You Built the Life You Thought You Wanted and Still Feel Trapped (Cathryn Lavery, Money Stories Ep4)

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.

I created something out of nothing that someone wanted to buy. Is pretty cool.

It's amazing.

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.

Knowing what you know now, what would you go back and tell your one business Catherine?

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.

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 gotta learn and integrate lessons. Okay, welcome back to another episode of the Money Stories Podcast. Today I am joined by my dear friend Catherine 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, you know, we can draw some of that out today for the listeners. Thanks for being on the— thanks for coming on the show.

Yeah, it's good to be here. I feel like Mike, you've seen me through so many big moments and now I often like, oh, what would Mike think about whatever decision I'm making?

Well, that, that means the world because, you know, I, I think one of the best gifts of entrepreneurship and, and plugging into other like-minded people is finding people that you can level up together. And I know things that you don't know and you know things I don't know. And so being able to plug in and share those and, 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.

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 the 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.

Totally.

And I think it's hard, and not in a negative way, it's more of 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 you're like, oh, this is the career path I could see happening.

I, 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. Of that journey. But you know, there are days when I, I wish that I had a job that I could just punch the clock, forget about it at 5 o'clock and go home and, and hang out. Right. But that's not the luxury that we have.

Yeah. It's a lot of jobs you could actually make more money than a lot of entrepreneurs do. Like going, working at Facebook and just leaving at 5, getting a nap room, getting a, you know, go for a walk on campus. I don't know if you saw this TikTok videos, which are hilarious, but I was like, oh, having a W-2 job where I'm— 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, like, as soon as I walked out those doors, did not think about it until the next shift. It was such a blessing.

Well, let's, let's back up to your journey and understanding how you got here and, and kind of what made you who you are. So Tell me, A, where you grew up and how you grew up and, and what maybe drove you to entrepreneur entrepreneurship in the first place.

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, 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— it wasn't even a thought. Even though when I look back, I was very entrepreneurial growing up. I had like— 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, so my mom had a PayPal. But I was just like a dropshipper at 13, dropshipping like Dawson's Creek DVDs from Canada because they didn't have them in the UK, and I'm always selling them. And but it was this weird thing, so I wouldn't talk to my friends about it at school. And there was 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 and IT. So then I was like, oh, well I should be an architect cuz that's like a profession and this kind of mixes with what I like doing. And so that, that's what I ended up doing. But I didn't— 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— I always wanted to live in the US because I went to New York when I was a teen. I was like, okay, if I can make it here, like, I can make it anywhere. But I— 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 over to the US.

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 did that look like when growing up?

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— like, we share an Adobe subscription because he doesn't want to pay the, you know, $30 a month or whatever. It's like, fine. Or he'll like walk 20 minutes instead of getting an Uber, things like that, where a lot of—

a lot of frugality.

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, like, 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 always like— I'm the person that was going around neighbors in the neighborhood, like 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, like to charge, and then it would have to give them back 'cause I had the charger. And so it was stuff like that where my parents are like, you are a monster.

Always scheming, always hustling, it sounds like. Where do you think that came from, that drive to make money? Was it because there was things you wanted to buy or were you just like solving problems? You like the game of it? Like, I'm, I'm really interested in this.

I think I, it wasn't even that I wanted to buy. 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, like I only was 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 trying to run a business here, mom. And there used to be like a computer room where like you would sit there. There wasn't any like being on your phone. And 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. It's like, okay, I'm gonna learn HTML and CSS so I can make my eBay listing look better than the next guy, you know?

Just like, it's like a native problem solver. Yeah, it sounds like it's just like, how do I do this?

And then slowly, like, do it better than I was before. And for me, I 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.

Yeah.

I, I, 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 and it's like, what does, 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, uh, use the 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, 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 is— was— became like, oh, What do I do now?

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.

So when I was graduating, you know, I have to get a visa to come over here. And so I got it 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, on a salary and then I'd done all the visa stuff, which is kind of expensive in itself of 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, and I'd worked for them for 3 months as an intern. It was paid, but it was like a stipend, so it was not very much. And so we did agree on like $40K a year in New York, which I was like, that, 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 by, 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 And then 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 go— like, I'll figure it out. And so I was just like, okay, let, 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 20— 12. And I get here, I have 2 weeks off, and again, I don't have that much money. And they, they email me and they're like, oh yeah, we're still a little quiet, so if you could start in like 6 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, 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 the So, so then I'm like kind of stuck. I'm like, okay, I basically have 5 weeks where I didn't plan to, to not be making any money. And so then I just started like literally learning. I'm like formatting Kindle books for people cuz I like learned how to do that. I, I'm just like hustling to make enough in the meantime and then also not really tell my family what was going on cuz 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 like 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.

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.

Yeah.

And not just survive, but eventually thrive. So, There you are for 18 months doing architecture.

Well, I started a side business on this side of the architecture job, probably like 6 months in, where I was designing like t-shirts and posters and stuff. And I, I had— 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 like offset printing or anything like that. And then I I was print— like, literally, my, 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 9 to 5, it was like 8 to 7. Like, I wasn't really leaving the office before 7. 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 going to do it forever. But I look at it now, looking back, is like, okay, that was my freedom vehicle. And I start, you know, I had like a 45-minute commute in the morning, so I would, I was like, okay, 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 2 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 Lizzy? 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, and 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'm not motivated. And then after a week I'm like, oh yeah, I'm good. The Wednesdays I was like, oh, I got to be done with this job. And then I told my bosses that I was going to, I made up the visa waiting for my green card excuses, the reason we had to do that sabbatical, but it was really me testing whether I could handle it or not.

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 Best Self. You find your big idea, the journal.

Yeah.

Right? Which was what started everything. And you win the Shopify Award in your first year of business.

Yeah.

Then you win it again. The next year. What was, 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 2 years? Like what, walk us through just briefly, like what that's like going from zero to hero essentially.

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, oh, I'm entering with this. And I even like put it on my wall like, you were going to win this. I posted, I printed out the official like thing that they did. I'm like, okay, best self is going to win this. Didn't think that we would, And my thought was like, okay, if that's my goal, but it's like sec— 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, you 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 in, hey, I'm thinking I'm gonna 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 figure out how to pivot.

Because you always had.

Yeah.

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.

Yeah. I'll just, actually with my wife now, she jokes sometimes because if I say I'm going to do something, I'm going to do it and there will be things that come up, but that's fine. Like I will just grind and get through it. Like, I remember when I, I was like, I'm gonna get my drive— when I moved from New York to Austin, I was like, I'm gonna get my driving license by my birthday on 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 3 lessons before I could get my test, and the second lesson I actually had to stop at a CVS on 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?

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, 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 it, and again, it's, it's, it's a superpower up until this point in your life. But what, knowing what you know now, what would you go back and tell your one business Katherine?

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. Figure out what the first step is and then I'll take it. And 8 times out of 10, that works out well. But the 2 times out of 10, I really like fuck myself. Yeah, because I don't— I also only see Like, I historically, I 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 specifics, 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 and I know design, but I don't know business. 'Cause I literally had never taken a business course in my life, not even in school.

Yeah.

And so even though I'd had these like little econ, you know, like my eBay store and obviously I would've had 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 solve. I thought, saw it as like, oh, I don't wanna 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, 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.

Yeah, 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.

Mm-hmm.

And it becomes really difficult to rely on other people. You brought on a business partner.

Yeah.

Didn't go great, to make a very long story short. What did you learn from that experience?

I mean, I learned a lot of things about myself. One of the things I look— 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, how did I show up that led to this? And 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 all, 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.

We train people how we want to be treated.

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 the— 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 I will try to smooth everything out, even though I'm not the one that made it rough in the first place.

Where did that role come from?

Oh, just growing up, managing my parents' relationship.

Yeah. Yeah, we're thrust into these roles that we don't ask for.

Yeah.

And if we don't have awareness and insight as to where they came from, they're going to run rampant. Until they force us to look at them, right? Which sounds like essentially is 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, uh, 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, on a partner.

Yeah.

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, on their own.

It's like partnering out of insecurity. Yeah, and I definitely, whenever I did the post-mortem 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 who was with is like, he's a very good talker. Yeah, very charming. Makes you feel good. And so I'm like, okay. And it's 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, I'll— he's a— I'll tell you how good I am. And 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.

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 are, that there is. But you've got to learn and integrate lessons. Yeah. And the only way you can do that is take responsibility. Understand what part you played in it, and, you know, then rapidly iterate and improve. So you knocked it out of the park with BestSelf. You became in many ways a leader and, you know, inspiration in the e-commerce space. What led you to the decision to sell the company?

So I'd been running it, started 2015, 2022, basically had gotten the business partner out. Like he'd been out essentially in everything but equity since 2018. Well, he also was taking money, but 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 we didn't have our factories closed on 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 your hatches, like, and I'm like, I have no reserves. I am like feeling really depleted, and I'm dealing with this—

no reserves cash-wise, no reserve energy-wise.

And I'm dealing with like, in my mind at the time, negotiating with a terrorist.

Yeah.

Where it's just like, I don't know where this is gonna go. And so— and it's funny because this standing up to the business partner thing, when I look back, it was, it was only when my teammates were gonna look like, my employees essentially were gonna be affected by the things that that 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 sign up for myself. No, it has to be like, oh, your guys's livelihood is on the line now, I need to do something. And so that was happening, and but, and it's just like a perfect storm. So because I'm distracted with the business, with the business partner stuff and figuring what that looks like, We have an inventory manager that's 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 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 cuz 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 2 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. 'Cause 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. If 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, uh, 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, uh, but maybe like 2 weeks after, because I'm like, okay, I'll have her, and then and then I'll be good to go, right? So, and I'll just— I'm not gonna go back. I'll just go there for a few hours and then I'll be good. Uh, and so then turns out she's a week late, and then I have to have an emergency C-section. So I'm actually like 4 days postpartum C-section when I do that commercial. And so when I— whenever it's like, I saw you on this, I'm like, please know I was 4 days postpartum. I'm as big as a horse. 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's 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.

Hmm.

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 would call inexperienced debt that I paid. So the business partnership, you know, the way you have technical debt where you start building on like clunky to just get to the next thing. That's how I was doing. 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 company for 7 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 take it to the next level.

Well, and 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?

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 DocuSign, you like click two things and then it's, oh, okay, I guess it's done. And then The wire didn't come, you know, like the wires in escrow while like everything gets completed. And so it's definitely like not as exciting. And then you go into 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—

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 my architecture job, I actually started a job like 2 days after graduation. Everyone else taking the summer off, I'm like, no, I'm going to work at this architecture firm because God forbid I would waste 2 months of my life. But it actually worked out because it was 2008, and, uh, the people that waited 2 months to try to get jobs in architecture didn't really— didn't make it.

Uh, so it had been a very successful strategy. But, but going back to like, I, I think exiting a company is one of the greatest gifts we can give ourselves.

I mean, just the idea that you like, I created something out of nothing that someone wanted to buy is pretty cool.

It's amazing.

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 wouldn't How long would I have to work to be able to make this amount of money?

It's just a long time.

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.

Yeah, it's, it's, it's amazing to kind of have that sense of completion. But you, 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 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 going to 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?

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 was a couple things. Some I listened to you and some I didn't know what she did. One of them was a lot of times there's an earnout component where— and my earnout was very reasonable. Like, I had other discussions where it was based on profit, which is not a good way to do an earnout because profit is— can be changed very easily. But the burnout 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 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%. I'm like, and I remember with you, you were like, well, you should negotiate. And this was 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 that, 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 out by that point. I think that's another thing, it's like one of my teams 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 don't know, kicked out. Yeah, which I totally get why they do it. But anyway, there was just all these like, oh, okay, oh, your email is going. I'm like, oh, okay. That's another thing that I 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?

Yeah. How did you think about deploying your money? And, uh, 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 take, 'cause 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 and 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 out, but I didn't put any in that I might've put in had I not done that.

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 a ton of.

I had also done that.

And you can do that when you have a cash flowing business, $25K here, $50K here. But for me, and this, this was something I was able to share with you, like once you sell, you start deploying in $50K chunks, the money goes fast and you can't access it.

Yeah.

So, you know, how do you think about investing now?

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 week automatically, even though it's coming from a savings account. It's just like, I don't even think about it. Yeah. And whether the market's down or up, it just goes in. And yeah, apart from that, I haven't, I don't think I have invested in maybe 2 other companies, like small, but it's like small amounts 'cause I still need to feel something. Yeah.

Which is I think a really important part, right? Is, hey, let's set aside a small budget.

Yeah.

To go do things that are fun, that I believe in and make impact that I want to make without doing what I did, which is deploy all my capital into—

And I'm— it's like small checks. It's like $5K, $10K, like literally nothing more than that.

And so you get a break and then what happens?

So I, I was trying to figure out what I wanted to do next. And I, you know, e-commerce obviously had been in e-commerce for 12, you know, 11 years at that point.

Yeah.

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.

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.

Yeah, well, from 2021 to 2023, between, you know, your, your container went from $3,500 to $24,000, and you just see— you— I remember just being on calls, we had 10 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'm— 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, 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 I, 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 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.

Yeah.

When you're starting your first company, quitting is kryptonite.

Yeah.

Like you've gotta, you've gotta 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.

And there was 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? You're a pure creator rather than Oh, here's a way to make money. I'm like, that's like, that's not really that enjoyable for me. And so, so there was 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. I'm like, Q4, we're up 20% because we had everything like already scheduled. And then Q1, we're— we had a worst Q1 since like 2018. It was Oh, 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 is actually bigger for us than Q4. And it's—

and they just punted.

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 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 figure something else.

So 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, and watching your baby dwindle from afar with nothing you can do about it, trying on these new things that aren't really working.

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 love the team that we created, but it also 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.

Less inexperienced debt.

Yeah.

And then what happened?

And then my— so I'm talking with the CEO of the, the company about my deal. So they sent me the numbers, are 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 CEO and he's— we decide to get on a call and it's like December of 20 '23, and he calls me, he's like, so bad news, you're not— the board aren't going to do any of the, uh, earnout, um, because we didn't hit your numbers. And actually, we are going to be shutting down. Um, we decide it's not real, 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, like, 6 months after I sold, we had like a 6-month agreement where I paid like a 3-month bonus and they paid a 6-month bonus to my existing team. And then they told the team like, okay, you're going to get your bonus, but after 6 months we're, we're, um, laying everyone off essentially. And So they'd come to me and I'd, you know, wrote a couple 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 same, I don't want to play the same video game again. Yeah. And, but then I started thinking like, okay, what, what, 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, am I getting back into the same game even though I'm out of it?

Like, is there sunk cost fallacy?

Yeah.

Yeah.

That's kind of how I—

or is there a bias that I'm not seeing? 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 of 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 like something like that.

I was, it's almost like, hey, I, I've like, I, I love the video game analogy. I've played this video game already. Do I really want to hit reset and come back in? What put you over the edge?

Well, so first the fact that I was gonna 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 of the products. And like, who knows like what I could do with it. And so part of why I bought 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. I, my, 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 now I have 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.

Yeah, I think that's, I think that's the, the point that I think is really important to bring out is you essentially structured it so you couldn't lose.

Yeah.

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 and attention and expertise that you had. To run your own specific business and you essentially get to buy it back for pennies on the dollar.

Right.

And beyond that structure, it's so that, yeah, if I just sell through this inventory, I've got my money back.

Yeah.

And have a line of sight to profitability. What's happened since?

Yeah, so, so I was like, okay, I'll, I'll buy it back. I could also turn around and sell it again, but I'm like, okay, I'll, I'll do it for a year and then I'll see how, how I, like it, what's interesting. It's been a, it's been a challenging year but good year. Like, 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 out when I sold the business. Yeah, that alone of just— there's a lot of minutia in business that, like, I also have ADHD, so I'm really bad. I'll pay— I'll like pay the weight tax on not dealing with something, whether it's like 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.

I'm stealing that. That's great.

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.

And it has access to unlimited information and all perspectives.

Exactly. And, and I, and AI, if you use it properly, it knows you better. There's that whole thing of 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. It hears, if you're using it to the level that I do, it can point out your blind spots and recognize patterns because it has so much information and you feed it so much data. And so that alone has been 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 said, the whole finance team where it was like, you know, uh, 2 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 on their screen, but I'm not like attached to it. Now I use this thing called Finiloop. So 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, that they're handling it. Whereas now I'm handling— I do have a fractional CFO that helps me, but we like get on a call.

There's responsibility, there's ownership. Yeah, it's one of the first things I have clients do is take ownership of numbers because there's— there tends to be only like 4 or 5 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 4 or 5 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.

Yeah. And I think another thing is like, sell 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, super talented designer that I worked with and a customer support person. But other than that, I was like, because I knew of, even though I love my old team, if I brought them back, it's kind of like you would like this, like a snow, snow like a snow mountain with no trails down it. You just decide what path. If I brought back old people, we're going to 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, 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.

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.

Yeah.

And like outsourcing my weaknesses. That's what I, that's what I've been better at doing.

I love that. So it's been a wild ride, right? Going from slinging Dawson's Creek DVDs in, in Ireland, becoming an architect, accidental entrepreneur, or maybe like default mode entrepreneur. Yeah, 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?

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 that— so I had a, a guy's— not even the— I've had several people steal money from me.

Yeah.

And it's because I will— I'm, you know, I've gotten better 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. I was 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 Best Self 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 up front 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.

Yeah.

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 business, had they sold it on 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, what you've done before.

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—

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 it like, is it a good like pro? And I'm like, oh yeah, is it? But then when I talked to other people, it was like, yeah, this insane. And a few weeks after, I, 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.

I mean, it sounds like it was a journey in self-trust ultimately. Yeah, going from outsourcing your confidence at the beginning, your your career to full circle. I'm actually gonna 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.

Yeah. But I, 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.

I love it. Catherine, 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.

Thanks for having me.