You know, like, well, let's just walk it back home. And I'm like, no, I got you, man.

I got a guy.

I got a guy. I'm your guy. But like, I'm so ashamed to admit who I was in this moment. I was like, it's going to cost you a little bit. So I charged him like, I don't know, probably was probably like a trade in Legos or something. But I remember I think it was like $2 or something. And he agreed to the price. I fixed his chain. We went back home. I think I probably proudly announced this to my parents later of like, I made $2 today from my friend Tim. And they were like, you jerk. Like, what do you charge your friend to fix his chain? I still, I'm just ashamed of that one to this day. Sorry, Tim. Uh, I owe you 2 bucks back. The early opportunist. Yeah, I was, I was, I was, you know, I was so excited about the economic value here. I sometimes, you know, didn't realize there were situations in which I didn't need to apply that. I saw an opportunity and I went for it.

So how does this opportunistic young kid go on to, to found a 9-figure company? What does that look like?

Next thing I, I was really doing after that kind of bike phase of my life was mowing my neighbor's lawns. And I think asthma saved me. I think the fact that in the southern heat, mowing people's lawns in like not the nicest neighborhood where everybody has a perfect lawn, like I was mowing lawns that were like 50% dirt and like 30% sticks and just going right over the top of it, you know, letting the mower do the work. And, uh, you know, dust in the air, it's 110 degrees, it's 100% humidity, and I just couldn't breathe.

Yeah.

This goes like getting paid $20, $25 to do a yard. And it was actually a pretty, pretty good gig. And I have two younger brothers, and so I'm now kind of like in middle school and high school, and so they're a little bit younger than me. And so I've brought them in and we're like, you know, schlepping two mowers all around and, you know, just where we could push them in the neighborhood, not even driving them anywhere. And we're, we're mowing lawns and we're making a couple of bucks here and there. And yeah, sorry, I lost my train of thought. Yeah. What was your question?

How does your journey into your first taste of success as an entrepreneur.

Yes. Yes. Yeah. So I'm feeling the pain from all these, all these hours out in the hot sun and sunburns and being unable to breathe. And I, you know, I see the opportunity in kind of early internet phase. And this is one where my dad really connected me to this as a professor. He was seeing this kind of on a technology side and seeing that the internet was coming. This was like '90, '94 to 1996 range. And, you know, he's like, there, there's this new thing coming. It's going to be marketing, it's going to be fulfillment for businesses, it's going to be all sorts of different things. And the opportunity that he showed me was that you could, you know, like businesses are going to need websites at some point. And so what does that look like? And so I had access to his computer lab at the university. And so I had access to really modern computers and we had a, we had a really nice computer in our home because my dad had actually been selected as an Apple Distinguished Educator for Apple Computers where they had been sending him all of the new Mac technology for about 10 years before that. So we had a computer that was way nicer than any family like ours should have. And he had a computer lab where there were 50 of them in a row hooked to high-speed internet.

And so I feel like I've heard this story before, a guy called Bill Gates.

Yeah, there's a couple of them. Yeah. Yeah. That's, I was one of those kids, like just hanging out. On campus with access to this stuff that honestly sat dormant 90% of the time when class wasn't in session in computer— computer labs even exist in this day? I don't know if they do at universities. Totally. Maybe they have quantum computers in them or supercomputers or something. But, you know, this was a thing at the time. So I had access to it and Dad kind of planted the seed with me of, you know, businesses are going to start to need websites. And so I built a website. I learned how to do it by reading like an O'Reilly software book on HTML programming. As a high school student, and I built a website for a fictitious business that I called Georgetown Mall that did not exist anywhere where I was, and I did not live anywhere near Georgetown. And, um, you know, like, here are the businesses that are in it, here's the hours of operation. And I built this whole thing with like fake photos on it and everything. And, uh, like, that's, that's the beginning of me like really nerding out with technology. I mean, I built a website for a mall that doesn't exist. Which I guess, you know, when you're in high school, you are kind of interested in malls. So maybe that's why it was top of my mind, like, let's go hang out with my friends at the mall. And I sold my first website to my basketball coach for $75 for his bed and breakfast. And, and that launched me into that business. It was both $75 upfront and then $10 a month to host it. And that created a little bit of recurring income. I mean, every 2 months I was making as much for just sitting there doing nothing as I was by mowing a lawn. And I got to do this indoors in the air conditioning in the summer heat when school was out and I had a lot of time on my hands. And I got— I totally caught the bug. I was like, this is cool. Like, I can make money. There's a recurring component. Everybody needs it. It was a huge just blue ocean opportunity. It was like websites in 1995, right? Everybody needed one and I could build one for somebody for $100. And any real business that was building websites was probably charging $1,000. So I had just an absolute corner on like the low-end market. I can build it fast and I don't have to be outside in the heat.

Yeah, it sounds like you found the superior business model pretty early on.

Yeah.

And, uh, your success only compounded from there. As you're getting into larger and larger opportunities, uh, I'd just love to hear about some of the challenges that you started to face in your, in your journey.

My most successful business, I started actually in my parents' living room still in high school. The software company that ended up becoming EyeContact, that ended up becoming a $50 million annual revenue business that we sold for $169 million when I was 30. That all started in, in my parents' living room. I wish it was like a garage or a basement. It's a better story, but it was right next to the kitchen, right in the living room. And it was, it was where I was building websites for people. And I started to realize that these website, these people that needed websites then started to have other problems related to marketing. And one of them just came up that they said, how do I, how do I keep in touch with my customers digitally now? And email newsletters kind of started to become that thing. And for me, it wasn't like I invented something new, certainly not email newsletters, but it just came out of like physical printed newsletters. One of my web clients said, I literally type up in like Microsoft Word a newsletter. I print it out on an inkjet printer, like 1,000 copies. I stuff them in envelopes and I mail them to my customers all over the country. This is a seasonal cabin rental business. And so their customers came from 1,000 miles away. And in western North Carolina where I live, they only come for like 4 weeks when the leaves change color in the fall. And so they were spending all of this time literally folding paper, putting in envelopes, paying for postage. And they said, well, I have been for the last year asking for everybody's email address. I have like 3,000 email addresses, but I don't know what to do with it. And I was like, well, you could just type. Literally built like in the admin area of their website a way for them to type in a message and then have it be sent to this list of email addresses that I like manually input into a database and then created a little way that they could add more to it. And that's how that business started. So I was solving a problem that my clients had and I didn't do much with that. It was just kind of bumping along. And I was actually then in at Carolina as a maybe a freshman when I got a call from one of those clients who said, oh, somebody else has asked me about this tool I have. They want to use it. I get connected with this guy named Wayne who calls me in my dorm room and he says, how much does it cost? And I was like, oh, like I've everybody. I just kind of include included it in their hosting packages and things for these web customers of mine. And so I had the immediate challenge of trying to figure out how to price this product. And I had done no competitive research. I didn't know this was even a thing. I was just solving someone's problem. Like, I didn't— to me, it wasn't even a product, right? It was just like, you have a problem and I can move these widgets around and that solves your problem. That's great. And so I came up with the biggest number I could possibly come up with. This is a person who sold like pet toys and pet supplies online. And, and so I said $400 and he was like, a month? And I'm like, no, no, a year. Oh, should have gone. Yeah.

Wayne, a week. No.

Yeah. No, I said, yes, $400 a year. And he's like, great. Like, where do I sign up? And the answer was mail a check to my dorm room. Like I had to give him a dorm room address, which he was somehow okay with. Mailed it because the price was so cheap. And I guess his friend Michelle had used the product before, who was my web customer. Uh, so I solved that problem and it still wouldn't kind of no clue what I'm doing. And then I started picking up customers here and there and it started to become Um, you know, as a, as a full-time college student, um, freshman year, maybe it was $15,000, $20,000. I think by my senior year it was $80,000. And that's really the underpinning that allowed me to not think too hard about going to grad school or getting a job after I graduated. Uh, the average salary of graduates from my computer science program was about $50,000 to $60,000 at that time in 2003. Which was a fair amount of money. And that number has gone up a lot since then. So it's a good, good career path that's proven out. But here I am making $80,000 as a full-time student and doing it in just a couple hours in the evenings. And so I thought, I'm going to just see where this goes. I'm going to try this out.

I mean, that's a tremendous amount of money for a, for a college kid who came from modest means. What did you do with the money? Were you reinvesting in the business? Were you investing in the stock market? What did you do with that success?

Yeah, I I wish I was saving it. There was nothing to show for it at the time. I mean, that was, that was top line revenue. And this was a business where I did have a couple of contractors. So how much I was probably grossing a little less than half of that or like putting in my pocket in the end, netting, you know, less than half. So yeah, so, but it was still a good amount of money, right? As a, as a college student. And I think my parents were still like paying for my car insurance or something. Right. So I still had not fully like launched from the, from the nest yet. And my apartment, you know, I lived in my buddy's kitchen on a futon because he— we were college kids, so nobody needs a kitchen. So I think the microwave was in the living room and I had a futon that folded out from a couch in their kitchen. And that's just where I lived. I paid $325 a month. So I had— this is when I graduated. So I had just the most incredibly low cost structure and I could get— I could, you know, afford food on a college campus pretty, pretty cost effectively. My wife, who I met in college, we were dating then, and she had gotten a real job upon graduation. So she had a salary of about $60,000, $70,000. So I felt super rich. And I had another, to this day, a good friend, a guy named Wes in North Carolina, who he and I had kind of gotten into business together informally, as in like when he needed $5,000, I spotted him. And when I needed $5,000, he would spot me. And like more than once, You know, he and I would walk down the street in Chapel Hill, North Carolina, where we went to school with an envelope of cash of like thousands of dollars because I've taken out of my bank account and he needs it by 1 PM today to pay somebody. Or it was the opposite the other way. I need to buy some servers. Can I borrow $5,000 for a couple of weeks? Great. Here's an envelope of cash. And, and so we start pushing and, you know, pushing that into like hiring more talented people in my business, building software that's more competitive and has like actually looking at competitors' products and saying, well, if we just added these one or two other, these other features, we could maybe charge twice as much or we could retain customers longer. So some kind of very early thoughts in, in how we would grow this business. But your question was where did the money go? Yeah, that's where it went. It went into like a real office, actually subleased maybe 3-room office from a law firm in downtown Chapel Hill. I think a lot of that early money went into things that helped me feel like I was a real business person that I didn't really need to spend money on. But it started to like, you know, have an office to sit in when I could have just done this in my apartment and have an office to see clients. Actually, that was helpful. And we still bought everything really cheaply, like our conference room. All the chairs came from university surplus, like we bought them for $10 each. We like reupholstered things ourselves. We had a projector that was the size of like a tube television in like 1975. It was like the biggest thing you've ever seen. I was always worried it was going to fall off the ceiling and kill somebody just to like have a screen in our conference room so we could like feel like we were in business. So we spent— we invested a lot of that and then it was just paying for, you know, my basic lifestyle needs at the time.

Two questions. One, when does the rocket ship start to take off? And then B, when was the first time you ever felt like, oh, I've made it, like I've got a lot of money?

The rocket ship really took off about 3 years after I grad— 2 to 3 years after I graduated from college. So there was definitely a period in there of kind of the first year or two after graduation where my parents are being good parents and circling a little bit and going like, you know, is this the— you know, it's like, cool, you've moved to, you know, LA and you want to become an actress, but you're working at a restaurant, right? And I was that person in that phase of like, cool, you want to become an entrepreneur, but like you are hanging out in this like tiny sublet office working till 2:00 AM, and like, is this really the life that, that you want to lead? And then around 2 years after graduation, kind of 2 to 3 years, we passed the $250,000 annual revenue mark. I think our first year in the eye contact business was $13,000 total revenue in the entire year. And so I'm still building websites for people, and my, my, um, co-founder Ryan is, is, is building websites and he's selling like a nutraceutical product off of a website and like we're just kind of making it work and that, that's what's paying for everything, right? And so then year 2 is, is $250,000. So we've gotten some things that are like working. And I think that was the first moment where I was like, this is, this is maybe going to work. And it wasn't even my own feeling of it. It was when I would talk to other adults that were more experienced than I was and say, yeah, like we, you know, because I'm just this like fresh-faced kid who I was 22, 23 and say, yeah, we're making $250,000 a year now. And they're like, wow, like that number exceeded most people I knew's annual salaries and other entrepreneurs that were in business didn't have a 2-person team that was making $250,000. And so I started to see the response in those people where they were like, wow, that's really cool. And like, oh, and by the way, we're growing. We're actually growing really quickly. The next year we did $1.3 million. So it was in that kind of $250,000 number is when I started to feel like maybe this is going to work. And I wasn't getting any of that money. We were pouring it back into marketing and everything, and $0 were coming out of the business to Ryan and I at the time. And then we hit $1 million in revenue and we're like scared. We're like, this is way bigger than we ever thought this would be. And I'm 24. And we're growing fast still. Like we, we hire our first full-time person to run marketing for us. We'd had a couple of part-time people filling in and now we go out and we look for a director of marketing to just direct marketing. There's no people in marketing. And that was, that was the first moment I think when I really felt like this is going to be, this is going to be something. And at some point there might be a way that I can get a bunch of money out of this thing to myself and actually build my own, you know, position in the world and build my own wealth, which was still $0 to my name at that point, probably negative zero. So car loan and just cash flow that was at breakeven. Yeah.

Well, I want to make sure we get to the second half of the story. So how did you get to $50 million? And then what was it like? What was the decision to sell and Yeah, talk me through that.

It was about a 7-year journey from that, like that $250K number to the $50 million ARR, which is really fast looking back on that. We grew really, really quickly. We grew to about $3 million annual revenue before we took any outside money from anybody else. So we just kept taking— this is why Ryan and I were making no money. We were taking every dollar we made in, we brought in the business and just putting it straight back into marketing because marketing was profitable. So we were like, how much can we turn the handle on this thing? And like, what can we turn this thing into? And so we're pushing and pushing and pushing. And then we get to a point where my co-founder Ryan went and had lunch with, with a guy named Judd, who's a really successful entrepreneur in North Carolina, who's about the same age as Ryan and I, but was a couple of years even further down this path already. And he'd raised a bunch of outside capital. And so Ryan comes back to me after this lunch with Judd and says, you know, everybody else is out there raising money. We haven't needed to raise money. But he said, I was having lunch with Judd and Judd was like, you can raise money really cost-effectively if you don't need to raise money. And that changed our minds. We're like, oh, we thought just because we didn't need it, we should never raise it. And he helped explain that, no, you'll get a really good valuation and you can probably give up a lot less of the company than other people might give up. And so we were able to raise over the first couple rounds about $6-7 million and give away like way less than a third of the company, maybe like 20% of the company or something like that. Where a lot of companies would have already given away 30% of the company at that point and then raised again. And, and so that put us in a position where we felt really confident to just keep raising capital. We were still the majority owners of the business. We didn't have to think through a lot of those tradeoffs of giving up control to somebody else. And so, and marketing continued to be profitable. We could, in the early days, we could spend $25 and it would bring in like $700 of revenue. In the, in the kind of mid-years where we spent most of our money on growth, in the years where we were spending $25 to $30 million a year in our, in our marketing budget, which was mostly Google Ads. We were spending maybe $200, $300 to acquire a customer, but they would spend $2,800 back with us over the lifetime. So we had the unit economics pretty well proven out and those softened over time and changed a lot. But in that core, we realized we could raise money, we could fund this economic model, and we could keep increasing revenue. And it was high margin. Recurring annualized revenue, which is the best type of revenue. It's a good kind in a business, in a software business where we weren't even shipping any physical type of product, right? Just ones and zeros as a service. And this, this started— we basically just continued to play that game. I mean, a lot of details behind it. Team grew to 250 full-time with another 100 spread across the world in contractors and people running kind of audits of communication coming in and out of our system and in India, software teams in Argentina, sales teams in London, call center in back in Wisconsin. And so it grew to some really, really cool scale and $50 million annual revenue. And I think one of the interesting things I like to— that's interesting to me that I like to share about that point when we sold in 2012 is that at that time, another company by the name of Mailchimp was the same size as us. And did about the same amount of revenue that year. So they were kind of a late entrant into the market. Even after us, they were growing much faster. We were at about that same level in 2012. We got a deal to sell the business. We'd raised about $75 million of venture and private equity at that point and had some bank support behind that from Silicon Valley Bank. And, and so we were in a position to return capital to our Series A and B investors at that point. And it just made a lot of sense to do the deal. And for Ryan and I, it made a ton of sense because we still owned a lot of this business. And so we were seeing companies like Mailchimp and others coming in and competing with us really, really intelligently and creating problems and causing that customer acquisition cost to come up and that lifetime value to come down. Still a good economic model, but both of those things were just slightly moving in the wrong direction. And so we could see that we were going to have to do something different in the next 5 years. Or we could sell. And we had been trying to do something different for probably the 2 years before that and hadn't been working. So we thought, this is a great business. Let's make this part of somebody else's business where they can package it with other products and cross-sell and upsell and use this in a way that, that'll work really well for them. So fast forward maybe 10 years later, you know, my exit, I'm now 10 years into having my exit and then Mailchimp sells for $12 billion. I don't know if you saw that number. So it's pretty good. Very impressive. Ben and his team were amazing and I think maybe never raised any outside capital. So very, very impressive software business. I'm kind of glad we didn't stick around and try and compete with them because damn, they were good. Yeah.

So, so you're 30 and after paying back investors, sounds like you put a little jingle in your pocket. What was that like?

Yeah, Ryan and I still own together about half the company and he had actually joined me 2 years into it. So though Ryan was always officially a co-founder in the business, I had built the product and had revenue and had a little bit more equity because of that. And yeah, it was life-changing. I mean, the number one thing that I remember is not the money at the exit. It's realizing that, that, that the big problems in our business that I've been trying to solve and just living and breathing 24 hours a day were no longer my problems to solve. Like, I just remember walking out of the office and it took a couple of days for that to occur to me. Like, I went right back into that cycle of like, all right, I got to dig in, you know, here are the problems. Let's try. And then I thought, Oh, thank God. No, I don't. Like, these are not my problems. No one is asking me to solve these. In fact, the people that just bought my company, it's now their problem. And they knew that coming in. And so that's, you know, that's why they have their talented people and the rest of our team to try and solve this. Just remember this huge weight coming off my back of just like, wow. And then I started to settle in to what, you know, what could life look like? And I got some advice from some, some fellow entrepreneurs at the time who said, don't spend any money, any real amount of money for the first year. And I really appreciated that. And I—

Man, I wish somebody had told me that.

Yeah. Yeah. And did you spend a little in the first year?

Yeah, a little or a lot.

Yeah, a little or a lot. So I had always had this, this personal value of I like to really reward myself when I make money. And so it was always about 10%. I would usually just spend 10%. So if I had made $100,000 before that, then I'd spend $10,000. We had actually— I'd actually sold some stock personally multiple times in some of our previous rounds before we exited. So early on, I'd taken $1 million off the table and then a couple more in a later round. And some other people at the kind of founding or executive level were able to participate at different levels, what they wanted to or not at that time as well. And so even then, it was kind of like, all right, like, what can I spend $100,000 on? And I did some things that were really fun with that. But then I had the big exit and it just felt like I couldn't just like completely blow 10% of that. That's just like, felt to me like so much money. So I didn't, and I didn't buy anything for, um, I bought a house about 9 months later, which I felt like that's pretty safe investment. Nice house in a nice neighborhood. So it's probably not going to be too much of a challenge to get value out of this in the future. But other than that, yeah, I did not. I didn't. Change a lot. I had bought a second home off of some of the money from one of those previous rounds and it needed some work. And so once the exit came along, I definitely spent some money on that, like finishing out the property and a couple of just cosmetic changes that I wanted to make to it. But I really, I really sat tight that first year. I kind of invested in some things that definitely cost money but were not invested. I spent money on things that were invested in my quality of life on some things that were, um, that were really helpful, uh, that I later ended up backing off. So like, we hired a chef, so we had all of our meals cooked in, in home for us, which was amazing. I was probably a little healthier back then too, so that was nice. Um, and, uh, and, and then I would use a car service to get around to a lot of business events. I'd have to travel over into Raleigh, which was a little bit of a bigger city at the time, and bigger city than Chapel Hill, and you know, I would be able to just go to these kind of like late night business events and things like that and have a driver, not even full-time, just like using a car service to go everywhere. Made me feel like a baller. And then, you know, eventually I was like, all right, I'll just drive myself there. This is fine.

Totally.

And then the chef was like, hey, I was like, ah, I like to cook. I'll grill some burgers, you know, I'll grill out. And so a lot of that stuff has come back around, but those are some of the first places we went. You know, we didn't even have like, housekeeper or anybody like doing laundry for us or anything. So we, we kind of stocked up on all that. And then we started having kids immediately. So our, my, our son was born like 10 months after the exit. So there was some, there was some timing there. I think the, uh, the stress just finally allowed that to happen. And then our daughter was born 3 years later. So we had, we got to go into having kids with a ton of resources. And with our first kid, we paid for a fair amount of support, which was awesome. And then with the second kid, we like tripled it. It was absolutely ridiculous. And then if we had ever had a third kid, we probably would have backed off that a little bit again, like a little too far, too many shifts, too many people in our house. And eventually got to a point where I looked at my wife and I said, you know what, I like to be able to walk around my own house naked and not feel like I'm going to, you know, offend somebody. And we had so much help and so many people helping, which was awesome. But it just felt like a lot of people in our space. And so we kind of pulled back from that and found what's a little more of a happy medium for us.

Well, and I want to dive into the psychological part a little bit because you touched on the weight that was lifted from running this company. Can you kind of dive into the psychological toll running a company like that when you're so young, relatively? What was that like and what was that transition like?

When we sold the business, I found myself feeling like lonely was kind of the word. It was, it was kind of unchallenged was another word where I just, you know, kind of had so much opportunity to choose my path that, and nobody really asking for much out of me that, you know, a little bit rudderless in that, like I needed to figure out what direction I was going to point my life in. And I actually felt a, I felt a pressure that probably not a lot of people have too much sympathy for. But a pressure of like, all right, I have the time and youth and health and intelligence and experiences to choose like any path that I want from this point forward. Like there was almost nothing that was off limits. And so that, that felt like a new weight of like, when I get to my deathbed someday and I look back on this, if I have not lived exactly the life that I want to live, There's only one person to blame. Like, there's nobody else I can point to and say, they made me do this, or they limited me. And, and so I, I, I kind of swam in that spaciousness for a while. I just couldn't figure out whether I should go left or I should go right. I had to, I had to really rediscover who I was because I had just been a guy who worked really hard for the last decade and I worked every minute possible and I loved it some days and I was exhausted and terrified other days. And so I'd come out of this pressure cooker, which, which came with two sides of it. One, people needed me. I felt, you know, like everybody, you know, came and asked me for the answers. So that must mean I'm smart or I provide some value. And then the second you sell, there's nobody asking you for anything anymore other than financial advisors knocking on the door saying, we'd like to speak with you and help you. And so I'd come out of that pressure cooker, which was constantly like reinforcing my ego while at the same time challenging, just, you know, not sleeping, not really making a lot of time for anything that I would consider like personally fulfilling. It was all about trying to maximize this opportunity. And I felt this like obligation to that opportunity too, because it felt so big. Like, who would I be to squander this opportunity? Like why, you know, I am a competitive person and I like to do things to the best of my ability. And so I just wanted to bring everything I could to every day in that business. And then, and then it all just sort of like the vacuum just sort of sucks it all away at the exit. And then it was, I'm left there sitting with like, nobody's asking me to do anything for them and nobody's asking me to solve their problems, which is awesome. But then like, hang on, am I a smart person? Do I have value? Because like, that's what was kind of propping all of this up of like, you know, yeah, I must be good at what I do because everybody asked me to solve their problems. And, and, um, yeah, and trying to really figure out the, the rudder, um, of kind of which direction to go in. And then the intensity of it. I found myself chasing intensity in other areas of my life, like trying to figure out how to go on a more risky vacation, let's say, or to do something crazier or something personally, because I had felt that like constant fear in, in my professional life of like, could this thing all go belly up tomorrow? And could, could I lose everything? And I had gotten kind of comfortable and built a craving for that level of intensity. As hard as it was, it was amazing to, you know, have a board meeting with investors flying in from all around the country in suits, asking tough questions, and then walking right into a product meeting and skipping lunch to try and solve a product challenge. And then, you know, going out to dinner with our CFO and trying to solve a challenging financial problem. And it just like felt so needed and it was so thrilling. And so I found this, this, you know, trying to fill that vacuum post-exit and trying to, you know, figure out what that looked like. I was definitely drinking too much alcohol because that just felt exciting and challenging. And it brought that sort of like kind of wildness to life that the business had brought. And I had to really kind of wrap my head around that one over time and have, you know, within 5 years was drinking way less and then the next 5 years drinking none. And I don't drink alcohol at all anymore. I had to really kind of graduate from that. And then I've, you know, I found excitement in other places. I had this moment and it's funny, it happened in Denver, sitting outside of a Starbucks in probably 2015. And I was out here with a group of entrepreneurs and still living in North Carolina at the time. And it just, it's funny that I now live in Boulder and have been here for 10 years, but a foreign mate of mine said, 'You know, when was the last time you were really, really happy?' In response to something I had said to him. And I just thought, 'Well, hang on a second, like, I am really, really happy. I have everything I've ever wanted.' And then I thought to myself, 'No, I'm not as happy as I could be. He's right.' And so I wrote down the answer to that question was in high school.

Wow.

He was like, 'What was it that was making you so happy at the time?' He just very point blank said, what did you do with your time then? And I was like, I mostly just hung out with friends and I played sports and I went mountain biking in western North Carolina. And I, you know, played some instruments and made some music. And he was like, well, when was the last time you've done any of those things? I was like, well, it's probably been high school. I've dabbled a little bit in it. And it really changed my mind about how to spend my time at that point. And it was the seed that helped me start to rediscover the things that I can actually control that make me feel great.

Yeah. And so the, the post-exit vacuum is, is well documented and a lot of people have a similar type experience, right? I mean, and I think you put it so succinctly, right? You're needed and there's voltage. You're feeling so alive. But it's, but it's, it's also driven by stress and anxiety and darkness. And all of a sudden, yeah, it's just gone. How do you rediscover who you are? From there.

Yeah. And I think it's also driven by what other people need so much too. And when you're part of a big organization or a system, everybody comes to you because you hold the purse strings, right? It's not necessarily maybe because you have the best answers, but, you know, you control budget and you control the things they need, right? And it's this kind of like two-way street that, that just continues to perpetuate. Sorry, I lost your question.

Yeah. So, so how do you, how do you discover who you are? Like, who am I without my company? Yeah, is the question I ask clients a lot.

Yeah, that's what I felt. And I mean, that was the number one question bouncing around in my head at the time of exit was, was like, what do I do? What do I like even? Right? Like, I've just been mostly trying to keep up with responding to what everybody else needed and wanted and trying to keep everybody else happy. So now for the first time in my life, nobody's really asking me to help keep them happy. And so now here I am trying to figure out what are the things that are going to make me happy? So having a computer science degree and being a little bit nerdy, I created a Google spreadsheet and the columns roughly, I can still pull it up on my phone, but roughly the columns were how strong was my mood that day? Like what did I feel depressed energy or did I feel more satisfied energy with my, with that day? I was still continuing to experience anxiety that I'd experienced as an entrepreneur, which had periods of time in my entrepreneurial journey had gone into full-on, like, crippling anxiety, like panic attacks, me changing my schedule, changing what I committed to significantly around things that I felt like were anxiety triggers for me. Some of that was still definitely hanging around. So I was recording, like, did, you know, did I feel like I was able to get through the day without it, without reaching some high level of anxiety that I wanted to try and avoid or figure out how to get in front of better? Um, did I do something that was challenging? Um, alcohol had already made the list. And so it was like, you know, no more than 2 drinks or something like that, which eventually I changed to, did I have zero alcohol today or not? And it wasn't an absolute rule. It was just a measurement. Some days I did, some days I didn't. Um, what else was in that list? Yeah, it was around, you know, these challenges. Oh, it was, um, did I leave my house and go into public today? Because I noticed that I could just stay in this mansion I lived in and it was really quite nice. Um, but after a significant period of time just sitting inside of my house and not going anywhere, it was kind of contributing to just feeling isolated and feeling alone and, um, and kind of diminishing value of relationships with friends. And so I was like, did I actually go out and experience energy in the world? There's maybe 7 or 8 of these things. And so I started following this pattern and, and, um, and just trying to see like what were the things I did on days where I didn't feel as anxious and I felt really satisfied about life and I felt connected with people. And I measured these things and I actually removed a couple of things from the list. One of the things that surprised me the most that I removed from the list was, did I feel like intellectually challenged that day? I felt like that was one of my core values of, I loved like using my brain to solve complex problems. And I still do like that to this day, but it fell off the list because I was like, eh, some days I do, some days I don't, you know, some days I want that challenge, other days Maybe I can go for 2 weeks and not have the challenge and actually do other things that make me feel really satisfied. So things that rose to the top ended up being like things like time outdoors. Part of why I ended up moving to Boulder was an optimization around this. So I was finding myself driving 2, 3 hours a week to go to mountain biking trailheads in central North Carolina, or just a little further away from the city where I was in to go get to these, these assets and things that were helpful to me. And so part of that calculation moving to Colorado was I could just not drive 5 hours a week to go to these things because I could ride to them right out of my house. And so there's 5 hours of my life I could get back. It was connection time with friends. It was the opposite of that isolation. It was just really getting out and connecting, making, being there for friends when they needed me, or volunteering time, donating, supporting causes that I appreciated. And still, and building, I think the intellectual challenge kind of shifted into a different one, which was just building things. Like, am I building something? So I built a house for a while. Like, I didn't build it, but I designed it and planned it and had a team build it. And so that was a really exciting project. I was creating something that I could see. And then I would write sometimes, would build software again and build tools to solve things. And that ended up being the thing, the intellectual thing that I really loved was like, am I creating something new in the world based on a problem that I want to solve or an opportunity that I see? Those are the things that have really brought a lot more value to my life in the most recent decade. Yeah.

And so it sounds like you took a very empirical-based approach to solving this, a very engineering-focused approach. Was— did you dive into any coaching, therapy, spirituality, any, any other modalities that, that played into the mix?

Yeah, therapy ended up being really useful, um, around drinking and reducing alcohol. Like, that was probably the biggest takeaway that started to come out of that. And then building some just general tools for trying to be the other side of like my anxious patterns where I would just get really intense into things and it would drive my anxiety. And so figuring out how to try and unwind some of those things. I never— I didn't hire a coach until many years later when I, when I kind of shifted into more of a— so one of the things that really frustrated me around the exit actually was, was everybody wanted me to come tell the eye contact story, right? So like I was on panels all the time. I was at conferences all the time. I was telling the story. and everybody only just wanted the big happy version of like the numbers and, you know, yeah, rah, rah, rah. And it was cool because we were a really big success story in the Southeast where there's not a lot of tech companies that get to the scale that we got to. Most companies there don't sell for more than $10 million, which is still a great exit, but just in compared to national and global standards, there's— we were kind of one of the big ones. And so everybody wanted to know the answer to, you know, how do we do it? And so we were telling that story all the time. And I just, started to feel like, you know, what, you know, was bouncing around inside my head at the time was what I really cared about at that point. And I was trying to balance that. I don't care about this story anymore, but it will provide value to other people so I can go out and tell it to the world. And with, you know, balancing that alongside, like, here are the things that I really care about, which is like, did this company damage my mind in a way that I will never recover or can I recover? You know, can I find happiness that isn't, you know, incredibly thrilling and terrifying? Can I find happiness outside of that intensity? Some of those big questions I was asking myself, and I wasn't talking about that outside of like therapy. And so a couple of years after the exit, probably like 6, 7 years after the exit, I hired a coach to help me start to understand how I could possibly be brave enough to share some of those things that felt like really scary parts of me. With the world and tell that version of the story, like the version of story that I actually cared about, the part that really felt really meaningful to me. And he shared a piece of advice with me that I've, that I've used from, from that point forward, which is anytime you share your story and these vulnerable and meaningful things from your life, the goal is not to get everybody to appreciate it. The goal is that one person might appreciate it. And that's been really helpful framing that I've used to this day of, of any conversation I have about this where the bar is so low that if anyone gets anything from this story, then I'll be satisfied, um, that I've, you know, taken the risk to put myself out there and to share, like, really tender and personal parts of my life.

So what is something along those lines that you wish you could have shared then that you can share now?

I think, I think the, the history of panic attacks is one that, like, I was so ashamed of having panic attacks as an entrepreneur. Just like, I felt like I was the only one that this had ever happened to. Um, I was terrified at what that meant about me as an entrepreneur. Like, does that just mean I'm not one of the ones that will ever be successful or that I'm just a complete phony? Everybody else is walking around looking so proud and confident all the time. And 99% of the time I was too, you know, perpetuating this problem. And so I wasn't— I actually, like, dreamed about in my mind, I would daydream about, like, maybe someday I will be brave enough to share this part of my life with the world and tell people that the stress often became way too much for me in my mid-20s, signing a $16 million lease, having 250 people working for me full-time, investors from all around the country. And, you know, that was— it was oftentimes it was too much. It was just too much. I didn't have the skills to handle it at the time. And it's been so fulfilling and powerful for me to start to share those dark corners with the world, which I started very, very small. I actually showed up for a speech to talk about my exit and, and changed the script 10 minutes before going in and talked for 30 minutes, almost in tears, about how hard it was. And that was right before I left North Carolina and moved to Colorado, so almost 10 years ago. And from that point forward, I've never looked back. But I had to— it took so much for me to break the seal on that and to get to let that thing out into the world. And finishing that talk, actually, 3 people came up to me. One of them had lost a sibling to suicide, and that sibling had been an entrepreneur. And that was like the immediate conversation I had coming out of that. And I was like, all right, hang on a second. Like, there's something really serious on the line here. Like, if I can share more of this message with more people, maybe I can help some other people see that they're not alone in this, in this sort of challenge.

So the question that's coming up for me is, knowing what you know now, was it worth it? And if you could go back and tell that guy something 10, 15 years ago, go, what would it be?

Yeah, it was, it was absolutely worth it. I have lived an extreme life because I was an entrepreneur and in a lot of other choices that I've chosen to travel to wild places in the world and challenge myself to do wild things. And I've also battled cancer twice in my life now before I'm 44 now, twice, two incredibly horrific, terrifying rounds with, with cancer diagnoses. And so I've gotten to like do some incredible things. And so I think the more I realize how finite life is, the more I appreciate that I took a lot of the risks that I took. And the more I've battled health on the personal front, the more I appreciate the times that I've gotten myself into tough situations versus the times that tough situations have just come up as bad luck. And so I've realized, I think that's really helped reinforce my appreciation for the risk I took in the business world and some of the personal risks I've taken as well. Because living in the illusion that I can control all risk away is, is so unrealistic now that I've, that I've had these two challenges with health where, you know, I didn't choose those challenges and I probably didn't do anything wrong to get in those situations either. And so I'm just glad that there were plenty of times where I chose the crazy route and the wild route and I walked myself into that, even if I got punched in the face, which I did so many times. So yeah, I appreciate the journey. And I think there was a period of time post— right post-exit when I started to realize, um, how many, um, you know, psychological patterns that I needed to unwind from the, the 10 years of busting my butt building that business, where I worried that these were things that were so unique to me that I would never be able to unwind them. And I've now had enough time and space from that to realize that they're absolutely unwindable and that when you intentionally try and break a habit, you can do it in maybe 1/10 of the time that it took to build the negative habit in the first place. And so that's created a lot of like empowered feelings in me that I can, you know, I could go back into a gauntlet like that again. And even if I didn't do it based on everything I've learned for how to do it better, even if I just let it absolutely beat me over the head for 10 years, I could still unwind it in, let's say, a year. So there's a, there's a path out even when it gets really, really tough. So that's given me a lot of confidence and appreciation for those risks that I've taken. If there's one thing I could go back and tell myself as a young entrepreneur, it relates to what I've spent the last 10 years working on, which is trying to figure out where my red line is. If you think about this as like an engine analogy, and I was talking to an entrepreneur just last week who has about a $10 million business and is pushing really hard to build this business. And he said, trying to figure out where my personal red line is, is like walking around in the dark trying to find where an electric fence is. I love this because it's like you have no clue where this damn thing is until you grab it and then you're electrocuted or you're at least shocked. He said, it's just, it's so hard because you don't know where it is, but you know that if you find it, it's not easy to just back up one inch. Like you're going to be attached to this thing and electrocuted and stuck, right? There's something almost really correct about that analogy of like when you're being electrocuted, you can't use your muscles because they're, they're being engaged by this. And so you're stuck and you can't actually get out of the situation. And I found that in myself time and time again. And so I've been building tools the last 10 years trying to help high-pressure, high-achievers for the most part, try and figure out where their red line is. And so I wish I had these tools back then. I wish they had been built. I think I'm the only person that's ever built them. Uh, I've found again, a problem to solve out of my own experiences in life and to share with others. And so we can do this pretty precisely. We call it optimal pace. It's how many hours you can push yourself today before the diminishing returns kick in. I mean, we all know that working 24 hours a day doesn't make sense. So then is 18 hours the answer? Is 16 hours the answer? What about 12? At some point you lose productivity, but you gain the reality of you probably won't burn yourself out or blow yourself up. Where do you draw that line? And so I've built tooling now that helps entrepreneurs all around the world figure out that answer with a check-in, 5-minute check-in they do every morning. They figure out what their optimal pace is that day. Sometimes they have to push a little further. Sometimes they can go a little bit underneath. And then we look at all these metrics behind. It's kind of like a physio lab, but for people's minds. So I wish I had that tool. I wish I had the confidence of knowing that, you know, 12 hours is enough today. Or maybe 12 hours is— I can go longer. I can go for 16 today. That was something that I realized was a consistent pattern in that time, was that I had an unlimited to-do list at all times until I sold the business. And so there was always more work to be done. And it was really hard to figure out when to stop taking that next book off the shelf and trying to process it and to then to be able to say, like, I felt a lot of guilt anytime I said, all right, I'm going to leave the to-do list right there for today. I'm going to pick it up tomorrow. I felt a lot of guilt behind that decision every time. And I think these tools that I've created now help people not have that guilt and just say it would be foolish to work one more hour right now. It's time to go for a walk or time to hop on my mountain bike.

When I think about this problem that we're talking about, this, this high octane, you know, high pressure but high reward lifestyle.

Yeah.

Right. Work-life balance has sort of got a dirty, dirty connotation now. But yeah, you know, there, there, there are two fixes typically an emotional fix, like what's the underlying psychology behind this, but then also the mechanical fix of how can I just look at the data and decide like what makes a good life for me? How do you think about that problem?

Yeah, I think about us as like each having both a player and a coach inside of us and like the, the player is just the core resource, right? It's the, it's the Jokic on the team, right? It's the just the person who can go out and get the work done, right? The blocking and tackling of like figuring out what the next day is or figuring out like, you know, what, what to do to fill the time to produce the output. And then the coach has kind of got like the gas pedal and the brakes and trying to figure out like, how much can I utilize this resource before I blow it up? And you can like— Jokic is a great example in some of the championship games where he's been pushed too hard. Guy can barely make it to half court. So, so what? He's a superstar. He's not actually playing in the offense because he's still trying to get back down the court. So we see this trade-off in sports, I think, more easily and maybe in physical pursuits than we see it in mental pursuits. And so that's something I'm really focused on in my own life now is trying to figure out when I'm, when I'm stuck just trying to be the best player there is of the game versus using myself as a resource correctly as the kind of coach mindset of like, how hard should I be pushing myself today? And And when am I even the right resource for the problem? So I think a lot of, a lot of trade-offs that are related to should I be working on this or should I delegate it are more of like coach-type decisions. And decisions around, you know, do I have the right skills for this problem I'm trying to solve or maybe more like player-type things if I need to figure out how to improve my 3-point shot in order to make more shots in the game or to help out my team in the best way possible. And so I'm trying to think about my life and how I optimize my, my time on this earth a little bit with those two hats of, of that player role and the coach role.

And what does wealth mean to you now?

It's trying to have the greatest impact on the things and people that I care about while I'm still on this earth and the ability to ability to really align those things, to, to, to be working on the things that are most meaningful to me, that I believe are, can be the most meaningful to other people, which is why I've chosen the things that I work on. And to share what I've learned and the vision for the rest of the time when I'm no longer on this earth, the vision that I have for what it might look like for others or what this whole human and consciousness experiment can look like, trying to figure out how to have that impact now so that, um, it's not that I don't have regrets later. It's like, I'll always want to have done more. Like, there's no amount of life that's going to feel long enough for me, right? Like, if I could live 1,000 years and keep doing this, I would take that gig. Um, but none of us can. So it's, uh, it's really trying to have the biggest impact on the things that I care about in the time that I'm here and, and to feel like I've made a difference in other people's lives.

And if you could just share one thing that may impact, uh, listeners of this show, typically entrepreneurs, let's say they're, they're building a $5-10 million company, what would you share with them?

My message is, is pretty clear, and I don't want to say the same thing over and over, but I do like to say the same thing over and over, which is work at your optimal pace. Figure out where your red line is. Do that through intuition, do that through tools, do that through coaches, whatever it is. Be curious about that question. How hard can I push right now? Because one of the things I've, I've learned about solving really big problems and doing things that are really impactful is that they are not hour-long projects and they're not week-long projects. Sometimes they're lifelong projects, but they're probably 2 to 5 to 10 years. And to optimize your output and your impact over that period of time, you've got to figure out how to jog instead of sprint.

Yeah. So, so well said. And definitely a message that I think isn't necessarily reinforced on Twitter a lot these days with hustle culture.

Yeah.

I so appreciate you sharing your story with us and it's It's so impactful to hear, you know, someone willing to open up about the dark side of entrepreneurship. How can people find you? How can they learn more about your work and the products that you've built to solve this problem?

I'm sharing a lot of these tools on our website, which is Thrive with Dory. It's D-O-R-Y, and it's named after those beautiful little wooden boats that go through the Grand Canyon. Have you ever seen these gorgeous little wooden boats that can They look fragile and they look frail, but they can navigate the biggest whitewater on earth. And I love that analogy. This is us, I feel like, as entrepreneurs, like we're often fragile and frail, yet we put ourselves into these wild situations. So yeah, so thrivewithdory.com, D-O-R-Y, that's the Instagram handle as well. That's where I'm sharing most of our research. And that's kind of how I've pivoted myself in the last few years is trying to really do direct research on this, which we do at the Dory organization. And we're measuring high-pressure, high-achievers to figure out what actually works for for them. This has become my mission to try and solve this problem because I feel like everybody else is trying to solve stress and productivity and hustle for everyone. And I'm really most curious about people that are in the pressure cooker, what actually works for them, not the person who's on vacation this week or the person that even maybe even has a 9-to-5 job and has a little more stability in their life. I'm trying to solve these problems for for people that are at, you know, 8 out of 10 pressure or higher, and they don't exactly have the bandwidth to sit back and try and decode this for 5 years like I did. How could I condense this in a way that they can solve it in the moment when they're still under fire?

Oh, what a beautiful and impactful mission. And, uh, yeah, I appreciate the work that you're putting into the world.

Thanks, Mike. Appreciate it.

Yeah, thank you.