I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson

25:13You're going to buy the building. Over time, you can get an increased yield by increasing the rent. But there's a ceiling on that rent, and you can't innovate to make more money. Whereas in a business, let's say a digital business like a web design agency or a software company, you can take your profits and you can actually grow the business and you can increase revenue. It's very difficult to do that in real estate without massive capex. Yeah, I think they do the same thing, right? They take the profits or they refinance and go buy a second property. What's wrong with that? That works. Yeah, I mean, you can do it.

25:48I don't know. It's just not something I've spent a lot of energy on. When someone tells me that they're going to go do it, I think of all the things they could do, that's a pretty solid approach. And I think one of the things I've noticed, I know a lot of really wealthy real estate people, and I've been fascinated by how illiquid it is. So you'll meet people who have$2 billion of real estate, but the actual profits that come out of it are like$20 million a year, which is amazing. right? It's made their family wealthy. The bank understands that they live a good life, but they don't actually have that much liquidity.

26:25And it's often tied up in the next project and the next project and the next project. So I think it's a great way to make your kids really, really wealthy and, you know, ruin a few generations and then they'll buy an F1 team and then lose all their money. All right. We have nothing in the S tier yet. So I got to try to get there. I think this is the guy to do it. So I have an icon here of Warren Buffett and this represents investing. So just being an investor generically, but I think maybe the way I was really thinking about this, because I think Buffett is a little unusual in the way that he's structured his company.

27:00So really this is to me owning an investment fund or being in the money management business, investing other people's money and taking fees and a profit off the top of it. Well, no, I would argue a little bit differently. I'd say investment management is an incredible business, but I wouldn't put Buffett in that category because he doesn't actually manage other people's money. Yeah, I know. That's sort of the exception here. So the distinction I would make, let's say you're a hedge fund manager, like my friend Bill Ackman. So Bill, for example, he went out, he raised hundreds of millions of dollars.

27:34He bought a bunch of stocks. He would go and advocate for these companies to improve, and then he would take fees on that. And if you think about that business model, you actually don't need to really put that much money into it yourself. And you can make a profound amount of money if you perform. The structure of hedge funds is typically 2 % of managed assets plus 20 % of the profits. So let's say that you raise$100 million and you triple it in a short period of time. You can suddenly make$30,$40,$50 million of carry and fees and stuff. So those are really tremendous businesses, in my opinion.

28:14The problem with them is that your investors can pull their cash out. And so what Bill has done that's so smart, and I would rank Bill as S and Buffett as S, and then other asset managers lower, they have permanent capital. That's the real distinction. And that means their investors can't pull their money out. They're going to make those fees no matter what. And they can literally, I mean, if you think about the simplicity. Sorry, why is it permanent capital? I can sell my Berkshire stock today. I can sell my Pershing Square today. What do you mean it's permanent? What's permanent about that part?

28:43Or are you not talking about that? Is there some other money? So you're just trading little stock certificates of ownership between the businesses. But what I mean is typically a hedge fund manager would say, let's say I give a hedge fund manager a million dollars. I can withdraw that capital. And the only way that they can give me that money back is by selling stock. So let's say you're the hedge fund manager. you go out, you invest in some company, the stock goes down, I lose faith. I say, Sean, I want my money back. You have to go sell part of your stake, potentially losing quite a bit of money.

29:20Whereas someone like Buffett or Ackman, people are just trading the stock certificates, right? Those are just ownership shares. Sure. Even when I'm out, whoever I sold it to, they're in. So the money is essentially there, even if the stock price goes down. Exactly. And if you think about it, just in terms of the beauty of their business model, Buffett's is more complex. With Bill's business, for example, he simply just goes out and he buys 10 stocks. And he has 50 employees and he makes hundreds and hundreds of millions. Sometimes, some years, I think he makes billions. Wait, wait, wait. So Bill Ackman's firm only has 50 employees?

29:56Yes. 50 employees. I think he manages, how much does Bill Ackman manage? 16 to 20 billion, somewhere in there. So, okay, let's call it 15 billion. So he's got$15 billion under management. You know what? We got to break the rule and we got to do a little public math here. I know. He takes a 2 % fee or he doesn't take the fee? He takes a fee on, I think it's a blended fee of between 1 % and 2%, depending on the pool of capital. Let's call it 1.5%. So let's say he's taking 1.5%. So his firm with 50 employees, whose job is to go and analyze and find 10 stocks to own, is making$200 million plus a year in cash flow off of just the fees.

30:40Well, you got to remember, so that's revenue, cost. There's cost to it, transaction, legal, all the other stuff. And again, I think that number swings around based on the performance and stuff as well. Right. But how high could that cost be? He's got 50 employees and it's legal. He's not doing M &A with private companies. He's doing public company investing. I believe, I mean, we don't need to do the public math. People can look it up. But if you look at Pershing Square Holdings, his public company, you can basically see what they pay him in fees every year. Okay, that's incredible. And let's not forget, that's no matter what.

31:12That's not the reward. That's not the 20 % reward. I remember talking to him in 2020. He was freaking out about COVID. And he had put$25 million into a derivatives position, betting, kind of buying fire insurance against COVID, dropping the market. he made$2.4 billion of profit or something insane off of that. I think it was$25 million bet. And you think about he got fees on all of that. Like it's unbelievable. And he also owns, let's not forget, he owns like$6 billion of that capital he manages. So that's his money. Okay, that's incredible. What about the other side of it where you talked about the hedge fund managers?

31:53So where are we putting them? So if Buffett and Ackman are your first S tier, where are you putting the general hedge fund manager, money manager, who's got assets under management, but not permanent capital the way you're doing? I'd give it a B, just because of the nature of the swings. And you can, you're pretty much guaranteed as a, let's say you're a very, you have a large venture capital fund or you have a large hedge fund. You're pretty much guaranteed over 10 or 15 years to become a decamillionaire almost no matter what, which is kind of a crazy thing about the model. But you might get blown up at some point.

32:31But explain the inconsistency, because I believe Ackman also has like blown up or almost got blown up, you know, a couple of times. What's the difference in your mind between what you're talking about? Bill keeps getting shot and then miraculously getting back up. And I think one of the - He's the 50 cent of the investment world. I mean, he has a great line. He just says the secret to success in business is just getting back up over and over and over again. And what happened to him was Bill has made so many incredible investments. But I believe in 2014, he bet against Herbalife, which was an MLM.

33:09And then he also bet on Valiant Pharmaceuticals, which was a pharmaceuticals company that was basically increasing prices. It was a very elegant, very smart model, but it was run in a kind of unethical way and the company blew up. So between Herbalife and Valiant Pharmaceutical, his investors lost faith in him and a lot of them pulled their cash. And so suddenly his whole hedge fund is blowing up. And fortunately, in 2012 or 2013, Bill had raised, I believe it was like$4 billion of permanent capital in Pershing Square Holdings. And Bill was able to basically bet on himself. He went to JP Morgan, he went to Jamie Dimon, who he's buddies with, and he got a$500 million or something loan to bet on himself and buy more stock.

34:00and he managed to come out the other end absolutely killing it. And I think the big lesson for him was don't short stocks because he was shorting stocks and be a lot more disciplined about investing in businesses with leverage or exogenous risks. I think there's this funny story. Bill went out and he bought these little plaques and he puts them on every single person's desk at Pershing Square and it's the Ten Commandments. It's like thou shall not short stocks. Thou shall not invest in a business with too much debt, etc. So Bill has really learned the lesson and been through it. Do you know how in venture capital, the sort of the normal VC fund isn't going to, it's basically like a pretty poor performing asset class because you're illiquid for 10 years.

34:50And then the sort of, you know, the IRR that you get out of it is less than if you just kept it in an index fund. So like venture capital on the whole is a pretty bad asset class. of course, the top funds perform pretty well. Is basically hedge fund management the same distribution or do they on average do better? So Warren, there's this great story. There's this guy, Ted Saeeds, who's a fund manager, a fund of fund manager. And he had lunch with Buffett and he said, Warren, I'll bet you, I think it was a million dollars that I can choose a basket of hedge funds and they'll outperform the S &P.

35:24And I believe he lost that bet to Buffett. Buffett basically said, on average, funds do not outperform, which is very true. I mean, most hedge funds, most venture capital do not perform. And I think that's kind of what's distinct about private equity. I think, I don't know for sure, but I think most private equity funds at least have a reasonable return. Hey, quick message here, because you know that feeling when you send a wire and it actually works? No friction? Well, I've used Mercury for years now, and let me tell you, it just works. And that's why I use it for not one, not two, but eight of my companies.

35:56From credit cards to invoices, I have everything in one place. There's no janky dashboard. I'm never told, please visit a local bank branch. None of that tomfoolery. And a few months ago, I landed a big client. And the first thing I did, I sent them a clean branded invoice. Boom, deal closed, cash in the door. That's the kind of banking experience I want. And that's why I use Mercury. So if you're running a startup and you want banking that feels like it's built in this century, well, go to mercury.com and get started in minutes. Mercury is a financial technology company, not a bank. Bankless services are provided through Choice Financial Group, column N8, and Evolve Bank & Trust members, FDIC.

36:30All right, we got a couple more I want to do. Local services. So you're starting a local pest control business, HVAC, you know, things that are, I got the handyman icon here because it is, you know, something that you do with, you know, a guy wearing boots and overalls that comes and does something in your local area. So I would say that's a C. Those are hard businesses. But if you can dominate a local industry, let's say you're really good at internet marketing and you own an HVAC business and you're able to hire great technicians. There's only so many technicians out there. And so they're kind of fundamentally difficult to compete with.

37:13And I think they're challenging. I know a lot of people over the last few years who have bought HVAC businesses or plumbing companies. And they're like, you know, guys that look like you and me. And they, you know, they come in and they're dealing with all these blue collar guys. And they're like, who the fuck are you? Why would I come and work with you? And so I think they're good businesses. If you're like, let's say you're a very enterprising HVAC technician and you want to start one of these businesses, you can do phenomenally well. But I think they're actually quite difficult to operate for a outsider.

37:45All right, I got a couple more. Venture capital slash angel investing. Although they're a little bit different. One's investing other people's money, and one's investing your own. I bucketed them together here. I would put angel investing as an E. I think I view angel investing a little bit like playing roulette. I like to play poker. It has better odds. I look at private equity or buying businesses more like poker. And I just know, I think the classic entrepreneur story that you guys have talked about a million times is you make some money as a founder, you want to pay it forward. You don't really get stocks in real estate and businesses or acquiring other businesses.

38:22Or they seem slow or they seem a little too boring, a little too common. And you hear a Jason Calacanis, I'm the first investor in Uber and whatever. And so you want to do that same thing. And it's a little bit like, you ever been pitched by a founder and they have a popsicle company and they say, well, I know we're tiny right now, but there's this one company that sold to Procter & Gamble for$300 million. It's all story-driven. And don't get me wrong, there's amazing angel investors like Lockie Groom and people that do amazing stuff. But I think for laymen, it's a terrible, terrible thing to do with your money.

38:58Yeah, it does feel a little bit like golf. It's an expensive hobby, but if you enjoy it, fantastic. Give it more power to you. We talked about this, I think, on the last episode or two episodes ago. When I first started out, I got in the habit of angel investing. I have$30 million or something tied up in angel investments. Completely illiquid. I have no access to it. I'd much rather own like stocks and real estate or something. All right. I have one more here that's buy a local sweaty startup. Oh, we have Cody Sanchez entering the chat here. I couldn't find a good icon. So I just put Cody on here for lack of a better term.

39:31It's a picture of Cody at a laundromat. And I think she's, I don't know. I don't actually know, by the way, if Cody really pushes that you should buy laundromats but I think that's a little bit of a narrative. I'll use her as a figurehead for this idea that you should find a local sort of brick and mortar, a sweaty business, you know, go buy a boring main street business and you're going to cashflow. Then you reinvest the cashflow and you buy the second laundromat and then you buy a car wash and you keep going in that direction. Where does Andrew Wilkinson rank that model on the tier list? I mean, I love Cody and I love Nick, Nick Huber.

40:06I think what they're advocating is basically, look, don't go and work for someone else when you can create your own job. And I think if you can be an owner-operator... But they don't say that. I think if they said that, it would be a lot more of an honest broker, right? You said one key word, which is what they say is own your own business. And you said own your own job. And I think there's a big difference between those two things. Well, I think that's a fundamental question. Are you buying your own job or are you buying a business? If the business returns more than the cost of the owner's salary, then I'd say that's great.

40:38I'd say that's a C. Chris and I always say, if you can skip the line and instead of working your way up and starting businesses, you can just buy a already working business and just improve it. I think that's phenomenal. I mean, it's really a lot of what we've done. So my story, I started the web design agency, Metalab. That business grew. I then took almost all my profits and I started like 10 other businesses and almost all of them failed. It was really exhausting. And at the end of that process, I had one business that I could sell, another one that was kind of alive, but I started 10 and I'd put almost 10 million or$15 million into all these terrible businesses.

41:21If I had just taken, you know, the a million, 2 million a year and just bought businesses and just improve them, I think I'd be much farther ahead than I am today. Well, that's what you eventually started doing, right? What you did at some point was you guys decided to switch into buying businesses that are already working as your main business to be in. And I believe you guys invested, you can correct me if I'm wrong, but I think the initial kind of seed capital was you took something like five or six million bucks from Metalab's profits. And you were like, this will be the base. And then we'll try to find these sort of compounding businesses that we can hold for a long time, what you guys call wonderful businesses.

41:59Great. And that's what has become tiny, the public company today. I think the market cap is something like$200-something million. Yeah, basically, we just started buying businesses in 2013 when we read about Warren Buffett. And we're like, oh my God, this guy's doing easy mode. Why are we doing hard mode? But to be honest, Buffett has this great quote, I'm a better businessman because I'm an investor. And I'm a better investor because I'm a businessman. man. And I think that in order to be a good investor, you need to have run or experienced the chaos behind the scenes at different businesses.

42:34And I think the beauty of what we did was we got really lucky. So we went to the gym. We didn't deadlift 300 pounds. We got really lucky with Metalab and it worked. So that built our confidence to go try more stuff. Then we tried every bad business model. We did drop shipping. We started a restaurant. We did a skincare company, like all sorts of dumb stuff. We always joke, we put forks into electrical sockets. We learned a lot. And then we started investing. And so what we could do is we could look at these businesses and say, oh, wow, this is actually a really high quality business. And I know that because I've operated a similar one.

43:12And do you remember how much capital you started doing that with? Once you stopped starting new businesses, you decided to go start buying? I think it was like four or five million bucks. We basically sat down and said, okay, we're going to start this thing called Tiny. I'm going to own 80%. You're going to own 20%. And that was only because I had more capital because I was the one who owned most of Metalab. And Chris put in 500K or a million bucks and I put in the rest and that's it. We never put any more money in. So that's because I was going to seed or did every year oh we found a new business let's take more metal lab profits and put it into tiny or no no nothing i mean we merged so it was interesting so i actually owned metalab myself i own 90 of metalab and then my brother and chris and a few other people were small shareholders in it and so um that that's what basically i diversified with so i went off and in my family office, did all the venture investing and bought some real estate and bought newspapers and restaurants and other dumb stuff.

44:19But tiny itself really just grew from that original amount. So that's pretty incredible. I feel like I got to ask you this because I think you get a lot of shit nowadays. I think a lot of people go look at the tiny stock. And basically you see, I think you guys went, or you like did this reverse merger. and so then the stock basically like shoots up in 2021 at the kind of like peak era at that time. And then basically it's just a downward trend since then. And I think a lot of people I see on Twitter want to kind of look at that and say, oh, this guy calls himself the Warren Buffett of the internet and he says he buys these great businesses, but what's going on?

44:58Look at your stock. And so they see that and they say, man, is this guy like many other people on the internet who maybe either overstate their claims or whatever, right? That's a common problem on the internet, I would say, on the whole, is that you don't know who's real. You don't know who's actually good. And so you have this public company that's a little bit of a public scoreboard in a way. And people get really riled up about that. On the other hand, and this is kind of like, you know, the two parts of the trial, right? You have the prosecution, the defense in a way. The other hand, you say, look, there's a guy who took four or five million, you know, first created this design agency that was really successful as a business.

45:35has generated, you said, over$100 million of profit lifetime. And then you took, you know, $4 or$5 million and you compounded that into a$200, between$200 and$300 million business that holds all these interesting assets. And, you know, cool, like the stock prices go up and down. That's not necessarily the end of the deal. And even if you said, look, that's how big it was, that's still fantastic. I don't know a lot of people who are listening to this that have done anything that's more impressive than that, you know? So I admire, even if your worst case, least generous interpretation is the today's current, you know, stock price, that's still pretty damn impressive.

46:11So I guess like, what's your reaction to this? Here's, you're sitting there. You don't want to go out there and, you know, fight all the internet trolls or anything like that. But like, how do you see this? What's your take on this? It's pretty funny. Cause like, you know, we started in 2006, basically 20 years ago, bootstrapped this business until 23, when we went public. And over the last 10 years, I think since we started Tiny, we've compounded our earnings at 25%. We do almost$250 million of revenue. We have$65 million of ARR. We do over$40 million of EBITDA. And Chris and I still own the majority of the public company.

46:53And these are all things, you can look at the public filings and see. Also, we talked about asset management. I mean, we also own or we manage a$200 million fund managed by the public company with$40 million of it, our own capital. And that owns AeroPress, Letterboxd, all sorts of other businesses. If we include that, that adds another$65 million of revenue. So we're over$300 million in revenue across 30 businesses. And all the businesses in the fund are profitable as well. I don't know. I'm kind of like, if that's failing, like sign me up. Right. And, and I don't know what to say to the trolls.

47:34Like, you know, don't feed the trolls. Right. Well, let's take the, the, the vulnerable side a little bit, correct? Cause I always ask myself this whenever I get criticized and my first reaction is like, what the hell are you guys talking about? Like, do you not see, do you not see? And I want to like kind of defend myself. But at the same time, I always ask myself this just for my own learning, which is basically like, what about this is fair, but what is the fair criticism. And I think that's always been an important question for me. It keeps me honest because, you know, look, either I'm just going to ignore it.

48:02I got nothing from it. I'm going to get mad about it and think they're stupid. I get nothing out of it. Or I mostly, you know, disregard what I think is the sort of like off base line of thinking. But maybe there's, you know, some things that some part of it, that's fair. Oh, it is fair that I said this. It is fair that I didn't, I didn't do this. Or it is fair that I thought it would be X and actually it turned out to be why. You know, those are some things that are fair, right? So what would you say is fair criticism about you? First of all, I just want to say I really empathize with people.

48:31I remember watching like Shark Tank and I'd be like, oh, wow, Kevin O 'Leary, you know, he sold his business for billions of dollars. And then you go read the juicy gossip that, you know, he got $10 million or whatever out of that deal. And I think it's very easy to kind of have the one blurb and then judge someone. And I think before I went through this experience, I would just believe what I read on the internet and kind of enjoy it, to be honest. I think there's this dirty, horrible part of humanity, myself included, that loves when somebody who's on an upswing falls. Talk about Bill Ackman.

49:10Bill's an amazing investor, but he's loud, right? And I'm loud too. I'm extroverted. I like talking what I'm doing. I like talking about our companies and everything. And it's really, really fun to watch someone loud like me fall in the mud, right? And I see this in myself. You know, you kind of cheer and enjoy it. Like celebrities go through this too, where it's like they're awesome and everyone loves them. And then all of a sudden, you know, they like to shit on them for a few years. And then they love them again. Like Justin Bieber, everyone hated him for the last five years. Now everyone loves him again.

49:42I just kind of think that's the course of things. And I think it's kind of, I just got to eat humble pie. And there's a lot of great things I get out of being loud on the internet and talking about this stuff. I've connected with so many incredible entrepreneurs. I've made so many new friends. I love talking about this stuff and teaching people about business and stuff. But this is the price. And I'm willing to pay the price. And it sucks. And for me, it's a button, right? When I was a kid, I have ADHD and I'd always fuck up. And I'd always be the one in our family that was blamed for everything.

50:17And so being misunderstood is a big button. And I really have to resist getting on the horn and trying to argue with everyone because it really doesn't help. So I think for me, we're just focused on delivering good results and building great businesses, which we're continuing to do. And people on the internet are going to twist it however they want to. The reality is 60 % of the businesses that went public in 2023 when we did are still under their IPO price. So Asana, Sweetgreen, Coupang, all these other businesses, they're all under IPO. Does that instantly mean that what the founder has built is invalidated and they're a moron?

50:57No. And I think the really fair criticism, though, of us is our business is a bit confusing, right? Even our stock chart, like starting businesses. So I made all this money from the web design business, started a bunch of companies. One of those companies became the dominant seller of themes in the Shopify ecosystem. And Chris and I always had it in our head. We were like, let's take a business public. We'd love to do that. And so we actually went and we partnered with Bill Ackman. We had sold the business to a family office. We bought it back and we took that business public. And we took it public in January 2021.

51:38Do you remember what was happening in January 2021? Every stock was going to the moon. And so you have this business that's doing 40 million or something in revenue and like 7 million of EBITDA. And it goes to literally the day we took it public, it jumps from a$250 million market cap to 1.2 billion. And so we didn't take it public at 1.2 billion. But that first day, that's where the chart starts, right? And then the mania is over and the chart starts going down. And as the chart started going down, we ended up deciding, hey, let's take tiny public. So we merge into it. So really, like the tiny story is this, right?

52:18We've been compounding at 25 % from almost nothing. And what people see, unfortunately, because that's what's in the public market, is this little, you know, this little dip down here. And to be honest, I get it. I think you really have to take the time to understand the business and the story and why it looks like that. But I'd encourage people to do their research and actually dig in and understand what we own. Because from my perspective, I think we own a lot of pretty incredible businesses. And you still own the majority of the business? I do. And is that still the majority of your net worth, basically?

52:56So how much skin do you still have in the game? Yeah, this is what's so funny is like people, I mean, I've even, people have said like, oh, you did a pump and dump. And I'm going like, what are you talking about? Like I've sold almost no stock. And the only stock, I did one large transfer, I think of$8 million. I moved it to my foundation so I could start doing philanthropy, right? Like I haven't taken any cash out. I still own all the stock. And like people will say like, oh, you're a pump and dumper or something. Like, I don't know. It's just, it's kind of sad. Yeah. And so you hear all this, and you've also talked about this idea of the courage to be disliked.

53:34I think, you know, maybe that was the right book at the right time for you during this period. I haven't actually read the book. It's a killer title. What is the thing that I can learn, you know, from that book? So Sam just did that great, I love that episode he did, where he basically said, here's the recipe to a miserable life, and let's invert. and one of my favorite inversions is that you actually want people to hate you. You do not want to be liked by everybody. I think that's a great signal that you're doing life wrong. And I think if you told me this 10 years ago, like I would think that's insane.

54:09I remember I read this Warren Buffett quote, it takes 20 years to build a reputation and five minutes to ruin it. And for me, I really internalized that. I was like, oh my God, I need to make sure that everyone thinks positive of me. Right. I better protect this reputation then. Every founder I meet for coffee, I have to woo them and make them like me or whatever. And I really felt that I had to be consistent and predictable. So for example, I buy companies and I'm a Warren Buffett, like a wannabe value investor kind of guy. But I also really like startups. I like starting restaurants and all this other chaotic stuff.

54:50And people don't like that. and I remember the moment I realized what was going on. My dad retired. My dad was an architect and he retired and I took him out for a beer and I said, dad, what now? What are you going to do with all your time? And he was saying he didn't really know. And I said, well, dad, I've got money. Why don't we team up and you can become a real estate developer? You can build the things that you've always wanted to build. and he goes, what do you think someone's going to say if I suddenly call them up? They know me as architect, David. And all of a sudden I'm pitching them on a real estate development.

55:29People don't like it when you leave your box, Andrew. And I was like, oh my God, I know that feeling. Have you ever had a restaurateur friend who pitches you on a tech startup they're starting all of a sudden? Or your yoga instructor gets their real estate license, they want to sell your house or whatever it is. my mental reaction, I hate this about myself. My mental reaction is stay in your lane. I don't like it. It makes me uncomfortable. I don't know why. And it's incredibly hypocritical because I'm a flip-flopper. I love jumping around. I'm an inch deep and a mile wide. And so it's like, I hate in others what I hate about myself.

56:06And I realized we're all like prison guards. We all have these labels. For me, it's like, I'm an investor and an entrepreneur, But then it goes deeper. It's like, I'm in tech, not real estate. You know, no real estate allowed. I'm bootstrapped. You can't do venture. That's weird if you do that. I'm pro-crypto or anti-crypto. And these labels kind of lock you into this identity. And I've seen this in a lot of big public figures. So like, do you remember when the CEO of Goldman Sachs, David Solomon, it came out that he was like a DJ? He loves to DJ, right? This guy on the weekends and evenings, he DJs.

56:45And the press went crazy. There's an article in The Economist about how, you know, is Goldman Sachs suffering because he's, you know, DJing? Do you think they would have said that if he was playing golf? Right? Or like, you know, we see like Kim Kardashian get passionate about prison reform. We're like, fuck you, Vanity Project. Jonah Hill starts surfing. Let's make mean memes about him. Michael Jordan plays baseball, you know, betrayal. And so I realized our brains are just prediction machines, and they get upset when things don't match. And so for me, I realized I don't fit cleanly in a box, and it's messy like everyone else.

57:24And so I remember I started asking all my friends about this and stuff. And I was sitting up at my lake house with a group of entrepreneurs. And I talked to these guys and I said, look, what would you do if no one was looking? And one of my friends runs this massive industrial business, like a billion-dollar business. And he says, my happiest moment is behind the oven cooking for people. And I actually would want to start a restaurant. And I said, oh, would you want to, you just want to own a restaurant? He said, no, no, no. I want to be the chef of like a Michelin star restaurant. And he said, I feel like I could never do it though, because I have so much of my ego tied up in being a business person.

58:08And everyone would think I would, that, you know, I'd gone insane. And at that moment I was like, no, like I wouldn't. But when I think about it, I would definitely be gossiping and going, oh my God, he's lost his mind. Right. You know, and so he, you know, he's escaped the prison and we need to beat him with our batons. And, you know, you see this with like legal degrees, bad marriages, disappointing your parents, you know, the industry you've spent 20 years in. And the issue is like all these promises were made by the person you were before, you know, not the person you are now. And so I realized like I'm in this quicksand.

58:48I don't know what to do about it. And in January, I found this book called The Courage to be Disliked. And it's one of these books where you see the cover and you just instantly kind of know. You're like, okay, I kind of get it. And it's really interesting. It's written in this very odd way where it's a dialogue between this wise old man and a young guy. And the core idea is just seeking recognition is a trap. It's impossible to make everybody happy. And if you try, you're going to end up living somebody else's life. And so you have to be hated. You have to have the courage to be disliked. And reading this book, it was like someone gave me the keys to my cell.

59:26You know, I'm in this cell and there's no walls on either side. They're like, by the way, there's no walls. You can walk out. And so my New Year's resolution this year was I'm done with the likability game. I'm going to have the courage to be disliked. And I'm going to say what's true for me. And so you might have noticed, like I've been writing a newsletter. I'm talking about all sorts of stuff. I'm talking about, you know, having ADHD and, you know, all my weird businesses or whatever. And I'm just saying, fuck it. If people don't get it, that's fine. And, you know, I'm going to keep buying businesses and doing great stuff.

59:58And on this side, I'm going to have a bunch of hobbies. You know, I like that. When I was in high school, I used to wear mismatched socks. I still wear mismatched socks, but I would like, I would leave the house and I would be wearing two different socks. And to me, I didn't even think twice about it because I don't know. I was just not even, who cares? It's just socks. But everybody would comment on it. My mom would comment on it about the way out the house. What are you doing? She was like horrified. Like, I can't believe you're doing this. And I was like, what do you mean? It's just, they're both socks.

1:00:27It does. Yeah. The pattern doesn't match. Okay. Who gives a shit? And at school, people would make fun of me for it. But they sort of realized like, oh, we made fun of him and he just continued doing it. But also I wasn't even doing it really as like some statement. I just didn't care. Like, I just didn't, I just decided not to care about socks the same way everybody else did. And I decided that the idea of matching stocks really didn't matter to me. And maybe it matters to other people, more power to you. But it just didn't matter to me. And I don't think I realized at the time how important of a mini lesson or trait that would be in the future.

1:01:01I remember moving to San Francisco. And we were self-funding, or not self-funding, but I had basically a billionaire backer. So Michael Birch was funding the lab we were using to do startups. We didn't take any outside funding. But one of our companies started to pop and we got, I don't know, like a million users, two million users, three million users. And, you know, VCs got a little bit excited. So there was an investor at Founders Fund that reached out. And I took the meeting because I was always intrigued by Peter Thiel. And I thought, I don't know, maybe this will somehow lead to me meeting Peter Thiel.

1:01:30So let me take this meeting, even though I really didn't want investment. And we go in and I started asking, you know, he's supposed to ask me about the business. I'm just asking him questions about Founders Fund. Because again, I don't really care if he invested in me or not. I'm just here to like learn about them. And I'm asking him all these questions that if you ask a normal VC, what stage do you normally invest in? Answer, proceed. What's your typical check size? Answer, 500K to a million dollars or whatever. Everybody's got like these predefined boxes, labels. What industries or what categories do you invest in?

1:01:58B2B SaaS, enterprise, blah, blah, blah. They have these labels that they were like, you know. And I went to the Founders Fund guy. I'm asking the same questions. He's like, we just, I don't know, we just try to find the singular businesses. And then we, I don't know, back up the truck. Like, how much money do you need? How much money can we put in? Let's put it, how much money do you need now? Then we'll put more money in later. What stage? Who cares? Let's go. And so he was, and he said that when Peter started Founders Fund, he had almost like a fight club style rule. And the fight club style rule was, the only rule is that there are no rules.

1:02:27The rules that we set as a fund are going to limit our ability to find the singular business. And this is why Founders Fund was one of the only VCs to own a shit ton of Bitcoin. And, you know, starting 2014, 2015. Most VCs couldn't even like buy crypto, like by their bylaws basically. And they didn't even see Bitcoin as a like, they were so blinders on to like, we need to find the next Facebook, right? We need to find the next Mark Zuckerberg that they didn't think that this anonymous Soshi Nakamoto open source project, creating a currency, like it broke all the rules. But that was the thing that mattered.

1:03:03And so Founders Fund has had a few of these really contrarian bets. They backed Anderil when Silicon Valley, like at the time, it was completely unpopular to back a weapons company. It was like so like the narrative at the time was that that was a bad thing. In fact, Google had to shut down their weapons project. They had a big contract with the Department of Defense and Google just turned it down because their own employees were like, this is not right. I don't want to sign up to be part of making weapons and killing, you know? And so the companies, you know, bowed down and the venture capitalists bowed down.

1:03:35And there was only a couple of investors and Elad Gill came on this podcast And he said, the day I saw that Google shut that project down, I knew there's a huge opportunity. If anyone was willing to go against the grain and actually build a weapons company, they were going to do phenomenally well. Like it makes total sense for the U.S. We're going to have a defense department, right? I think everyone agrees in that. And the defense department is going to need weapons. And if the weapons are built by a high tech company, that's going to be better than building low tech old school weapons. Like this all makes sense.

1:04:03And that's when he backed Anderil and Founders Fund backed Anderil. And so I just saw the payoff, you know, in Silicon Valley, they call it being contrarian, but what does it feel like in practice? I think it's what you're talking about. The courage to be disliked, the courage to look stupid, right? The ability to think differently, right? All these terms that have been floating around, they all sort of apply to this thing. And I'll share one more story that kind of reminds me of this, which is one of my business heroes is Jesse Itzler. And he came, you came to one of our hoop group events, the basketball camp we do.

1:04:33So Jesse was there and Jesse was laughing. We were at the table. He's just laughing. He's like, all these guys, he's like, they're all talking about their like crazy ambitious plans. Like this guy's building a city. This guy's building a religion. This guy's building rockets. This guy's building this. And he goes, I'm literally selling a calendar because his project right now is called the big ass calendar is literally a calendar you put on your wall. So you can be a little more intentional about how you're going to spend your time this year. And he's like, I think it matters. But like in the grand scheme of this, I sell a$19 calendar.

1:05:03You know, it's just funny. I'm even here. And here's a guy who reinvented himself 10 times, did not stay in any box, right? Started as a white guy rapper, then wrote, and that wasn't really fully working out. So he writes a jingle. It becomes the New York Knicks song. He sells a sports jingle company. When he sells the company, he gets to ride on this guy's private jet. He's like, this is amazing. Starts a private jet company, gets involved in a coconut water brand. He now hosts a big running event because he loves running. He has a sauna company because he loves sauna. And he basically he's just like almost productized himself and none of the labels that you try to, whatever label you try to apply to this guy, like, oh, he must just be a biz, a brand builder.

1:05:41Then he tells me about how he, you know, invests in this, like, he decided that water was going to be really important. He bought, he invested in like land that produced really pure water. And I was like, oh wait, so you're an investor. He's like, well, no, I don't really, I don't really care about investing. I just, so he was unlabelable. And so I really find a lot of inspiration and people like this. And the thing that he said that really stuck with me, I was like, so what are you going to do after this? And, you know, in this room, when you're surrounded by these hyper ambitious, hyper talented people, it's very tempting to just be like, oh, I need to ratchet up how big my thing sounds, you know, that I'm working on.

1:06:17Otherwise I'm sort of low status in this room. And he told me, he goes, oh, I think I'm going to go be an assistant basketball coach with this like local, like, like this all black college that's nearby. Like, I want to go be the assistant coach. Like I love basketball. He's like, but dude, I was like, I was like, what are you, why assistant basketball coach? Like clearly not for the money. Like, you know, because you want to get into basketball. He's like, no, dude, I just want to be on the bus. He's like some of the best times in my life were on the bus going to a game. He's like, if I can just be on the bus, oh dude, that's going to be good for the soul.

1:06:46And I just admire this guy having the courage to be like, yeah, I'm going to go do this thing that sounds completely random. But as soon as he says it, it instantly resonated. And like, I'm actually now an assistant coach for a high school basketball team near me because I was like, dude, I want to get on the bus. That actually makes total sense to me. That was a huge part of my childhood. I would have so much fun doing that, even though I don't know how that fits with the rest of the stuff. It doesn't really need to fit. It just needs to be something I want to do. All that totally resonates. I mean, I think, do you ever listen to Invest Like the Best?

1:07:16Amazing, amazing podcast. He has some great guests, but there's definitely an archetype. And the archetype is the autistic super genius investor who's like, I, you know, I buy laundry or not laundromats. Let's say, you know, it's like Brad Jacobs. He's like, I just, you know, I choose an industry. And then for five years, I buy every company in it and I take it public and then I make, you know, I compound at 30 % and then I go do it again and again and again. And there's a very clear formula. And I have never, I've never had a formula. And I think the benefit of like, there's okay. Like I was on Kauai, the Hawaiian Island.

1:07:52And someone goes, you've got to go to this donut place. They fry their donuts in coconut oil and they're these purple donuts made of sweet potato. And I'm like, okay. So I go and it's amazing, delicious donuts. And I start talking to the guy behind the counter and he says, oh yeah, we're expanding. We just did one in LA. And I said, what? You're like a little tiny donut shop on Kauai. How did that happen? And he goes, do you know Kevin Rose? And I'm like, yeah, yeah, I know Kevin Rose really well. What are you talking about? And he goes, Kevin came and he ate these donuts and he loved them. And so he invested like$10 million in our business.

1:08:30And now we're scaling it across the country. Now, Kevin is a fascinating guy. I mean, last time I talked to Kevin, he's like, yeah, I did the donut company. And then I'm flying to Sweden tomorrow. And I'm meeting with a teenage engineering, which is like this audio file company or whatever. And then, you know, he told me about this Alzheimer's company, this company that's doing an Alzheimer's drug he invested in. None of those things fit together in a box. And Kevin is a great example of, when I see Kevin on a podcast, I jump. Like, I have to listen to it. Like, the random show with Tim Ferriss is like my favorite show in the world.

1:09:04And both of those guys have been so good at not allowing anyone to put them in a box. And as a result, they've created this magnet. Like, the guys on, if, like, I had two options. Let's say I can be value investor Andrew with my formula. It'll be very good for raising money. I can go and invest like the best. I can tell my clean story. I'll look like a duck and quack like a duck, right? There's a lot of positives to that. You get less hate, easy to raise money, you know, investors like it, whatever. But if you're just interesting and you share what you're doing, like Kevin Rose does, really interesting things come to you.

1:09:39And I would argue like most of our best businesses come from me. It's like, I was a barista and I got obsessed with coffee and I bought AeroPress. I love movies and I tried to invest in film. So I actually had this period where I was flying down to Hollywood and meeting people and looking into investing in movies and stuff. And I looked at it and I was like, I'm going to lose so much money. And at that same time, I happened to be in Auckland with Tim Ferriss randomly. And I was in town and I went, oh, there's this guy who runs Letterboxd there. I should have a coffee with him. And that coffee, literally, I had coffee with Matt, and I made an offer for the business within four hours.

1:10:22So these things happen randomly. And I think you need to create that magnet for interesting people and entrepreneurs to seek you out. And I don't know that anybody listens to the autistic super genius talk about his formula and spreadsheet for buying a type of business and goes, I want to do business with that guy. I want to sell my business to that person. Maybe there's a certain type where that is appreciated, but that's not my jam, you know? And, and, and, you know, I'm going to get my two to 3 % hate quota for that. And that's just fine by me. Well, you're going to get the hate either way.

1:10:58You think those often, you think the, the ASG crowd doesn't get the hate? Of course they do too, right? Totally. You're going to get the hate either way. Yeah. If you're not getting the hate, you probably haven't, you know, it's just a signal you haven't really done enough yet. And how jealous are you, by the way, of those guys, right? I wish that I could be that focused. I wish I'd get that excited about buying waste management businesses. I do, but it's just not true. It's not true to me or you. Exactly. Why would I be jealous of something that I would be miserable of? Can you imagine my first million if every time you just talked about one vertical would be the most boring podcast of all time?

1:11:32Dude, the greatest hack in the world is if you're going to be jealous, be jealous of the inputs, not the outputs. All right? I just said something profound. Pull over your car. Write this down, okay? Listen, everybody looks at the result that somebody has in their life and they get jealous of the result. And that leads you astray because you don't even really know what it takes to be that, to get that, to have that, right? If you're going to be jealous, it's hard. So most people try to just turn off the jealousy knob. I'm just not going to do it. Well, good luck with that. It's a pretty tough thing to do to really, truly kill envy inside you, right?

1:12:07There's a certain level of enlightenment and wisdom you need to reach to truly just never feel that envy again. So instead, just redirect it. Get envious of people whose inputs you're jealous of, their day-to-day, the work that they do. And if you're like, man, I would love for my day to look like that. I would love to work like that. Not the results of the work, but the work. And so, for example, Bill Simmons is a guy like this. I don't know how much you know about Bill Simmons, but he's a sports podcaster. But before that, he was a blogger. He tried to get hired by a newspaper. they rejected him.

1:12:38So he starts his own Boston sports guy blog. And he's just sitting there writing about his hometown sports because, you know, since he was four years old, his dad's been taken to Boston sports games. And he somehow like blogged his way literally to like ESPN ended up giving him his own section. Then when he's at ESPN, he's like, I'm not just like any, and by the way, they're like, he's a call. He's a journalist. No, well, he doesn't do journalism. He's just writing as a fan. So I guess we'll call him a columnist. No, he's not really a columnist. I guess he's a blogger. We couldn't, by the time they were trying to figure out one label, He goes and creates 30 for 30.

1:13:06He reinvents the sports documentary space. And he pulls that off. And then he gets fired at ESPN for speaking his mind. And he goes and he leaves and he starts The Ringer. And it's a podcast network. And now he's Bill the Podcaster. He sells it to Spotify. He makes hundreds of billions of dollars. And there's this great clip the other day that came out of like this big trade happened in the NFL. And there's this clip in The Ringer office. And Bill is carrying a microphone in one hand and a chair. and he's like basically like jogging through the hallway because he wants to go join one of the other Ringer podcasts to come talk about this trade that just happened.

1:13:37Like that's not his podcast. He doesn't need to be there. He's got all the money in the world. He could be on a yacht. He could be on an island. And he's sitting there running with a chair and a mic because he really wants to go talk to friends about what's going on in the world of sports because that's what he loves to do. So I'm jealous of Bill Simmons, not because he sold his company for hundreds of millions of dollars or has a popular podcast, but because the guy gets to talk to his buddies about the thing that he loves all day when he doesn't have to be, right? And so I'm jealous of the inputs.

1:14:01And so, you know, I think that's a thing that if more people did, you could kind of use your jealousy as more of a compass to figure out what do you really want to go do? I think if more people knew the behind the scenes of a lot of these super wealthy people, they wouldn't want that life. Like there's a lot of sad, very wealthy people, as you know. I think the trick is, how do you figure out what you're great at and you actually enjoy? Because there's things I'm great at that I just don't enjoy. Like sales. I love pitching and selling and talking to people. Or sorry, I'm very good at it. But I actually, it drains my life force.

1:14:37It's misery, right? And so I think like, you know, for me, I started out headphones on, coding, making websites. 20 years later, I've realized I can write and talk about things I'm passionate about. And that creates opportunity, which I can then funnel into all my various businesses. Like I think being a human router, and just doing the thing you're great at. You're doing this too. I mean, it's like Ben might run all the day-to-day operations. You just get to go and do the thing you're amazing at, and it benefits your business in a profound way. And I think that's the trick. Well, I would even push back.

1:15:11It's not even that, oh man, there's all these wealthy people who are miserable. There's a lot of wealthy people who are happy doing something that you would be completely unhappy doing. I remember when we got bought by Twitch, and I was like, oh, you know, I get to meet Emmett. He was my boss. He's the founder of Twitch. He did the thing that I had been trying to do. He started a tech company. it like took over the space that he was in. It became like one of the few social networks that was out there. That's what I was trying to do before that. And, you know, the guy sold his company for a billion dollars and here he was running this thing.

1:15:38And it was like a big part of the internet. I think Twitch was like, I don't know, the second biggest consumer of bandwidth or something that year. Like, it was crazy. And I saw his day and he was happy doing it, which was basically he sat in the boardroom on the ninth floor of the office on a long table and he sat at the front and the CEO sat next to him And then teams would come in 30 minutes at a time and they would sit down, they would put a memo in front of him. He would read it. He would ask them questions. He would grill them. And sometimes he'd be like, this sounds fantastic. Can't wait to see what's next.

1:16:04And sometimes he'd be like, this doesn't make any sense to me. And he would kind of rip them apart. And then they would be like, leave, go back. They would do a week of work and come back again the next week for their weekly 30 minute meeting with him. And that's what he did all day. And I just remember looking at that and being like, thank God I saw this because this is not what I would want. I thought this was my dream. I thought like literally what he was doing, what he had done was the dream for me, dream outcome. And I realized like, that would be kind of a nightmare of a life. And so wait, what, if that's the nightmare, not the dream, then what's the dream?

1:16:32And then you start asking that and you start looking around and you start thinking about what would be really interesting. And that's when I started the podcast. Cause I looked at Tim Ferriss and others and I thought that sounds pretty fun. And so an easy hack, cause I'm starting a new content project, my first new kind of big content project since my first million. And the hack, the trick is instead of asking, instead of trying to think about what would be really popular, what would get millions of views, what would get millions of subscribers, the better question is, what would I have fun doing 3 ,000 times?

1:17:00Because if I do it 3 ,000 times, I'm probably going to get good at it and I'm probably going to stick with it and probably going to get a good result, sure. But more importantly, I'm going to go do it 3 ,000 times. I better really be like, let me optimize for that instead of optimize for what might work. Let me ask you this. Are you leaving your cell? Are you breaking out of your cell? Is this something that people go, wow, this is like crazy. It's like when Tim Ferriss launched his card game or he wrote his, like, he made that weird crypto project. Is it one of those? I've explored that wide, like totally weird, totally weird.

1:17:32Go make a movie, create a Broadway play. Like I've explored all that. And there's like things, but that's not the active thing I'm working on. One of them is, I would say, different in that it's a different mode to be in. So for example, this podcast is live, it's improvised, it's unedited. I get on here and I just do me. And then I don't really think about it after the fact. There's a team that basically takes it, they edit it, they title it, they package it, they set it out there. And I don't really think about it again. Whereas the thing I'm doing right now is a little bit more of a craftsman approach.

1:18:02It's like, I'm not just going to improvise it. And it's this like, you know, three weeks later, that's kind of gone. I'm going to make a new one. It's like, no, I'm gonna make one thing. It's gonna be great. But that means I'm going to really like have to be a craftsman about this. And I'm going to really have to go and take a scalpel to this and try to like make it as great as I possibly can, which is not a mode I'm normally in. That's awesome. I mean, it's like the happiest I've been in the last 10 years is writing my book. Just headphones on, doing something and actually shipping something that will be relevant, hopefully in 20 years that you can go back to.

1:18:33Yeah. There's something so ephemeral about podcasting and tweeting and all the other stuff. So nice to zoom out. Totally. Well, Andrew, thanks for coming on again, man. It's always good to hang. And yeah, you want to shout out anything, your newsletter, anything you want to shout out? Yeah, I mean, that's mostly, I haven't really actually been tweeting very much. I've been posting on my newsletter and I really love it. I sit down like once a month and I kind of do like what Tim Ferriss and Kevin do. I just like write about all the random things I'm excited about. Sometimes it's about business, sometimes it's about other stuff.

1:19:06But yeah, people can sign up neverenough.com, the newsletters there. And I love it. Like it's, it's been so, it's been so much more enjoyable to just sit down and actually write something formally and take my time instead of like tweeting out toilet thoughts randomly and then fighting with trolls. All right, man. Good to see you. Yeah. Great to see you, dude. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. Hey, let's take a quick break. I want to tell you about a podcast that you could check out.

1:19:40It is called The Science of Scaling by Mark Roberge. He was the founding CRO of HubSpot, and he's a guest lecturer at Harvard Business School. The guy's smart. And he sits down every week with different sales leaders from cool companies like Klaviyo and Vanta and OpenAI. And he's asking about their strategies, their tactics, and how they're growing their companies as head of sales or chief revenue officer. If you're looking to scale a company up, if you're a CRO or a head of sales, just looking to level up in your career, I think a podcast like this could be great for you. Listen to The Science of Scaling wherever you get your podcasts.