Chris Cooke's Net Worth is £5M. His Goal? Living a Buddhist Capitalist Contradiction.

We spoke to Chris Cooke in this week's episode of Moneywise, and let me tell you – this conversation was WILD!

Chris is easily one of the most fascinating contradictions I've ever met: a self-described "capitalist Buddhist" who built and sold a software company for £30 million, then blew through his entire £5 million share in SIX MONTHS on a weed farm, a comedy club in Thailand, and luxury beachfront properties! 

Like all Moneywise episodes, Chris breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart – and believe me, there was plenty to unpack here.

We also went deep on the mind-blowing paradox at the heart of his success: how his Buddhist detachment from money became his secret superpower in business, the painful lessons of losing friends after lending them money, and the philosophical rollercoaster of a socialist who accidentally won at capitalism. Just wait until you hear how he managed to go from £5 million to £200K in debt while still maintaining a multi-million portfolio!

Below you'll find my summary of the episode along with the entire transcript.

And by the way...this podcast, the concept of it came from Hampton, which is a private member's community for founders, CEOs, high net worth individuals where we're having conversations exactly like the one I had here with Chris. That typically only happened in private. And my favorite thing about it is the fact that there's such a range of folks in there, people that are VC backed tech people, bootstrap founders, and people like Chris, who just frankly have very, very different stories and perspectives on life. So I think it's awesome. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.

Listen to this episode on:

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• Spotify
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• Amazon Music

Now, below are the notes and the full transcript.

The Numbers

• Company sale: £30,000,015 upfront + £15M contingent on targets (which they didn't reach)
• Personal take: £5 million after splitting with co-founders
• Tax bill: Unexpected £500,000 tax bill (could have saved £400,000 by spending time offshore)
• Major investments:
  • Weed farm in Thailand: ~£100,000 (failed investment)
  • Comedy club in Thailand: ~£100,000 (passion project, losing money)
  • 5-bedroom house in England with sea view (now on Airbnb)
  • Beach house in Thailand
• Current situation: £200,000 in debt on paper, but net worth around £5 million in assets
• Monthly income: £10,000
• Monthly expenses: £10,000 (currently paying off tax bill)
• Early salary: £18,000/year while building the company

Building Wealth Through Detachment

Chris's journey into wealth began with an unusual premise – a Buddhist philosophy that encouraged detachment from money. "I discovered Buddhism and I saw these rich international school kids and they were miserable," Chris explains. This observation led to a fascinating thought experiment: "Imagine being a Buddhist capitalist, using the power of meditation to just not care, be detached from money and yet still pursue business success."

This detachment, counterintuitively, became his competitive advantage. When he was playing poker to supplement his scuba diving business income, he noticed: "I just got very, very good at poker the less I cared. If you're too nervous of losing, you're playing against people who are a bit scared. Once I let go of that attachment, I was just scarily good and able to make much better, calmer decisions about money without panicking."

This same principle carried over to his business ventures. Chris found that when he wasn't desperately chasing money, he made better decisions and attracted loyal team members who stayed "because we had this love of each other and the work unstoppable, and it just prepared us for this sudden meteoric growth."

From Scuba Instructor to Software Exit

Chris's path to a £30 million exit wasn't straightforward. After university, he headed to Thailand during the 2008 financial crash to become a scuba diving instructor. "Going out to Thailand and being a scuba diving instructor seemed like a completely sensible plan," he recalls.

Eventually, he returned to the UK and started working in software, experiencing significant imposter syndrome: "Complete start from zero imposter syndrome out of my depth, furiously googling how to do my job every night." But his entrepreneurial instincts kicked in as he moved up the ladder: "The higher I got, the more I realized, damn it, I'm smarter than my bosses again."

Starting with five co-founders (eventually narrowing to three), they built a charting app that reached £1 million in annual recurring revenue. The path wasn't easy, with the team accumulating around £500,000 in debt during the growth phase: "The only way we managed to do this was setting up payment terms with a bunch of people... and when five months came, we said, 'Look, things are looking good, but we need a bit more of an extension.'"

When pressure mounted to sell the company, Chris was the last holdout: "I said, why sell? We're literally right. All I would do with the money is found a company like this." Eventually, an honest conversation with his co-founder changed his mind: "He just goes, 'But, Chris, I'm scared. I'm out of my depth. I don't know what I'm doing, and I don't know how to grow this company anymore.'"

The Buddhist Millionaire Paradox

After receiving his £5 million, Chris found himself in a philosophical crisis. "I resented that money. It was burning a hole in my pocket," he admits. His conflicted relationship with wealth led to spending his entire windfall in under six months—and ironically, he spent it before even officially receiving it.

His first purchase reflected his values: "I bought a holiday for my whole family to go to Disneyland Paris... I just bought the fanciest suite with all the upgrades." But then came the more ambitious investments: a weed farm in Thailand, a comedy club, and real estate.

The weed farm ultimately failed completely: "The market just dropped out. It's a terrible investment." The comedy club became a passion project but continued losing money. Fortunately, his real estate investments provided a safety net: "I'm really lucky. I knew myself well enough to have invested enough in property. And that's enough that just renting that out will put my son through a good school."

Chris's spending spree wasn't just about money—it reflected his identity crisis after selling his company: "I'm the world's saddest millionaire... You're still debating with lawyers and advisors and accountants and none of which I wanted. You're then working for the company you've just sold your company to... And having to watch them fire or encourage your whole team to quit."

Money and Relationships

Chris's newfound wealth created unexpected challenges in his relationships. "For a couple of months, I bought everything for everyone. Just didn't think, didn't look at the price and just said yes to everything," he shares. "But it just wasn't me. And it was awkward, and I was attracting the wrong kinds of people."

He began lending money to struggling friends, which seemed natural at first: "It costs £300 to fix [their car] and they're losing sleep over this. And it's a rounding error for me." But this generosity created complications: "Good people don't like that you're throwing money around. It makes them a bit awkward."

When he later faced a large tax bill and asked friends to repay loans, "some of the responses I got [were] quite hostile." He learned a painful lesson: "When you lend money to someone, say bye to it. Be Buddhist about it."

Despite these challenges, Chris received messages from people expressing gratitude for his help during difficult times: "For every one of those [fallouts], there are people who just let me know, send me a message that they really appreciated, and it really meant a lot to them at a time when they were down."

Other Key Quotes

"I don't have imposter syndrome. I am an imposter. It feels incredible to be so out of my depth, surrounded by people so much smarter than me. The reason I was successful is because I wasn't smart enough to realize how dumb I was."

"I'm very comfortable with the paradox. I'm very comfortable with the contradiction. I think that's the beauty of life."

"If I wake up every day and I do what makes me happy and it makes other people happy too, then I'm winning. The rest will take care of itself."

"Too much of the financialization... I just worry how many geniuses in society end up working in finance, making rich people slightly richer when they could be making society slightly better."

"When I'm in that mode where I'm enjoying the journey, the right path reveals itself to me... I find when my head and my heart are aligned, I'm on a really strong path in that flow state."

Full Transcript

[00:00:00] Chris Cooke: I don't have imposter syndrome. I am an imposter.

[00:00:03] Harry Morton: Chris Cook is a capitalist Buddhist. He also sold his company for $30 million and then promptly blew most of it on a weed farm, a beach house, and a comedy club in Thailand, among other things. If you're already feeling like that doesn't really make sense, well then good. You're in for one hell of a story. Because it's not just about money. It's about what happens when your ego, your values, and your bank account all collide.

[00:00:24] Chris Cooke: This is more money than I ever thought I'd make in my life. This is incredible. I'm very comfortable with the paradox. I'm very comfortable with the contradiction. That's not going to get me out of this hole. Now I'm confessing all my flaws. And since I'm a flawed Buddhist.

[00:00:37] Harry Morton: I'm Harry Morton, and this is Moneywise, a podcast. Not about how to make money, but how your life changes after you already have. And this is the insane story of what happens when a socialist Buddhist becomes a millionaire, and what we can all learn from his very unique and frankly inspiring story. And really quick. This is a podcast for Hampton, a private member's community for founders, CEOs, high net worth individuals where we're having conversations exactly like the one I had here with Chris. That typically only happened in private. And my favorite thing about it is the fact that there's such a range of folks in there, people that are VC backed tech people, bootstrap founders, and people like Chris, who just frankly have very, very different stories and perspectives on life. So I think it's awesome. Go and check it out. Join a socialist Buddhist millionaire. Sounds like a complete contradiction. And frankly, it is. But the world is full of contradictions, and it's in those contradictions that the most interesting things usually happen. Chris story is part value test, part financial experiment, and part philosophical roller coaster. He grew up skeptical of capitalism, beat the game anyway, and then went about spending his winnings like a man who hated having them. But buried inside that chaos is something important. A deeper understanding of happiness, detachment and purpose. Oh, and spoiler Chris did make some smart moves along the way as well. So this isn't just a story of blowing through cash, but let's start with what I assume is the most important thing for a Buddhist. The money.

[00:01:58] Chris Cooke: So we sold for 30,000,015 up front and 15 contingent on earning a target based bonus.

[00:02:07] Harry Morton: How much did you walk away with yourself?

[00:02:09] Chris Cooke: Uh, five. So we didn't hit the target? We didn't get any of the bonus. Uh, and then. Yeah. Three co-founders. Five. And then, in my classic carefree Buddhist fashion, uh, didn't really look into too much how much tax I'd end up paying. I could have, uh, gone offshore. If I'd have spent four months out of the U.K., I would have saved £400,000 on a tax. But that felt a bit against my socialist values and also not good with the young family. So I was like, I'll pay the taxes. Fine.

[00:02:43] Harry Morton: Fair. And so what was the what was the first thing you bought when that money landed?

[00:02:49] Chris Cooke: Well, so I resented that money. It was burning a hole in my pocket. Um, and I actually managed to spend it all in under six months.

[00:03:01] Harry Morton: Now, look, we'll get to the comedy clubs and the weed farms. Don't worry. But Chris did also make some more solid financial decisions along the way as well. Real estate, beach properties, assets that ended up honestly being the thing that saved him from a full on financial faceplant. But first, we answered the question that I'm sure you've been wondering since you clicked on this video. And that is, how does a socialist Buddhist end up essentially winning capitalism? Well, the story starts in the capitalist haven, Thailand. Well, firstly, you grew up in Thailand. That's that's news to me. You're a British man. You grew up in Thailand, or you sound British, I should say. Um.

[00:03:34] Chris Cooke: Yeah.

[00:03:35] Harry Morton: Yeah.

[00:03:37] Chris Cooke: So what's the story there? Yeah. My dad, uh, was working for Canada's oil and gas industry, LPG, and they got bought up by a Dutch multinational. And so he got given the opportunity to travel with the young family. So from the age of nine, we were living abroad, Hungary in the mid 90s, then Brazil, then Thailand at 15. So strange experience. Definitely in education and yeah, sort of gave me my first contact with Thailand and then, you know finished university 2008 big financial crash. So going out to Thailand and being a scuba diving instructor seemed like a completely sensible plan and.

[00:04:19] Harry Morton: Absolutely.

[00:04:20] Chris Cooke: Worked quite well for me there, actually I did, I did well doing that. So just have always been an entrepreneur, saw how hard my dad was working and kind of wanted to be my own boss and find my own way, but found it was better to be a cool guy in a nerdy space than a nerdy guy in a cool space, if that makes sense.

[00:04:37] Harry Morton: So growing up in in Thailand, like, what were your early views on money?

[00:04:42] Chris Cooke: Well, I discovered Buddhism and I saw, like, these rich international school kids and they were miserable, their families were miserable, and they never saw their parents. So so I kind of, you know, simultaneously was in my dad's shadow and so wanted to have a level of success to prove to him I wasn't a failure, but also kind of had this contempt for money, which so saw me well into life. Like it was weird, though. I remember, you know, reading and studying Buddhism and saying how like, all of this teachings could be used by the wrong person for evil purposes. And that that sparked me. I was like, imagine being a Buddhist capitalist, like imagine like using this power of meditation to just, yeah, not care, be detached from money and yet still pursue business success. That would be a weird paradox that I just the, you know, the obstinate capriciousness of me. I wanted to pursue that path.

[00:05:41] Harry Morton: That pursuit or experiment, really. It worked. But it also taught Chris something really interesting. You don't need to twist Buddhist values into capitalism. They actually play pretty well together. In fact, Chris credits those values for the reason making money came so naturally to him. Key word there. Making. Keeping it, growing it. That's a whole different beast. All that is coming. For now, let's continue on the story of how he went from running a scuba diving school for tourists, which he ended up losing to selling a rapidly growing SaaS business.

[00:06:10] Chris Cooke: The first thing is seeing how hard my dad worked to climb up the corporate ladder. He never finished school even. And so for him, starting on the bottom rung of a minimum wage job, literally loading bottles onto a truck right all the way up to Country Manager was incredible. And he was rightfully so proud of that. But he worked so hard and I going to boarding school, coming home for three weeks holiday and then him having to be away for half of that because work, um, just made me kind of always commit to the fact that I thought it was better to do your own thing. And that was really confirmed when I started in the world of work and I was working seven days a week. Minimum wage for someone who wasn't that smart and was making loads of money. And I was like, okay, so why work really hard to make someone else rich when you can just do it yourself? Um, that sort of changed, I think, when I came back to the UK, having had a few successes and failures, entrepreneurship in Thailand that had kicked a bit of the confidence out of me. And then I started working in software and, you know, complete start from zero imposter syndrome out of my depth, furiously googling how to do my job every night. Um, and but then the higher I got, the more I realised, damn it, I'm smarter than my bosses again. So fine, let's start a company. Um, that and I'm just unmanageable as a person. It's just incredibly difficult to tell me what to do. Uh, just just made it a natural thing, really.

[00:07:53] Harry Morton: And so you kind of started this company while working your, your job, right. So how did the transition sort of happen?

[00:08:00] Chris Cooke: Um, quicker than I would have liked because we had a very young, aggressive co-founder who was, uh, had hadn't, hadn't had it kicked out of him like I had yet. This is why we were a good combo. I became the rare for me, but the voice of caution. Uh, so there was a few of us, uh, five co-founders originally, and then a couple that didn't work out with. We were misaligned. Um, and one guy quit his day job. And one by one, we would quit our day jobs as the thing started getting ready for us. And then. Yeah, uh, it was nerve wracking. Um, you know, I just started getting a good salary. Um, and with sales and software like, you land a big deal, get 50 K commission. Oh, my God, this is amazing. And that client would have just kept paying me more and more money. Um, so it got to a point where I was like, this is more money than I ever thought I'd make in my life. This is incredible. And I just gambled it all. And again, this is partly this. This was the Buddhism, not the greed, because I was happy with the amount of money. I didn't want more, but say yes to the opportunity to take the chance. Get on it. Don't fear losing it. Um, and you know, it's easy in hindsight, having been successful, to be glad with that decision.

[00:09:18] Harry Morton: You went into massive debt to grow the business. So how much was the debt and did it? Was it scary? Did it scare you?

[00:09:25] Chris Cooke: It was probably at its peak, half $1 million. The only way we managed to do this was setting up payment terms with a bunch of people. So everyone we dealt with, they would offer us a discount because they could see we were young and ambitious and struggling, and we'd be like, instead of a discount, this could repay you over the next six months. And they were like, okay. And then, um, and then. Yeah, when, you know, five months came, we said, okay, well, look, things are looking good, but we need a bit more of an extension. There's that old expression. If you owe the bank $1,000, it's it's your problem. If you owe the bank $100,000, it's the bank's problem. Numbers are probably higher these days, but, uh, that was really what it came down to was just faith, charm, uh, naivete. Uh, and a bit of this bit of fearlessness. I had one sleepless night and then kind of woke up the next morning. Well, that's not going to help. That's not going to get me out of this hole.

[00:10:29] Harry Morton: When did you realize the company was taking off?

[00:10:31] Chris Cooke: Then we made 100 K in revenue to date like total. Right. And that's when the graph just started looking very good. Um, and you know, you never know when it's going to plateau, but from 0 to 100 K felt huge.

[00:10:49] Harry Morton: And then how much were you paying yourself then?

[00:10:51] Chris Cooke: 18 year. We're on.

[00:10:53] Harry Morton: And I'm sorry. Were you living? We didn't. Sorry, Chris, I keep interrupting. Were you living in the UK or were you living in Thailand throughout this entire period?

[00:11:00] Chris Cooke: This was in London. So this was most of it was going to rent, as I'm sure you can imagine, a small place. I was very lucky because it was a lovely little cul de sac in Camden. Would you believe that? Had a little woods in the back of it and we were on the ground floor, which people are scared of. I'm six foot seven, not scared of anything. So I had this lovely ground floor flat with a woods I could walk around in. Amazing. And so that was beautiful and stunning. But that was all my rent was that and we were sometimes not paying ourselves. So I got my wife a job in a restaurant just so she could bring home free food that covered us.

[00:11:43] Harry Morton: At what point did your co-founders want to sell?

[00:11:45] Chris Cooke: Yeah, well, this was the big problem. So the first co-founder we lost, uh, had a mortgage, and he was a tech consultant. He was on 60 K. Yeah. And he said he couldn't go with us full time until we paid him more than that. And we were like, well, that won't work. Like, we were thinking 18 KS. That's what we're paying ourselves. Um, and this is it, like just different people at different stages of their lives. It's very hard for a 50 year old with a mortgage to start a business. Um, they get trapped in the golden cage, you know? And so, yeah, that was the first one that fell, by the way. Um, and then, yeah, the second big one was just as soon as we hit a million annual recurring revenue. Um, it was just different for him. It was fascinating. He was the, you know, young, hungry guy that had propelled us to go so aggressively, so quickly, so hard. And as soon as we hit that, he just could see the path and he was no longer interested in it, like he liked it when it was unsure. The uncertainty. And as soon as it was like we were on a train heading in one direction, he was like, cool, I'm getting off. Um. And a million was enough for him to buy his parents a house so they could get divorced.

[00:13:04] Chris Cooke: It was stuck in a house together and unhappy. So that was just a life changing amount of money for him. And at the time, it felt like, as I say, such a betrayal. Uh, because, you know, I thought we were building this company to last for life, and I was I was loving it. And I said, why sell? Like, we're literally right. All I would do with the money is found a company like this. So why would I sell? It makes no sense to me whatsoever. And he got more and more desperate. A combination of breaking up with his long term girlfriend, getting stuck in London during lockdowns and being incredibly burnt out. He just was like, we need to sell now at all costs and I can appreciate that. I've always said the the CEO, the co-founder that takes a business from, 0 to 100,000. It should be really a different person that takes it from 100,000 to 1 million, 1 million to 10 million, and then 10 million beyond. Those are very different skill sets, very different personalities, very different temperaments. Um, and very often the co-founder, sometimes they can evolve and change through that. Sometimes they enjoy it. But I've worked many places where you can just sense that the company is has outgrown one of the co-founders who is still sticking around.

[00:14:18] Harry Morton: One by one, the team of co-founders either left or decided to sell. Chris was the last one to hold out, and because he never started the business as a big financial play, the decision was really hard.

[00:14:27] Chris Cooke: One wasn't that it wasn't enough money. I just again, I said, all I, all I want to do is take this money and buy this company again with these same people.

[00:14:38] Harry Morton: Who didn't want to.

[00:14:38] Chris Cooke: Get off the ride. No, I was enjoying the ride. I was enjoying the journey. And I think at the time it was heartbreaking. Like I lost my team. I lost my sense of self. Um, I lost my friends and co-founders because we really disagreed on this and were arguing I had to spend two years arguing with lawyers and accountants. It was an Erin Brockovich moment where they were like, oh, why don't you have this spreadsheet? And I'm like, yeah, I do have it. It's all in my head. Okay. Like, I have the spreadsheet. And, you know, even the the last co-founder standing. I had a good chat with him recently. Um, and there was this beautiful moment where I was just so upset that he wanted to sell, and I didn't, um, and he just had a moment of honesty with me where he just goes. But, Chris, I'm scared. I'm out of my depth. I don't know what I'm doing, and I don't know how to grow this company anymore. And I've been lost for some time. And that just that honesty was so disarming to me and took the fight out of me because he was the sales co-founder. Right. And had he tried to charm me or talk me around. But that just moment of just beautiful, vulnerable honesty. Was was why we sold. Because I, I appreciated it, um, I respected it, and we are still friends. I still tell him it was a massive mistake selling, but at the same point, it's like those relationships that didn't work out.

[00:16:09] Chris Cooke: And you go, oh, if only the person could change this one thing about them. That would have been fine. And again, hopefully you get wise enough to realize that that isn't people. People can't change that. One thing about them, and a lot of relationships are glued together with the hope that maybe one of you will change. Enough. Um, and this was it. Like, I just had not found the right co-founders who wanted the same things. We've all learned from it. Next time I have less of a chip on my shoulder. Less to prove. Um, but but I. I don't need to try every desperate hack to make the thing work. I'd like to build a sustainable company with work life balance and love and find some people that share my values, whereas these people were the people that were prepared to join me. A guy that had recently come back from Thailand as a failed scuba diving entrepreneur. Now I have more options. Now I know what I'm doing. And yeah, I stuck around longer than I should have even after we sold the company because I wanted to learn. Okay. Now I'm working for a company with 100 plus employees, making 100 million annual recurring revenue a year. And I just wanted to see behind that curtain. How does that company get run? And the main thing I learned is I never want a company that big. Right. It's not fun.

[00:17:26] Harry Morton: Remember this quote?

[00:17:27] Chris Cooke: I resented that money. It was burning a hole in my pocket. Um. And I actually managed to spend it all in under six months.

[00:17:36] Harry Morton: Yeah. It's time to expand on that.

[00:17:38] Chris Cooke: In fact, I spent it before we got it. So the sale L had been signed and completed. But because of the way because we were trying to, we had a Polish co-founder registered in Cyprus and a German co-founder in May. So trying to deal with all that meant that we had the money sat in a bank account for far too long. And so what we ended up doing is just lending the money to ourselves, knowing that an amount would be transferred later when the sale was finally completed. Completed. And I spent it in under six months, the amount I'd have lent to myself. It wasn't even really mine yet I hated it. But to answer your question properly, the nice thing I bought. I bought a holiday for my whole family to go to Disneyland Paris, and we just. Yeah, I lied to them about how much it cost. And I just bought, like, the fanciest suite with all the upgrades, and it was just. Yeah, lovely and pimping and very nice for my younger sister and her young family and yeah, just beautiful and fun. And then I invested in a weed farm and a comedy club in Thailand.

[00:18:43] Harry Morton: Okay. So there were there were some. So you spent it all. But they weren't they weren't just you didn't just spend it and then start from zero again. You spent it on some on some businesses at least. Um.

[00:18:56] Chris Cooke: Oh, yeah. I mean, the most sensible and the most of it went towards was actual property.

[00:19:01] Harry Morton: So the weed farm, the company. How much did you pay for both of these things?

[00:19:06] Chris Cooke: Uh, all in probably £100,000 each.

[00:19:10] Harry Morton: Okay. Okay, so. But that doesn't. So that does not account for the 5 million that you made. So then where does the rest? Was the rest purely on the house or.

[00:19:20] Chris Cooke: Uh, mostly real estate. Yeah. I've got a very nice house in England. Uh, five bedroom. Uh, yeah. View of the sea in Devon right now on Airbnb most of the time. And then we go back to England to visit my family, my parents. We can stay there. Um, and then. Yeah, very nice beach house in Thailand. Um, when I had the scuba diving in school, that was one of the things I bought was a house by the beach with the success from that. And then the problem with Thailand is you can't own anything. So I put it in my ex-girlfriend's name. Wow. And she ended up taking that and the dive school. Yeah. So you just have to start again. There's no legal recourse. Like, yeah, you just have to be Buddhist about these things and move on.

[00:20:05] Harry Morton: Okay. Wow.

[00:20:07] Chris Cooke: So buying another beach house felt like okay.

[00:20:11] Harry Morton: Yeah, sure. Okay. But then cashflow wise, what was your situation at this point?

[00:20:17] Chris Cooke: Um, well, I still had plenty. So the investments in the weed farm and the comedy club, I estimated like, oh, okay, well, eight months runway. I'm really lucky. I knew myself well enough, uh, to to have invested enough in property. And that's enough that just renting that out will put my son through a good school. Uh, the income from that I'll survive. But, yeah, the both the Weed Farm and the Comedy Club lost a lot more money than we projected for a lot longer.

[00:20:47] Harry Morton: And do they make money now?

[00:20:50] Chris Cooke: No. The weed farms folded completely. The market just dropped out. It's a terrible investment. It was something that, you know, 16 year old Chris thought was cool. And I wanted to help a friend out. You know, she was growing weed for her. This is all legal in Thailand, by the way. But she was growing weed for her boss. And, you know, he was making money. And I was like, well, you could do that for yourself. And the reason that failed was simply, I just didn't know the industry at all. So when it was struggling, there were no levers I could pull to help. I was like, okay, then it's struggling. And the other thing was we got a sales guy involved who was also a friend, who knew how much money I had made from the sale of the company. And then he started telling people, oh, this guy's got loads of money. So then a bunch of parasites came at the tea and just yeah, that quickly got drained. The scope of it ballooned. Yeah, that's a whole story. Probably for my therapist. But. And then the industry dropped out. Thailand got flooded with weed. You know, you're competing with, uh, the waste products of Canada and America. Just the FDA doesn't approve. And then they send here because it's industrial waste. So the price went from £10 a gram to $0.10 a gram over the last two years. And so that was the whole thing. The comedy club is my passion and my love. And so even though the thing has been losing too much money once we hit this thing, especially because the weed farm was losing so much where it was dipping into my wife's savings pot, she got involved.

[00:22:22] Chris Cooke: And I think the important lesson there might seem obvious wasn't for me. I'd been meteoric successful by avoiding ignoring my conservative, risk averse wife. Right. And then once it started dipping into the savings pot, she got involved and she was always an entrepreneur as well. An Asian businesswoman was doing like retail and stuff. Um, and then learning to work with her and a newfound respect for her and having her, like, pull one of the businesses out from the brink and then scramble together enough savings to pay this massive tax bill I wasn't expecting. Uh, that that was an important reset for me. Definitely brought me back down to earth and just refocused my values. So one level of fool on his money was soon separated, and I actually got some advice from a mentor who told me, don't invest in anything for two years, because just the heady rush of selling your company gets so excited, you know? Um, and maybe I should have followed that. But at the same point, I'm true to myself. I've enjoyed the journey. I've learnt a lot, and it's hard to have any regrets. Like what got me there? Got me here. I'll keep mumbling. I'll have some hits. I have some failures. But I'll keep growing. Keep learning, keep loving it.

[00:23:46] Harry Morton: See? Yeah. So. Okay. I mean, it's incredible. You definitely didn't stick it in a Vanguard ETF. Most people invest in stocks and bonds and crypto but you avoid those things. So why is that. Or you did avoid those things. Why is that.

[00:23:59] Chris Cooke: I did I mean I played crypto for a bit because the, uh, you know, socialist and anarchist in me love the disrupt the banking system narrative. Uh, so so I got into crypto 2017. Good time to get involved. Invested a bit in it. Um, likewise, playing stocks did it to learn, but hated it. And it reminded me of when I was had my scuba diving school in Thailand. I'd be making more money at night playing poker online during the big online poker rush of the 20 tens, if you remember those heady years. But I realized I was just spending all my time on a computer, staring at us, staring at numbers and graphs. Um, yeah. It's boring. It's just not fun. Like it's not adding anything to society. And again, I try not to judge for those people that have learned that and enjoy that and are passionate about that. Good for them. And the irony is the company, the product that ended up making me so many millions was graphs and reports. It was a charting app, so I ended up staring at reports anyway.

[00:25:07] Harry Morton: Yeah, right. There you go.

[00:25:09] Chris Cooke: Life is funny that way.

[00:25:10] Harry Morton: It is funny that way.

[00:25:12] Chris Cooke: But yeah, I think too much of the financialization. And there's this quote, like, I'm really I'm not worried about the measurements of Einstein's brain, but deeply concerned that there were loads of geniuses that died as slaves in the cotton fields. Uh, not quite as dramatic, but I just worry how many geniuses in society end up working in finance, making rich people slightly richer when they could be making society slightly better. Mhm.

[00:25:38] Harry Morton: Yeah. That's a really that's a nice question.

[00:25:40] Chris Cooke: But you probably have to cut from your podcast.

[00:25:43] Harry Morton: Just so you know, we'll never cut things on the basis of the views or the plays. However we will cut the boring parts. How did your lifestyle change. Um. Or not change I guess. Like, you know, it sounds like you didn't totally screw yourself over in the sense that you bought some real estate. You know, you set yourself up in that respect. Yeah. Did your lifestyle shift in any way?

[00:26:03] Chris Cooke: Uh, for for a couple of months. I bought everything for everyone. Just, you know, didn't think, didn't look at the price and just said yes to everything. Um, but it just wasn't me. And it was awkward, and I was attracting the wrong kinds of people. There's definitely a cautionary tale there. I think I was scaring away. You know, good people don't like it when you throw money around. Uh, the people that do are the people that you don't really want to hang out with. So I really liked events like Baby Bathwater, um, and DC in Bangkok because you'd meet like minded people. And so there's already like a filter where it's not awkward that you're talking about money. People understand it. That's why. Yeah, I've enjoyed some of the guests you've had in your podcast.

[00:26:47] Harry Morton: I've got to do it. He set it up so nicely. Another great place to talk openly about money. It's Hampton. Go and check it out. Join Hampton.

[00:26:54] Chris Cooke: But yeah, I think at certain point I just had to come back down to earth and reset and come the hell down to stop burning money. Like I resented it, like I resented having it because I didn't want to sell my company.

[00:27:07] Harry Morton: You did give some money to friends, and it left to lead to losing some of those friendships as well. So I wonder, like what? What went wrong?

[00:27:15] Chris Cooke: So I, I've always wanted to help friends out. I've always been generous even when I had nothing. And it just feels very strange and tough when you know your friends are struggling, uh, and you have an unbelievable amount of money, a life changing out of money. And so there were a few people where anytime they were struggling. Sure, I have it right. And the first few times it just, you know, makes sense. Their car breaks down, it costs £300 to fix and they're losing sleep over this. And it's a rounding error for me. And it's embarrassing to say that but but yeah, for someone on 20 K a year who can't afford a a bill of £500, like, yeah, why? Why the hell not? But unfortunately, a few things happened. Good people don't like that you're throwing money around. It makes them a bit awkward. And it's just even if they don't resent you for it, it's just a bit gauche. It's a bit classless. And then, yeah, you do attract the wrong sorts of people. And I think the saddest was when I lent money to people, and then when I got this huge tax bill, I'd sent a message around saying, hey, like, I understand blood from a stone. If you don't have it, that's fine. But, you know, could you start paying me back? And some of the responses I got quite hostile. And in some way I think this is just guilt and people's first response lashing out defensive.

[00:28:42] Chris Cooke: Um, but it was a real shame to lose money and friends that way. And I think part of that is just having to learn to recalibrate. So now I don't go around talking about my wealth and I don't throw money at people. Um, and this seems obvious, but like, for me, why wouldn't you help someone if you could? And we all help each other, right? Like you'd lend your friend a tenner. And this just seemed a comparatively relatively similar sort of mechanism. Um, but, I mean, I spoke on a podcast last month about this, and I just lost a bunch of friends, and it was really sad. Bunch of people heard that podcast and have been messaging me this week saying how, uh, I lent them money when they really needed it and it really helped turn their life around, and they've been forever grateful. And that was wonderful to hear because because, you know, the most salient, the one that sticks to your mind first are the the fallouts and the people that were rude. But for every one of those, there are people who just let me know, send me a message that they really appreciated, and it really meant a lot to them at a time when they were down. So yeah, you just have to accept when you lend money to someone, say bye to it. Be Buddhist about it.

[00:29:57] Harry Morton: Okay, I know what you're thinking. Wow, this guy is horrible with money. And to be honest, he probably wouldn't argue with you on that. But the question is, does it really matter? Well, of course this is money wise. So the answer in this case is yes in this context. But the purpose of money and really the thesis of this podcast is that it won't bring you happiness alone, but it is a tool to help you figure out what will increase. Happiness is detachment in some way. He's happy being silly and having fun and not putting pressure on himself to be something he's not. And by the way, I'm not saying go and be stupid with money by any means, but the reason that Chris was frankly a bit stupid with it is because to him, that money was a symbol of loss, and this is a trap that any founder can fall into. If you treat the money as a replacement for something else that you value and cherish, you can end up feeling completely empty and losing sight of all the other benefits that having money can bring to your life. And that's exactly what happened to Chris. Spending £5 million in six months is quite fucking impressive, honestly. So, like, so can you just can you can you just go back there a minute? Can you just tell me a bit more about those six months and what they felt like and what that experience was, and like what your life was on a day to day basis, spending 5,000,000 in 6 months.

[00:31:10] Chris Cooke: A lot of drinking, a lot of traveling, a lot of stress.

[00:31:14] Harry Morton: So it was stress. Okay. That's interesting.

[00:31:17] Chris Cooke: Oh, God. Yeah. Yeah. No, I, I mean, and again, you're still debating with lawyers and advisors and accountants and none of which I wanted. You're then working for the company you've just sold your company to 22. And having to watch them fire or encourage your whole team to quit and having to work on. And then you're filled with remorse and regret for that. I'm the world's saddest millionaire. I'm sorry. No, but.

[00:31:44] Harry Morton: This.

[00:31:44] Chris Cooke: Is.

[00:31:45] Harry Morton: It is a really interesting one, though, like, because, um, what was it I was reading recently? Felix Dennis, How to be Rich. Um, and he talks about, like, there was like a ten year period where I think he spent £100 million in ten years or something on, just like coke and hookers and parties and booze and and nearly killed himself. Um, it doesn't sound like that's the journey he went on, although he did do some drinking. Like, I'm just really interested in that, like, really heady. Kind of like, I just, I just can't. It just sounds like a fever dream to me. I cannot imagine.

[00:32:17] Chris Cooke: It is mental and the way I describe it. So going to the tech conference in our business industry, just after having announced we sold the company, and you have to realize I'm famous in my industry for telling people not to sell and telling people I would never sell. That was like my line. I was going around telling people, don't sell them, sometimes I don't. And then and then I sold. And so it was like the big news. And the way I described it is it must be how women feel like at their wedding. I was going around, I was the center of attention. Everyone was coming up to me and saying, oh, congratulations, you must be so proud. You must be so happy. And I was like, thank you, thank you. So it was this beautiful, surreal moment, but it very much feels like peaking, right? Like plateauing. And then you're scared like, well, what comes next? How do I outdo this? And it's terrifying. Like, I already had imposter syndrome. And part of you worries I was I great or was this luck? And a lot of it's the fear of that. And so I think, you know, that led to the heavier drinking plus, you know, unlimited budget to do things. Um, I think if I wasn't so vain, I would have been more attracted to prostitutes, but I just. I need to believe the girls love me to be.

[00:33:36] Harry Morton: This period, these mistakes. They're definitely more of a how not to guide, but it's a trap that lots of post exit founders can fall into. Even if you decide you don't particularly care about growing your wealth or leveling up, that doesn't mean you shouldn't be smart with your money. Money is a tool for survival. That's not something to neglect unless you're willing to completely Bear Grylls it and go off grid your whole life. Although that does sound kind of enticing given the state of the world. Anyway, like I mentioned before, even in his most frivolous phase, Chris did make some smart decisions. He made some responsible choices around real estate and creating reliable cashflow for his family. So yes, he blew a fortune, but he did also accidentally end up building a safety net, and that's what ended up saving him.

[00:34:13] Chris Cooke: My son will never have to want for too much. His school is done. He's got a house by the beach. He'll be fine, right? He won't have to struggle.

[00:34:25] Harry Morton: And here is the lesson I think is crucial. Having conviction and nuance is important. But being too rigid and never leaving yourself room for contradiction can leave you feeling stuck and back you into a corner. I'm sure there'll be people that disagree with this, but life is a balance between values and survival. What survival looks like and how important your values are to you will vary from person to person. Where you sit on those scales will ultimately decide the kind of life you live. Like most spectrums, extremes are where most issues present themselves because of his willingness to experiment with his ideas and to challenge himself, he's learned even more about himself and his values than he would have done had he not.

[00:35:00] Chris Cooke: It'd be different if I was trying to be a Buddhist monk and live. But even Buddha said like, it's not about having being an aesthetic and denying yourself anything. It's about not clinging onto things. I'm not saying this is exemplifying good Buddhist behavior. Um, but I think you have to be prepared to live in the moment, uh, prepared to let go of things and just live in the present and feel it.

[00:35:25] Harry Morton: Do you think your life is too contradictory. Do you ever feel like an imposter in both spaces?

[00:35:31] Chris Cooke: I don't have imposter syndrome. I am an imposter. It feels incredible to be so out of my depth, surrounded by people so much smarter than me. The reason I was successful is because I wasn't smart enough to realize how dumb I was. I took the chances anyway. I went for it, and I got lucky. Um, likewise. And it is funny. It's so contradictory. But so many Buddhists you meet, uh, they're boasting about how they're more Buddhists than other Buddhists. And you're like, I don't think that's the case, bro. I don't think we're here in the competition to be the most holy Buddha ever. Um, but that's the trap of ego and pride. I'm very comfortable with the paradox. I'm very comfortable with the contradiction. I think that's the beauty of life. God bless those people that can put themselves in a in a pigeon hole, in a bucket Bucket and say, I am this, uh, I am forever walking those tight ropes. I am, uh, yeah. Contradiction wrapped in a paradox.

[00:36:33] Harry Morton: In a moment, we'll get back to the numbers Chris is spending and his net worth, which is particularly interesting given the way he spent his earnings post exit. But first, I want to get into the contradictions that define Chris's life. His Buddhist values taught him to want for nothing. But it's exactly those values that brought him everything.

[00:36:51] Chris Cooke: I think having an unhealthy contempt for money, and yet striving for success has combined with my feelings towards Buddhism, um, and made me appreciate the journey rather than destination. So never having a destination in mind, but just wanting to make work my life's passion and find something that I enjoyed and felt like the way to me and where I could be my most true, authentic, natural self. And I found that when that happened, I would just get in this flow state where, you know, everything just worked out. Like, even though I just was making a small scuba diving school in rural Thailand, it was this up and coming place and I'd started at the right time. Lots of people were fleeing there because of the financial crash, and there was like a new Novotel, a new Marriott hotel. And I was I'd set up a tour company in a place that kind of made no financial sense at the time, but because I was the first mover there, I just suddenly started getting all these opportunities. And because I was prepared to take tours out during the low season, which again, would make no financial sense, but I didn't care too much about the money. You end up having these, you know, really enthusiastic return customers, word of mouth recommendations. So yeah, I, I found the same with like my poker game.

[00:38:08] Chris Cooke: Like I just got very, very good at poker. The less I cared. And if you're too nervous of losing, uh, you're playing against people who are a bit scared. I just found, like, once I let go of that attachment, I was just scarily good and able to make much better, calmer decisions about money without panicking. Then what I found for myself is that when I'm in that mode where I'm enjoying the journey, the right path reveals itself to me. And that sounds a bit hippy and esoteric, but it it can't all be done by logic. Some of it is gut feel, and I find when my head and my heart are aligned, I'm on a really strong path in that flow state, feeling in your natural sense of things. And if you just wake up desperate to make money or stress that you don't have enough or you're in debt, I feel you do yourself a massive disservice. Like creativity. Um, and your best ideas come from from when you have a more relaxed approach, when you're not trying to grip hold of money in the short term. And I think, like a lot of things, the tighter you grip onto some things, like if you're if you're climbing, right, if you've ever been rock climbing.

[00:39:16] Harry Morton: Yeah.

[00:39:16] Chris Cooke: I mean, if you're trying to if you panic, right. And you're trying to grip hold as close to the wall as you can sometimes happens when people first start. You lose or you lose all your strength. It's such a waste of energy. Whereas when you push away, your arms are extended in more natural pose. You have more options. And I think that's what I've taken from Buddhism. Um, and, you know, the other thing I'll say is that, uh, trying to put at the heart of myself like a good, a good life, a life well-lived means that I've done things where I've done the right things by my customers, I've done the right things by my employees. And that has been a good investment as well. Like, caring for people has meant I've had really loyal people that could have taken jobs for more money elsewhere. But just because we had this love of each other and the work unstoppable, and it just prepared us for this sudden meteoric growth.

[00:40:12] Harry Morton: All right, let's get to some updated numbers. So what is your current net worth?

[00:40:18] Chris Cooke: Uh, I'm 200 K in debt.

[00:40:21] Harry Morton: Okay, Nice. That puts you. That puts you I. That puts you firmly at one end of the spectrum of guests on this podcast, I tell you. Um. So congrats. Congratulations. Which, by the way, while true on the liquid front and a comedic number, it's not really the case. He does own a lot of valuable assets, and so realistically the number is more like 5 million. Uh, so tell me more about that though. Like, what does that mean?

[00:40:46] Chris Cooke: Well, I got some bad financial advice on what my tax bill would be. I thought I'd be able to write off my losses for my businesses in Thailand. Uh, and I thought I'd be paying a much lower percent than I ended up paying. So my tax bill came for half £1 million. I wasn't expecting it. Now, part of that is just. And again, I can't use Buddhism as an excuse for all of my behavior. I just don't worry about money. I just don't think about it. It just isn't a priority for me. And sometimes that's great when you have, you know, your business is going in debt, but you persevere and it makes loads of money anyway. Sometimes you get a tax bill that that that high and you're like, oh, I wasn't planning for that at all. Damn.

[00:41:30] Harry Morton: And what's your monthly spend then?

[00:41:33] Chris Cooke: Incredibly low. I'm out in Thailand. I've bought all my houses. No mortgage. So I earn ten K a month. I spend ten K a month on my tax bill.

[00:41:45] Harry Morton: Chris is far from the typical post exit founder. Not because he didn't win big, but because he carries this. Money's not the goal energy. And to be clear, he's not saying everyone should stop caring about money.

[00:41:55] Chris Cooke: I don't want to venerate being poor. Like, I'm sure very few of the listeners or guests on your podcast do, but but I used to as a young, idealistic teenager, I used to really, like, have contempt for the wealthy people that inherited a lot of money. Um, and I think now I've just like, we're all on our journey. Um, but as I say, if you're if you're grabbing at things that just aren't naturally on your path in the right moment, then you'll always be frustrated. I do also know that as I've had success, I see the game. So my co-founders and I fell out because at various stages the money got enough. They wanted to walk away, and I saw that as a personal betrayal because I thought, well, we built this beautiful thing together. Let's keep going together. And the money just got too much. And I, you know, it's easy for me at the time to see that as greed or resent it. Um, but at the same point, like, I've just realized, like, for them, that was their path and that was the right decision for them at the time. Um, but but the real problem is that, you know, what we do learn from Buddha, it is that whatever you get, whatever your happiness is, it'll never be enough. So it's taken me a long time to be like, okay, what is my next step? And so instead, I've just decided now, you know, a new level millionaire for the first time in my life, but I just feel like I'm at this new chapter in life where I'm having to start again and think, okay, calmly, rather than try and do a bigger number in a shorter amount of time. Can I do it where half the team doesn't get burnt out? Can I build a sustainable life? Can I enjoy the journey rather than desperately reach a destination of one? The game of capitalism? Awesome. Now can I start something that's sustainable, enjoyable, has work life balance, and actually work with a team and build a company that's going to last decades rather than be this incredibly explosive flash in the pan?

[00:43:58] Harry Morton: How does a Buddhist entrepreneur define success?

[00:44:01] Chris Cooke: If I wake up every day and I do what makes me happy and it makes other people happy too, then I'm winning. The rest will take care of itself.

[00:44:11] Harry Morton: So yeah, Chris Cook is a walking contradiction. He's a socialist, that one at capitalism. He's a Buddhist with a real estate empire. A guy who burned through millions and feels richer on the other side. And while it might not look like the traditional success story, it's a hell of a good one. If you like this story, why not check out the complete other end of the spectrum? We did an episode recently with Tommy Mello, who wants to be making $1 million a day, or if you want a lifestyle business. We did an episode with Laura Roeder, whose goal was to get to $5 million and actually managed to take her foot off the gas once she got there. And if you want to get even more stories like these ones that aren't on Moneywise, you've got to be inside a private member's community like Hampton. It's a highly vetted members community for founders, CEOs, high net worth individuals where we have these kinds of conversations that really only happen in private unless they're on money wise. Now, uh, that's the only place you get access to them. So if that kind of thing is interesting to you, you've got to go and check it out. Join Hampton. And finally I've got to give a plug to Lower Street. That's the company that makes this podcast. It's actually my company. If you're the founder or the CEO of a company and you want a podcast for your organization, check us out. Lower street.