Cathryn Lavery: Founder & CEO of BestSelf

Episode 536

In this captivating episode of The Kara Goldin Show, we sit down with Cathryn Lavery, the innovative Founder and CEO of Best Self. Cathryn shares her entrepreneurial journey, from launching Best Self with a vision to create products that foster personal growth and goal achievement, to propelling the company forward through a highly successful Kickstarter campaign and high-profile endorsements from figures like Daymond John and Tony Robbins. Despite selling the company in 2022, Cathryn’s passion led her to reacquire it in 2024, a testament to her dedication and belief in her mission. She opens up about the challenges she has navigated, the critical lessons learned, and the importance of mentorship and a strong business foundation. Grab your pen and paper—you won’t want to miss a minute of this enlightening discussion. Tune in now on #TheKaraGoldinShow!

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started.

Let’s go. Let’s go. Hi, everyone. And welcome back to the Kara Goldin show where we sit down with some of the most fearless and inspiring leaders, entrepreneurs and innovators to uncover their journey towards making significant impacts. And today, we’re thrilled to welcome Cathryn Lavery, who is the founder and CEO of Best Self. I absolutely love her story for so many reasons. So she’s the visionary founder and leader and launched a Kickstarter campaign back in 2015, that you may have heard about, it was pretty incredible. It was an astonishing amount, it was $322,000 in 34 days pretty kick ass for sure. And best sell for those who aren’t familiar with it creates innovative products designed to help achieve personal growth and goals. You may have seen some of the journals, but my personal favorite are the conversation card decks. So we are definitely going to get her chatting about that she was endorsed and Best Self was endorsed by Daymond John from Shark Tank, and also won the Shopify build a better business competition and has also been mentored by Tony Robbins. I mean, she is just absolutely incredible. But we’re also going to get into She sold her company and then repurchased it back. And so I can’t wait to hear more about all of this journey. So welcome, Catherine. Thanks.

Cathryn Lavery 2:07
It’s so good to be here. Thanks so much for the kind intro. I’m gonna send that to my parents. Absolutely. Well, it’s

Kara Goldin 2:12
so funny when your public relations individual reached out to me, I just I love your story, and so many ways, because I always say that being an entrepreneur, and certainly being a founder is never a straight line. Right. And I think that this is, this is just such a great example for a lot of different reasons. But what were you doing before starting Best Self.

Cathryn Lavery 2:34
So I did another Shopify store before WsL. But I actually was an architect. So I grew up in Belfast, I went to university in the UK, and then I moved to New York to be an architect, and, you know, study, got my master’s, worked in it for two years. And then was like, Oh, I don’t know that this is what I want to do. And I started designed shop on the side of my regular job and, and not sort of doing well. And so that’s kind of what got me started entrepreneurship. But I didn’t grow up in any sort of entrepreneur family, like my parents have normal jobs. When I told them, I was thinking of getting out of architecture, it was like, red flags, what’s going on, but neither happy and see me like thriving. But at the beginning, I think they were like, Oh, my goodness, you were an architect. And now you’re doing this stuff online. But I had an eBay store when I was 13. So I was like, very entrepreneurial growing up, I just didn’t know you could do this, like as a job. And so looking back, there were like signs my parents would say, but at the time, I just didn’t know that this was a real thing.

Kara Goldin 3:39
That’s so so amazing. So what inspired you then to start Best Self? And how did you actually get it started? What were the first products but also just where was your mindset?

Cathryn Lavery 3:51
So when I got started with Best Self, I didn’t think it was going to be a company, I just wanted to create the first product, which was the self journal because I had a previous business. And as I got more into personal development, and like learning about how to have successful habits, and like manage my emotions, and doing a lot of things that I didn’t grow up knowing anything about, I don’t think I read my first personal development book till I was 23 or 24. And so then I was just like, I would be so much further ahead if I had known this stuff before. Like, why don’t we learn this stuff at school? And so the first product was the self journal, which was a three month based structured journal as far as like, Okay, how do I take all these successful habits and create a system for myself to be able to get what I need to get done and be productive. And at the time, I actually had ADHD, and I didn’t know what it was not diagnosed for a few years after. So I’d come up with all these frameworks for myself to be able to push my life forward without getting caught up. And that’s what the self journal was in the beginning. So it’s just like, here’s a framework that I can take all these books that I read bacon into something and if I just follow this framework every day, I’ll get where you need to go. So that’s essentially your Best Self started. So it was the self journal. And then I call it the company Best Self, because I was thinking, Okay, if I want to grow more products, sometime like, what’s the essence I don’t want to be like just a journal company. And so that’s why I call it the company Best Self. And then the first product was a self journal, which was very, like type A, let’s be productive, get all our goals achieve everything. And that’s where the company started.

Kara Goldin 5:26
And so did you sell fun? That part of it? I know, you did the Kickstarter campaign, when did that sort of come into the timeline?

Cathryn Lavery 5:34
So the Kickstarter was what launched the whole thing. Because when I looked up, you know, I had another physical products company, and I done previous Kickstarter. So I knew it’s basically a way to pre sell a product that doesn’t exist yet, because I didn’t have the money to, you know, fund it myself. And I showed it to friends and they wanted it. So I’m like, if I kickstart it, then I can have this thing created. And then the Kickstarter went so well, I will. I was like, Oh, wait, what if this was the thing, so I didn’t start the Kickstarter with the goal of like, Oh, I’m gonna start this company, I started the Kickstarter, because I couldn’t afford to make the product just for me. So I was like, if I Kickstarter, I can pre sell a bunch, because anyone I showed the prototype to wanted it as well. And then, when I saw the traction, I was like, wait a minute, what if, like, this passion project that I just wanted to exist, was the business. And so that’s how it started. But it was not the plan to start this, like Bessell was not a plan to start this big business. It was just like, I want to create products. And this is a way to do it.

Kara Goldin 6:33
So for those who aren’t familiar with how a Kickstarter campaign works, can you explain it a little bit? I mean, are you repaying this money eventually? Or how does the How are the economics setup.

Cathryn Lavery 6:44
So Kickstarter is just a way to pre sell a product before it exists is kind of like a concert ticket. So a lot of times people like oh, well, people really buy something before it exists. But concerts, if they can’t sell enough tickets, they just won’t have the concert. And so it’s a way to make sure you don’t end up with a garage full of product that nobody actually wants. And so if you are telling people what the problem is describe the problem, oh, here’s the solution to it, and you can pre sell enough of them, then you can use that money to essentially fund the production of it. And so that’s, I say, we’re like Bootstrap, but we bootstrapped, did the Kickstarter, and then the Kickstarter raised enough funds that we went into production. And then from then on, it was just sales from that initial production run was able to fund the company. So

Kara Goldin 7:35
interesting. And so did you have a business plan that you were, you know, or prototypes or anything like that, that you showed? What strategies did you really use? Because you killed it with your campaign? I mean, that was that’s pretty fast. And also significant amount of startup money for a lot of companies. Yeah.

Cathryn Lavery 7:55
So I had a sort of strategy around launching the Kickstarter was just grow an email list. So it’s very targeted, like people who are into productivity, we did a giveaway, I put out a lot of content. And this was back in 2015. So it was people weren’t as burned died on that. So I was like, How do I give so much value that it’s like a no brainer. And so it was, I think we funded in like, just over a day for the initial 15,000. And then it was like, how do we add more and more value? So it’s like, okay, this is a no brainer. So we did a partnership with plinkus when it first started. So if you bought our products, you also got a six or a year free premium membership with that, which was more than the cost of, and so it was like, okay, and it didn’t cost us anything. And so it was like, how do we keep adding value to the backers we already have, and then add additional products without complicating fulfillment, because a lot of people go into a Kickstarter, and they, they have the main thing, and then they create, like, oh, we’ll do a T shirt with my name on it and stuff. And, and I actually have coached people on crowdfunding because I’m like, okay, don’t do that. Don’t create a bunch of random projects or products with your name on it, first of all, because nobody knows who you are yet, and they don’t care. And secondly, people might want to support you, but they don’t actually want the t shirt or whatever, they just want to support you. But now you’re complicating your fulfillment. And you’re going from like, oh, this was a hard enough project. But now I have to come up with a bunch of random items with my name on it that nobody actually wanted anyway, but it’s just going to complicate my fulfillment. So I always tell people, like people just want the main thing and then multiples of the main thing for the most part, I want one, or two or three or four. And so don’t make your rewards like super complicated or really confusing on the back end, because once you come to deliver them that you’re like, Well, why did I do this? And so really just being strategic with like, what actually people want and how you give them the most value for their backing.

Kara Goldin 9:47
Such great advice for sure. So what are some of Best Selfs most popular items? So

Cathryn Lavery 9:54
we started with the self journal, which was the first guided journal right And you set a goal, you break it down, and you hit it in three months, because I was into, you know, yours too long you procrastinate. And so it was like really teaching system people systems of how to goal set and actually achieve them because we don’t learn that at school, which is insane. And then the, you know, the business that was doing really well. And I think in about Sep 2017, everything business wise was just like, amazing. And, but my personal life I was going through, I got divorced. And I was just like, wait a minute, I thought if I was super productive, like, you know, Best Self was like, at that point was like your most productive self. And I was like, wait a minute, I think we need to expand. And so I started going down this trait of like, okay, I never want to go through this again, even though like we were not me and my ex are still on good terms. But it was just like, doesn’t matter what business goals you have, if you go through something where your personal life is just upset, so much. It, like wrecks everything else, because you’re completely distracted from your business. And so if you really want to achieve your goals, you have to make sure that your personal life is good. And then your business life is good. And that time I was only focused on business and goals and like, what am I doing over here to be the most productive. And so the team used to joke like, the product line would kind of expand wherever cat was going in her life. And so then I went on that line of relationships, and like, what tools can we create, basically, for me, to make sure that my relationship was good. And so that’s where the conversation decks came from was like, almost like a Trojan horse of personal development. Like, what is your relationship it looks like again, but it’s just cards around having conversations that allow both people to be open without one person being defensive of like, Oh, why they asked me questions like, Oh, they’re not the questions are. And so it was just like going down this route. And so no, I our biggest products are actually these, these conversation decks. And you know, people still buy the journals, but it’s really about like, Okay, what is your Best Self, and it very much started, like, type a productivity like that was the goal. And then I was like, oh, wait a minute. Your Best Self is like grid relationships, personally, professionally. Yes, you want to be productive, but you don’t want to let everything else in your life kind of fall by the wayside. Yeah,

Kara Goldin 12:19
that’s so true. So can you share how the endorsement from Daymond John, and even the mentorship from Tony Robbins not only influenced best sales journey, but how did those come about?

Cathryn Lavery 12:30
So we won the shop five, build a business awards, that was an award that used to have for to get people like starting a Shopify store, and I’ve been on Shopify, since 2012. And it’s funny because I’d entered the competition with like a previous business didn’t get anywhere close to winning, but it was always like, Oh, this would be so amazing, because they create this prize. So you get to ring the New York Stock Exchange Bell, you get to get mentored by like Tim Ferriss and Tony Robbins, and Daymond, John and other like Marie Forleo. And so we went to the Gotse mansion. And Damon was one of the mentors there. And what’s funny is we had a mentor, ship session with him, but the affiliation like partnership, and come from that it came from the first or second night. Turns out he like travels with like this crazy Monopoly board. And he plays Monopoly with the, like, entrepreneurs, because he can’t. And he said this after is like, you can kind of judge people by how they play a game of like, are they strategic? Do they try to cheat? Are they paying their bills, like they should be? Are they paying attention, and so he said this after so anyway, I played a six hour game of Monopoly. So it was probably like eight or eight or nine of us at the beginning, but then it got down to me versus him. It’s like 2am. And he ended up winning. But afterwards, his business binder, like gave us his card. And then later he ended up like, posting about the journals, and was just like, I love this product. I use it for like achieving our goals. And so it was very much like a Oh, I, I met the entrepreneurs. We’ve played Monopoly together. I liked the founder. And so then we ended up doing a just like a straight affiliate thing. And he sent us pictures of him using the self journal on Shark Tank, which is really cool. So it was fun. And then Tony Robbins was one of the mentors for that. And then we ended up scaling from the first year we want to build a business award. And then the next year they they announced the build a bigger business award where it was like for companies that had scaled and we ended up being in the top six for that and got to go to Fiji and stay with Tony Robbins at his resort. So it was it was awesome. Yeah,

Kara Goldin 14:45
that’s that sounds absolutely incredible. So the Shopify build a better business. You mentioned that they’re not doing that anymore, or did they stop doing it?

Cathryn Lavery 14:54
I don’t know. They haven’t done it in a couple years. And I’m not sure why if it was just I I have no idea why they stopped doing it. I hope we didn’t ruin it. But I thought it was the coolest. I thought it was the coolest thing ever. And I always think of them when I hear about like competitions, where it’s prizes that you can’t actually pay for. And so because if you build a, I’m actually when I, when we finished our Kickstarter, the the competition was announced, like the day after. And I actually put something on our wall on my wall in the office and was just like, We’re gonna win this. I didn’t think it was gonna happen. But I’m just like, okay, best case scenario, we win. Second best case scenario is we build a great business, and it doesn’t even matter anyway. And so that’s kind of the goal. I think Tim Ferriss came up with the idea and told Toby, like, how do you create something that gets people off their couch to like start a business, you have to inspire them and like a cash prize, if you have a successful business? Isn’t that inspiring, but like, being around these people, and getting this, like, once in a lifetime experience, is something that will inspire people to actually get started.

Kara Goldin 15:56
So what led to the decision to sell Best Self in 2022? Were you sort of was it growing? Was it COVID? Was it? You mentioned, you had been through some personal changes? So what led to that pivotal point in the business? Yeah,

Cathryn Lavery 16:15
so when I started the business, I didn’t have a clue what I was doing, you know, I didn’t plan to start this big business, I really plan to I want these products to exist. And I’d run it from 2015 to 2022. And they had a baby at the beginning of 22. And, you know, the business has been on hardmode for the last two years between like COVID and supply chain. And I dealt with an embezzlement issue with an employee, there was just like, a lot of stuff happening. And I’m kind of seeing the writing on the wall, as far as like, you know, you turn on the news, like, Oh, we’re going into recession. And, you know, I had all these employees counting on me, and it just adds more pressure. And it’s also this, have you heard the term like technical debt with like a software startup, where you just like, throw things together, and you kind of build on top of it with the plan to like, fix it at some point. And so I had what I call an inexperienced that where I’d like, just put all the stuff together and like, didn’t know what I was doing. And when you run something for long enough, like, there’s just like, bloat. And it’s really hard to go fix it after the fact. Because, you know, you have a team, and it’s just difficult to like, go back and like fix past mistakes, you know, whether there’s just so many you can make. And so when I was thinking about selling, you know, I got a good offer. And they were like sold me this big idea of what they were going to do. And I really wanted to see that self grow into this bigger thing. And I wasn’t sure that I was going to be the person to take it there. Especially, you know, I just had this baby. And I was like, there’s just a lot of pressure, especially Yeah, bootstrapped without taking any extra funding, like what was gonna happen. And so that was the decision I made to sell it and also just figure out what I want to do next, like, how do I wipe the slate clean, and then start something else with everything I’ve learned over the last few years and be able to do more faster with less mistakes.

Kara Goldin 18:09
So interesting. And then so in 2024, you bought the company back. So how did that conversation come about?

Cathryn Lavery 18:18
Yeah. So it’s funny because the company that bought, my company was like, they just started, they were trying to do a new version of private equity. And that was kind of what was exciting because they were supposed to be doing it like differently. And so they bought us that was our first acquisition. And then they were kind of starting their main, like holding company and then buying brands. And I think they underestimated how much harder EECOM is when you’re in it. And the other brand they bought, there’s just a lot of things happening at one time. I think they were trying to do too much. It was like, instead of focusing on the brands that they bought, they were like, oh, what should we buy next? Because they had this funding, and I think they had a second round of funding that was supposed to come. And I don’t know, the full story, all I know is that the second round of funding never came in came. And so they added all this expense, and hired all these expensive people. And I, you know, I don’t know the full story. But essentially, when they found out they weren’t gonna get any more funding, it was like, Oh, God, and they moved to a skeleton crew, and then was like, Okay, we’re gonna shut down and sell off the brands. And so I got on a call with the CEO, and he was like, Do you want to buy it back? And to be honest, at first, I was like, not really, because at the time I was, you know, they’d actually let go of the team after six months, which I knew about it because I’d given them a three month retention bonus, and then they’d given them a six month retention bonus, and then said, Okay, we’re actually going to let everyone go and move to a more agency model. And so I’d already gotten a few of them jobs at Friends companies. So So I had no idea I was gonna buy it back. And then when I was like thinking about it, I was like, How do I do this? In a way, because I love the brand. And actually the 14 months, I wasn’t working on it, I was like, Oh, that was such a, like fun brand, I hope I can create something like that, again, that I really believe in. Because I was trying to come up with all these new business ideas. And I like, I could have done them, they didn’t really care about them. And so it was hard for me to get motivated to work on them. And so when this came up, I sort of journaled around, like, Okay, how would I make this fun in a way that I don’t have to buy the company back in order to sell it? So like, how do I just run it better come up with like, products I enjoy? And it’s that idea of, you know, the fisherman story? Yeah, where fisherman is that on a boat, and he catches the fish. And there’s VC funding guys there. I’m gonna butcher the story, but, but I believe in it. And I that I’ve kind of seen both sides of it. And the VC guys like, oh, how long did that take you? And he’s like, an hour. It’s like, well, if you bought all these boats and scaled and grew, you could actually have a whole fleet of fishermen and make way more money. And he’s like, and then well, you know, and then what? And he’s like, Well, and then you could retire eventually, after 20 years, and how old is money and spend this time with your wife and kids? And the fisherman’s like, Well, I do that noi. And so I realized, after I sold the business, I was like, Okay, what do I do now? i And so no, I that. I was like, Okay, let me get it back. And then just take all the inexperience that I had before. And I the the slates clean, and I can continue to work on it without the pressure of, you know, everything that I’ve done when I didn’t know what I was doing.

Kara Goldin 21:36
Yeah, definitely. And so when you brought it back, then the first things you talked a little bit about how you how you thought about this, it was, I guess, kind of a turnaround, to some extent, you had to rebuild your team, you had to, you know, you looked at all the existing products, and figured out exactly what you would do differently. When you think about it now, what do you think you would have done differently? What advice would you give to other founders who are sort of sitting in that position that you were in 2022? Thinking, you know, should I actually move forward with something like this? Would you look at the buyer differently? I mean, you know, like, how would you sort of overall, think about that?

Cathryn Lavery 22:23
I mean, it’s easy to look back and think I would have done this differently. And I got asked that a lot as, as far as like, Oh, would you still sell and I would still have sold it when I did because of the information that I had at the time. And what was best for me personally. And then I got some time off, because I was kind of burned out when I even though I had people working on the business, it’s always this, even when people are running the day to day, at the end, like the buck stops with you. So if something goes wrong, like you’re the one that’s going to be on the line for it. And so, despite not really being in the day to day anymore, I still had that in the back of my mind. So it’s difficult for me to like, disconnect from it. And so the sale led me to like disconnect, figure out what it is that I was really wanting to do with my life. And then the opportunity came up, but I never, you know, the first year and a bit, I wasn’t thinking I’m gonna get this brand back, it was more of just like, Oh, I’m glad that I did that. Here’s what I learned. And here’s what I would do differently next time. And then it just so happened that this came along. And I was like, Okay, well, how would I do it differently. And like thinking of that ahead of time, as far as like running it more efficiently, not knowing more about just like cash flow and inventory and building a team and culture and who’s a good fit and who’s not a good fit, which I didn’t you know, I’m literally like, building the plan as I’m flying it the first time. And so you just, there’s just things that I didn’t know at the time. And so now I can do it in a much more effective way, while also getting a break. So it’s kind of this unique situation, and I’m glad that it happened. And I was just like, well, this is gonna be a good story. Whatever happens.

Kara Goldin 24:02
Yeah, definitely. So what do you think was one of the biggest challenges outside of sort of having to go through this? I mean, when you look at your business, and and as we discussed earlier, you’re, you know, looking at all the different MCS and people, you got to kind of You almost got to hit restart, right on your company, and in many ways, so what would you say you are doing differently today versus right before 2022? Before when you were scaling? Like, I almost think like I look back on things and the things that you reacted to or you view it now as reacting to it. You know, how would you change things for yourself? Or how are you changing things now?

Cathryn Lavery 24:43
Well, I mean, when I first started the business, like we didn’t even have a CFO until you’re four or five and that’s actually I find the embezzlement at the same time. I’m like hiring and so you know, then I put that I didn’t play. So there’s a lot of things that like I learned, oh, this should have been done differently, managing cash flow and inventory with physical products, as I’m sure you know. And then also things like a chat GPD didn’t exist when I sold the company. And I use it for so many things, that it like, relieves a lot of mental load for founders to just make things more efficient. And I actually train the team that I’ve since hired and like, Okay, here’s how to do this effectively, and, and create training for them to be more efficient and doing things that used to take us way longer, and create training where we’re all using AI to do things more efficiently. So it’s like silly things like responding to a sales tax letter, which before I would like either send to my accountant or for the first few years, I would just ignore it until it wouldn’t stop annoying me. And so there’s just a lot of minutia that now is removed and frees up my time to be more creative. And so that’s kind of how I’m looking at. It’s like, how am I spending my time? And then how am I empowering my team to be more effective with more resources than we’ve had before? But less people?

Kara Goldin 26:12
So interesting. Yeah. And I think the world has definitely, you know, even changed since 2022. I mean, there were so many things that have changed that have made the business so much easier. So really, really exciting. So, last question, best advice for anyone wanting to start and build a new company?

Cathryn Lavery 26:33
I think the best advice, if I was thinking about it, I would find companies like the one I’m trying to start. So if you’re trying to start a physical product business, you should not be looking at like reading stories about software founders, because it’s a whole different model. So I will be talking, I’m looking at companies in a similar space and what they’ve done. And a lot of founders are very helpful. Like, if you reach out like I’ve, on my blog, I’ve shared Oh, this happened, you know, when I got embezzled from it was like, Oh, this is how it happened. Exactly. So here’s the mistakes I made. And so a lot of founders are very open and transparent with, here’s what we did. And here’s how it worked sometimes out on blogs, but you know, on Twitter or so starting a group or getting into a community of people where you can ask questions, is the best way to sort of shortcut your learning so that you’re not making the same mistakes that someone else has made 100 times because no business unless you’re creating like robots, or something is brand new. And so someone else has been there. And so the best thing is just like talk to people who’ve already done it, so you can like shortcut mistakes that they made. And that’s kind of what I’m doing as is I’m looking back at, oh, don’t do this again. I know everything’s much simpler, because if you start things off with sort of a better foundation, it will set you up. It’s kind of like a Jenga thing. You know, when you’ve played Jenga, and people, the bottom is just like so messed up that this thing is not going to go very far. That’s how what I did to myself, I feel like as far as the inexperience and it’s hard to go back and fix that later. And so if you start speaking to founders, looking through exotic reading books around the people who’ve done businesses that you want to create, that’s the best way to like, get started and learn what it is you’re trying to do. So true. So Cathryn Lavery, founder and CEO of best sell. Thank

Kara Goldin 28:17
you so much, and your wisdom is incredible. Good luck with everything. Very, very inspiring. We’ll have all the info in the show notes as well for Best Self products. So thank you, again, appreciate it. We

Cathryn Lavery 28:32
also created a discount code golden. If anyone wants to buy anything from the store. You’ll get 20% off Perfect, perfect. Perfect.

Kara Goldin 28:39
All right, great. Thanks again. Thanks so much, Kara. Thanks again for listening to the Kara Goldin show. If you would, please give us a review. And feel free to share this podcast with others who would benefit and of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin. I would love to hear from you too, so feel free to DM me. And if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book undaunted, where I share more about my journey including founding and building hint. We are here every Monday, Wednesday and Friday. Thanks for listening and good bye for now.