April 5, 2025
Imagine selling your company for millions – and then buying it back for pennies on the dollar.
That’s precisely what I did.
In this episode of Money Stories Podcast, you’ll learn:
- How our superpowers eventually become our limitations
- The importance of setting boundaries as a founder
- Why so many entrepreneurs outsource their confidence
- and more!
Video
Watch the full podcast episode on YouTube by clicking here.
Or watch it below:
Full Transcript
Mike Brown: The things that are our superpowers, left unchecked, eventually become limitations. This curiosity, this natural problem-solving, this ability to use money to keep score for what you’re learning makes total sense with who I know you as. Now, studying to be an architect, you get your first job, you’re living in New York. I believe you came over with, like, $3 in your pocket. Kind of take us back there and walk us to starting BestSelf.
Cathryn Lavery: I created something out of nothing that someone wanted to buy, which is pretty cool.
Mike Brown: It’s amazing.
Cathryn Lavery: If you look around and no one that you hang out with is who you want to be like, then you need to go to another circle.
Mike Brown: Knowing what you know now, what would you go back and tell your younger business self?
Cathryn Lavery: Cathryn, if you delay a hard conversation, it’s just going to get harder and harder and harder. And often, in a business context, it’ll become more expensive. When you don’t have boundaries for a long time, people will start to treat you however they like.
Mike Brown: We train people how we want to be treated because entrepreneurship, I think, is the greatest school of personal development that there is. But you’ve got to learn and integrate lessons. Okay. Welcome back to another episode of the Money Stories podcast. Today, I am joined by my dear friend, Cathryn Lavery. What can I even say to describe your journey and your career? Shopify award-winning e-commerce builder. But that is just the surface, really. You are one of the most brilliant minds that I know. I’m so honored to be sitting here with you today. I’ve learned so much from you, and I hope that we can draw some of that out today for the listeners. Thanks for coming on the show.
Cathryn Lavery: Yeah, it’s good to be here. I feel like, Mike, you’ve seen me through so many big moments, and now I often think, “Oh, what would Mike think about whatever decision I’m making?”
Mike Brown: Well, that means the world because I think one of the best gifts of entrepreneurship and plugging into other like-minded people is finding people that you can level up together with. And I know things that you don’t know, and you know things I don’t know. So being able to plug in and share those and help each other just continue to level up, get better, and become the best versions of ourselves really is kind of what makes it worth it because it’s a lonely path.
Cathryn Lavery: Oh, yeah. And it’s also difficult if you didn’t grow up with, like, entrepreneurs. I remember when I used to be an architect, and I was, and I wanted—I had a Shopify store on the side—but all my friends were either, like, architects or comedians. And so I was like, I need to get outside of this circle and start meeting other people. Because if you look around and no one that you hang out with is who you want to be like, then you need to go to another circle.
Mike Brown: Totally. And I think it’s hard, and not—
Cathryn Lavery: In a negative way. It’s more like, do you aspire? Like, are you asking advice from someone that you aspire to be like? And if not, then you need to get in a room of people where you’re like, “Oh, this is the career path I could see happening.”
Mike Brown: I think you make a great point here because I think a lot of times, from the outside looking in, people might think entrepreneurs think they’re better than other people or think that it’s just—it’s not better, it’s just a different path, and it’s a much harder path. And yes, there are potential rewards at the end of that journey. But, you know, there are days when I wish that I had a job that I could just punch the clock, forget about it at 5:00, and go home and hang out, right? But that’s not the luxury that we have.
Cathryn Lavery: Yeah, with a lot of jobs, you could actually make more money than a lot of entrepreneurs do—like going to work at Facebook and just leaving at 5:00, getting a nap room, going for a walk on campus. I don’t know if you saw those TikTok videos, which are hilarious, but I was like, “Oh, having a W-2 job where I can just clock out and stop thinking about it.” I’ve had one job ever where that was the case. I worked at a stationery shop when I was at university, and I literally, as soon as I walked out those doors, did not think about it until the next shift. It was such a blessing.
Mike Brown: Well, let’s back up to your journey and understand how you got here and kind of what made you who you are. So tell me where you grew up and how you grew up and what maybe drove you to entrepreneurship in the first place.
Cathryn Lavery: So I grew up in Belfast, Northern Ireland, which is very—not an entrepreneurial space. You know, you just go to school, then you go to university, and then you get a job. And my parents both had normal jobs—like, my dad’s a doctor, but he works for the National Health Service. Same job for, like, 40 years. The idea of me not going to university was just, like, not even a thought. Even though, when I look back, I was very entrepreneurial growing up. I would sell cupcakes on the playground. I had an e-commerce—or an eBay—store when I was, like, 13, which I wasn’t even able to have a PayPal account for. So my mom had a PayPal, but I was just, like, a drop-shipper at 13, drop-shipping, like, Dawson’s Creek DVDs from Canada because they didn’t have them in the UK, and I was always selling them. But it was this weird thing, so I wouldn’t talk to my friends about it at school. And there were all these things where I was like, “Oh, it’d be so much easier to, like, have this online store.” So I was even, at, like, 13—you look back and you’re like, “Oh, the things I was interested in.” I just didn’t know you could do it as a job. And so I was good at design, art, and, like, physics. So then I was like, “Oh, well, I should be an architect, because that’s, like, a profession, and this kind of mixes with what I like doing.” And so that’s what I ended up doing. But I literally did not know anyone who had their own business, who did anything outside of having a normal job. And so I just kind of followed the path that I was told was the right one. And then when I came out, I always wanted to live in the US because I went to New York when I was 18. I was like, “Okay, if I can make it here, like, I can make it anywhere.” So I got an internship for the summer, and then that internship brought me back after I graduated to work as an architect. And so that’s how I first came—
Mike Brown: Over to the U.S. Well, again, backing up to 13, selling Dawson’s Creek DVDs. How did you grow up in relation to money? Were you poor? Were you middle class? Like, what—
Cathryn Lavery: What did—
Mike Brown: What did that look like when growing up?
Cathryn Lavery: I think we were middle class, but we were—I think my parents grew up very poor. And so we were middle class, but I think we didn’t have access to the money. Like, my—I think my dad has money, but he still will, like, think about—we share an Adobe subscription because he doesn’t want to pay the, you know, 30 bucks a month or whatever. It’s, like, fine. Or he’ll, like, walk 20 minutes instead of getting an Uber.
Mike Brown: Things like that where there’s a lot of frugality.
Cathryn Lavery: Yeah, which—but he also taught me a lot about—I remember he, like, set up our first savings account where he was like, “Okay, for any amount you save, I will give you a certain amount, like, extra more.” So then I’m, like, scheming. I was always, like, trying to find ways to make money. So I was always, like, the person going around neighbors in the neighborhood, knocking on doors to see if they needed their lawn mowed or their car washed or whatever I could to, like, make money. And so I was always, like, with my brothers, even figuring out how to have them do stuff for me for money or something. So I would, like—I bought these rechargeable batteries, and then they needed them for their toys, so they would—I would have them, like, either pay me for them to charge, and then they would have to give them back because I had the charger. And so stuff like that where my parents were like, “You are a monster.”
Mike Brown: Always scheming, always hustling. It sounds like, where do you think that came from, that drive to make money? Was it because there were things you wanted to buy, or were you just, like, solving problems? You liked the game of it? Like, I’m really interested in this.
Cathryn Lavery: I think it wasn’t even that I wanted to buy things. For me, it meant, like, the freedom to be able to do stuff that otherwise I wouldn’t be able to. And so I remember with my eBay store, for example, I was only allowed on the computer, like, an hour a day. So that’s very limiting. So I remember, like, buying a laptop with the money that I was making so that I could, like—you know, I’m, like, “I’m trying to run a business here, Mom.” And there used to be, like, a computer room where you would sit there—there wasn’t any, like, being on your phone. So for me, it was—it was, like, I like learning, and, like, “Okay, how do I figure out this game?” Or, like, figure it out. And then once I figure it out, it gets a little more boring, and I can, like, move on to the next thing. But everything is, like, figuring out how to win at that thing is, like, “Okay, I’m gonna learn HTML and CSS so I can make my eBay listing look better than the next guy.”
Mike Brown: You know, just, like, it’s, like, a native problem-solver. Yeah, it sounds like—just, like, “How—”
Cathryn Lavery: “How do I do this?” And then slowly, like, do it better than I was before. And for me, like, I like learning, and if I can—and making money doing it is just a way of, like—it’s, like, a scorecard for the skills.
Mike Brown: Yeah, I—
Cathryn Lavery: Which I actually never thought of before. But for me, it was always, like, it’s, like, a metric that you can actually track because sometimes you’re learning stuff, it’s, like, “What does this mean? Like, is this actually useful?” And so, because some things you can’t really track, it’s, like, money is the one thing you can use as a metric stick. But it’s bad because sometimes—I remember, I don’t want to jump ahead, but when I sold my business, I’m, like, building this in-ground cold plunge in the backyard. And so I’m, like, learning plumbing and electrical. And Emily was coming back, and she’s, like, “How was your day?” I’m, like, “Not great.” She’s, like, “Why?” It’s, like, “Well, nothing I did today made any money. Like, I can’t—I’m not gonna be a plumber or electrician.” And so tying my worth to, like, money was—became, like, “Oh, what do I do now?”
Mike Brown: Well, this is great foreshadowing because the things that are our superpowers, left unchecked, eventually become limitations. And this curiosity, this natural problem-solving, this ability to use money to keep score for what you’re learning makes total sense with who I know you as now. But let’s go back to studying to be an architect. You get your first job, you’re living in New York. I mean, I believe you came over with, like, $3 in your pocket. I mean, kind of take us back there and walk us to starting BestSelf.
Cathryn Lavery: So when I was graduating, you know, I had to get a visa to come over here. And so I got, like, this scholarship that paid for part of it. And then I was basically coming over, and I think I had about $800. And then I was, like, “Okay, I’ll get paid in two—” you know, I had two weeks off. And then—and then I was, like, “I’ll work for two weeks, and then I’ll get paid.” Then I—and another big curveball was—so we had agreed on a salary, and then I’d done all the visa stuff, which is kind of expensive in itself, like going through that whole process. So then I got it, and then a month before I was supposed to come out, the company—and I’d worked for them for three months as an intern; it was paid, but it was, like, a stipend, so it was not very much. And so we had agreed on, like, 40K a year in New York, which I was, like, “That works.” And then a month before I came out, they were, like, “Actually, we don’t have a lot of work right now, but we still want you to come out. But maybe you’ll work for 30,000, and then we can increase it once we get more work.” And at the time, I was, like—I was, like, “That’s pretty tight.” But—and I was talking to a few friends about it. I’m, like, “Well, I already made this plan,” so I’m, like, “I’ll figure it out.” And so I was just, like, “Okay, let’s go.” And so my plan was, like, “Okay, they’ll get more work, and then I’ll get paid more, and I’ll just have to be very careful.” And so then I—so then I’m gonna make 30,000 pre-tax in New York City. And this is 2012. And I get here, I have two weeks off, and again, I don’t have that much money. And they email me, and they’re, like, “Oh, yeah, we’re still a little quiet. So if you could start in, like, six weeks—” and, you know, “I know that you just graduated, and I know when you graduate, people want to travel, so you could travel.” And, like, I did travel—I traveled from Ireland to here. And that was a point where it was, like—and I also couldn’t get another, like, full-time job with someone else because the visa is tied to them. So then I’m, like, kind of stuck. I’m, like, “Okay, I basically have five weeks where I didn’t plan to not be making any money.” And so then I just started, like, literally learning—I’m, like, formatting Kindle books for people because I learned how to do that. I’m just, like, hustling to make enough in the meantime and then also not really tell my family what was going on because I didn’t want them to have me come home or, like, feel like they had to give me money or anything. So I was really just hustling to make money until the time I was supposed to start that job, which I ended up starting and worked there for 18 months.
Mike Brown: But all of a sudden, this natural curiosity and the natural-born problem-solver selling Dawson’s Creek DVDs all of a sudden becomes a skill to survive. And not just survive, but eventually thrive. So there you are for 18 months doing architecture.
Cathryn Lavery: Well, I started a side business on the side of the architecture job probably, like, six months in, where I was designing, like, T-shirts and posters and stuff. And I was coming at it from, like, “Oh, these are things that I would want to exist.” And I didn’t have a marketing plan. I had a Shopify store. I bought a printer because I didn’t know anything about offset printing or anything like that. And then I—I was printing—like, literally, my architecture firm had this printer. I was, like, “This is really good quality.” So I just bought the same one. And then I would do the prints, and then I would, like, go to the post office. I didn’t even have, really, a lunch break—you were kind of expected to just work through it. But I would, like, leave the office to go for a walk, and then I would mail stuff at the post office, and then I would go back to the job. And I remember a couple of designs I did that kind of went viral. And I would get back from work, and it was not—it wasn’t, like, nine-to-five. It was, like, eight-to-seven—like, I wasn’t really leaving the office until seven. And I started hiring a TaskRabbit to come in the morning—like, I’m, like, packing orders because I also didn’t know about a 3PL. So I’m doing everything myself. And I pretty much did a lot of stuff. Then, eventually, I think after I was, like, “This is making more money than my job, and I’m spending way less time on it.” But I knew I wasn’t gonna do it forever. But I look at it now—looking back, it’s, like, “Okay, that was my freedom vehicle.” And I started—you know, I had, like, a 45-minute commute in the morning, so I would—I was, like, “Okay, I can’t quit my job until I know more about, like, the business side of things.” So I started reading—like, I’m, like, “Here’s—” I think I picked, like, 22 books. I’m, like, “I have to read these before I can quit the job because I have no idea what I’m doing.” And then, eventually, I ended up quitting the job when I felt, like, “Okay, I know a little more.” And then, over time, I, like, gradually—that was, like, my cash flow while I tried to figure out what the next thing was. But BestSelf didn’t come along until, I think, two and a half years after I quit the job. Because I was—I tried a few other things in the meantime, but I also, like—I’m very calculated-risk because even when I quit the architecture job, I didn’t want to leave them in the lurch because I had a few other—I had some projects that were on-site, but I didn’t want to do any new projects. I’m, like, “I’ll just go one day a week, and I’ll do all the site stuff.” And then because I’m, like, “What if I quit this job, and then I turn into, like, lazy, and I just—” because I’ve never not worked, I think, like, literally every summer I’ve worked. And I was, like, “What if I—” because I’ve just never had—not had a job. So I was, like, “Okay, if I can just control my time—like, what if I—I’m actually not that productive, or I, you know, I’m not motivated.” And then after a week, I’m, like, “Oh, yeah, I’m good.” The Wednesdays, I was, like, “Oh, I gotta be done with this job.” And then I told my bosses that I was gonna—I made up, like, the visa waiting-for-my-green-card excuse as the reason we had to do that, like, sabbatical. But it was really me testing whether I could handle it or not.
Mike Brown: I love that. So there is a through-line here of entrepreneurship as a freedom vehicle. Now you take the leap, you eventually find and found BestSelf. You find your big idea—the journal, which is what started everything—and you win the Shopify award in your first year of business.
Cathryn Lavery: Yep.
Mike Brown: Then you win it again the next year. What was it like going from slinging whatever you can online to winning one of the most prestigious awards in the industry in that period of two years? Walk us through, just briefly, what that’s like going from zero to hero, essentially.
Cathryn Lavery: Well, it’s funny. So I’d entered that competition with my previous Shopify thing—wasn’t anywhere close to winning, but it was very much, like, a goal. And I feel like whenever I Kickstarted the Self Journal, they launched the new competition, like, the day after the—the day after the Kickstarter ended. I’m, like, “I’m entering with this.” And I even, like, put it on my wall—like, “You are going to win this.” I posted—I printed out the official, like, thing that they did. I’m, like, “Okay, BestSelf is going to win this.” Didn’t think that we would. And my thought was, like, “Okay, that’s my goal.” But it’s, like, second running up is, like, you create a great business. So for me, it was—it was, like, kind of, like, a roller coaster of—it felt, like, “Okay, I made it. I know kind of what I’m doing, at least,” because you get all these, like, accolades, and then the people that were, like, “Wait, you’re quitting architecture? You, like, got all your—you know, your degree and your master’s, and you’re just gonna, like, work at it for 18 months and then be done?” And so I could tell, like, my parents were supportive. My mom was just, like, “Yeah, you’ll be fine.” And my dad was definitely, like, “Oh, I’m a little nervous about you quitting your job.” And I kind of framed it—like, I framed it as, “Hey, I’m thinking I’m going to quit my job in a few months,” like that, knowing I’m going to quit my job, and I’m just giving you, like, some leeway that this is happening. I mean, it wasn’t, like, I was taking money, so I didn’t need to explain myself, but it was very much, like, a “This is what’s happening, and I’m just giving you some time to warm up to the idea.” But that was, like, the first time I was, like, “Okay, maybe she knows what she’s doing,” like, that this is happening. Because it’s really difficult to, like, explain to people that aren’t in the business world—it’s, like, “I think I, like, know what I’m doing. It’s gonna be fine.” And I didn’t know what I was doing—I was just figuring it out as I went. But I have very—I was, like, “I’m fully confident I’ll—I’ll figure out how to—”
Mike Brown: Because you always had—yeah, this—this was a default mode for you. It’s, like, you find a problem, you solve it, and there’s actually no question of whether you’re going to find a solution.
Cathryn Lavery: Yeah, I’ll just—actually, with my wife now, I—she jokes sometimes because if I say I’m going to do something, like, I’m going to do it, and there will be things that come up, but, like, that’s fine—like, I will just grind and get through it. Like, I remember when I—I was, like, “I’m going to get my driver’s—” when I moved from New York to Austin. I was, like, “I’m gonna get my driver’s license by my birthday this year.” Then I break my collarbone the week I moved to Austin. But I mean, I already set this goal. So I have these, like, lessons, and I would just take my sling off before the lesson. And I remember I took these three lessons before I could get my test. And the second lesson, I actually had to stop at a CVS during the lesson to get some, like, Advil because I’m, like, “I’m in pain.” And she’s—I was, like, “I broke my collarbone.” She’s, like, “You what?”
Mike Brown: Like, these things are starting to make sense now, right? And what I want to point out is just this—this spirit that seems to be tracing through all of these stories of—it seems completely normal to you to see a problem, find the solution, and just execute. But that is a rare quality that most people don’t have the ability to follow through with that level of commitment. And again, it’s a superpower up until this point in your life. But knowing what you know now, what would you go back and tell your younger business self, Cathryn?
Cathryn Lavery: Hmm. I don’t know. I mean, I think—I mean, we’ve talked about this—is just this idea—I’m very quick to action, so I don’t do a lot of research, really—not at all. I’ll figure out what the first step is, and then I’ll take it. And eight times out of ten, that works out well. But the two times out of ten, I really, like, screw myself.
Mike Brown: Yeah.
Cathryn Lavery: Because I don’t—I also only see, like—I historically will just generally assume that other people are like me. So if they say they’re going to do something, they will do it. And I realize it’s actually not the case. And so I have gotten into things where, rather than have a contract laid out with very specific terms, I would default to trust. Because—I mean, another thing is I was very insecure when I first got into business. I was very, like—I remember I was just, like, “Oh, well, I—I’m an architect, I know design, but I don’t know business,” because I literally had never taken a business course in my life—not even in school. And so, even though I’d had these, like, little e-commerce—you know, like, my eBay store—and obviously I would have to do stuff around that, in my mind, like, the business was just—was not very interesting at the time because I didn’t see it as a problem to solve. I saw it as, like, “Oh, I don’t want to be in, like, spreadsheets or whatever.” And so when I first got in, I was, like, “Oh, I’m going to be at a disadvantage because I don’t have this background.” And so I was very much, like, I would never ask for anything, but I always would try to show up and give as much value, which ended up serving me well over time because I made a good network. But I would never ask for help or feel like I could, like—put, like—God forbid someone—I would put someone out to, like, help me with something.
Mike Brown: Yeah, the—the ruthless self-reliance. Yeah, your superpower starts to become a limitation because now you’re so used to this being all just figured out, and it becomes really difficult to rely on other people. You brought on a business partner.
Cathryn Lavery: Yeah.
Mike Brown: Didn’t go great, to wrap—to make a very long story short. What did you learn from that experience?
Cathryn Lavery: I mean, I learned a lot of things about myself. One of the things—I mean, you can look at—I think for a while, you can look at, like, “Oh, this person did this negative thing to me,” which might be the case, but it’s, like, “Okay, what—how did I show up that led to this?” And what—one of the things I’ve learned is, like, “Oh, I wasn’t—” because I was bad with boundaries, there wasn’t any. And it was only—you know, it’s when you just kind of let—when you don’t have boundaries for a long time, people will start to treat you however they like.
Mike Brown: We train people how we want to be treated.
Cathryn Lavery: Yeah. And I had trained where I was just letting things go and not having hard conversations. That’s probably one of the biggest learnings—is, like, if you don’t have—if you delay a hard conversation, it’s just going to get harder and harder and harder, and often, in a business context, it’ll become more expensive—not only just, like, in my case, like, legal bills, but also just energy, and it’s, like, a weight that you’re carrying. And so if I could go back, it’s, like, have hard conversations early and learn how to set boundaries and talk about things that are difficult. Because I think I grew up—I’m, like, the peacekeeper, where I’m just, like—Emily will point this out after. She’s, like, “How come when people do something negative or treat you badly, like, you’ll be tripping over yourself to make it okay?” As in, like, “God forbid there’s, like, any tension.” I’m, like—even though you did the bad thing, I will try to make it okay—as in, like, I will try to smooth everything out, even though I’m not the one that made it rough in the first place.
Mike Brown: Where did that role come from?
Cathryn Lavery: Oh, just growing up, managing my parents’ relationship.
Mike Brown: Yeah. Yeah. We’re thrust into these roles that we don’t ask for.
Cathryn Lavery: Yeah.
Mike Brown: And if we don’t have awareness and insight into where they came from, they’re going to run rampant until they force us to look at them, right? Which is—sounds like, essentially, what—what happened here. You know, your experience with your business partner actually led to me coining a term that is “outsourcing your confidence.” You actually had everything that you needed to run that business and had run businesses before. But you already mentioned just a little bit ago that you weren’t confident about business. So you went out, and you—and you outsourced your confidence to bring on a partner. And this is a recurring theme I see time and time again with people—is they go find a 50/50 co-founder because there’s just a little part of them that isn’t confident that they can do it on their own.
Cathryn Lavery: It’s, like, partnering out of insecurity.
Mike Brown: Yeah.
Cathryn Lavery: And I definitely—whenever I did the postmortem on that and what I learned from it, that was one of the things where, if I look back, I was, like, “Oh, I was fine.” I just didn’t, like—I would have been fine. Now, I do think, even though that partnership didn’t end up good, I think it was a good—because the person I was with is, like, he’s a very good talker, very charming, makes you feel good. And so I’m, like, “Okay.” And he is very, like, self-promotional in a way that I’m not. And so my wife will say, like, “Oh, it was good for you in the beginning because you’re not like that.” I’m always, like, “Oh, I’ll show you—” he’s, like, “I’ll tell you how good I am,” and I’ll—I’ll be, like, “I’ll show you how good I am, and I won’t say a word.” And that’s not great when you’re, like, starting a business.
Mike Brown: Here’s—here’s what I love, right? Is that—that hindsight being 20/20. Yes, maybe there was some outsourcing of confidence. And what I hear is you taking responsibility for your part and how you showed up to the relationship and giving credit for what you learned. And I think all of that is so important. And, you know, if you’re going to learn and grow—because entrepreneurship, I think, is the greatest school of personal development that there is. But you’ve got to learn and integrate lessons, and the only way you can do that is take responsibility, understand what part you played in it, and then rapidly iterate and improve. So you knocked it out of the park with BestSelf. You became, in many ways, a leader and inspiration in the e-commerce space. What led you to the decision to sell the company?
Cathryn Lavery: So I’d been running it—started in 2015. By 2022, I had basically gotten the business partner out—like, he’d been out, essentially, in everything but equity since 2018. Well, he also was taking money apart from that. And so—but getting him out in 2020—2020 was just, like, a really rough year. It was, obviously, COVID. I mean, I came into that year where it was going nuclear on the business partnership, so—which is a huge distraction. I had COVID coming up where our factories closed because of this thing called COVID that we were hearing about. We were almost out of our best-selling products. We didn’t have, like, a bunch of money in the bank. And so I’m kind of going into 2020, and everyone’s, like, “Batten down the hatches,” and I’m, like, “Batten—I have no reserves.” I am, like, feeling really depleted, and I’m dealing with this—
Mike Brown: No reserves cash-wise, no reserves energy-wise.
Cathryn Lavery: Yeah. And I’m dealing with, like—in my mind at the time—negotiating with a terrorist.
Mike Brown: Yeah.
Cathryn Lavery: Where it’s just, like, “I don’t know where this is gonna go.” And so—and it’s funny because the standing-up-to-the-business-partner thing—when I look back, it was—it was only when my teammates were gonna—like, my employees, essentially—were gonna be affected by the things that he was doing that I, like, stood up and was, like, “No, this is not happening anymore.” And it’s just funny because I’m, like, outsourcing—it’s, like, “God forbid I would just stand up for myself.” No, it has to be, like, “Oh, your guys’ livelihood is on the line—now I need to do something.” And so that was happening, and it’s just, like, a perfect storm. So—because I’m distracted with the business—with the business partner stuff—and figuring out what—we had an inventory manager that was, like, embezzling from us, which I discovered in 2020, around the same time. So I’m just, like—there’s just, like, multiple wars on each front. And by the end of 2020, I got the business partner out. And I was, like, “Okay, now—” and it was great because it’s great, and it’s stressful because you’re, like, “Well, now—now I don’t have this other person to blame. Now it’s, like, totally on me,” which is great and empowering. But also, it’s, like, “Okay, now it’s for real.” And so, for the next two years, essentially, it was, like, getting us back profitability-wise, product development. And the goal wasn’t to sell, but it was, like, “How do I get into a place where I could sell it if I wanted?” And then I had a baby in March of 2022—at the end of March. And it was, like—that, I think, was the impetus for selling because then it was—I’d always, like, poured everything back into the business. And—and then someone came to me with an offer, probably in, like, May or June of 2022. And it wasn’t a great offer, but I’d read this book, and it was just about these, like, binary decisions of—it’s, like, “Oh, do I sell to this person or not sell at all?” And I was, like, “Well, let me just start having more conversations with people.” So that’s kind of—I just started taking calls with people and, like, putting it out there that I was maybe thinking about it, with the goal of, like, “Okay, if a good offer comes along, I could take it, but if it doesn’t, like, whatever.” And so I hadn’t taken any time off after Quinn, really—like, I literally—like, I thought your due date—like, I didn’t plan a C-section or anything, but I was, like, “Okay, well, she’s due on this day.” And then I had been talking to PayPal about doing a commercial thing with them, and so they’re, like, trying to nail down a date, and they’re, like, “Okay, this day.” I’m, like, “Well, that’s my due date. So I don’t think I’m gonna make it that day, but maybe, like, two weeks after,” because I’m, like, “Okay, I’ll have her, and then—and then I’ll be good to go, right?” So I’m, like, “No, I’m not going to go back—I’ll just go there for a few hours, and then I’ll be good.” And so then, it turns out she’s a week late, and then I have to have an emergency C-section. So I’m actually, like, four days postpartum from a C-section when I do that commercial. And so whenever—like, I saw you on this—I’m, like, “Please know I was four days postpartum—I’m as big as a house.” And, like—anyway, so I didn’t—all that to say, I didn’t really take time off. So the decision to sell was a lot of things—it’s, like, I’m hearing about a recession coming, I’m seeing margins getting tighter, I have a big team in the US—we’re remote—but, like, I’m also seeing margins getting smaller, and it’s getting more difficult, and, you know, the interest rates are going up. And I’m just seeing, like—you know, I’m running this business in a zero-interest environment, essentially—what does this look like moving forward? Should I take some money off the table and just, like, chill? Because I, like—I love the brand and the business and the products, but I—oh, there’s a lot of what I call “inexperience debt” that I paid. So the business partnership—you know, the way you have technical debt where you start building on, like, clunky stuff just to get to the next thing—that’s how I was doing it. And I had this debt from, like, paying off the business partner—I took a personal loan to do that. So there’s all these, like, mistakes that I made where I’m, like, “I don’t know how—I just—I can’t really—” at some point, it’s easier to get out and start something new than to fix this over here. And because you also have all this baggage that comes along with anything when you’ve been running a company for seven years. I really loved my team, and it’s hard to also—and I didn’t have the energy for it—I’m, like, postpartum—I didn’t have the energy to turn the ship the way I knew it needed to be turned. And so I was, like, “If I sell it, I take money off the table—everyone there is going to get a raise, and they’ll—they’re all business people—they’ll figure out how to, like, take it to the next level.”
Mike Brown: Well, and I—I remember you called me to ask about my opinion, and I told you something one of my original mentors told me, which is, “You’ll never regret selling your first business.” So you get the check, you get the wire—how did it feel exiting that company?
Cathryn Lavery: It’s kind of an anticlimactic event, mainly because you build all this—you spend so much time building up this thing, and then it’s a “do connect”—you click two things, and then, “Oh, okay, I guess it’s done.” And then the wire didn’t come—you know, like, the wire’s in escrow while, like, everything gets completed. And so it’s definitely, like, not as exciting. And then you go into a scarcity mindset, which is where I went—where I was just, like, “Oh my God.” I went from, like, having a cash-flowing business and an asset I could someday sell to, like, no cash flow and just money that is going to deplete because it wasn’t enough that I was not going to work again. And so then I’m, like, “Okay, what am I gonna do next?” Even though I had plenty of time and resources to figure it out, suddenly I was, like, “Oh my God, I don’t know, like, what I’m gonna do next.” And all this time where I’m, like, “I can take time off,” and I’m, like—I wanted to learn how to code and do all this stuff, which I did do—but I didn’t enjoy it because I felt like I had to—there’s pressure to figure out what the next thing was. Because I’ve always—since I was, I don’t know, 14—always knew what the next—like, working every summer—when I graduated from my architecture job, I actually started a job, like, two days after graduation. Everyone else was taking the summer off—I’m, like, “No, I’m going to work at this architecture firm because God forbid I would waste two months of my life.” But it actually worked out because it was 2008, and the people that waited two months to try to get jobs in architecture didn’t really—didn’t make it.
Mike Brown: So it had been a very successful strategy. But going back to, like—I think exiting a company is one of the greatest gifts we can give ourselves.
Cathryn Lavery: I mean, just the idea that you—like, I created something out of nothing that someone wanted to buy is pretty cool.
Mike Brown: It’s amazing.
Cathryn Lavery: Like, I would never have made—you know, like, I was always thinking, like, “Oh, I would always tie things back to the architecture job—like, oh my God, I would—how long would I have to work to be able to make this amount of money?”
Mike Brown: It’s just a long time.
Cathryn Lavery: Or, like, if I had to stay in that job—like, I hired a bunch of people, and they all made, like, way more than I made, which I was able to do, which is just wild.
Mike Brown: Yeah, it’s amazing to kind of have that sense of completion. But you touched on something I think really important for other people thinking about selling their business or maybe they’ve recently sold their business, which is—you go from a cash-flowing business and an asset you can sell to, “Now I’ve got a lump sum, and I gotta decide what to do with this, and if it’s not enough to never work again, what the hell am I gonna do in between?” So what did you do? And, I guess, what are some of the lessons learned, or what do you wish you had done differently with your lump sum post-exit?
Cathryn Lavery: Well, I went to your Unbreakable Wealth. I hadn’t exited at that point, but it was, like—I think I’d signed the LOI, and we were negotiating things. But there were a couple of things—some I listened to you, and some I didn’t—I wish I did. One of them was—a lot of times, there’s an earn-out component where—and my earn-out was very reasonable—like, I had other discussions where it was based on profit, which is not a good way to do an earn-out because profit can be changed very easily. But the earn-out piece—you know, things change, especially with private equity. I actually think that the people I did the deal with were, like, pretty forthcoming—like, I’ve heard some, like, shady stories. We did end up having to renegotiate a couple of things at the very end because we had an Amazon issue, which did actually put a risk on the business that hadn’t been there before. So I did see that. So they didn’t change the price, but they did say, “Okay, this cash at close,” which I believe was, like, 10% when we first started, became 25%. And I’m, like—and I remember with you, you were, like, “Well, you should—you should negotiate.” And this is close to the end of the deal—I’m, like, ready to be done. But you were, like, “You should negotiate maybe a lower overall price but more upfront.” And I was, like, “Yeah, but then it’s not as much.” And it’s, like, the ego—it’s, like, “Then I can’t say I sold for this much because it’s—it’s gonna be less.” And—and the—the scorecard that we’re working on—like, “They’re gonna be fine—like, they would have to be idiots to not hit that goal.” Yeah, I said that. And so—and then I’m completely—I—by that point—and that’s another thing—it’s, like, one of my team’s, like, “Oh, yeah, I have to remove you from Slack now.” I’m, like—and I was an ambassador—that’s for a year—but I’m, like, “Oh, okay.” And it’s so weird because it’s, like, “I started the Slack, and now I’m just, like—I know—”
Mike Brown: Kicked out.
Cathryn Lavery: Yeah—which I totally get why they do it. But anyway, there’s just all these, like, “Oh, okay—oh, your email is going—” I’m, like, “Oh, okay.” That’s another thing that I’d do differently now is, like, don’t mix personal emails and business emails together—because if you lose that business email—if you sell your business—also, if you are negotiating selling your business, do it from your personal account with your lawyer—because those emails could all be accessed by a—you know, an owner—if they come in again—they—I don’t know if they did that, but, like, that’s something you should be thinking about. What other—what—what was the question?
Mike Brown: Yeah, how did you think about deploying your money? And—
Cathryn Lavery: Oh, yeah—so when I went to your program, I think one of the big things I learned from that—it was just, like, taking your risk in your business instead of taking—because I was, like, very into crypto—I did have some stocks, but, like, to be honest, like, a lot of my net worth was either in my business or crypto, and I’m, like, “Oh, yeah, I should be doing more.” So after that, it was, like, deploying it into, like, the stock market and things that, if I needed to get access to it, I could. And so I diversified and didn’t put any more money into these, like, risky bets—I didn’t take any—I—but I didn’t put any in that I might have put in had I not done that.
Mike Brown: Yeah—I mean, one of the big conversations I remember having is just, like, the thought process of investing in our friends’ companies, which is something I had done—
Cathryn Lavery: I’d also done that—
Mike Brown: And you can do that when you have a cash-flowing business—25K here, 50K here. But for me—and this was something I was able to share with you—once you sell, you start deploying in 50K chunks—the money goes fast, and you can’t access it.
Cathryn Lavery: Yeah.
Mike Brown: So how do you think about investing now?
Cathryn Lavery: I mean, now I’m—sometimes I’m, like, “I should send, like, my—my thing of how much more I have invested in just the stock market than I did before.” I’ve just—again, I can—I can access it anytime—so that’s, like, a big piece of having a plan and just automatically—I mean, I did the lump sum into the market whenever I sold, and then—even though, technically, I should have just put more in, just, like, every—every week automatically—even though it’s coming from a savings account—it’s just, like, I don’t even think about it. And whether the market’s up or down, it just goes in. And yeah—apart from that, I haven’t—I don’t think I have invested in maybe two other companies—like, small—but it’s, like, small amounts because I still need to feel something.
Mike Brown: Yeah—which I think is a really important part, right? Is, “Hey, let’s—let’s set aside a small budget—”
Cathryn Lavery: Yeah—
Mike Brown: “—to go do things that are fun that I believe in and make the impact that I want to make without doing what I did, which is deploy all my capital into—”
Cathryn Lavery: And I’m—it’s, like, small checks—it’s, like, 5K, 10K—like, literally nothing more than that.
Mike Brown: And so you get a break, and then what happens?
Cathryn Lavery: So I—I was trying to figure out what I wanted to do next, and I—you know, e-commerce—obviously, I’d been in e-commerce for 12—you know, 11 years at that point—
Mike Brown: Yeah—
Cathryn Lavery: —different stores, but—but I’m, like, “E-commerce is hard mode.” It’s just—there’s a—and it’s, like, “I don’t want to do that again because it’s a lot of headwinds.”
Mike Brown: Well, and the reality is, right—there’s always—there’s controllables and uncontrollables, and e-commerce from 2015 to 2023 got a lot harder.
Cathryn Lavery: Yeah—well, from 2021 to 2023—between—you know, your container went from 3,500 to 24,000. And you just see—I remember being on calls—we had ten containers, and I’m just, like—something that should have cost 40K is now 240K—it’s, like, insane—I’m, like, “Public math that I—” yeah—so it’s things like that where you don’t really have control. So I’m thinking, like, “Okay, if I go into a good cash-flowing business—” so I’m, like, “Okay, I could do this agency.” And you actually told me something really good—you were, like, “Try it on and see if you like it—you don’t have to make any decisions.” And so that actually gave me the permission to try it on. And then I realized after two—I’m, like, “Oh, I don’t like this at all.” I don’t like—I like product creation because I like creating something once, and I don’t like feeling like I have a boss with all the clients. And so I was getting more into AI—learning, like, coding and things like that—but a lot of the stuff—it’s, like, I like solving problems, but I didn’t have a lot of problems to solve when—I mean, I have everyday problems, but—but I was struggling again because I think everything I’ve ever started, started as a side quest from something else. And when I didn’t have the structure of the main thing, I really struggled with figuring out what I wanted to—
Mike Brown: Do—which is definitely a common journey. And why I give the advice of “try things on.” Because what tends to happen is, as entrepreneurs, we have this “burn the boats” mentality—we start a new thing, and, like, “Well, I guess this is it.” And then we just go heads down, and, like, “Hey, wait a minute—you have no pressure to actually work right now—you have a lot of runway, and trying on a new thing, going, ‘Actually, this is not for me’—like, quitting becomes a superpower when you’re post-exit.”
Cathryn Lavery: Yeah—
Mike Brown: “When you’re starting your first company, quitting is kryptonite—like, you’ve got—you’ve got to make it through. But, like, once you make it through, then quitting becomes a superpower—like, saying ‘no’ becomes a lot more important than saying ‘yes.'”
Cathryn Lavery: And there were all these ways of—you know, it’s, like, “Oh, how are you going to invest your money?” And there’s just so many ways to make money—but I realized I’m, like, “I don’t—” I think I thought of myself as an entrepreneur, which I think I am—but I think I come at it from, like, an artistry—like, “Oh, what can I create that becomes a business?”
Mike Brown: You’re a pure creator, for sure.
Cathryn Lavery: Rather than, “Oh, here’s a way to make money.” I’m, like, “That’s—that’s not really that enjoyable for me.” And so—so there were all these ways—I’m, like, “Yeah, I could do that—not really interested in it.” And so—so then I’m seeing—you know, I’m hearing from—so I was an ambassador, and I’m supposed to be on these calls with the—the sellers—but it was, like, “Okay, well, if they don’t schedule it, then there’s not much I can do.” So I would just send emails into the void of, like, “Here’s what I think.” And I’m just doing it because I’m getting paid as an ambassador—and, honestly, I’m also thinking of the 20—you know, 20% of 25% of money that is tied up with this thing. And I still have access—I can see the Shopify—and, like, Q4, we’re up 20% because we had everything, like, already scheduled. And then Q1, we had the worst Q1 since, like, 2018—it was—and I was, like, “Okay—” yeah—I was just, like, “Okay, well, I have to mentally say goodbye to that money now because there’s just no way to catch up between, like—Q2 and Q3 are quiet—Q1’s actually bigger for us than Q4.” And it’s—
Mike Brown: And they just punted.
Cathryn Lavery: Yeah—because they didn’t—because they were, like, a new private equity company—so they’re, like, trying to set up their business while buying brands, but then taking autonomy away from the team—and—and then they can’t make purchase orders—and guess what? If you don’t have inventory, you can’t make sales. And so it’s just, like, this death spiral—yeah—and so I’m, like, “Oh, shit.” So then I kind of, like, “Okay, I’ll—I’ll figure something else—” I—and it’s funny because it’s—I think I had a more stressful year not working than when I was working—I was, like—
Mike Brown: And watching your baby dwindle from afar—with nothing you can do about it—trying on these new things that aren’t really working—
Cathryn Lavery: And I was thinking, like, “I’m glad—” I was glad that I sold the company, but I was, like, “I hope—” in my mind, I’m, like, “I hope I could build something like that again because I loved the ethos, and I still believed in a lot of what we did—I just—it had become something that felt like more of a prison than, like, a freedom.” Because—you know, I loved the team that we created, but it also had just become, like, very difficult to manage. And then it’s hard to, like, be nimble and change things when people’s pay—like, people’s pay and their whole families are dependent on you. And so I was, like—it was just very difficult to, like, think of how I would want to do things—but I just—it was—it just felt too—too hard, and I didn’t have the energy to do it. But in my mind, I’m, like, “I hope I can build something like that again and just not make the same mistakes next time.”
Mike Brown: Less inexperience debt.
Cathryn Lavery: Yeah.
Mike Brown: And then what happened?
Cathryn Lavery: And then my—so I’m talking with the CEO of the—the company about my deal—so they sent me the numbers—they’re, like, 11% off goal, and it’s, like, an all-or-nothing thing—so then I’m, like, chancing my arm, seeing if I could get, like, some sort of prorated thing—so I’m talking with the CEO, and he’s—we decided to get on a call, and it’s, like, December of 2023, and he calls me—he’s, like, “So, bad news—you’re not—the board isn’t going to do any of the earn-out because we didn’t hit your numbers. And actually, we are going to be shutting down—we decided it’s not really—our thesis isn’t really working, and we are going to sell off the brands that we bought—so do you want to buy it back?” And, to be honest, when he first brought that up to me, I was, like, “Oh, no—” because I was thinking of it—I mean, by that time, they’d already told me—like, six months after I sold, we had, like, a six-month agreement where I paid, like, a three-month bonus, and they paid a six-month bonus to my existing team—and—and then they told the team, like, “Okay, you’re going to get your bonus—but after six months, we’re laying everyone off, essentially.” And so they’d come to me, and I’d—you know, wrote a couple of references, helped a couple of them get jobs at other places. And so I knew kind of what was going on—but when he said to buy it back, I was, like—I pretended I was interested because I was curious, but I wasn’t that interested in buying it back because I was, like, “I don’t want to get back into the scene—I don’t want to play the same video game again.”
Mike Brown: Yeah.
Cathryn Lavery: And—but then I started thinking, like, “Okay, well, in what way would I buy it back?” Because I thought it’d be a cool story—I was, like, “Interesting—like, what—what’s the same, and what’s different?” And so then I—at first, I was going to have someone run it—like, someone to come in and be, like, the operator—and I would just own a small piece of it and still say that I owned it without getting into the weeds again. And then that did not work—did not work out—and we’re just negotiating this deal—I actually sent all the numbers to Mike because I’m—because I’m also wanting to look at it from, like, “Is this a good investment versus am I just doing, like—I’m—am I getting back into the same game even though I’m out of it?”
Mike Brown: Like, is there a sunk-cost fallacy?
Cathryn Lavery: Yeah—yeah—yeah—that’s kind of how I—
Mike Brown: Or is there a bias that I’m not seeing?
Cathryn Lavery: Yeah—and also, it’s just, like—I exited this company—what is it—it was also, like, “What does it look like to buy a company back?” And so that was on my mind—like, “Am I—am I—what’s the word—like, going back in time—like, am I—yeah—I mean, evolving back into something that once was—something like that—I was—”
Mike Brown: It’s almost, like, “Hey, I—I’ve—I love the video game analogy—I played this video game already—do I really want to hit reset and come back in?” What put you over the edge?
Cathryn Lavery: Well, so—first, the fact that I was going to have an operator running it, and looking at just, like, the numbers—I was, like, “Well, I’ve done this before—I know how to do it.” And the price point was just, like—it is basically, like, I got all this inventory—I’m, like, “If I sold the inventory, I’d make my money back, and then I would own the IP and all the products and, like—who knows—like, what I could do with it?” And so part of why I brought it back was, like, “Well, I’m not working on anything else.” To be honest, I didn’t have a great vision for buying it back—my thoughts were investment-wise—I thought it made sense because the numbers—I was, like, “Well, I know how to do this—the numbers make sense—I’m not working on anything that I’m very excited about—I’ve also been learning a ton on, like, AI coding, automation.” I was, like, “How would I—how would I get this company back and then run it in a much different way than I did it before?” Because I had the freedom to—there’s, like, no team—which is good in that I can start from a clean slate, but bad in that there’s no—there’s no team. And so I was just thinking of, like, “Okay, what’s the—” and I negotiated, basically—it wasn’t a risky deal.
Mike Brown: Yeah—I think that’s—I think that’s the point that I think is really important to bring out—is you essentially structured it so you couldn’t lose.
Cathryn Lavery: Yeah.
Mike Brown: And this is a common story—people sell their companies—private equity doesn’t work out for whatever reason, right—they’re running a lot—they’re running a lot of portfolio companies—they may not have the time, attention, and expertise that you had to run your own specific business—and essentially get to buy it back for pennies on the dollar.
Cathryn Lavery: Right.
Mike Brown: And beyond that—structure it so that, “Yeah, if I just sell through this inventory, I’ve got my money back—”
Cathryn Lavery: Yeah—
Mike Brown: “—and have a line of sight to profitability.” What’s happened since?
Cathryn Lavery: Yeah—so I was, like, “Okay, I’ll buy it back—I could also turn around and sell it again,” but I’m, like, “Okay, I’ll do it for a year, and then I’ll see how I like it.” What’s interesting—it’s been a challenging year, but a good year—from where I sold it, we’re, like, 50% of the revenue, but we’re, like, 4x profit where we were, as far as, like, percentage. And I’m running, like, super lean—I’m also realizing—so, for example, there’s just, like, technology upgrades that weren’t—weren’t, like—ChatGPT wasn’t a thing when I sold the business—
Mike Brown: Yeah—
Cathryn Lavery: That alone—just—there’s a lot of minutiae in business that, like—I also have ADHD, so I’m really bad—I’ll pay—I’ll, like, pay the “wait tax” on not dealing with something—whether it’s, like, a—dealing with a state tax—I gotta call someone or fax someone—something that’s gonna be kicked down the road. And so there’s been a lot of things where ChatGPT has become, like, a—it’s, like, a digital co-founder is what it’s become—
Mike Brown: I’m stealing that—that’s great—
Cathryn Lavery: It’s, like, someone that is there 24/7—I can brainstorm with—I can give, like, “Here’s the problem—” and I have, essentially, access to it—to geniuses—at all times—at any time of the day—
Mike Brown: And it has access to unlimited information and all perspectives—
Cathryn Lavery: Exactly—and AI—if you use it properly—it knows you better—like, there’s that whole thing of, like, Google knowing you better than your partner because you Google stuff that you probably wouldn’t be telling other people—AI is, like, 10x that because you’re asking it questions—if you’re using it to the level that I do, it can, like, point out your blind spots and, like, recognize patterns because it has so much information, and you feed it so much data. And so that alone has been, like, a game-changer—so between, like, the technology of both leveraging that for all my weak points is just, like, a complete superpower—then there’s things like—we used to have a whole finance team where it was, like—you know, two weeks after the month closed, they’d close the books—but it’s all in, like, Excel, and I would never open—I’m, like, on the calls—I’m, like, seeing it on their screen, but I’m not, like, attached to it—now I use this thing called Finaloops—I literally will see my live P&L all the time—I don’t—I’m the one, like, seeing what comes in and what goes out—and I’m book—like, I don’t need a bookkeeper—it takes me, like, 10 minutes a week—and I’m just, like, so dialed into how much everything is—which is why the—so it’s, like, taking responsibility over everything—where before, I would—I’m, like, “Okay, they’re handling it,” whereas now I’m handling—I do have a fractional CFO that helps me—but we, like, get on—
Mike Brown: There’s responsibility—there’s ownership—yeah—it’s one of the first things I have clients do is take ownership of their numbers—because there tends to be only, like, four or five numbers that really matter in business—and when you get a—you know, P&L from your accountant a month later after it’s completed, you’re actually—first of all, it’s not organized in a way that your brain works as an entrepreneur—B, it’s totally forensic—so I think it’s really critical to find the four or five numbers that matter in your business—right—some version of top-line revenue, bottom-line profit—you know, money in, money out—like, getting some of those dialed, and then go, “Okay, how do I leverage these to make actual decisions?” And I think every founder needs to have some ownership over their numbers if they really want to be successful in the long run.
Cathryn Lavery: Yeah—and I think another thing is, like—selling it—I sold the business, and it was—it’s kind of, like, a clean slate where, when I got it back, I also didn’t rehire—I brought in a designer that I—a super-talented designer that I worked with—and a customer support person—but other than that, I was, like—because I knew—even though I loved my old team—if I brought them back, it’s kind of, like—you would, like—this, like, a snow—like, a snow mountain with no trails down it—you just decide what path—if I brought back old people, we’re gonna take the same path that we’ve done because—and it’s really difficult to, like, go where I wanted to go if we just follow the old pattern—so even though it’s been very difficult—both, like, running the business and then hiring people for it—it’s definitely been good for me because I realized, like, “Okay, what I’m good at, what I need to hire for—do we even need a person for this? Or can we use, like, AI automation to do this one piece well?” And—
Mike Brown: No longer outsourcing your confidence—yeah—right—like, you’ve done this thing before—you’ve knocked it out of the park—now you get to come at it with such a different mindset of, like, “Oh, I—I know what I’m doing—”
Cathryn Lavery: Yeah—but I also know—I know what I’m doing—but some of the stuff I do on a day—like, I’m still too in the weeds with it—and one of my things—like, I need to get out because I, like—I have these—I’m learning, and, like—I’ve been building these apps with—now that I can code with AI—I’m, like, “Okay, what’s the business we need to be in?” And what’s the business we’re in right now is the one that we’ve been in—but I need to figure out where we’re going next—which I need some free space—so I’ve been trying to have the team that I have get on board—we’re not there yet, but that’s—I told, like—like, creating a scorecard where everyone’s attached to a KPI and why that matters—so that I can be, like, “Okay, I don’t—I’m not a good micromanager—I don’t like managing people—and knowing, like, the confidence to know what I’m good at and what I’m not good at—”
Mike Brown: Yeah—
Cathryn Lavery: And, like, outsourcing my weaknesses—that’s what—that’s what I’ve been better at doing.
Mike Brown: I love that—so it’s been a wild ride, right? Going from slinging Dawson’s Creek DVDs in Ireland, becoming an architect, accidental entrepreneur—or maybe, like, default-mode entrepreneur—side hustle became the main thing—award-winning business builder—and then buying back your company after exit—through all of that—what would you want to leave listeners with as some of the lessons learned that maybe you had to go through—some of these things that were maybe painful experiences, but now, on the backside, you can go, “Ah, yeah—I’m so—like, I’m so glad I went through that because I learned what—”
Cathryn Lavery: I mean, I learned a lot—I think one of the big things was trusting your gut—so when I look back at things that turned into a complete mess for a time in my life, there was a time early where I—something wasn’t right—so—so I had a—a guy—not even the—I’ve had several people steal money from me—
Mike Brown: Yeah—
Cathryn Lavery: And it’s because I will—and we—you know, I’ve gotten better at protecting myself—sometimes you deal with unscrupulous people, unfortunately—but the last time I dealt with that, I had a bad gut feeling in the beginning, and I overrode that gut feeling because—for—in this example, we needed inventory—so I was willing to—and I—other people had seemingly worked with them—like, “Okay, cool—” so I think listening to your gut—because your gut is actually—it’s the first reaction—we think that it doesn’t mean anything, but it’s actually a lot of our life and subconscious, and it’s our body telling us “no,” even though we don’t know why it’s “no.” Now I listen to my gut when I feel that because I—I can look back and be, like, “Oh, these were bad gut feelings that you had that you overrode at the time.” Also being better at protecting myself—whether in a business agreement—so one of the examples was the person I was gonna get BestSelf back with and have run it—you know, I’d obviously gone through this business partner thing—so I’m, like, “Okay, let’s have the hard conversations upfront and lay out things—” and it was during that process of, like—where I—things came up where I’m, like, “Oh, actually, I don’t—this isn’t a good person to go into business with—” and even though I knew it was gonna be way harder to do it myself—like, I knew I could do it, but I didn’t want to, and I knew it was gonna be much harder—and actually, my wife at the time—originally, she was, like, “You—” because at first, you’re thinking, like, “Buy it back—have this person run it—or not buy it back—” and that was the binary thing—and she’s, like, “This is a great—you negotiated a great deal—there’s other options—there’s the option to sell—the option to buy it at that price—there’s buying it back—” and so looking at everything not as a binary decision—it’s, like, “What else is possible? Like, what assets do you have here that—like, the option—like, I could have gone—” and I did talk to people—I was, like, “I could easily raise money for this—I could easily get people who wanted to buy this business at this price—” so don’t just think, like, “Oh, just because I don’t have this person run it—I don’t have anything anymore—” and so now I look at everything—I was, like, breaking it apart into, “Okay, what do I have, and what would be valuable to other people,” and then also not rushing into anything—so it’s, like, I realized I was, like, “I don’t need to make any decisions right now—I can buy it back, figure it out, and then, potentially, if I want to sell it later—but do I want to rush into a partnership when I don’t need to?” And so that’s kind of why I ended up buying it—and I’d even had, like, pretty big people interested in it—but I was, like, “I don’t want to rush that—” so I was just, like, “No, I’ll—I’ll—I’m just going to do this solo—” and then once I have a better vision of, like, what it is that I could—because I don’t want to—I can—I can pay for it myself—why would I want to—and I’m getting this deal because it’s me—the—the business—had they sold it on the market—would have been much more than that—but that’s kind of one of the things—like, “Oh, I could—like, know what you’re good at and what you’re—what you’ve done before—”
Mike Brown: Well, there’s just, like, an endless optionality—yeah—it sounds like—and breaking out of that black-or-white thinking was so beneficial because it allowed you to see a whole—
Cathryn Lavery: And actually, I’m glad that it happened, and I’m glad that I took that step back, and I went through with it—because I remember—even within a few weeks—I was, like—and what I realized—and after talking to you and other people—and I showed the numbers—because the person I was going to do the deal with had been nagging the deal the whole time—like, “Oh, I don’t know if—like—is it a good—like, pro—” and I’m, like, “Oh, yeah—is it?” But then when I talked to other people—like, “Yeah, that’s insane—” and a few weeks after—I’m just, like, “Oh, this was such a good decision—like, I’m—I don’t like the way it happened, but I’m glad that it happened because it forced me into doing it myself so that I, you know, I have so many more options now.
Mike Brown: I mean, it sounds like it was a journey in self trust ultimately.
Cathryn Lavery: Yeah.
Mike Brown: Going from outsourcing your confidence at the beginning, your. Your career to full circle. I’m actually going to trust myself here. And I’ve got endless time, I’ve got endless options, and then I’ll bring on a partner if and when it makes sense.
Cathryn Lavery: Yeah. But, yeah, I think maybe I was falling into old patterns of like, oh, I need this person to help me run it when I, you know, I didn’t need that at all.
Mike Brown: I love it. Cathryn, thank you so much for sharing with us. Your journey is incredible. Your story’s incredible. You’ve got a ton of lessons learned. What a valuable conversation. Thanks for being here.
Cathryn Lavery: Thanks for having me.