The 2021 Milly Awards

Dude, that's crazy. That's a $10 million mistake. Yeah. Andrew, what's going on, dude?

Are you pumped to do that? I'm really young. I'm excited. I've worked out this morning and feel good.

It's a nice sunny day. We have a big dump of snow here, which is actually incredibly rare. Usually it never goes below freezing. So yeah, it's nice.

What'd you do, play? No, actually one of my treadmill. It's weird. I was feeling a little low energy over Christmas.

And I realized it was kind of worked out. And so I was like, oh, I'll take, you know, am I eating the right thing? Am I doing the right routines? Am I doing my gratitude journal?

I can't really. I can't remember that. I've had compliments in my taking. He's never had that much work done.

Yeah. I just realized working out is all you need to do. There's a great quote. It's in this book.

I was reading, called The Body. And it basically said, if we could put in pill form all the benefits that exercise gives you, it'll be the most successful medicine of all time. And the whole point of the book was it was called The Body by Bill Burson. Bill Bryson, I love that book.

And he's just like, basically like sleep and exercise are the cure to most everything. Yeah, it's crazy. I love his writing. He's great.

Do we want to get into this, Sean? Yeah, let's do it. We did this last year. And I think it was probably my favorite episode last year.

We called it the Milly Awards. We did an awards ceremony at the end of the year. Andrew came on and we did it in 2020 at the end of the year. And I actually went back and I listened to it, which is cringy to listen to your own voice recorded.

But it was a really entertaining episode. We made a bunch of predictions. I actually even kind of noted some of them down. I don't know if you guys saw that.

Like some of the things that we had said last year. And so we're going to do it again. And we're going to try and make this an annual tradition. We'll see how it goes.

And all right. So without further ado, here we are. The 2021 Milly Awards. We are back.

And we got a bunch of different categories. The three of us did our research, did our thinking about who we think is the winner for each. We did not tell each other, did not show each other. So if we have the same answers, just coincidence, great minds think alike.

And we're going to react to how each one goes. And I have a little side game here, which I'm going to play. I have a little notepad. I'm just going to kind of take notes of who I think wins each category in terms of their answers.

So we'll see who brings the heat during this thing. I got Sam. I got Sean. I got Andrew.

I'll put a little tally for. And I'm the only judge or you guys can chime in on that. But I'm just going to keep note of how we do for this all episode. All right.

So did I miss anything, Sam? Are we good to go? Yeah. All right.

So I have two documents. I have one document with my answers. And then I've got the other document that have last year's answers. And so I think what we should do is you can lead.

And you could say the category of the news. Here's what last years are. Right. OK.

So we'll start with breakout company. So this is the 2021 breakout company. It's a company that kind of exploded. No, a billion of the years first, Sean.

OK, you want to go in the actual order? All right. So a billion of the year is number one, then. We do billion of the week sometimes on the pod.

So this is Billy of the year. It doesn't have to be somebody who's a new billionaire. But it's just a billionaire who had a hell of a year. Last year, Sam said Chuck Feeney, who is a guy from Blockbuster and all that stuff.

Or that somebody else? No, he's just a he started a business where they sell airports but he gave away like duty free. He gave away all of it. He gave away all of it.

We gave away $10 billion. Andrew had Mark Leonard, who's I think the CEO of Constellation Software. Is that right? Who's maybe somebody respect who runs a similar playbook to you, buys great companies, owns them for a long time.

Very stealthy, secretive guy. You shared a bunch of cool stories about how he keeps a low profile. And I had Eric Yuan, who was the CEO of Zoom, because I thought Zoom sort of saved the world during the pandemic. I let the world continue to run.

And so I had Eric Yuan. So who do we have for this year? We'll start with Sam, Billy of the Year, who you got? Darmash, the CTO and co-founder of HubSpot.

He came on her pod. Just sucking up to your boss. Well, yeah, I mean, I guess. But he just had the idea outlook on life.

And I think he had an amazing job. Like he basically said, no one reports to him. And he doesn't report to anyone. I don't know what's he worth.

Like $2 billion, whatever HubSpot stock is worth. I thought he was pretty amazing. I got a good outlook. And what was the outlook that you liked?

The most interesting thing with Darmash is exactly what you said. Instead of, I think so many entrepreneurs are like, OK, I'm either all in or I'm all out. And he kind of said, you know what? I'm just going to do this stuff I like.

And he's kind of a floater. Like he just kind of floats around within the company. And I thought that was really cool. And he was nice.

The thing about Darmash is that he's nice and he's friendly. And he's calm. And I really enjoyed that about him. He has type A in that he's competitive, but he's not trying to out alpha people.

He's very comfortable. Or Andrew, who you got? Billy of the Year. So mind the way it was actually a guy I randomly met.

So I was at this cocktail party at just a house in my neighborhood. And I was talking to this guy. And I started asking him what he did. And he said he was in the kind of beverage space.

And he started seeing names that kind of knew like Mission Hill Winery, which is like a big winery up here. Anyway, it turns out this guy's worth $8 billion. And he owns a beverage-focused holding company called Marc Anthony Group, this guy named Anthony von Mandel. And his story is pretty crazy.

So he started a little like wine importing business in Vancouver. And made enough money to buy a winery called Mission Hill. Took on a ton of debt. It was like dirt floors.

Had only a few barrels of wine. Turned it around. Turned into a real solid business. And then he hit it big when he was trying to diversify.

And he started a company called Mike's Hard Lemonade, which I'm sure you guys heard of. And this is like an insane story. Like in the 90s, people would have fights in the liquor store over the last couple of bottles of Mike's Hard. It went into the States.

And sold to him. In America, we make fun of people who drink. Like it's like a joke like Mike's Hard. Well, the idea they had was like man or two embarrassed to drink coolers.

So like let's make a cooler. They can kind of not be too embarrassed to drink. But anyway, he ended up building that into a massive business. He ended up also starting White Claw a couple years ago, which is like the same idea, but healthy.

And now they do $1.4 billion of revenue last year in 2020. And the craziest thing about this guy is he owns, I believe 100% of the business. And he has no debt because he's been almost in bankruptcy multiple times. So it was just totally crazy local entrepreneur who just knocked out of the park.

And I'm obsessed with these guys who have just like taken a risk. They've done it 100% themselves. They didn't have VCs, didn't have investors. So just an amazing story.

Wow, that's a good one. I didn't realize that the company has Mike Hard also does White Claw, which is amazing. It's basically a reboot of the similar concept. Totally.

OK, I went about it. My Billy of the Year. So I had two. All right, so I have the I-Roll one, which is Elon Musk.

But it's not for the reason that most people would think. As you know, one of the maybe top three slogans of this podcast is, bet on yourself. And Elon, several years ago, did a bet on yourself compensation plan that you guys probably remember. I don't know if everybody knows about this.

I'll summarize it. And I'm kind of hand-waving through some of the details just to be quicker about it. But basically, Tesla at the time, his five years ago, was at about a $50 billion market cap. And the rumor was, Elon's going to leave.

And he might go just focus on space, full time. And he had a negotiation with the board and basically said, OK, I'll stay. But here's the compensation plan I want. And he sketch out a plan.

He said, look, you only pay me if I increase shareholder value. No guaranteed money. And he basically did it in rough strokes. Every $50 billion in market cap they added, he would get another 1% of the company.

And so it was at $50 billion. So he'd have to get it to $100 billion to get anything. If he got to $99, he got nothing. And so he had to get it to $100 to get any more for all his hard work.

And I remember there's a great clip. If you go to YouTube and you just search for Elon Musk compensation plan, CNBC, there's this clip of the anchors making fun of them. Because they're like, oh, yeah. And this plan is unprecedented.

It has this far-fetched idea that if you could get over $600 billion, Elon would get this huge unlock if he gets to that reward. But I think we could safely say, it's never going to happen. Why even include that in there? And sure enough, this year, Tesla crosses all that.

He hits every single part of the compensation plan, I think. It's now a trillion dollar company. And basically, the guy called a shot. He bet on himself and hit all of it.

So I really like the betting on yourself aspect of it. So that's why I give it to Elon. But what was the second one? The second one, again, a little bit of an expected answer, but not for the reason you think.

So Vitalik Buterin, who's the co-creator of Ethereum, he's worth himself probably $1.6 billion, I think, based on the value of Ethereum today, something like that, $1 or $2 billion. But there's all these new projects constantly launching. And one of the ways that projects were trying to get hype and marketing is that they would just send some of their projects into Vitalik's wallet, his public wallet. And they would say, look, Vitalik holds our coin.

So you should too. And then the other thing that they would say, that was the first marketing scheme people do. And then people fell for it. They're like, oh, Vitalik's investing.

And that's all investing in it too. But he didn't actually invest in it. They just sent it for free, just shoved it in his wallet. The second thing that people were doing was they were using Vitalik as sort of like a lock up.

They were like, look, we sent one coin that came out, the Shiba Inu coin, which is like another dog coin, like Dogecoin. They sent I think $6 or $6 billion worth of their coin to Vitalik's wallet to essentially lock it up. They're like, look, that's all there. It can't be sold.

And so you're not like, it's there. So you don't have to worry about who owns this thing, Vitalik owns this thing. And it was partly marketing. It was partly their way of locking away some of the supply.

And what Vitalik did was pretty awesome. India was going through a really tough patch of COVID. So he got this thing. And what he did was he donated a billion dollars of it immediately to India.

And then he dumped the other $5 billion and just burned it. And just said, you know, so that the price, if he sold it all in the open market, it would crash the price. So instead he took $5 billion and just eliminated it from the pool and gave a billion dollars to India, kept none of it for himself and helped a lot of people in India out. And he did this like overnight as soon as he got it.

And I just thought that that was like, you know, a pretty remarkable thing from a pretty remarkable guy who. He's the guy's amazing. It's really cool. That guy and the Sam Bankman guy are probably the two most interesting people I think in the world at the moment.

Yeah, the cool thing about that for those who don't remember the Sam Bankman freed guy, he's currently the wealthiest person from crypto, wealthiest known person from crypto. So you know, nobody knows who Satoshi is, but Sam Bankman freed is the next one. He's got like 15 or $20 billion net worth from crypto, including the exchange he created. And if you listen to interviews, he's like, not like any other crypto zealot.

He just is like, he's a kid on care about crypto. Like I don't believe in it. Not believe it. People want this.

So I made a product. And like that's his whole mindset. And he also is like obsessed with this idea of like, I forgot it's called. There's some like philanthropic thing.

He's really like, Sam, do you remember the name of this? It's like charitable ambition or something like that. It's like, yeah, he basically, he was basically the idea is like, I'm just going to get as wealthy as possible and give it all away to different stuff. And it's okay for me to be incredibly ambitious and do this thing, these things I don't really care about because I'm just giving it away anyway.

And he's giving it away like during his lifetime. The last year's all right breakout company, you go for breakout company. I have, I have open sea. So just to give you a sense of open seas, crazy growth.

I had that too, by the way. Started in 2017 and the bear market hit like pretty much immediately. And I know people who were building like their competitors and they ended up folding because it was just like, there was no interest. And these guys were like, you know, the cockroaches that just stayed alive.

And in 2020, basically they in 2020, so last year, they did $24 million in GMV. Pretty small overall. And they get 10% of that. They have, I don't know what their take rate is.

Something like, I think it's even lower than that. I think it's 5% of something. They, so it was very small, 24 million in gross sales across the platform. That's not their sales, that's what people buy from each other.

So they just get a small take. This year, 15 billion. So going from 24 million to 15 billion in one year, that's 650X. To me, that's a breakout company.

I know we've talked about it before, so it's not a big surprise, but I had to give it to them. So I had that as well. But I came at the back up because I actually thought that you were gonna pick that. So I had open sea as well.

I think it's amazing that they basically just kind of created a market. I think that's a pretty bad ass. Or at least they were part of a market that was not existing a couple years ago. All right, so my second one is someone who we talked about.

I'm gonna botch his first name, but his last name is Love. What's his first name? Peter Love? Is it Peter?

Is it just Peter? I think it's Peter. I thought it was a weird person. But let's go in Pieder, just to bother.

I thought it was Pieder, to be honest. But I'm gonna call him Peter. All right, so this guy. It's Peter like a theater.

That's how it works. I thought it was. I thought there was an eye in there in some weird area. All right, we talked about this guy a couple of episodes ago.

I've actually been paying attention to him for like three years. And as far as I can tell, it's a one person business. And for the longest time, he would reveal all of his revenue. And for years, it was like two or $300,000 a year in revenue.

And he has a bunch of different products. He's got Nomadlist.com, remoteok.com, workers.co. He even has a cool website called Rebase, which is all about going to Portugal, moving to Portugal. So he's got like eight different websites.

But the longest time, only like $3,000, $500,000 a year in revenue. Like, neat, but not that cool. This year, he got close to five million in revenue. And for a one person internet business, that's pretty phenomenal.

And the remote thing has basically kind of caught up with him. And he's crushing it. And this guy's an artist. I love him.

I think so. He's kind of his own entity. And I think that he, for me, was the breakout person of the year behind opens. I think that guy kind of has my dream life, which is funny that I say that because I do own similar businesses.

But I've always, I've always like fetishized the idea of being a one person entrepreneur and being able to do that level of revenue. I just kind of got ahead of myself. And it's so interesting. I think I have a lot of respect for him because I think he still shares his numbers.

Most of the guys that get to the scale, they almost always stop sharing because everyone realizes how much money they're making. I have a story of a guy who's going to come on the pod soon. And I've been talking to him. And he made 10 million a year in profit in the early 2000s from a lyric website.

That was around for years. So I have a one person. Wait, is it Maloon? Maloon Tessovic?

No, but he is similar story. He's a Russian Jewish guy. Is that guy a Russian Jewish guy? Yeah, I also make like a drink.

I don't know what he's. Not a drink in European. Oh, my guy. No.

Okay. That guy, didn't he do something else that's really remarkable now? Like he did the lyrics thing. Isn't he doing some other interesting stuff?

He works at Expo. He's a partner at Expo. Gotcha. Andrew, who you have Sam has this like weird indie breakout company.

That's not a company. Bro, I chose OVC. That's the most obvious one. I chose that one too.

So I had to get you. Before I'm Mr. obvious, Sam's Mr. Suck Up and let's see what Andrew's got to get here.

So I'm trying to be better. I'm just trying to be different. So if there's one thing I really, really don't like. It's middlemen, realtors, investment bankers, that kind of stuff.

So I love this company Microacquirer. For a long time, if you wanted to buy a tech business, you were going to these crappy listing websites with really like really sketchy sites with really low quality businesses. And this guy Andrew basically came along and started this company called Microacquirer. And it's for generally like profitable, SaaS businesses on the web.

And he's just done a really, really nice job of doing it. I'd say it's kind of like Zillow for buying a tech business. And I, you know, he got to replace Flippa and all these other kind of crappy websites. So I'm a big fan of what he's doing.

And he can fight to people. He's like 10 million bucks or something like that. We're all investors, I think, right? I am.

I didn't invest, but I think it's a good one. Well, I invested a small, a very small amount, like $5,000 or $1,000 or something like tiny. But he's picking fights with people online too. He's kind of making himself a kind of a villain to a certain group of people, which we'll see if that ends up being a good idea.

Who's he going after? I forget. What do you think? I think he's going after like, he's basically saying like, he went after two groups.

He's like, first like bootstrappers need like some love. Like, you know, if you're a profitable company, like, why is that getting no attention? And then the second thing is he's going after tech crunch because they don't cover those types of companies. They just, they basically work for the VCs.

It's kind of like his angle. It's like, he's a good angle. He created a rival publication, I think, called the Bootstrappers to just take a shot at TechCrunch. Like, I will cover these companies if you guys aren't going to.

But then the only hypocrisy is that he's raising a bunch of travel. So I think, you know, that part, you know, breaks down a little bit. But I think he's doing a good job of picking a fight. And this is general's Twitter strategy, which is if you like totally sell out to your mission, which is like both a good and a bad thing, you could just like, there's a guy who, I was friendly with a Chris Heard, he created a company that's around remote work.

And they help basically like manage companies, like laptops and desks, their desk set up, when you work from home, they'll help you as a company manager, workers, desk setups. And so he just every tweet is just about how remote work is taking over and how everything else is going to die. And he'll just be, he's just, that's the propaganda machine. And he just keep beating that drum every day, every day, he just keep talking about how the office is dead, remote work is going to happen.

But he cannot be wrong. And yeah, and then it's just like, you know, a total like brainwashing of contents. But you know, it's pretty effective when people do do that. I can't really bring myself to do that exactly, but it works.

Okay. So who I would give it to OpenSea. Oh, I'm getting it. Okay.

Great. I love it. Right. Yeah.

Great. Microquirer is cool, but OpenSea is just, there's levels. And microquirer. Honestly, I would do yours, man.

I think yours is the most unique, right? I think OpenSea had a big win, but it's like, you know, I think venture backed kind of like of the moment, crypto stuff mine I think everyone knows about. But I think what Peter's doing is very unique. And it's just when you think about lifestyle, I think he has the best possible lifestyle of any of the people.

And what's the story where a guy goes to a party hosted by whoever, like, you know, some rock fella type, it's like, you know, his friend is saying, this guy's the richest man in the world. He's got everything. He's got this. He's got that.

He's got cars. He's got servants. He's got everything. And then the guy who's the guest goes, but I have something he'll never have enough.

Enough. And yeah, that's the Kurt Vonnegut. Yeah, it was Kurt Vonnegut and Joseph Heller, I think, right? Mm-hmm.

So that's the version of, you know, Andrew, you had Peter levels, but you didn't have enough. And so you kept going. And there's a part of you that envies lifestyle still. All right.

We're giving it to Sam. Once you start, once you start, once you get an office, once you have employees, you have this beast to feed, whereas Peter could just check out. Right. One of these days, we should do a story of someone who has done that, who went one way and then just said, oh, fuck it, we're going to go the opposite and went back.

I love those stories. All right. I get this one. All right.

So the unsexy simple business that you saw this year, I'll go first. We talked about it. This guy named Quinn, I think his name is Quinn Emmet. Is that the guy's name?

Right. Is it Snyder? I don't remember what it was. He had a vending machine business and he started, he was just worked in sales at like some tech company.

And I did like a little checkup on him. He's doing like $30,000 a month in revenue and half of that is profit. And he basically started with $1,500. He's got some vending machines throughout his city.

I forget where he is. California, I think started with $1,500. Now he has software that tells him when the things need to get refilled. And he says, he only works 10 hours a week on it.

I think that's pretty cool. I think that's pretty awesome. I love that. Like Quinn Snyder's a basketball coach.

So definitely not Quinn Snyder or something else. I think it was Emmet. Quinn Emmet. Andrew, who you got for best unsexy or simple business that you saw this year?

I feel like you see a ton of these. So this probably the easiest category for you. I see a lot and I looked at a bunch of ones that people had brought us and I just, I can't really share. But this is when I came across recently that I think of genius.

So some guy, he went and he basically built a fake interior of a private jet in Los Angeles. They used a movie set or whatever. And then they just rented out to influencers so that they can take photos where it looks like they're on a private jet, but they're not. And they charge 70 bucks an hour.

I think it's booked out 12 hours a day, probably doing 20 to 40k a month. And I can't imagine the margins would be less than 80%. And I was like, that's fucking amazing. You could just build this thing, hire a bunch of people in the movie business to build it over a weekend.

And then you can own that for years. What was it called? It's LA private jet studio. It's on pure space, which is like a photo shoot studio list.

That's awesome. That is so that's a great one. All right. I have one.

I'm going to steal this from our friend of the pod Cody Sanchez. Sam, you sent this link earlier. And I think this is a great one. Did you take the one that I said?

You could see the one. I saw one. I'm taken. It was better than the one I had.

So I was like, Oh, this is what I used this one. Instead. So she, by the way, her TikTok is blown up. So she's always on my feet.

She's crazy. Dude, her last one just got 10 million views. That's insane. Like her, she has half an million followers on our TikTok.

I always see them. I use TikTok a bunch. And I'm always like, Oh, like, I was in my head. I would just see like, I don't know 30 comments.

I'm like, Oh, you know, it takes so hard. And like when I saw that it actually has added up, it's just yet another reminder of the value of just keep going compound the the winds over time. So she was doing this thing. She goes, here's a boring business that that you love.

And it's called American Striking. And all it is is this woman owns this business. And it just paints the white line that you need for like a road like lane, basically, or like a parking spot. You know, it's like, I need to paint these white straight lines.

And so she's a company American Striking. I think it started about three years ago. And you know, $400,000 the first year, seven million the second year, 15 million, almost the third year. And just crushing it, just absolutely crushing it.

And according to Cody, 70% profit. Yes, exactly. Some of the 60, 70% profit margins. I don't know.

I don't know much about it. Because again, my research was watching this TikTok five minutes before this pod. But what a beautiful business. And what a, you know, what a great reminder that like, you know, you read about Elon Musk, you're like, Oh, I have to like send rockets to Mars.

And then you read about the girls, like I dropped straight white lines and I can make millions of dollars a year. And I just remind you, you know, you can win the game anyway. So she's my pick. I love that.

I vote for that one. Okay, I'm going to take that in honor of Cody. So we are at 111 right now. So we're one each.

By the way, I have a little honorable mention here, an unsexy business that's extremely well. Have you guys looked at Crocs stock? Yeah, crushing it. It's the post Malone.

Dude, 2020 when the pandemic happened, so March 2020, you could, you could bought a pair of Crocs for I don't know how much Crocs go for. Let's call it a hundred bucks. Maybe there's a little less. You could buy a pair of Crocs and you could buy the stock for $10 a share.

It's now up 13x in one year. Just the pandemic was good to Crocs. And I just thought that was like an amazing winner out of this like pandemic time. Is it post Malone?

Yeah, that's just you driving it. He was, he kind of hopped on that trend really early. And then they created this new thing called like Crocs. I forget what they're called, but they're like charms that you put on your Crocs.

And if you drive around the Midwest or in the South, like every- How do we make it clear? What could we do? Ah, let's dangle Charms off of- Do you know what I'm talking about? Like my wife is obsessed with these and she buys them for kids and puts them on a Crocs.

Yeah, it's like, like a, you get like a soccer ball like pin or like a football pin or like some cartoon and the kids are obsessed with it and they're crushing it right now. Post Malone started making the popular in a lot of country music people like Luke Combs, you probably have no idea who that is, started wearing camouflage Crocs. Gotcha. Yeah.

Who knew? Who knew? By the way, Sam, I got another real quick pop quiz for you. Hands up.

So I see you're not you're not looking it up. I want you to guess the monthly visitors to OnlyFans.com. 20 million a month? Okay, you're close.

It's 250 million. Tell you're off by 10 acts in order of magnet. Is it really? That was going to be my other unsexy business was actually the business of sexy, which was like, I had no idea they get 250 million visitors per month.

That's insane. That'd be one of the top websites in the world. Then there's another one called Chatterbait. That's, you know, a broke man's version of OnlyFans.

It's 300 million. Oh my god, it's insane. So, they didn't only fans, did they say that they're no longer allowing nudity? They did for a second and then they reversed course on that.

Stupid version. Like no more porn. Yeah. Facebook, no more photos.

You know, it doesn't work. That's so stupid. By the way, average visit duration. Four minutes.

All right. We're going to the next category. Your best investment. Okay.

So what was your best investment of 2021? Let's kick it off with Andrew. So I would, the boring answer is AeroPress. I never really talked about that on the pod.

We bought that maybe four or five months ago, and that's been awesome so far, but that story hasn't played out yet. So the one that we haven't really done that much in the last year. So the best one thing that I've been buying myself is actually a company called Persian Square Holdings. I don't think I've talked about it.

So I have about 95% of my net worth in tiny and our kind of core businesses, but I've been quietly building kind of a backup forever rich retirement portfolio of stocks, real estate, brick and mortar businesses. We own a chain of restaurants and a hotel, a bunch of conventional stuff. I just own a bunch of restaurants in Victoria. I know what is that.

We own a hotel in St. Louis. Oh, Marshall. Yeah.

Yeah. With Marshall. Exactly. It's the hotel business.

It's amazing. I'm basically, we bought this that we bought like a apartment building and converted it into all Airbnb. And we took it from we bought it super cheap and now it's yielding. And maybe you're my billy of the year.

I don't think not yet. Working on it. It sounds like a get to think about it. That means you might be round up into it.

No, I don't think I am. I don't really have a good picture on that stuff. That's a good answer though. If the answer is I don't think I am, then the answer, then that's a good sign.

Yeah. What's that? People say, I don't spend a lot of time on that stuff because a lot of people who are billionaires on paper, it doesn't really matter. You could invest in some startup.

It could get valued at $20 billion. You can own 1% whatever. I just don't, I don't spend too much time on that. Anyway, I've been thinking about this and I go, if everything goes pear-shaped, I want to still be rich and I want to have enough money to live a great life.

Isn't that's why that guy you like, right? Yeah. Yeah. So I've been following Bill for five or six years and I found that he had this holding company called Pershing Square Holdings.

And what he did is really smart. So he had a hedge fund. And when you have a hedge fund, you have a whole bunch of investors and they give you cash to invest. But at any given time, they can freak out and they can take their money back.

So you could be in a down, you could own an amazing business and you could be forced to sell at the wrong time because an investor redeems. And so he created this holding company in Amsterdam. I think he raised $4 billion and he called it Pershing Square Holdings. And it's basically a public holding company that just owns a bunch of stocks and owns really great stuff.

It owns Chipotle, Domino's, Hilton, Lowe's, Restaurant Brands International, so like Burger King, Popeyes, that kind of stuff and universal music. And so it's this really diversified blue chip stock portfolio. And as I dug into it, I realized that it perpetually trades at a discount to the net assets there. So if there's $100 worth of stocks, it trades at about $70, meaning that the market could go down 30% before you've lost any money in the portfolio.

And then on top of that, you have Dilakman managing your money and he does crazy shit. Like he last year, he turned $25 million into $2.7 billion. And I got to ride along with him on that. So anyway, I've been buying that almost exclusively.

I've got probably like 60% of my portfolio in this. And I just keep buying more and more every month. And I've quadrupled my money, I think, over the last couple years. Did he do the crazy trade that he made last year of the COVID trade?

Was that out of these vehicles or was that a separate vehicle? Yeah, that was in this vehicle. And anyone could have bought that. You told me about this at a digital buy actually last year.

Last year or something like that. Yeah, you've talked about this. You like, okay, great. So that's a good one.

Sam, what you got your best investment? Sam, what you got your best investment? I bought a big lot in Austin, kind of boring, but I bought a big lot in Austin. I used an asset back loan.

So I used cash to buy it. Like I told them I bought it in cash and reality. It was a loan at a 1% interest rate. And it's not the story again, it hasn't played out, but it's already appreciated because I've got offers on it.

But I'll make about $500 in tax free profit with very little work. And the work that I've been doing on it is fun. I'm learning a skill. I'm learning how to develop a home profitably.

So that's going to be my, it's probably not my best. Just like investing in S&P 500, that's up 30%. I mean, that's not much of an investment. I didn't do anything.

And so my Austin Real Estate project will be the most actively active thing that I'm managing and make the most. That's a good one. By the way, the YouTube video on your personal YouTube channel, is it Sampar or the Sampar? Yeah, just my name.

You show the lot, the rundown shack that's there today. It's great. It's fun, right? It's way more and watch that.

And what you just said will be way more entertaining. It's great. But I also, I feel like you might make 500 grand, but if you made 5 million passively, it wouldn't feel as good as you can. Exactly.

That's why I'm saying, it's because it's fun. Like it's, I'm basically developing a skill and anything quite fun. And the tax implications are quite nice. Yeah, that's great.

Okay, good. My best investment, I'm going to go with this startup that I invested in. So last year, I think it was last year, I created a rolling fund. And it's basically said, Hey, if anybody wants to invest in startups alongside me, you know, you don't have to have the network, you don't have to have the knowledge.

All you got to have is the cash, you can do this. And I was like, okay, I wanted to start it. I was like, I want to start this off. I want to make it enticing for somebody to join because you could invest in a number of people who are professional full time investors who've been doing this for a decade.

So I was kind of thinking, why would somebody invest in me? So let me juice it up a little bit. Let me put three of my personal angel investments into this deal, into this like fund. And so they'll be able to say, look, I get to sort of like, I get grandfathered into these deals that you've already done.

That's very kind of you. And self-serving, like I wanted my fun to get subscribers quickly. So I was like, how do I provide more value here? Here's some free value.

Now looking back, it actually has turned out to be very kind because the very first deal that I put in is a company called deal, DEL. And what deal does is it's the easiest way to hire a contractor. So like I was paying, I wanted to hire this guy in Australia, the guy who actually was editing our podcast, I kind of paid this podcast editor in Australia. And so I was like, oh, do I need to go get a lawyer to make a contract?

And how do I pay them in his local currency? And then what are the compliance rules around that? How much taxes do I need to pay? I don't understand all this.

So I went to deal in literally five minutes. I was like, here's the guy's name. Here's his email address. Here's where he lives.

It's like, here's a contract. It's like, would you like to add a confidentiality clause? Yeah, yeah, toss that in. It's like, walk on my burrito.

Like, you know, I'll go for that. And then it was like, great, it's sent for signature and the payments will come out of your bank account and it'll pay him in Australian automatically every month. And I was like, wow, that was like kind of magical. It basically replaced, you know, what a bunch of humans would have to do.

So I loved it. So I ended up chasing down the founder and I was like, yo, your product is amazing. How do I invest in this? And he was like, oh, you know, I'd love to have you.

And I didn't invest right then. And then when I followed up, he was like, oh, dude, we just closed the thing. Sorry, I forgot like, you know, you didn't follow up. So so I missed the first round.

And then I almost missed the second round. What was the valuation of the first one? First one might have been I don't remember exactly, but it's like a startup, you know, like maybe 12 million caps or 20 million caps, something like that. And so he's like, don't worry, I'll get you into the next round.

I was like, okay, great. So he messaged me one day. He says, brother, like, you know, I got your spot for your next round coming together. Let me know.

I'm like, oh, I'm in 25k. No questions asked. He's like, great, got you in. And I was like, I was like, actually, you know, one question, I guess, what is the valuation actually?

What does it happen to be? And he's like, you know, I don't know if I can say this probably I can say this. It was like, it was like, a million. And I was like, what?

And I was like, okay, and I didn't want to go back on my word because I like the product. I like to founder a lot. And I was like, I said, I'm in, so I'm in. And I was like, Oh shit, okay, whatever.

And I was like, you know, do you have like crazy traction? Like, how are you getting this this thing? He's like, you know, we're doing well, but like, you know, he told me the number and I was like, that's an absurd valuation for this thing. I was like, who's doing this deal?

And there's an entry, some of those deals like these guys are nuts. Well, I don't know why they're doing this, but whatever the check did it anyways. It was valued this year at five and a half billion, like, you know, two years later, they said he and they found a tweet in the south, so I can share this. They ramped up revenue from four million to 50 million in ARR in one year.

And they went from 15 employees to 550 employees in one year. And so this is just like an insane amount of traction actually, I actually knew what they were doing. They, you know, they bet on this before because I think the revenue was definitely less than four million at the time. It was valued at 200 million.

And so, you know, the value investor and Andrew would have been dying in that moment. It just didn't make any sense. It didn't make sense to me even, but this has turned out to be a pretty amazing deal. So if not including dilution, which is a big factor here.

So take that for what's worth. So 12 million into five and a half billion is 458. So your $25,000 in that 12 round would have been worth over $11 million. Yes, exactly.

And my buddy Ryan did that deal at that at that round and reminded me as such about like the crazy markup. And so, you know, the 25 days turned into half a million, but man, that's the difference between half a million and 12 million was following up. Oh my God. All right.

Good. So wait, this is my best investment of words. Maybe this is my worst investment actually. 25k that I have million.

Well, it would be good. And then I put it in the rolling funds. So now, you know, most of the economics went to my investors. Dude, that's crazy.