How Andrew Wilkinson Built a $400M Fortune (And Why He's Giving It All Away)

We spoke to Andrew Wilkinson in this week's episode of Moneywise.

Andrew became an entrepreneur when he was very young, making six figures before he was even out of his teens. He founded MetaLab, a design agency, and later created Tiny, acquiring numerous businesses and growing his empire to a net worth approaching half a billion dollars.

Like all Moneywise episodes, Andrew breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.

We also went deep on: what's actually worth spending money on when you're wealthy, the surprising downsides of having multiple homes, and why money often creates more problems in families than it solves.

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 group that I run, which is a community for CEOs and founders. And the reason we created this podcast is because in Hampton, we noticed that everyone was asking about money, but typically there's very little talk about money in public. And the communities that I'm a part of or that I run, I've noticed that the best ones have the most transparency. So at Hampton, we have radically transparent conversations about money, from how much money we've made from our companies to how we invest it to how we spend it and all of the personal issues that come with having money. Hampton is a group of CEOs and founders, and we'd love to have you apply. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.

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Now, below are the notes and the full transcript.

The Numbers

• Started making $5,000/month as a young entrepreneur, which gradually increased to $15,000, then $30,000, then $50,000 per month
• Paid himself $250,000-$500,000/year in the first 2-3 years of his business
• By year 5, his design agency was making $30,000-$100,000/month in profit (~$1.2M/year)
• First significant liquidity: $7 million from selling a business at age 27
• Income at peak: $5-7 million/year
• Net worth at one point: $75 million (mostly in privately held companies)
• Personal stock in WooCommerce alone: worth over $200 million
• Total business portfolio value: approaching $1 billion
• Living expenses: $250,000-$500,000/year, sometimes up to $1 million/year
• Lost approximately $10 million of his own money over 8-9 years in various business ventures
• Expensive purchases: $50,000 watch (Steve McQueen Rolex Explorer), $4,000 everyday Rolex, $5,000 Fender Stratocaster, €200,000/week yacht charter

Starting Young: The Best Money He Ever Made

Andrew started his entrepreneurial journey as a teenager, quickly realizing he could build a business by hiring others to do coding and design while he focused on running the company profitably.

"It was just whatever was left over at the end of the month went to me. And over time that became $5,000, then 15,000, then 30,000, then 50,000. And the number just kept going up. And it got to a point where, you know, I just couldn't spend it, and I had to figure out what to do with it," Andrew explained.

Unlike many founders who underpay themselves while building toward an exit, Andrew prioritized paying himself well from the beginning. "I think businesses need to make their employees happy, their customers happy and their shareholders happy. And I think one of the mistakes a lot of people make is they don't really make the shareholders happy, and that's themselves," he said.

This early cash flow allowed Andrew to start investing in other businesses, beginning his journey of building a diverse portfolio of companies. But making money at such a young age came with challenges.

"I was being completely fiscally irresponsible. I would, like walk into a electronics store and there'd be like a $5,000 camera, and I'd just be like, I want that," Andrew admitted. "When I grew up, my parents basically said no to everything... so as soon as I could afford them, I was so desperate to experience what it was like to have money and to spend it recklessly that I did with abandon."

What's Actually Worth Spending Money On

After experiencing significant wealth, Andrew has developed strong opinions about what expenditures actually improve quality of life and which ones don't.

Among the items that weren't worth it:

• Luxury cars: "I bought a Porsche 911 turbo. It was loud and uncomfortable... I kept thinking like, eh, people think I'm an asshole when I'm driving around like nobody looks at you."
• Expensive watches: "I have one $50,000 watch... But otherwise the watch I wear every day is like a $4,000. Not crazy nice Rolex. And I've got a cheap omega, and I don't know, I don't get any joy out of that."
• Yacht charters: "Chartering a yacht is insane... it costs as much as a lawyer's salary for like, a week, right?... At first I was like, wow, this is so beautiful. We're in the middle of nowhere. But pretty quick, I was like, why would I want to be isolated in the middle of the ocean, away from everybody?"
• Multiple homes in different cities: "Having multiple houses is really... a total pain in the ass. You know, that trite phrase, the things you own end up owning you."

What Andrew does find worth spending money on:

• Private jets: "That's one of the only, like, rich people things that I think is actually worth the money."
• A lake house close to home: "The lake house, though, was the best thing I've ever spent money on, and not because it's a second house or flashy, but because it's not about anything except for family and friends... it's about family and friends and disconnection."
• A beautiful primary residence: "I have a beautiful house on the water. My primary house. There's something really lovely about investing in amazing space for you and your family."

The Complexities of Wealth and Family

One of the most surprising revelations from Andrew was how challenging wealth can be when it comes to family dynamics.

"I think money really ruins families. I know more families that have been ruined by money than families that have been brought together by money. I think it's a very corrosive, toxic force," Andrew shared.

He explained how money created tension between him and his brothers when they worked together, and how it complicated his relationship with his parents. "There's something odd that happens when the son is wealthier than the parents," he noted.

Andrew also detailed how difficult it can be to use money to help others, even with the best intentions: "Everybody has these fantasies about money and being able to shower it down on those that deserve it... But I would be so worried that that million dollars would pervert or corrupt that friendship. Make them feel weird and indebted to you, or you feel like they owe you."

This extends to philanthropy as well: "Even donating money can be fraught... if you talk about the charity you're doing, you're a douche because you're bragging. And if you don't talk about it, then no one knows you're being charitable and they criticize you for not being charitable."

The End Goal: Dying With Nothing

Despite all the complexities, Andrew has settled on a clear goal for his wealth: giving it all away before he dies.

"Giving money away is joyful, right? It actually feels really good to shed it and help others. Why wouldn't you want to do that in your own lifetime?" Andrew explained.

When asked if he planned to leave money to his children, Andrew was surprisingly resolute: "I think I'd give them proportionally a small amount... I think the goal would be to effectively give them a really awesome version of Social Security, where they always know that they're going to have a house and medical care and all those basics, but ultimately they're on their own. But as of right now, I don't think I'm going to give very much to my kids at all. I think it's all going to go in the foundation."

Andrew's journey with wealth has taught him that money itself doesn't solve the fundamental human problems of anxiety and unhappiness: "Wealth is a little bit like travel. You know how everybody fetishizes like, oh, I'd be so happy if I just, like, moved to Hawaii or if I just travel to Europe, everything's better in Europe. The problem with travel is that your brain comes with you, and your brain is what causes the feelings of anxiety."

He concluded with a powerful insight: "Taking a SSRI and anti-anxiety medication has helped me more than having any amount of money."

Other Key Quotes

"I remember going to the ATM and printing out the slip and seeing this huge number with a bunch of zeros on it and being like, oh my God, I'm done. I can retire, I can do anything I want. I never have to worry about money again. And obviously that's not what happened."

"In the first 2 or 3 years of the business, I was paying myself 250 to 500 K a year, and I have continued to pay myself really well and live the lifestyle that I wanted."

"My net worth was probably 75 million. And I was living in a $2 million house. Driving a Tesla wasn't doing anything crazy."

"I've done quite a few things where the goal is not to make money. Like I'm doing something for the community and I've lost like 5 million bucks on it or something like that."

"In 2008, the stock market crashed. I was literally in this situation where I was gonna go bankrupt. I had this client who demanded a refund... the refund was going to basically empty my bank account down to about 500 bucks."

"I'm sitting here right now and I've got a $5,000 Fender Stratocaster that I haven't played in two years. Like I should not own it, right? It's like I bought the best one in the store and I barely play guitar."

"I poured about $10 million of my own money over the course of 8 or 9 years, and ultimately I lost it all, pretty much."

Links You Might Like

• Tiny Capital - Andrew Wilkinson's company that acquires and holds businesses
• MetaLab - Andrew's design agency
• Andrew Wilkinson on Twitter

Full Transcript

[00:00:04] Andrew Wilkinson: I remember going to the ATM and printing out the slip and seeing this huge number with a bunch of zeros on it and being like, oh my God, I'm done. I can retire, I can do anything I want. I never have to worry about money again. And obviously that's not what happened.

[00:00:21] Sam Parr: That's my friend Andrew Wilkinson. He became an entrepreneur when he was really young, and before he was even out of his teens, he was making six figures.

[00:00:29] Andrew Wilkinson: It was just whatever was left over at the end of the month went to me. And over time that became $5,000, then 15,000, then 30,000, then 50,000. And the number just kept going up. And it got to a point where, you know, I just couldn't spend it, and I had to figure out what to do with it.

[00:00:45] Sam Parr: Andrew never planned to be super wealthy, and he didn't grow up that way either. So throughout his 20s, he learned the hard way which things were worth spending time and money on and which things weren't.

[00:00:54] Andrew Wilkinson: I just found that my life turned into a series of questions from my assistant.

[00:00:59] Sam Parr: He also made a ton of major mistakes along the way that nearly brought him back to square one.

[00:01:04] Andrew Wilkinson: The day after the stock market crash, they were like, we're totally unhappy. We want all of our money back. And the refund was going to basically empty my bank account down to about 500 bucks.

[00:01:14] Sam Parr: Andrew tells us about all of the crazy ways he spent his money, from luxury items like cars and houses to investments and attempts at goodwill. He'll tell us what he regrets, what he'd do differently, and how he lives his life now. After all the lessons he's learned through founding Metalab and creating tiny.

[00:01:37] Sam Parr: I'm Sam Parr, and this is money wise. Just scroll through Instagram for 30s and you're gonna see a ton of stuff out there on how to get rich, but none that really teach you how to handle life after you've already made a little bit of money. I'm co-founder of Hampton, a community of CEOs and business owners. Our members range from new startups with ten employees to public companies with hundreds of millions in revenue. And because I run Hampton, I'm able to see all types of private conversations about money, and I think some of those should be done in public. Hence this podcast with money wise, we provide advice by speaking to people who have made a lot of money, and they're radically transparent about all of their numbers, which means their monthly expenses, their portfolios, and more importantly, all the personal issues and problems that come with being successful and how they're solving them. And of course, if you're the CEO of a startup, you guys got to check it out. Join Hamptons.com. You'll be part of a group with eight people who are similar to you, meaning they have similar sized businesses, similar problems in their lives, and we have thousands of members and hundreds of in-person events. So check it out. Join Hamptons.com. Having a lot of money in your late teens and early 20s is wild. Of course it's awesome. However, it is difficult to navigate all of this when you haven't really finished maturing. You're basically still a kid. We've had a few people on this podcast who have made money later in their lives, and pretty much everyone is grateful that it happened that way. But what if you're like Andrew and you make a lot of money at a really young age? As a young guy with access to a lot of cash flow at an early age, Andrew made a lot of spending choices that he thinks simply weren't worth it. And through trial and error, he found choices that he thinks are worth it. But before we get to those, I want to tell you a little bit of background about how Andrew made his money.

[00:03:22] Andrew Wilkinson: I figured out that I didn't want to do coding, and so I started hiring other people to do the coding. And then I realized I could hire other people to do the design. And before I knew it, I had a business without meaning to. And I ran it really profitably.

[00:03:37] Sam Parr: Right away, Andrew started paying himself really well, which, by the way, he thinks all business owners should do instead of building towards an exit.

[00:03:44] Andrew Wilkinson: I think businesses need to make their employees happy, their customers happy and their shareholders happy. And I think one of the mistakes a lot of people make is they don't really make the shareholders happy, and that's themselves. I mean, ultimately, you're the one doing all the work, and I've always felt that you should get paid well. You know, you should make sure your employees are paid first and your customers are happy. But if those two things are true, there's no reason why you can't pay yourself well. I mean, in the first 2 or 3 years of the business, I was paying myself 250 to 500 K a year, and I have continued to pay myself really well and live the lifestyle that I wanted. And I think that one of the mistakes people make is that they don't pay themselves well. They kind of starve themselves, and it puts them in this zombie like fasted state where they'll do anything for food, and they think they need to sell their company instead of just going to the bank account and paying themselves really well and making dividends or living off cash flow. So that's where I focused is ultimately, my businesses were there to build a great life for me, and I did that from pretty much day one. I gotta say, like the best money I ever made was that money going from making 650 an hour to suddenly having this design agency and making tens of thousands of dollars a month was incredible. Not having to worry about my rent, being able to go buy steak dinners, pick up the bar tab. Everything else pales in comparison to that. That is the best money you'll ever make.

[00:05:17] Sam Parr: With the cash he was making, he realized he could build more businesses and increase his cash flow.

[00:05:22] Andrew Wilkinson: You know, I started out in the first couple of years and I had one business, but pretty quickly I started a lot of other companies. And so, you know, my design agency was making pretty good money. I was probably making like between 30,000 and $100,000 a month of profit within the first five years. But I got really excited about trying to diversify.

[00:05:47] Sam Parr: So by year five, you're around 1.2 a year in profit. Is that right?

[00:05:53] Andrew Wilkinson: Yeah, yeah. So I started trying to diversify. It's the classic story where everyone fetishizes a different kind of business. And for me, the business that I wanted was a SaaS software company. And so I was taking almost all that profit outside of the 500 K or so I was paying myself. And I was pouring it into those businesses. And so on paper, I'd kind of be up 100 K of net profit, and then I'd take between 70 and 80 grand a month and just pour it into all these new businesses.

[00:06:26] Sam Parr: What age were you when you started doing that?

[00:06:28] Andrew Wilkinson: Probably like 21, 22. And that was really hard. That was exhausting. And at that point, uh, a couple years in, I sold one business. I had maybe 3 or $4 million a year of cash flow coming in. And I decided that I wanted to start investing. And I basically copied Warren Buffett and started buying small tech companies and just growing them over time and holding them.

[00:06:54] Sam Parr: Andrew continued to hustle with this focus on cash flow through most of his 20s. And then he got his first taste of real liquidity.

[00:07:06] Andrew Wilkinson: So I'm 27. I'm running these five companies. I wake up every day in a cold sweat. I'm kind of like just madly jumping between all the companies. And, you know, I'm making good money. But like I said, it's almost all going out to these other businesses, and I don't really have any sense of what my net worth is. I thought net worth was the money in the bank, right? So I always felt broke. I think I might have felt a little bit different if I understood how to value the businesses and earnings and all that kind of stuff, but I didn't get any of that. So in 2014, I sold a business for $7 million, and that was the first time that I'd had ever had like a large amount of money all at once. And I remember going to the ATM and printing out the slip and seeing this huge number with a bunch of zeros on it and being like, oh my God, I'm done. I can retire, I can do anything I want. I never have to worry about money again. And obviously that's not what happened.

[00:08:07] Sam Parr: So let's back up here for a minute. Throughout his 20s, Andrew starts making significant money, which at the time he's just putting into a bunch of different businesses, basically throwing a ton of ideas at the wall and seeing what sticks. Unfortunately, not all of them stuck.

[00:08:21] Andrew Wilkinson: I poured about $10 million of my own money over the course of 8 or 9 years, and ultimately I lost it all, pretty much.

[00:08:29] Sam Parr: Meanwhile, he's spending a lot on himself.

[00:08:32] Andrew Wilkinson: I was being completely fiscally irresponsible. I would, like walk into a electronics store and there'd be like a $5,000 camera, and I'd just be like, I want that. And the reason I was like that was because when I grew up, my parents basically said no to everything, right? And my parents didn't have a lot of money, so I didn't resent them. But I was obsessed with computers and electronics, and I never got them. And so as soon as I could afford them, I was so desperate to experience what it was like to have money and to spend it recklessly that I did with abandon. I will say, like, it really kind of took the fun out of it. I would be so excited to, like, buy a new laptop a couple years before. Suddenly I'd just, like, buy a new laptop because I felt like it and it was just kind of empty. I was very consumeristic, and I'd go on these shopping sprees and get home and be like, what am I doing? Like, why do I have all this stuff?

[00:09:28] Sam Parr: And so in 2008, Andrew got a really big wake up call.

[00:09:32] Andrew Wilkinson: In 2008, the stock market crashed. I was literally in this situation where I was gonna go bankrupt. I had this client who demanded a refund. Literally, they were happy for the month before the stock market crashed in 2008, and then the day after the stock market crashed, they were like, we're totally unhappy. We want all of our money back. And the refund was going to basically empty my bank account down to about 500 bucks.

[00:10:01] Sam Parr: Let's move back up the timeline to when he's 27 and he gets his first real big liquidity. Here's how his spending changed.

[00:10:08] Andrew Wilkinson: I went through a long period where I really wasn't spending very much, and I was living way, way, way below my means.

[00:10:15] Sam Parr: What's your definition of much, though?

[00:10:17] Andrew Wilkinson: Well, I was probably spending 250 to 500 grand. Maybe. Some years I'd spend up to a million. Let's put it this way. My net worth was probably 75 million. And I was living in a $2 million house. Driving a Tesla wasn't doing anything crazy. And I'd say the big thing that I started doing that was expensive and silly. Was flying private, and I've always been someone who hates traveling. And there's something just so magical about just rolling up and getting on a plane and going. And I used it mostly for business to meet interesting people. And the way I thought about it was, you know what? I wouldn't do this trip otherwise. Like, it's such a pain in the ass to go on a trip just to meet one person or something. But if it's someone interesting enough, I'll spend the, you know, 15 grand or whatever to charter a plane to fly to San Francisco for the night. And I'll go have dinner with someone amazing. And I found that it really paid off. And so I got totally hooked on that. That's one of the only, like, rich people things that I think is actually worth the money.

[00:11:23] Sam Parr: One of the only. We'll talk more about what's worth spending money on and what isn't in just a minute. And no, we're not going to settle for the usual fast cars aren't worth it narrative. Andrew made some personal spending decisions that didn't exactly pay off. But first, I want to get a better understanding of what that $75 million net worth looked like. That's coming in just a moment after this quick ad break. So let's talk about the 75 million. At this point, Andrew is basically using all of his cash flow to buy more businesses. So what does that look like for his net worth?

[00:11:56] Andrew Wilkinson: Well, his all in privately held companies pretty much.

[00:11:59] Sam Parr: Surely not all of it. Surely you had you didn't have 10 or 20% liquid? No. What was your income.

[00:12:05] Andrew Wilkinson: 5 million. Maybe 7 million. Something like that.

[00:12:09] Sam Parr: How do you not have any liquid savings or public equities when you're bringing in 5 to $7 million a year, though?

[00:12:15] Andrew Wilkinson: Well, I mean, I poured it all into buying businesses, so I took the money I made from selling that business, and I put it all into buying businesses. So I was growing my cash flow pretty rapidly. I wasn't that liquid. I would sometimes have some cash, but I would almost always deploy it into another private deal. I mean, I was just buying businesses Business is constantly one after another.

[00:12:37] Sam Parr: That's a pretty wild portfolio. And that's because I always talk about safe investments. I prefer index investing. And so this is sort of the opposite of what I like. But that's totally cool. There's a lot of different ways to go about it. And yeah he's getting a lot of cash flow. But then something happened, something he had no idea that was coming and changed his perspective completely.

[00:13:02] Andrew Wilkinson: We had grown a ton, and the business was doing tens of millions of dollars of profit. And we also took a business public. And I remember looking in my trading account and seeing my stock portfolio, and suddenly this previously private business, which, you know, I owned, but I didn't really know what it was worth, was worth hundreds of millions of dollars. That kind of slapped me in the face. And when I saw that, I was like, man, what am I doing? I'm building up all this cash and I'm not converting it into anything interesting.

[00:13:39] Sam Parr: How much was it worth at that point, you think?

[00:13:41] Andrew Wilkinson: My personal stock in WooCommerce was worth over 200 million.

[00:13:47] Sam Parr: That's insane. Right?

[00:13:48] Andrew Wilkinson: It was crazy.

[00:13:49] Sam Parr: That was probably the first time that you actually crossed. Like, not only did you cross nine figures, but you crossed it in a fairly liquid. Actually, I don't know how liquid things are when you're the CEO or the founder. I don't know if you're actually allowed to sell it, but liquid enough that you could get loans on it probably fairly easily. So that was probably like the first time that a you passed some huge number or at least the next threshold. But B it's like real money.

[00:14:14] Andrew Wilkinson: Yeah, it felt like a big, big jump. And I mean, I already knew I was there on paper. Woocommerce was actually one of the smaller businesses that we owned at the time. And so I knew that if that was worth 200 million, then, oh my God, you know, the rest of the businesses could be worth close to a billion or something like that.

[00:14:38] Sam Parr: Crossing nine figures in net worth was a major turning point for Andrew, and this is when his spending habits changed again. This time it's not shopping sprees at Best Buy or whatever he used to do. Instead, this time it's a lot bigger, and he quickly learns that it's not all that it's made out to be. But there are some exceptions.

[00:14:57] Andrew Wilkinson: I bought a Porsche 911 turbo.

[00:15:00] Sam Parr: No, that's not the exception.

[00:15:01] Andrew Wilkinson: It was loud and uncomfortable. And, I mean, it's an amazing car. Don't get me wrong, but I just kept thinking like, eh, people think I'm an asshole when I'm driving around like nobody looks at you. There's a great Morgan Housel line, he says. Nobody looks at you in a fancy car and says, I want to be like that guy. They go, I wish I was that guy, right? Nobody cares. And they might actually be thinking, what a prick. It would always be like a 65 year old man. It's never a hot Instagram model. It's always a 65 year old man. Girls don't care. They're like, oh wow, what is that like? And they'd ask me questions about it. And I like, don't even know anything about the engine or the specs. Like it was just meaningless. So I felt like a bit of a prick. And it wasn't that comfortable. And so I ended up selling that. I have one $50,000 watch because. And it was more aesthetic. Like, I love the aesthetic of it. It's the Steve McQueen Rolex explorer. But otherwise the watch I wear every day is like a $4,000. Not crazy nice Rolex. And I've got a cheap omega, and I don't know, I don't get any joy out of that. And I've sold most of those. I don't know, man. I like I'm sitting here right now and I've got a $5,000 Fender Stratocaster that I haven't played in two years. Like I should not own it, right? It's like I bought the best one in the store and I barely play guitar. I haven't played guitar in like 20 years, so it's like things like that actually just make me feel guilty and shitty about myself. I tried chartering a yacht. Chartering a yacht is insane. This is never going to be a budget vacation. Typically a weeklong yacht charter and somewhere like the south of France is going to be upwards of €200,000 per week for just 12 guests.

[00:16:45] Andrew Wilkinson: It costs as much as a lawyer's salary for like, a week, right? Like, what do you mean, ludicrous? I'm seeing a lawyer's annual salary. No, it's like over $200,000 for, like, a week. And that's not even, like a crazy. I mean, it is a pretty big boat, but it's not even that crazy. Like, I'd show my really rich friends. Oh, I chartered this yacht, and they'd be like, oh, that's cute. Like, it's not like a crazy one.

[00:17:09] Sam Parr: Who did you charter a yacht with?

[00:17:11] Andrew Wilkinson: Just my girlfriend and some friends. And at first I was like, wow, this is so beautiful. We're in the middle of nowhere. But pretty quick, I was like, why would I want to be isolated in the middle of the ocean, away from everybody? Like, I find this to be really weird and lonely. That all these rich people fly to these amazing places and then never meet any of the people that actually live there.

[00:17:30] Sam Parr: All right, so we'll check off car. We'll check off chartering a yacht. What else is on the list of things that you were able to check off?

[00:17:37] Andrew Wilkinson: So I tried buying multiple houses. So I bought another house in Vancouver. I was spending a lot of time over there, so I bought a place there, and I bought a lake house that I'd always wanted. Having multiple houses is really. Yeah, it's a total pain in the ass. You know, that trite phrase, the things you own end up owning you. And I just found that my life turned into a series of questions from my assistant was like hey, the pavers on this pathway need to be redone, and it's going to be $5,000. And the roof needs to get redone. And this person is staying there this weekend and they want.

[00:18:15] Andrew Wilkinson: This or whatever it is. I just found it to be a total pain in the ass, and I ended up selling one of those houses. The lake house, though, was the best thing I've ever spent money on, and not because it's a second house or flashy, but because it's not about anything except for family and friends. When I go there, I'm bringing friends up there. I'm hanging out with my kids. I'm away from work. I'd say that and flying private are both worth it.

[00:18:41] Sam Parr: How far away is your lakehouse from your main residence?

[00:18:43] Andrew Wilkinson: 45 minutes. And that's another thing, is people do this stupid thing of buying a house that's like three hours away or a flight away or whatever. I think, like, yeah, it's hard to it's hard to use something that you can't get to. You know, you're going to go like for ten nights a year or something like that otherwise.

[00:18:59] Sam Parr: I bought a second home that was two hours away, and my wife, over the course of it, was just me. We didn't have a kid at the time. Over the two years, she slept there five times.

[00:19:09] Andrew Wilkinson: Yeah. It's ridiculous.

[00:19:10] Sam Parr: It was completely unused.

[00:19:12] Andrew Wilkinson: And when you get there, you're like, dude, why isn't the Apple TV work? Oh my God, these blinds suck. I got to fix this thing. I got to fix that thing. So it would.

[00:19:19] Sam Parr: Have been much better to rent an Airbnb each of those times.

[00:19:23] Andrew Wilkinson: Totally. So in terms of things that are actually worth it, I have a beautiful house on the water. My primary house. There's something really lovely about like investing in amazing space for you and your family. I think that has been worth it. I think having the lake house has been worth it because it's about family and friends and disconnection. I think the private jet definitely is worth it, but there's a lot of downsides. Like there's a lot of downsides to money.

[00:19:51] Sam Parr: When we started this episode, I made a promise. I told you we weren't going to make this episode. That tells you the obvious things like buying fancy cars and how they probably aren't going to improve your quality of life at all. And we did obviously just get into that a little bit. But this is where it gets deeper. A lot of people have this idea about money that if they have a lot, they would use it to do good for friends, family, community, the world, things like that. And we end up building up these grandiose ideas about how we're going to do that. But these ideas, I think, are a lot more complicated than people think. Andrew tried in a few different ways to do something good with his money, and he learned a tough lesson. Despite your best intentions, money on its own doesn't do good. His first run in with that lesson was with his family, and he's going to tell us all about it right after this quick break from our sponsor.

[00:20:39] Andrew Wilkinson: I think money really ruins families. I know more families that have been ruined by money than families that have been brought together by money. I think it's a very corrosive, toxic force. I don't think having too much of it is a good thing. I think, uh, you know, it causes a lot of perverse incentives.

[00:20:56] Sam Parr: When you say family, are you talking about your brother and sister? Are you talking about your wife? Your children amongst themselves? What are you talking about? Where it ruins family.

[00:21:04] Andrew Wilkinson: All of it. When I was a kid, my parents would fight about money. And so growing up, I just embedded in my brain was this idea that if I get money, everyone will be happy. And I'll make them happy with money. And that hasn't been the case. You know, I worked with two of my brothers, and that caused a lot of conflict. We've worked a lot of it out.

[00:21:24] Sam Parr: Are you guys close now?

[00:21:26] Andrew Wilkinson: Yeah, we well, we we go through phases. We we love each other and we get along fine, but it's like there's a lot of hot button topics and things we don't talk about and disagree about politics and all the usual stuff. You know, with my parents, it's been a little complicated too. And there's something odd that happens when the son is wealthier than the parents.

[00:21:46] Sam Parr: It's like the age where your father gets old enough and you get strong enough to where you learn that you can beat him up. Like, I remember like the moment I realized that my parents are not infallible and they can make mistakes and maybe the things that they did to me when we were younger were mistakes on their end or weren't like the right decision. I was like, oh my God, you're just human. And then when I sold my company, it was in the Wall Street Journal or something like that, and they were like, I don't understand, you have health insurance. Like that was their immediate response. And then over the next 6 to 12 months, when I was able to take them on vacations and things like that, and they started understanding a little bit more, and I revealed to them the number, it changed from excitement a little bit to intimidation to where they felt intimidated. And at times I think they felt embarrassed, like I'm not used to these things and I don't want to bring you down. I'm embarrassed. Or why are you embarrassed of me? Things like that. And it did create like a weird power dynamic that I felt very uncomfortable with because at the end of the day, I still Revere them and like, hold them up to where I will bend over to please them versus they should do that for me. I don't think they should.

[00:22:53] Andrew Wilkinson: It's totally bizarre because I think everybody has these fantasies about money and being able to shower it down on those that deserve it. Like, let's say you have a friend and your friend is like a professional violinist and they're amazing. And, you know, you think the world of them, but they have a hard life because they're not making very much money. And you just go to them and you say, hey, here's $1 million. Dollars. I would be so worried that that million dollars would pervert or corrupt that friendship. Make them feel weird and indebted to you, or you feel like they owe you or I just I think it's really, really hard to actually use money in positive ways. Even donating money can be fraught. Like, I've done quite a few things where the goal is not to make money. Like I'm doing something for the community and I've lost like 5 million bucks on it or something like that, and all. It's resulted in like very, very negative experience and even charity. People can see through a negative lens. And it's like if you talk about the charity you're doing, you're a douche because you're bragging. And if you don't talk about it, then no one knows you're being charitable and they criticize you for not being charitable.

[00:24:09] Sam Parr: It can be very complicated to use your money for noble causes. Money doesn't solve problems or make things better, but it is a tool to help. One of many tools. Another one of those tools is time. We talk a lot about how one of the biggest perks of this lifestyle is having autonomy over your life. You get to choose if you want to continue working. You get to choose if you want to travel full time. Or you can be like a good friend of mine who decided to quit working and spend a lot of his time at water parks. True story. You can also choose to spend time embedding yourself in what you're passionate about, and do good that way and gain knowledge, make connections, and build useful skills. There really isn't a shortcut to make that happen, and even the seemingly small projects can suddenly take up a lot of your time in a way that you didn't really expect, which is something that happened to Andrew.

[00:25:01] Andrew Wilkinson: I bought a building that's near my house. It's this amazing building. It's on a great corner, and I have all these awesome ideas for what I could do to it, and I think it would transform the neighborhood. I think it would be a really positive thing, and I could put a lot of great businesses in there that I would love to use and my neighbors would love to use. So I buy this building and I say, yes, and I'm very, very excited the day I buy it. You know, the first week or two, I'm excited. I'm texting people about it. I'm.

[00:25:27] Sam Parr: And then you learn about like the permits that you need.

[00:25:30] Andrew Wilkinson: Exactly. So now it's like, oh, I'm negotiating leases and oh, there's financing documents that need to get signed, and I've got to go and do a bunch of meetings with all the people that might want to be there. And, and I just get dragged in.

[00:25:44] Sam Parr: In reality, unless you plan on committing to doing something really intensely, I think donating is one of the best things you can do. And even with donating, there's a lot of nuance to be aware of. And so once again, I will direct you to one of our episodes that we did with this guy named Mike Beckham. It's one of my favorite episodes of all time. And like Mike, Andrew has come to love donating.

[00:26:05] Andrew Wilkinson: Giving money away is joyful, right? It actually feels really good to shed it and help others. Why wouldn't you want to do that in your own lifetime? Right? Like Bill gates has basically said, like all the money will be hopefully spent before he dies or close to.

[00:26:19] Sam Parr: So why don't you do that?

[00:26:21] Andrew Wilkinson: That is what I'm doing.

[00:26:21] Sam Parr: Do you think you're going to give it all away before you're dead? I mean, are you going to die with nothing?

[00:26:25] Andrew Wilkinson: That's the goal. I want to die with certainly no assets to myself or close to.

[00:26:31] Sam Parr: Would you give it to your children at all?

[00:26:33] Andrew Wilkinson: I think I'd give them proportionally a small amount. Right. I don't know what that looks like. I think the goal would be to effectively give them a really awesome version of Social Security, where they always know that they're going to have a house and medical care and all those basics, but ultimately they're on their own. But as of right now, I don't think I'm going to give very much to my kids at all. I think it's all going to go in the foundation.

[00:27:02] Sam Parr: When it comes to having a lot of money, like anything else, I think the idealized version is always better in your brain than it is in reality. It's still great, but I think that people think it's going to be one thing and oftentimes it's something else. Of course, that's not saying having money doesn't make life awesome. I think it can, and it does. It'd be ignorant of me to say that any of the luck and the money that I've made hasn't made my life better and easier, because I think it has. But the whole point of this podcast is to help people not fall into the trap that makes people think that everything gets better automatically when you make money. Money itself will not make you a better person. I don't think money itself is going to make you a happier person. And like we saw with Andrew, just because you buy a really nice fancy guitar, it's not automatically going to mean that you can play it well. Andrew had an analogy that I liked a lot when I asked if he was afraid of losing everything that he's built.

[00:27:57] Andrew Wilkinson: Wealth is a little bit like travel. You know how everybody fetishizes like, oh, I'd be so happy if I just, like, moved to Hawaii or if I just travel to Europe, everything's better in Europe. The problem with travel is that your brain comes with you, and your brain is what causes the feelings of anxiety. And so what I've realized is that the feeling of anxiety that I have is actually just inside of me. Taking a SSRI and anti-anxiety medication has helped me more than having any amount of money. It's just my personality. Right. Like, only the paranoid survive. And even now, I'm like, what if democracy falls and we have a dictator? What if I need a second passport? Do I need, like, gold bars in my basement? Like I just have a paranoid mindset.

[00:28:51] Sam Parr: Andrew's one of my great friends, and I love him to death. I love that I've been able to live through him a little bit, because he's so transparent with all of his numbers and some of the issues that he's had and some of the things that work, some of the things that don't. Things like that. And what I've noticed with Andrew, along with a lot of my friends, is that they have this issue that my buddy Ramit Sethi always says, which is that spending money is like a muscle, and the muscle to earn is a little bit different than the muscle to spend. And I love that Andrew is super transparent about using that muscle and letting me know what worked for him and what didn't, and things like that. And so a big takeaway for me is that money is easy to spend, but it's hard to spend well. And so I want to give a shout out to Andrew. Andrew, thank you for doing this. You're always transparent. I really appreciate that. And if you want more transparency like this, we're going to keep releasing these episodes of money wise. However, if you want to dive a little deeper, you guys have to check out Hampton. It's Join Hampton Hampton's my company. We're a community. We're a network of CEOs, business owners, things like that. People who have businesses that are a little bit smaller in the 510 employee range, all the way up to companies that are much larger.

[00:29:56] Sam Parr: We're talking publicly traded companies that are doing hundreds of millions in revenue. I'm able to find a lot of the conversations for money wise in the Camden community, because people are super open about money, about growing their companies, about winning, about losing all these things that typically never happen in public. So if you want to check it out, go to join Hamptons.com. You'll be able to go to the website. You can apply. My partner and I, we watch 100% of the interviews, and then we'll put you in a group of eight people who have similar sized businesses as you, which also means similar types of problems, things like that. It's pretty life changing in my opinion. And you'll also have access to hundreds of events throughout the year, as well as thousands of other Hampton members. So check it out, join Hamptons.com. And of course this podcast is made by Lower Street. I always like giving them a plug because I'm super happy with their work. If you are a company that wants to make a podcast like this, it's a pain in the butt to be honest, and lower street makes it a lot easier. So check them out. Lower street. All right guys, we will see you next week for another episode of Moneywise.