Nathan Chan (2:59)

Look, first of all, thank you for sharing and. And first of all, opening up because I was saying to you before we started rolling, not enough people talk about this, that when you sell your company, it is a massive loss of identity. And, you know, I have an M and a friend where he said to me, like, Nathan, like, 50% of the time, like, like, people are miserable after they sell their company. And, you know, we see through Instagram all these highlight reels, and it's so easy to compare yourself to other people that most people looking from the outside would look at your journey and be like, wow, you sold it. You started this really cool watch brand. You've seen it grow and you had $100 million exit. People be like, what? What? Why wouldn't you be happy? Like, you never have to work a day again in your life. So. So talk me through, like, how did movement start?

Jake Casson (3:48)

So, yeah, movement started as an idea because I was basically a dropout in college and I had a roommate who was also very entrepreneurial. I had other businesses growing up that would get to a hundred thousand in sales and then kind of fail eventually. But so I was always entrepreneurial, always wanted to start something. I knew college and uni wasn't for me. So when I met my college roommate, we were both just like, brainstorming different ideas. And at the time, we were just thinking about things that resonated to us. And we were constantly scanning crowdfunding websites like Kickstarter and Indiegogo and finally realized that there was this gap in kind of the fashion world where none of these brands we really resonated with deeply. At the time, Nike was still is, but Nike was a brand that we really loved. And. And just because it evoked this emotional feeling within us. And so that was kind of movement. It was. There was. There was no watch that we could afford that had this kind of emotional feel to be inspired. And the combination of, like, let's build a brand with design and price that we really loved, that was for us young men and women. And like, that was the idea. And because of our e commerce experience prior, it just took off. The Indiegogo crowd, or Indiegogo crowdfunding page did 300, 000 our first year we did a million. Second year we did 7:30. I think at our peak, we did like 75. And then I think we sold it. After like six and a half years or something like that for 100 million. But yeah, that was kind of the concept.

Nathan Chan (5:23)

And did you raise money?

Jake Casson (5:24)

No. I mean, fortunately, a couple small, like, competitions that we won, we would get 50, 000 or I think his grandma loaned. The crowdfunding was, you know, $300,000 from $5,000 of credit card, you know, debt. We basically got the samples, got pictures, edited the video, marketed it, wrote everything, and then just sent it out. And we were just scrappy. It was just like early days before Instagram was really big or, you know, YouTube was still kind of figuring itself out and really Reddit is where we kind of like went and like sent it and. And then the crowdfunding platform just kind of took over.

Nathan Chan (6:04)

Did you ever think you wanted to sell the business? Did you start with that intention?

Jake Casson (6:08)

I think I always knew that I wanted to. I heard Tony Robbins say something about financial freedom. It's the first time I heard that word or that, that term. And I always knew that, okay, like, I want to. I want to find financial freedom. I didn't know how much money that meant, but in my mind it was, yeah, millions of dollars. And. And as the business was growing and we were doing, you know, 40, 50, 60, 100 was kind of always that. That view because we can kind of see it at the finish line. We actually went out to go raise money because we needed. We wanted to continue to scale the business, and we just needed outside capital to do that. And then kind of at the same time, we started talking to Movado and who acquired us. And it just was kind of like, right place, right time.

Nathan Chan (6:54)

And how long did that deal take?

Jake Casson (6:55)

I can't remember exactly. I think we were talking to them for maybe like, I think three months. Four months?

Nathan Chan (7:01)

Yep.

Jake Casson (7:02)

Maybe it was like four months.

Nathan Chan (7:04)

Yep.

Jake Casson (7:04)

Could have even been longer. But there's like this, you know, just. It starts as like, conversations, and then you go into exclusivity and you kind of start running from there. But I think the entire from. From day one of having a conversation with them, it was like a four month period. Yep.

Nathan Chan (7:17)

Got you for due diligence. Always a deal.

Jake Casson (7:20)

Yeah, I believe so. Yeah.

Nathan Chan (7:21)

Okay. All right, so take me back to the moment that the deal went through.

Jake Casson (7:28)

I didn't tell my parents until. So I've been talking to them for four weeks. For four months. Sorry. Talking for four months. Didn't tell my parents until the week before because in my head, it's not done until it's done. So I just didn't want to jinx it. I don't want, I don't want anyone else to feel the excitement or what pressure, whatever it was. I didn't want to feel more pressure, excitement. I didn't want to get let down. So eventually it goes through. And the next day, you know, you wake up and you kind of look at your phone and your bank account, it looks like a phone number and you know, you have this like, it's hard to explain. You have this moment where you're like, there's gratitude. You're, you're, you're grateful for what you did, you're proud, all these things. Your phone starts blowing up but, but you still have, you don't. You just stay in bed and just like look at your phone all day. You get up and it's like, well, what am I going to do today? And you know, at the time I was still working at Movement, so I went to the office. Like I did. My routine was exactly the same, right? So you go to the office, gym, whatever. And then the next day, the next day. I think the best part was just hearing from people, you know, who I knew through throughout the, the journey or whatever. It was just like that was like this and maybe it's external validation, but it just felt good. The people who had seen the work put in, who I had crossed paths with across the world, just be able to like share a small moment with them, I guess was like, nice. And then, you know, you fast forward a few months later and yeah, I started to, you know, I bought, I bought a condo, like a nice condo. I didn't need a house because, you know, I'm single by myself. So I bought a condo and, and then you spend money on the areas you want but like you're not, I don't know, your life doesn't change drastically. Right. I was still working, so it was amazing. But I was still living the same life in many ways.

Nathan Chan (9:24)

And so was it, did you have an earn out or it was an all cash deal and like that. How did the transition take place?

Jake Casson (9:30)

Yeah, basically it was all cash deal. There are some incentives, but yeah, basically, you know, I wanted to stick around because like we just sold in the business and I wanted to do right by them. They just changed my life. And also there was like still kind of, you know, a mission that I wanted to see through and there was incentives. So I kind of like kicked the can down the road or I like moved the goalpost. I was like, all right, well like I can't celebrate until we win this. So almost instantly, I kind of tried to convince myself that, like, there's more. There's more money on the table. There's more to do here. But then Covid hit, and I just realized that we weren't going to get those incentives. And I didn't even care about those incentives because, like, I had money in the bank. I wasn't, you know, I didn't. I didn't need more. I didn't know what more money was going to give me at this point. And that's where, like, my whole. I started to become a little unhappy. And I started to realize, like, more money wasn't going to solve that. And I didn't know what would solve that. And that's where, yeah, things kind of started to come in.

Nathan Chan (10:33)

So talk me through that. Like, so what happened next? So you. You eventually finished up at movement. Did you start in, like, I know you invest in brands now, but. Yeah, like, did you start. Like, did you look at starting another E Comm brand or what happened?

Jake Casson (10:44)

Yeah, so I was. I turned 30 when I left. And, you know, at 30 years old, a lot of your friends or all your friends are working, doing this, doing that. The people that might be able to relate to you in terms of financial, you know, freedom or wealth are usually in their 60s, maybe some athletes, but a lot of these people are just, like, they're still involved. Like, they love to work still, or they don't know what else to do, so they're still working on something. I kind of realized that I didn't want to work on an E Commerce brand anymore. I thought about other brands. There's just nothing that, like, I loved the creative part of movement and I loved, I think, just accomplishing and being good at something. But now that I, like, kind of done it to the degree of that Movement did it, I didn't want to just do it over again for the sake of trying to do it bigger. And. Yeah, so I just struggled with what it was that I wanted to do next, why I wanted to do something. I had a lot. I started investing in brands, thinking, well, maybe I'll learn a little bit about this, or maybe I'll be, you know, I'll be able to mentor and help other people, which I realized, you know, some people I'd give money to and I'd be involved in the. More like the conversation around the highs and the lows rather than tactical, because I'd make introductions. But I don't want to come in and be tactical. I don't. I'M not an operator. Like, that's not what I love to do. Sometimes I'd give more money, sometimes I'd get less. Didn't really change that feeling in my gut about like. Like I was kind of chasing this fe. This high of what it felt like running my business and just accomplishing things and building something, getting good at something, and I just couldn't find that anywhere else. Um. And yeah, I kind of just started to casually invest and I kind of just started like, trying to enjoy life as much as I could. I ended up moving to San Diego. You know, I bought all the things that I wanted, I thought I would want to buy, you know, and I traveled and I played video games and smoked weed. Like, I was just doing stuff that I was like, I earned this, you know, like, like, I can, I can. Like, I'm not just a bum. I'm like, I worked and I can do this. And it would mask some of that, that feeling, I think, for certain times. But there'd always be a moment where I'd just be inside at my, you know, my tower, I'd call it, because I'd be high in my, my, My condo. I'd be high up in the condo and I just, Just feel lonely. Feel like there's more to life than just that. Like, like my peak story doesn't. Shouldn't end here. And the thought of it ending here just felt depressing.

Nathan Chan (13:25)

You know, Tim Ferriss, I never forget, he talked about, like, it's so hard to build a company, then you sell it. And then when you situation, you invest in companies, that, that excitement, you can, you can kind of get that through investing in companies, but you don't have to do the work. Did you, did you feel that or. Not really.

Jake Casson (13:45)

Not. Not really. Honestly, not really. And I, you know, I think it's just different frames of minds. Like, I think understanding what drives you. What about. Like I really had to think about what was it, what was my happiest day as that movement and like, what made me the happiest. And when I thought about that, I think there's kind of two parts. It was like working with people. So, you know, I think having this community around me that I was kind of like, like all these people starting their careers at movement and like movement succeeded. So like, they're all, you know, have accelerated their careers in many ways because of movement. And also, you know, pretty much everyone made some amount of money with Exit as well. So just having that felt amazing. It's like these lifelong relationships and I Think life's all about relations. I think getting better at something, like just being an expert at something feels good, just having this knowledge and learning. But I think the biggest thing, like the early days of movement, thinking of this idea that and, and the vision for where it could go, and then being on my computer, you know, early days, even before, like me and my business partner, like, he lived in San Diego, I lived in Los Angeles at the time. And I would just be on my computer at my house, just like, you know, just, just brainstorming, trying to be creative and think about how we're going to grow, how we're going to do this. Like, what's the messaging, marketing channels. And I think the creative part for me, like the creation of something was really what I found. But again, some people love operations, some people love investing. They're good with money, they're good with investing. Like, I think for me, I just, I really realized that, like, it was a creation of something that I enjoyed the most.

Nathan Chan (15:25)

Yeah, I'm the same. Like, when it comes to operations and all that kind of stuff, it's not my strength. I can do it, but it doesn' Bring me energy.

Jake Casson (15:33)

Yeah, exactly. And when you have money is a good motivation, a good money is a good motivating factor. But when you have it, you have to find what motivates you to be like that operator or to be. To do things that you don't want to do. And that was, that's. That's been one of the hardest things for me is like, you know, everyone is. Some people are motivated by money simply because of ego. And like, that just wasn't me. Like there wasn't more, more money didn't. There's nothing that I wanted. And again, I knew it, that money wasn't going to make me happier. I'm. I still like the game of money. I still like, you know, thinking about certain things in my life and gamifying them. But I'm not going to sacrifice certain things in my life, my health or relationships just for money anymore. And that's where I realized I have to find something that, that motivates me just intrinsically that I, I would love to get better at. I love to do. If money wasn't involved, I want to do it, still incorporate money, but just need to find something at a base that I can really love for you.

Nathan Chan (16:40)

When you started movement, at the start, did it like, or even throughout that journey, it was, obviously, there's hard times, businesses are tough, but the calling for you was the creation and the Building.

Jake Casson (16:51)

Yeah, I think the creation of. I think the calling at the time was, was money. Like, I think I, I just, I think for whatever reason at an early age I was just motivated by, by, yeah, trying to make money. And not that I had like, grand tastes. I just like, wanted to, I wanted the financial freedom. I wanted to help out my family, I wanted to take care of the people around me. I wanted to be able to, to do what I wanted when I wanted in some ways. And I've heard other entrepreneurs say this, but like, I can be very, very lazy and I opportunity to kind of. I can do things on my time, right. I can pick and choose and, and, and say yes to things and say no to things and not let money run my life. And I think there's good and bad in that, as I've, I've come to realize. But I think money was a big motivating factor. What I found that I enjoyed though, and the reason I always. There's lots of ways to make money. The reason I liked creating these businesses was the creation process. The idea of like, all my businesses that I've had, I've sold like T shirts. I've sold obviously, watches, sunglasses. I've sold a bunch of other products. And I've also, I've always seen them on other people walking around in like random places. And that's always been a really great feeling to be like, I created this from nothing and then I've kind of seen it, you know, transform into the real world.

Nathan Chan (18:14)

Most would kind of go, you have a unique skill set, you know, how to grow brands. Why wouldn't you go again?

Jake Casson (18:20)

I just couldn't think of a product that meant enough to me to like, build it and for this. And you know, I think I, I again, I enjoy that the beginning, first couple years, but I don't know, I just, I don't enjoy the operations. I'm not, I'm a, I'm a people pleaser. I'm not good with confrontation. I'm an introvert. So dealing with, like, dealing with the shit of, of managing people and headaches and, and just, you know, I was like a nice boss. I was like a very friend. Like, I think, I think everyone liked me. I was friendly, which isn't necessarily a strength. It can be good. But also I think you need to be. Yeah, you need to be tough. You have to have tough conversations. And I'm not good at tough conversations. I've gotten better, but it's just not, it's just not something I enjoy. I Did it. And I'm proud that I did certain things and. But, yeah. So there just wasn't any idea, you know, like, there just wasn't any idea. I thought about. I like clothing. I thought about different clothing brands, but, you know, I'm just like, do I really want to go and create a brand that does, you know, I don't know, 5 to 10 million, and I can, but do I really want to do that? Like, operating that brand? The idea of, like, creating my own product sounds fun, but, like, do I really want to, like, have a business deal with inventory and go fly to manufacture? Like, no. I think, you know, there's brands that do that well, and I like the brands that are out there, and they. They want to do it more than I do for whatever reasons. Like, they're driven, maybe because they intrinsically love it or they're chasing money or whatever. But for me, it was like, well, what is it? I remember when I sold to. I, like, looked at the big list of hobbies because I always said, I have no hobbies. Like, you know, I watched. I watched, like, TV and movies. I worked. I listened to, you know, podcasts, books, and then I hung out with friends. Like, that was kind of it. So when I. When I sold, I looked at a list of hobbies. I tried golf. I tried guitar, and I just kind of went through different hobbies. And, like, you know, there was a few that stood out when I was a kid that I was like, okay, I did this when I was a kid. Let me try that. But, yeah, starting another business just didn't. Didn't scratch that itch.

Nathan Chan (20:26)

Didn't excite you?

Jake Casson (20:27)

No. And again, I'm not gonna say never. The thing is, it's funny. When I sold my business, I told people I was like, I'm never gonna start anything again. I was like, that's. I'm telling you, I'm like a lazy person at heart. Like, I don't want. I don't. I don't want to do this again. And I'd done it three times. Like, I had other. My other business I had for five years. Like, I started when I was 17, and at its peak, it did 250 grand. Like, and I had a retail store, like, at 20. Like, I was doing stuff, like, before this. So I just didn't. I just. Commerce just wasn't something that I wanted to do. Also, the people. A lot of the people in commerce, like, I just. They loved it. And, like, I just. I just felt like I wasn't connecting with the joy of, of creating another business. Like these people were, they wanted to like, take over. And I just, I just, I just didn't feel that desire anymore. So, yeah, I just wasn't there.

Nathan Chan (21:20)

Yeah. And look, I think when you've, and I've seen this in friends as well that have sold their business when, when you've done the hard yard, you don't really want to go back to that grind. Right. And it almost, for some people, they love it, but for others it's like, well, that was tough. I don't want to go back to that.

Jake Casson (21:38)

Yeah, for sure. And it's funny, I've listened to Alex Ramosi and like Chris Williamson talk about this, but Alex articulated well where, you know, he loves the game of just, of just building a business. Like that's his game that he wants to play. And I respect that. Like, if that's what you love, that's what you get energy from, like, then you're going to be the best at that. You'll sacrifice, you know, time and energy elsewhere to do that thing. And some people create new businesses because they do love running them. I think some people, I've also met people, founders who have exited who are, as you mentioned, like, I have founders who have exited that are completely lost. I have founders who have exited who go and just start another, you know, company with just a different name or slightly different category. And I think they do it not because they necessarily want to, but just because they don't know what else to do. Like, they literally don't know what else to do. And it's painful to go and like shed this identity that you have one world that's propping you up. I mean the E commerce world, entrepreneur world. Like, I could have kept building my name. I could have, you know, done more podcasts, I could have wrote a book. Like, there's a lot of stuff that I could have just done to like become this personality. And it just wasn't what, it wasn't true to me. Like, it's not what I wanted to do. I didn't want to be this expert in that world. I still love it. I still do. There's still a love for it. Like, and I like helping people, but for me, I just knew that there was something. It just wasn't that burning feeling kind of inside that you have that. I had early days. Right. You know, probably when you had, when you first had that five dollar sale and you just, and maybe what you have now, it's just like, like when, when that's gone you can't force it. Just it, it, you know, and some people chase the next big, okay, we did a hundred, let's go for 200 million. But like, I just, I, again, I knew, I knew money was not going to make me happier and I didn't want more. I didn't want to, like, rub shoulders with people just for the sake of like, oh, I'm wealthy or, oh, I'm powerful or, you know, successful. So I wanted to find something that I just wanted to do at my time, my pace, that I loved.

Nathan Chan (23:47)

I'm sure after you launched that video where you got half a million views around, you sold your company for $100 million and you felt really lost and all these different things, a lot of people would say, maybe even watching this was easy for you to kind of say, okay, well, I just want to do what makes me happy a lot. Like, some people just don't have that choice. And you've earned that privilege to find out what's next. What would you say to people?

Jake Casson (24:10)

Yeah, yeah, I guess I think that you have to go through that process. So I think, you know, you have to go through a point where you, you think you have to work towards money, right? It's hard. Or work towards something that you really are, you think you can be good at. Like, you have to have some interest. I had interest in E Commerce. It's not like I was doing something that I hated. I just realized at some point that, like, I wanted that more of this wasn't going to give me more happiness. So I think that's like, yeah, I think that's kind of where I, I, I, I sit as I was working towards money, but I also enjoyed the experience that I was going through. And then at some point, you know, I just realized that, okay, there's, I do want to start something else outside of this. And I, and I know it's going to take time, but yeah, I did have money also at like 30, I'm 33 now. But it's like, you know, if I was back in my 20s, like, I was, I was willing, I went into $5,000 of debt to start the company. Like, you know, had I wanted to do something else, I would have gone into debt, taken a second job to like, fund whatever it was that I wanted to do. Like, I think money has to be some motivating factor. I mean, it's, it's just, especially, especially in the States. Like, you need money to survive everywhere in the world. But like, you know, some money is just like it, it is a necessary evil. And I think you have to focus on it. But if you. If you only focus on money and you are miserable with what you're doing, like, more money is not gonna make you less miserable. It could give you the time to then dedicate elsewhere. I have a friend who. Who has an agency that, again, he's. He enjoys to some degree, but it gives him a lot of time to focus on other things. And I think that's another example of just, yeah, money can give you time. So I don't know, it's like you need money to play the game. So still focus on money, but just understand that more money is not going to make you the happiest person, especially if you're already unhappy. If you're happy and you're. And you're making money, then great. It'll. It'll probably make you happier. But the more money you make, you alienate yourself from other people. Less people can relate. You kind of change relationships potentially with family, friends. Like, it's just the world kind of feels and looks different at times.

Nathan Chan (26:24)

Did you work out who your true friends are?

Jake Casson (26:26)

Yeah, I think, like, I have a lot of. I had a lot of friends that. I just had a lot of friends at the time. A lot of friends because of the business, connected to the business, employees, this, that. I think they're all. I'd still call them all friends, right? I don't think I had any, like, falling outs, but I just think that I just didn't want to talk about the company anymore. I didn't want to talk about the past. You know, I was like, winning a sports championship and, like, talking about it for the next decade. It's like, I, like, that's. That's. That thing doesn't define me. Right? It's a. It's a big important moment in my life, but I'm more than just my business. Then the sale, and I didn't know what. That. I didn't know what I wanted to talk about. I just knew I didn't want to talk about this. And that was the hard part. It was like I was saying yes to anyone who would hang out to learn more about myself and trying to connect with people and moving to new cities and trying new things, which I think is important. I think that's like a big thing of. It is just you have to try new things. You know, you have to, like, experiment to learn more about yourself.

Nathan Chan (27:30)

So what would you say to founders that are in the early stages of their journey to make sure that your identity doesn't get so trapped in the success of your business or not the success of your business because it is such an all encompassing thing.

Jake Casson (27:47)

I think to some degree you're gonna have like, you're gonna have to go through it. You know, I think you're gonna have to like, I think everyone's gonna focus on, I can tell you whatever you're, I want to tell you, but like your, your eyes are going to be on the, you know, mission critical and that's building the business, selling the business, getting to a certain revenue. Like that's the dreamers who are just wanting to like accomplish their, you know, kind of goal that they have for themselves. But I think that if I could go back in time, the only thing that I would really have done differently was just try and figure out ways to invest in myself outside of the business. And I think like the health and fitness stuff, like I was drinking a lot too. Just not like, not a lot by any means, but just like a lot for me, right? Like I'd go out on, on weekends or if I would dinners, like business dinners. Like I was just, just wasn't treating my body as well as I treat it now. And I think had I focused more on health, had I invested in certain relationships, I just think those things would have like, helped keep me a little bit more balanced and just think about this. I think also like being self aware about how like we think and associate identity or money or what our values are in life, like, I think that just helps the transition. So a lot of founders that I have who are trying to like getting ready to sell or hoping to sell just my story, I see them like thinking about this stuff earlier, you know, like before they sell. They're already thinking about like fog. Well, what would I, what I do if I sold today? Where would I live? Like, why am I happy with my life right now? If there anything that like, is money limiting me right now from being happy or is it just like I could go on a walk today, I could go to the gym, I can go to a concert. Like, you know, like we can. A lot of people have the money to do a lot of the things that make them happy, happy day to day again, Fulfillment, it comes from building something and, and also understanding what about the business fulfills you. I think just thinking about these things is the only thing that I can really say because it's hard for me on this side of, of you know, the sale to be like, oh, like this is, this is how you do it. I'm Just, these are just things I didn't know and now that I think about. And yeah, I wouldn't take away the way that I learned them, but it would have helped me a lot, you know, avoid some, you know, mental pain over the last five, six years.

Nathan Chan (30:11)

I think a big lie that we often tell ourselves is if we hit this revenue target or if we meet this goal, then I'll, I'll feel this or when we hit this, it'll be amazing. Was this something that, that resonates with you?

Jake Casson (30:23)

Yeah, I mean, you always move the goal post, right? And yeah, I mean, I didn't know similar to how you built this. I knew that. Okay, we can start a Watch brands. Watch brands are $100 million businesses. But, you know, we did 300 grand, then we did a million. I was stoked. Then seven, then third, like our. And then every year we'd be like, then you start forecasting. So the first few years were great because there was no forecasting. It was just like, let's just do as much as we can. Then you start forecasting. And if you don't hit a number now, you're not on, on plan. And that's when you're like, well, we're below plan. We're. But. And that's when things start to feel like, well, we're not growing as fast as we should or we can. And then you sell the company and then you, and then you think about, well, this is where the company's still growing. Can we turn into a 200, 300 million dollar business? A billion dollar business. And then you leave the company and it's like, yeah, do I need to. In order to be fulfilled again? Do I need to create something that successful? And is that. Yeah. Is that where the story kind of ends? Which is such a weird thing, I think, for. I don't know, maybe it's, maybe it's narcissistic, but it's like, I do think about myself. Joe Rogan talks about this, like, think about yourself as like, you know, you're the main character in a movie. And I, I just try and like, I get excited just about my, you know, I want to make myself proud. I want to make my younger self proud, my, you know, future kids proud. I just, I think about, I like to do things that's. That scare me or that I think I can't do at one point, and then it kind of becomes this goal that I, you know, latch onto. So, I don't know, it was just, it was a weird thought to be Like, I'm not gonna find something that I can, like, dive into the same way and feel as fulfilled with that scares me the same way as when starting the company did. I mean, I used to look at entrepreneurs when I was starting that company and, and see what kind of personality traits, because again, I'm introvert, people pleaser. The entrepreneurs I knew were a type, you know, like, dominant in terms of, like, the presence in the room. Like, you know, they were definitely intimidating people, and they were not. I didn't see myself as like, this. This figure on, you know, especially watching Shark Tank or this and that. Like, you know, so, yeah, it was. It was used to be scared to pick up the phone and call a buyer at a retail store when we first started company or get on meetings with people. Like, everything scared me. So, you know, succeeding and then also just getting more confident in all my abilities was like the best feeling. Just getting good at something, proving to yourself that you can accomplish and conquer kind of these limits that you thought that you used to think kind of were set for yourself. And again, selling the business, it was like, well, you know, where do I go now? And that was that. I think that's where, like, yeah, you were so fulfilled. And just losing that kind of just messed me up a bit.

Nathan Chan (33:29)

You've really, you. You really touched me with your video. That's why I reached out. And it just so happened that you were in Australia. You're based Australia in Sydney. You've flown down to Melbourne to this interview. So thank you for taking the time to share, give back to our community. So you talked about kind of finding your next thing and kind of really delving into going back to, like, what made you happy. So what is that now? And how did you find it?

Jake Casson (33:55)

Yeah, I mean, for me, I think that I went back and thought about what I enjoyed when I was a kid. And again, I watched a lot of movies, tv, but I also, like, somehow stumbled into video editing. I was doing bar mitzvah video edits for friends and stuff like that. And then in school, I did some video editing, but I just. At the time, YouTube was still like, like hardly around. I just didn't see a path to, like, YouTube wasn't a path at the time, you know, so when I looked at that list of hobbies, like in. In video production, editing was one of them. I was like, what if I just, you know, buy a drone or a camera and just like, just start, like, you know, every day, every week, just filming stuff, just trying, trying and do it for a month. And it was. It didn't look like this. It was like up and down, up and down. And, you know, I'd get one good shot finally. Because the beginning sucks. The learning curve. And anything that's complex is like, the beginning is usually you're bad at it. But I also understand that that concept of just, like, show up to this, like, if I want to find my love. I was looking around for something I loved, and there was nothing. I had no hobbies, so I knew that I had to, like, really just find something that at one point I enjoyed. I think. I think I will enjoy being bad at this thing if I just don't burn out from it and just show up for, like. Like as long as I can, really. And I just started showing up as much as I could. Sometimes I'd go weeks without touching the camera, but I'd always come back to it. I tried to be disciplined, and eventually I just started to enjoy bits of. And pieces of it. And. And, yeah, I just got better and better and better. And now I'm at a point now where I'm like, I'm still really bad at it, but, like, I got a YouTube channel that has subscribers now, and I have a video that touched a lot of people and. And I'm enjoying this. This process of it. And I'm still just showing up, like, even now, I'm just like, it's every day I put in hours. I treat it like work. I treat it like, again, I have the flexibility to not necessarily have a 9 to 5 per se, but like, I try and put in, you know, four good hours a day of just something that involves either, like, learning, editing, filming something in that world, and then the end product. I really enjoy when I put out a video or I share the art and I create this thing that people watch or comment on, and it touches, you know, someone or relates to someone. So kind of comes full circle in terms of, like, you know, a physical product. But again, I think that for entrepreneurs, it's like, it's not always. It's something that you can be good at. Is, like, more important than something that you just love? Because even this, it's like, do I love every piece of it? Like, I don't love every piece of it. I didn't love every piece of running a company. But if I can be good at creating companies, and, like, I would. I would continue to do that if I needed money. Like, if I just needed money, I would probably have just jumped into, like, skill sets of maybe either creating my own company creating an agency for people. Like, you know, I'm focusing on getting, building a skill set that's, that has equity and is worth something. So, you know, now I'm in a place where like, I do have time because I have money and I'm just focusing that energy into building a skill set in this video world which there will be money. And the learning curve's tough. Like, you know, if I needed money right now, my YouTube videos would probably look very different. They'd be quick, you know, fast. But I mean, yeah, the last video was on track for a million views. It ended at like 500,000 because it got flagged for some things. But like, I could have made money on like I could make money on my channel right now if I wanted. And you know, that essentially was like two and a half, three years. Granted, I have the story to tell, but like, you know, I see a lot of people on, on, on YouTube who, you know, have 3, 400,000 followers from a few years of just like working on it. So it's tough. Like I think, I think it's, it's a saturated market, but I think if you can kind of figure out your story, like you can win there.

Nathan Chan (37:47)

But yeah, yeah, look, the, the creative movement is, is massive. I'm even starting now days to really start to go deep on my personal brand and create. And it's, it's really fun. Like it's, it reminds me like, so I've made a commitment to myself this year that I'm like a daily non negotiable as I post every single day. And I started with 90 days. I'm about like, I think 60 days into that 90 days and I posted every single day. And when I started I was like, geez, I should have been doing this a long time ago. But it felt like old days founder.

Jake Casson (38:22)

Yeah.

Nathan Chan (38:22)

And that's how it feels for you, right? Like it does it feel like old days movement?

Jake Casson (38:26)

Yeah, for sure. You're bad at something again. You're scared about certain elements like how you're perceived or, you know, there's so much to it and also how much time and energy it takes to get to that final like part of it. I think for me, what I love is like 90% of the work that I do. The thing I'm working on doesn't look good. Right? Like you're just, you're trying to like edit it, you're trying to color, you're trying to build this thing. And then the last 10%, it's like, oh, it finally Looks good, but you're still nervous about posting. And then you post it and then you get that there is this external validation from it. But it's, It's. I think it's like, especially when the content's meaningful or you worked hard on it, it's. It's art at the end of the day. And I think art is supposed to be seen and even in physical products, right? Like, there's just different elements to creation again. And that's the part of, like, this, of business and everything that I love the most. Like, you know, some people just love crunching numbers and, and that's great, but like, for, for me, understanding that this is what I love has just been really special. But I think being scared. A lot of this has been me being terrified, terrified to. I have this brand of movement. Right. Just my personal brand that's, that's tied to it. And the expectations of what I put out, even if it's just internal, could just be my own. It's like no one else probably cares, but my own expectations of, like, the story, how people are going to perceive me talking about mental health stuff and money, am I going to be, you know, like, like, you kind of ask the question, like, what about the people who kind of say it's easy for you to say you have money. And it's a, It's a, It's a question that, like, I don't know entirely how to answer. I'm just sharing. I'm not telling anyone else how to live. I'm just sharing my experience for what I went through. And if there's someone who's on that same trajectory or even not going to. A lot of people who don't ever get to the exit, it don't sell the company. So I hope that just like, just my story is. Is helpful to other people. And I think that the people I'm creating for is, again, it's my younger self. It's, you know, the younger generation. I just, I just, I think it's just my lessons in my life, and that's what the whole channel is. It's, It's. Whether it's business or my life, it's just lessons that I learned and kind of have taken away from my experiences that I'm just, just. I'm just sharing, like, take it or don't, I don't care. But it's just, it's just my art, what I'm sharing at the end of the day.

Nathan Chan (40:48)

Yeah. And that's, and that's what entrepreneurship is. It's like entrepreneurs are modern day artists.

Jake Casson (40:54)

Yeah.

Nathan Chan (40:54)

Like we get a blank canvas and we're able to paint. Right. That's how I see business and entrepreneurship and that whole, you know, Alex, he's referred to as the game. But that there's ups, there's downs. But yeah, it's, it's, it's art. Like that's, that's how I see it. So we have to work towards wrapping up. Man, we could talk about this all day, but I have a few questions just around I guess lifestyle, something I think about because I'm in the thick of it running found a day to day, all those kinds of things. Like how does it feel to be able to wake up and not have an alarm and not worry about what day it is, not have anything on your calendar. You don't have to be anywhere and you don't really have a care in the world.

Jake Casson (41:46)

There's good and there's bad. Like some days it feels great, some days it, you feel lonely as ever. You know, I think if you had your life, that's why I say like investing in life outside of business. If you had relationships, you had, you know, wife or kids or just other things that were other responsibilities that were pulling you down. If you have no responsibilities and then you wake up after being so driven and fulfilled to the things that you were doing and you're then, then you, then you come to a place where you're just trying to kill time all day which kind of get bored. You get bored and it, but it just eats at you from. Some people are, and they're usually not entrepreneurs. Some people who just can live on the beach all day like that, that's. They're living on the beach without any money and just barely making by because they can live that lifestyle. But entrepreneurs have been driven and are fulfilled by what they're doing to then be in a position to lay on the beach all day. Like they don't. That's not the way their brain works. You know, like again it goes from thinking your brain is going outward to then inward and it just starts to eat away at like yeah, that, that the happiness or the fulfillment. And it just, it can really get, you can really get in this spot where you just feel like you don't know how to get out. You don't see a way to get out of it. And I think so there's days where it's like I love my sleep and I, and I sleep like eight, nine hours, no problem. So it's like I do love the Fact that, like, I can wake up, but at the same time, like, I feel like a piece of. If I wake up at 10, like, you know, I want to still get up, you know, 7:38, and. And. And still, you know, win the day. And. And I like. I actually, like, kind of create a schedule now for myself again. I know that I'm going to spend four hours or so doing stuff with the. The video stuff, but for the last five years before kind of really getting into this, having no schedule, although it was good at times, like, it really probably was a net negative. And, like, for my mental health, and this is just my personal experience, I feel like some people with money maybe can just go and. But also some people, yeah, they're like, they spiral into different, you know, areas. They're chasing, like, you know, drugs or, you know, certain, like, vices that, like, don't take them to a good place either. For me, it was like, I just. It was just my mental health that started to erode. So it's good and bad. Depends on how you look at it. Depends on what day it is.

Nathan Chan (44:09)

Yeah. Well, look, dude, we have to work towards wrapping up, but I just wanted to share. Thank you for just you. Such open openness, honesty around, really the dark side of entrepreneurship. Right. In many ways, like, we, we, we. It is a. It is a sport in many ways that is often glamorized, and it's easy to compare yourself to all the crap that is online. And don't get me wrong, the highs are high, but the lows are low. But building a business is incredibly tough, and it's an incredibly fulfilling thing as well. But, you know, you've shared your story on, you know, you've had a successful exit, and it hasn't been what others might be perceive it to be, but you're on your path. You're working it out. But thank you so much for sharing.

Jake Casson (44:54)

Yeah, thanks for having me.

Nathan Chan (44:55)

All right, so if you love this episode, make sure to check out my interview with Alex Hormozi on how he scales companies from zero straight to $2 million a month in less than a year.

Alex Hormozi (45:07)

You were like, how have you achieved? Like, there's five years of my life that disappeared. In fact, I lost all the money, which I talk about in the book. I had all the gyms, I did the turnarounds, and then I had $0 five years later because of mistakes that I made. But the things that I was gaining was not the money. It was the skills. It was the character traits and the beliefs.