Asking A Billionaire Investor How To Prepare For The Economic Collapse (#371)

I'm mostly holding cash and waiting for winter to come, and I'm going to buy businesses personally as well. At the end of the day, I just— yeah, I just want— I want businesses.

You don't own any like Vanguard index fund shit. You just are literally sitting on, I imagine, tens of millions of dollars of Treasury bills.

Yeah.

All right, on today's episode, we got Andrew Wilkinson joining. If you don't know, you gotta know, Andrew is the creator of Tiny. Tiny owns like, I don't know, 20, 30 businesses at this point. They own Dribbble, they own AeroPress. Basically, he buys and sells businesses of total value, maybe over a billion dollars at this point. Um, definitely over $100 million in revenue. And, um, and he's sort of known as the Warren Buffett of the internet, or that's the model that he chose to create. So he didn't do the startup path where he creates one genius idea. He didn't do the investor path where he's just putting small checks into these companies. Instead, he was finding these little gems of businesses, buying them, and he's been doing this for like, you know, I don't know, 10, 15 years now. And, uh, Andrew's become a good friend. He's a friend of the pod. He listens to the pod, so he knows the vibe. He's probably the most well-liked guest that we have, so we're always happy to have him back. In this episode, we talk about preparing for winter. So what moves he's making or has made in order to prepare for what's going on in the economy. So what he's doing in his business, what he's investing in, that sort of thing. We talked about a couple of his new ideas or businesses that he started, one like negotiating as a service or procurement, as I'm told, or this other company called— actually, I don't want to give it all away, but he talks about a couple of the ideas that he's working on. And then we go on some tangents about why you should only rent your house and not buy houses. We talked about, you know, different ways that he gets together with other entrepreneurs and groups. It's a good episode. So about an hour and a half. I think you'll like it. All right. Enjoy this episode.

Dude, wait, hold on, Sean. I haven't seen you in a minute. Where are you? You good?

Oh, dude, I've been literally sitting at Tesla charging stations for like the last year of my life. It feels like I made a horrific mistake of renting a Tesla for a road trip.

Where'd you go?

Just from here to LA, from the, from the Bay to LA. And I thought, okay, that's cool. Might have to stop once or twice. It stopped 5 times. Basically every 90 minutes I had to stop for 30 minutes. It was awful.

How fast were you going? Were you going above 80?

No, nothing. Not fast. 2 kids in the back and a bunch of, you know, snacks. Like, this was not like some— this is not me. It was you. That's how I felt. That's how I felt towards the car. I was like, Apparently this isn't what most Teslas would be like, but the Tesla I had rented, you know, was, uh, was not the greatest. And which kind of sucked because this was my sell my wife on a Tesla as the next car trip. And, uh, yeah, I had the opposite effect.

You know, it's interesting is like I bought a Tesla like maybe 8 or 9 years ago and it was insane. It felt like, you know, going to the future or whatever. And I just bought the new BMW iX, which is like their electric SUV. And you realize that the main feature of the Tesla is how quiet and fast it accelerates. And instead of being a Tesla feature, you realize, oh, that's just an electric car feature. And then as soon as I get in my BMW, I plug in CarPlay. So it's like the Apple interface. You realize like at the end of the day, these electric cars, like there's really not any competitive advantage. Um, you know, and Tesla, frankly, the interior is so much worse than BMW and all these German and American manufacturers. So like, I'm really curious to see how it all plays out now.

Yeah, they've done such a good job of rebranding, uh, fake leather to vegan interior. And, uh, that's what they say. They say it's vegan-friendly interior. I'm like, oh, you're just low quality, like the fake leather. And whenever I sit in them, they feel like plastic. I'm not a Tesla fan. I also think that they're like super not sexy.

Yeah. Like the Model X looks like a weird big toe or something. I mean, I think like it's, they're great, they're great cars. Like I really like them, but I just think that everyone overestimated their competitive advantage and that at the end of the day, you've got all these legacy manufacturers and, uh, you know, ultimately if Apple and Google are providing the interface that most people use, it barely matters. Right. It's just like a platform with an electric motor. That takes you from A to B and then, you know, does it work with your iPhone or your Android? Uh, and if you look at the Tesla interface, it's like really bad. It, you can't sync your maps up on the screen or anything like that. It's, it's not great.

So Sean, you're not getting one.

Uh, actually I still probably will get one, but, um, yeah, I gotta like do research and shit now. Like I joined the subreddit for Tesla fans. Fans. It's so crazy, by the way, how many products are just for Tesla owners, because you basically have— I don't know how many million, but like, like in the subreddit alone, there's 2 million members. And that's, and that's Reddit. Reddit's like the niche part of it, right? So like, I don't know exactly how many cars Tesla has sold now, but, um, somebody, somebody can grab that. I think they're doing— they did like a million this quarter delivered or something like that. Something crazy, like a huge, huge jump. But let's say that there's 5 million Teslas out there. Those are 5 million high net worth people who can be targeted with specific products. And I've seen some people do this. Uh, one guy had this thing called Tesla— I forgot what it's called— like Tesla Camper or some shit like that. And it basically would turn the trunk of your Tesla— if you fold down the back seat and you open up the trunk of it, it would turn it into like a sleeper van. And, um, it was just like a bed that goes in the back of a Tesla. It's perfectly made to fit the back of a Tesla. It looks sleek like a Tesla thing. And it was like, and they were doing like, you know, they're doing pretty well. These guys would do 7 figures on just, just this one product with very minimal ad spend because they can go highly targeted with content, Instagram and stuff like that to, to reach Tesla owners. And then same thing, people selling these adapters that let you charge everywhere, or there's an app because I was like trying to plan the road trip and I just typed in the destination and like, you know, it gives you a suggestion on where to stop to charge, but it wasn't great. That's why I stopped 5 times. I was like, there had to be a better, more optimal route. than this. And there's some old-ass app called A Better Route Planner or something like that, ABRP. And it's like the number one ranked thing. The interface looks like it's, you know, from the '90s. And, um, it just does a slightly better job at like giving you some custom control over what, what charging stations you should hit on a, on a trip. And I just realized like, wow, there's, this is like a, um, it's like Rolex owners or things like that. Like these high net worth communities that are super passionate and they're locked into that ecosystem. Uh, you know, Apple being the biggest example of this, like the big, like the Apple blogs that's, that were out early on got huge over time. Uh, this is like, there's the same opportunity with Tesla and other products like that.

That's awesome. Yeah. Maybe, maybe I'll be getting one too, but we'll see.

Um, so we should, so we should reintroduce Andrew. So Andrew Wilkens is back. Uh, definitely the, the number one guest of the pod, both in our hearts and the fans' hearts. So, uh, and I don't know why we don't schedule more of these because like we should, but, uh, every quarter or so Andrew just texts us. He's like, hey, I want to come on, I got stuff. And we're like, great, pick it, pick a day, let's do this. And so he's back. He's the, uh, founder, CEO of, uh, of Tiny. And they buy beautiful internet businesses. He's done a bunch of pods with us in the past explaining that stuff, but he's also, he also listens. Do you still listen to the pod regularly? I know you used to listen in the sauna at night.

Yeah, all the time. I take little breaks because I get too pumped up sometimes when I listen, like, in the sauna. That's a nice way to say it. I listen in the shower or the sauna usually.

All right.

If that lasts for more than 4 hours, you can call your doctor.

I'm always fully nude when I listen to you guys.

Would it make you feel comfortable now if we turn the cameras off and take off our clothes?

That would be ideal.

So you had a bunch of ideas or topics, Sam, you want to go to?

Yeah.

So you got— you have a bunch of good shit.

You—

what do you want? So we're going to talk about like what you're doing for winter, meaning like what you're doing, which are personal and business finances, given that the economy may not be going well. We're going to talk about like different ideas that you have. Um, I want to talk about the anonymized workers. So you, like, you've been hiring some anonymous folks and then you also have, uh, like 5 or 6 companies that you've started and we're gonna do like a postmortem on them and like say like what went well and what didn't go well. So Sean, you're—

yeah.

All right, great. I was gonna say you, you drive, Sean, because Andrew already told me a lot of his stuff. So I want you to tell me what's most interesting.

Yeah, let's start with Wynter. So Andrew, maybe tee it off, which is, uh, I think there is a consensus now that we are either in a recession or going to be in a recession and that this is not going to end soon. Give me your take on what your view is of the market and then what are you doing to prepare for that situation?

Yeah. So I mean, there's this great quote by Andy Grove, "Only the paranoid survive." So ultimately, none of us know what's going to happen. We could have a rebound. I was super terrified when COVID hit. I thought the world was going to fall apart and it didn't. But what I do when something like this happens is I stress test my business. So if you think about it, like, um, if you're about to drive your family in a minivan across a large bridge, that's like, you know, a kilometer in the sky, and there's a 1 in 20 chance that bridge can't take the weight of your car, you don't want to drive across, right? Doesn't matter if you're probably going to be fine, you just don't want to go across. And so I think you want to stress test and overengineer your business for all the worst-case scenarios. So effectively, that's what I've been thinking about a lot. And I think what people miss is there's two ways that something like this can go bad, right? The worst way it can go bad is total loss, right? You go bankrupt, your business fails, you're embarrassed, it's terrible. I think that's the worst. But the less bad option that no one really talks about is missing opportunity. So you get presented with something incredible you're illiquid, you can't take advantage of it. So for example, let's say you're an e-commerce company and suddenly ad rates drop, you know, 5x, and you could go out and take the market and sell shitloads of your product. Uh, you can't do that because you're, you're illiquid or you're just barely holding on. You don't have any cash reserves. Maybe there's an amazing acquisition, you can merge or take over a competitor or something, but you can't do that. So you get— instead of errors of omission, you get errors of commission, you're not able to actually execute on those opportunities. And so I've been thinking a lot about this over the last couple months, and generally we operate quite conservatively. Our goal is any debt we have, we want to be able to pay it off pretty much at any time. We try and keep as much cash as we can at head office, but there's a couple specific things that we're doing that I figured I'd share that could be useful. So number one is—

Can you start with what is a stress test? So that sounds cool. I want to stress test my businesses. Great. I sit down today. What the heck am I doing to do that?

Okay. So you would say, okay, what happens if revenue drops 50% in this business? Are you able to lay people off? Is that a possibility? Are you stuck in a bunch of long-term contracts and leases that you can't get out of? Do you have a lot of debt? That you can't pay, um, you know, you're really modeling out, like, what, what I'll do is just do a simple spreadsheet and say like, okay, if revenue goes up by 20%, here's what it looks like. If it goes down by 20%, if it goes down by 50%, if it goes down by 70%, or for example, one thing that often happens is you still have customers, but in many businesses they have accounts receivable and people stop paying. So people, they're gonna pay you, but they might just pay you late, maybe in 90 days or 120 days. And so what happens if no one pays you for 2 or 3 months? Do you have enough money in the, in the bank? Do you have credit lines, et cetera? So, um, I think, you know, it's really wise to kind of do that shadowboxing and imagine a bunch of nightmare scenarios so that you can sleep at night.

Great. What is it?

Yeah, go ahead.

Actually continue where you're going. Continue where we're going. And then I'm going to ask you a question.

Yeah. Okay. So I'll talk a little bit about like what we're specifically doing. So everyone always says, you know, the best companies get started by— and during a recession, which is absolutely true. But at the end of the day, I am not going to be putting a lot of money into crazy venture bets. And what I mean by that is I'm not going to be taking like a lot of risk, right? So I'm not going to go and invest in the e-commerce company with $500K of revenue at a $12 million valuation. I'll still keep betting on new companies, but I'm doing it in a much more conservative way. So for example, we have an AngelList rolling fund. We invest about $12 million a year there, and I'm pivoting it to totally focus on secondary and minority buyouts. So for example, a founder who gets cold feet or wants to buy out their business partner, something like that. Um, I'll do non-binary deals. So what I mean by that is like, if Revenue and earnings get to where they say they're going to be, the valuation is one thing. If they don't, the valuation is another. So kind of our investors win in either scenario. Um, and then the other one is strat, uh, like structured deals. So for example, saying to someone, look, I'll give you a $5 million valuation, but I want a guaranteed 15% return, uh, in the case of liquidation or, uh, dividends and that kind of stuff. And then also, I mean, you guys have talked about this a lot, but the idea of default alive. I want to be investing in businesses where if they can't raise the next round, they're not going out of business. And then the other thing with venture is we've realized too, we can do venture internally by incubating businesses with low downside. So for example, turning our P&L expenses into businesses in and of themselves. So for example, we want better procurement internally. We want to negotiate rates and get our P&L under control. And so we started a business to do that. We want to get better credit across all of our businesses. We started another business to do that. So that's the kind of stuff we're doing with venture.

We just talked all about that the other day.

And what was your take, Sam?

On what?

On what he just said.

I think it's—

I'm— I should do that, I am doing that, or I'm doing something different.

Uh, part of me thinks that like that's a little— well, I personally wouldn't do that because I'm like, man, when shit gets bad, I get afraid and I just want to focus, focus, focus. And when I think of like you starting something new, I'm like, whoa, aren't you gonna have to like allocate like another $500,000 to this salary for buyer.co and like or, you know, like however many the salaries and however much it's gonna cost to do a new website. And so I get, I get nervous about that. So are you not, are you baking those into like new expenses? Are you saying like, look, I could just go and cut costs and save a little bit of money, or I could go spend a little bit more money and build a company around it?

Well, I'm looking at businesses, like there's been businesses where, okay, here's an example. So when we started Buyer, which is our, um, negotiation service for software, that we launched 2 years ago and we ended up selling it to Ramp. So I think we started that business for $50K. At the end of the day, we were looking at it and going, this is a very low-risk bet where we're basically finding someone who, you know, they want to start a company, we're giving them all the tools to do it, and we're going to partner with them, provide all the capital. But at the end of the day, we're looking at really, really simple capital-light businesses that can get revenue within like 2 or 3 months. I don't want something. I mean, I've done, I can talk about this later, but I've done businesses where we go for 10 years and are never profitable and we're just pouring good money after bad. I, you know, I don't do that anymore.

What are you doing with your personal portfolio at the moment? What's that like? What's those percentages look like where, where each thing is?

So, um, basically it's cash. So I have treasury bills. Um, and then I also have a, the only stock I hold right now is Pershing Square Holdings. And the reason I really like that is, A, it's trading for far less than the value of the underlying assets. So it's a holding company that owns a bunch of blue-chip stocks and it's trading at about 66% of the net asset value. So if there's $100 of stocks, you're paying 66 cents. And then they also are—

But that's by design. Don't most of these holding company types trade at a discount anyways?

Not to this degree, right? At the end of the day, like, this is— why is it for the type of fund it is? Uh, well, I think there's a variety of different reasons. I mean, it's illiquid, it's traded in Europe, uh, it's run by Bill Ackman, who has had, you know, a few blowups, and people associate him with blowups. If you actually look at his record, he's killed it. Um, and the other thing I like about that business, by the way, is that they own a very large position in interest rate swaptions. So as interest rates go up, the fund actually does better. So over the last, if you look at the net asset value over the last 4 weeks, it's barely moved while the larger market has gone down significantly. Um, but anyway, I'm mostly holding cash and waiting for winter to come and I'm going to buy businesses personally as well. Uh, at the end of the day, I just, yeah, I just want, I want businesses.

You don't own any like Vanguard index fund shit. You just are literally sitting on, I imagine, tens of millions of dollars of treasury bills.

Yeah.

And that's wild. What do you do? I guess, where's your main focus with your balance sheet? Like, uh, how much of your worth is in your personal accounts versus, let's say, if you think about, okay, my, my net worth, how much of it is associated inside Tiny? And you need to be smart about what you're doing inside Tiny versus on your personal? Because I think for most entrepreneurs, most of their net worth is in their business, and then their personal checking accounts, savings accounts, and stock trading accounts are much smaller in comparison.

Yeah, I'm like 90% in Tiny. But what I have done is I've had liquidity and other things outside of Tiny. Tiny is a holding company that I co-own with Chris, and there's been other assets, like legacy assets that have sold. Or cash flowed. And so I've taken that money and compounded it and done stuff with it personally. And the way I look at the personal money is if everything goes pear-shaped with Tiny, I still want to make sure that I, you know, can retire and be free and have enough money to do stuff. So it's a little bit more conventional, but I, you know, what's funny is, you know, you're like, oh, you don't have ETFs and stuff. As far as I'm concerned, I do have an ETF because Pershing Square Holdings owns 10 positions. Right. So it's a diversified stock portfolio and it just happens to be managed by Bill.

What percentage of your net worth— or sorry, if you have one number in Treasury bills, how's that compared to the other number in Pershing Square? Pershing Square?

I think it's 50/50 right now.

And one thing that I've been following is basically like 2 years ago, so, or a year ago, you own or you're a majority I actually don't know what your percentage is. I think, uh, it's in the, the annual report, but, uh, I, you own WeCommerce, which is a collection of Shopify plugins as well as a few other products. That's like a really, really good business. I forget what it said in the annual report, but it's publicly traded. It's like $50 or $60 million a year in annual revenue. And its peak stock was like $600 million. It was crushing it. Now, like the rest of tech, it's just been decimated to like, I, I, what is it today?

I think it's like $80 million or something.

So how's it feel like you're the only person I know who's like this wealthy? Well, I know we talked to Dharmesh. Dharmesh was like, yeah, I lost like $200, $300 million the other day. Uh, how's like, what's it feel like? What's it, what's, where's your perspective and where's your emotions when you're seeing this thing destroy it and be amazing at $600 million? All the way down to 80. Like, how do you feel about that?

So I think if I was just like a pure— one of the interesting phenomenon I've seen is people who are great entrepreneurs often are just great entrepreneurs. They don't become investors. They, you know, they don't like thinking about the stock market and finance and stuff. I actually really enjoy that side. And so I've spent the last 10 years learning about investing and reading about Warren Buffett. And Warren Buffett's mentor, Benjamin Graham, has this whole idea of Mr. Market, right? So the stock market is like this moody person. It goes up and down. At the end of the day, if you know what your business is worth, it's irrelevant what the stock market says it's worth. So personally, I mean, yeah, like sure, there's a little bit of an ego hit seeing your net worth have some zeros pulled off of it. But at the end of the day, I know that number is made up anyway. So for me, it really doesn't affect me day to day. I just go, do I still own a great business?

Well, and it— you're, you're personally, you're fine. Like you've got liquidity and you've all these other things going on, but like, um, I imagine—

let me put it this way. There's a great Buffett story and he says, you know, Sam, let's say you own a farm and it makes you a million dollars a year of profit, right? And some yokel walks up and goes, hey Sam, I'll give you $50,000 for that farm. You just go, go away. Like, no, I'm not going to sell. And then someone else one day comes along and says, Hey, I'll give you $20 million. Maybe you consider that. But the idea is that at the end of the day, these yokels will yell numbers at you and you don't have to sell, right? Unless you sell, that's when it matters, right? If you sold for 50 grand because you're panicked, because you're going, oh, the economy's in a recession, maybe my farm will crumble and you sell for 50 grand. Yeah, that sucks. But if you ignore the yokels, it's irrelevant. And in the same vein, we all own houses. And the houses, the values fluctuate constantly. We don't feel that, right? Because you don't see a ticker. Or if you own The Hustle, there was times where if The Hustle had been publicly traded, it would've been worth next to nothing. And then there are other times where it would be worth crazy numbers, right? And you, at the end of the day, you know your business, you know what it's worth. Yeah.

Dharmesh said this thing, he goes, valuation oscillates around value. And I just had this images, you know, so imagine you're creating value in this business. The line is going up and it's pretty steady. It's really, it's quite hard actually to have like dramatic jumps in the value of your business or dramatic downs and then dramatic highs again. It's like, that's not really how value's created in most businesses. And, um, and he's like, but then value is this like crazy moody line that's swinging up and down on like higher and lower than the value at any given time. And if you have to be able to differentiate between the value of a business in the valuation of a business. And that's, I think, what you're, what you're talking about.

Totally.

You want to talk about some of these? What do you want to get to now, Sean?

Well, I was going to say I have the opposite strategy as Andrew, as I often tend to do with most of my friends. I have the opposite strategy, not by design. I wish that was not true. But like, for example, right now I'm doing more— I'm putting more attention and energy and doing more deals in venture than I did in the past year, the past 2 years, really, because with your personal money. Uh, well, though, the fund money, but I'm, you know, I'm the steward of that capital, right? So, and it's, and the, the returns of that, I have personal money in there as well, but like the returns of that, I think are going to be pretty meaningful personally. But, um, this amazing thing has happened, which is that all the founders have just read bad news for like 6 months straight. And this has done 2 things. One, a bunch of like not a bunch of people who would have quit later quit now, which is fantastic because picking is really hard in startups. And so like, you know, thanks for making it easy where like you meet a founder who's just sort of like, yeah, so what? Like, okay, okay, you know, who cares about what's going on in the world? I'm still going to do this thing. I was obsessed with it before. Just because there's a war in Ukraine and a pandemic and the stock market's down and crypto is down doesn't change my interest in this like niche thing. So you see that person, you're like, okay, great. They're, they're in it for the long haul. You see other people who are pivoting like crazy and you're like, okay, they're not really in it for the long haul. The second thing is that they've cut all their valuations by like 40 to 60% or more. The same deal. Yeah.

Or more.

Uh, so the same deal you could get, you know, for $10 million, you're now getting for $4 or $5 million, right? $20 million, you're now getting for $10 million. And so, but, but the reality is that that same business was going to exit 7 to 10 years from now where like, The market, they're reacting, they're changing their valuation based on today's data, but you're going to get paid out. So you get to buy cheaper, but you get to sell 7 to 10 years from now when the market conditions are going to be dramatically different than today and likely a lot better than whatever this next down cycle of the market looks like over this year, next year, whatever, however long it lasts.

My worry is anchor bias. So I mean, if you think about it, everyone was saying venture valuations were crazy in 2019. Let's say the average seed and, you know, or, or sorry, angel valuation was say $5 million in 2019, which was much higher than it was in 2016. In 2016, I'd see deals for $1 to $3 million. So then it goes to $5 and then in 2020, 2021, let's say it goes to $20 million, right? And then it comes back down to $5 and we all go, oh wow, it's a crazy deal. Right? So my worry is that these businesses should actually be valued at $1 to $3 million because If anyone came to me with most of these businesses, uh, you know, as a, as a cashflow real-world investor, it just looks insane.

Yeah.

But you said the only way to get your money back is to have a massive exit, right?

But that's always, that's always been true for venture, right? Venture, uh, a venture deal will look horrible to any private equity type of buyer. And in the same way, a private equity deal to a venture capitalist will look also horrible because their, their criteria and their lens and their model, they're based on fundamental, like totally different factors.

And Andrew, on this point, you said both. You said, I didn't invest in Slack when I had the opportunity. I didn't invest in this or that or this. And you've made, I don't know, dozens or maybe even hundreds of investments. So you, you, you walk the walk as well, but you, you've said, oh, I wish I could have done this. I wish I would have done that. I made a huge mistake to do that. An exercise that I do all the time, that I try to do all the time, is I try to ask myself what, like, you know, like we constantly say like, oh, I wish I would've known that this company was gonna be as big as it was. And I wish I would've pounced on that. And I had that opportunity, or there was this opportunity that I had and I missed it. And I always ask myself, what is happening this second, this week, this month, where I'm gonna look back and there's a chance that it's gonna say, I really just screwed that up. Like that was a, a, like for example, for me it was when I was running The Hustle, Facebook ads, I could buy users for a dollar and they were worth $10 to me. So like I knew at the present this is a good deal and I didn't go harder on that and I missed that opportunity. And so right now I am wondering, you know, I, uh, about 8 months ago Sean and I were like, dude, we're never gonna make money on angel investing because like the valuations are $20 million when a company should be $5 million. And like these whole, this whole like idea of like a Tim Ferriss, investing $15,000 into Uber and making $50 million. That can never happen with us. The numbers just don't work. Now I'm seeing these numbers and I'm like, is that happening right now? Is this opportunity— does this exist this second?

I would say you guys have a very unique opportunity because of your profile now. Right? I think like Tim Ferriss was able to get into the best deals because people wanted him in them. And you guys are going to have that same opportunity. But I guess the question is, Are you playing roulette or are you playing poker? I play poker. I want to play with very good odds in my favor and I want to know the odds. I don't want to play roulette where it's almost totally random. I still think venture is totally random. I do it for fun off the side of my desk. And don't get me wrong, when I see, I look back and go, I could have predicted maybe not Slack, but Certainly there's some of the businesses where I could see it was quite obvious that they were going to be winners and I could have pushed harder to invest in them. But I still look at that as kind of random because I've had that feeling on businesses where I've lost everything. So for me, what I'm saying is you're about to enter an environment where anyone with cash who has a large sum of cash is going to be able to buy a business at, say, a 20 or a 30% earnings yield. Meaning you can buy a business and pay yourself back in 2 or 3 years, maybe 5 years, and you can buy good businesses, right? Because everyone's going to be panicking and wanting to sell. There's going to be great opportunities. To me, I'd just rather play that poker game than venture right now. And I'm focused on it. It's not to say I'm not going to do venture long-term. And if a friend of mine who's amazing comes to me and says, hey, I need $100,000 for my company, I will invest all day still. I'm just saying I'm not focusing any energy there right now.

What's an example of a company that you tried to buy recently and they wouldn't sell? Or an example of a company that you can, you can reveal now and it's no big deal because it just, it won't happen. But is there any companies that you, that, that are good examples of this?

Uh, well, there's one really weird one. Um, bridgebase.com. I started playing bridge like 5 years ago and it's kind of like chess.com. There's all these nerds that play. The website isn't particularly good, but I was quite impressed by all the numbers behind it. I think it ended up selling to someone else. We looked at chess.com. That ended up obviously blowing up with everything that happened with Queen's Gambit. I mean, there's all sorts of businesses. I won't kiss and tell because we still might look at some of them, but we've looked at a lot of kind of off-the-beaten-path, interesting businesses like that. Where you find a nerdy cohort of people that have a dedicated place where they all gather.

How much do you think bridgebase.com sold for? I'm looking at it now. It looks like it has 8 million monthly unique visitors. It's pretty huge.

Yeah, I think my mom uses this. By the way, that little kiss and tell line, I have this sheet on my phone where I just save little throwaway lines that I call them get out of jail free for phrases, where it's basically like, how do you use a phrase in specific situations? I'll give you another example. So Andrew just did one where it's like, you get kind of put on the spot and you don't really want to share. So you have a phrase that gets you out of it smoothly, safely, securely, and no damage done versus— there were many other things that he could have said in a response that just would've been sort of awkward. And another one, my uncle told me this once. He goes, he was like trying to do this deal and it wasn't really working. And I kind of, we all kind of felt like, I feel like this deal is doable, but we're just not there yet. And like, maybe we just need to like, you know, if you just wine and dine this guy a little bit, like I think it would happen. But you can't just tell somebody, I'd like to, you know, wine and dine you. That doesn't really work. And he's just like, you know, my mentor told me you gotta meet someone belly to belly if you're really ever gonna do a deal with them. And like whether it happens or not, you never regret meeting another He says, okay, yeah, sure. And he used that as the— to get what he wanted, which is I'd like to meet you in person in a kind of informal way. And I have no agenda. Like, I can't come up with a new agenda to do it. I'm just telling you that this is something I believe fundamentally, that the two people need to be belly to belly if they wanted to, if they ever want to do it.

You have an entire folder dedicated to these phrases. What other folders do you have? And what other words are in that folder?

Like, you use one all the time. Like, don't piss on my leg and tell me it's raining. It's like, how do I— How do I get my point across, you know, with a little bit of humor, a little bit of showmanship, and a little bit of like, uh, ambiguity versus just speaking so fucking— like, cause I have this problem, I'm really direct. So I kind of needed these tools in order to do stuff. And I stole this actually from Neville. Neville, in his copywriting course, when I was creating my copywriting course, I had taken other people's to see what do they know that I don't know? What are, what are some things, useful things they've taught? And one of the things he teaches in there is he goes, um, What does he call it? He's like transition. He has this long list of transition phrases and it's like, or he calls it slippery transitions or something like that. And basically it's like, we all know that you should kind of start with small talk and then get to the meat. If you just go straight to the meat, it's a little bit aggressive and upfront, but also it's hard to be like, small talk, small talk, small talk. So anywho, do you want to do that? Would you like to buy my product? And it's like, oh damn, awkward. And so he, he has this long list of like his little connector phrases. And I was like, oh, that's really useful actually. Like, this is a useful thing to get out of a course. So when I created my course, I started creating like these banks of like phrases, headline formulas, transition words, like different things. I'm like, this is your go-to when you need to sign off or like say hello in a fun way, sign off in a fun way, give a, you know, transition or like, you know, give somebody something that's direct. And I, so I started creating those for myself.

Dude, belly to belly is a good one.

Yeah, it's a good one, right? Like face to face doesn't have the same touch. Belly to belly gets a chuckle and you're like, okay, I understand what you're trying to do.

Andrew, are you doing any writing at the moment? You're all, you've always been a great writer, but you haven't, it doesn't seem like you're really producing a lot. Are you writing for your companies or anything?

Yeah, I'm working on a book actually.

What? Really? On what?

Yeah. Yeah. Just about, um, The story of building our business and just, yeah, like the experience that I've had over the last 15 years.

What's it going to be called?

I don't know yet. I'm still figuring it out. I just signed like a book agent and, uh, I think I, I think I sold it, but yeah, we'll see. It's fun. I mean, it's fun. It goes back to like, um, I think I've spent so many years frantically writing like Twitter threads that disappear into the ether. I love the idea of actually building a narrative story and writing something more substantial. I'm really enjoying that process. It's a new thing. It's a totally new thing to learn. I'll share some stuff with you guys.

I'm going to tell you a little book story that will give you— When you tweeted out you're coming on, you're like, "Oh, what should we talk about?" There's a bunch of questions, a bunch of good ones, honestly. But one that stood out to me was this guy goes, "Give us— Can you guys each tell us an example of a butterfly effect moment in your life?" Meaning, A chance encounter you had with somebody or somebody or something that just nudged you in a different trajectory that kind of changed your thing. And at the time, it didn't seem like this monumental decision or event. It just seemed like this kind of harmless chance encounter. And your book thing reminded me of my answer to that, which is that once upon a— I think I've told the story before. Once upon a time, my dad was supposed to come to this meeting and he's like, he was supposed to go to this meeting in San Diego. He's like, "Oh, you should come with me." I was a college kid at the time, I think a junior or senior in college. And he's like, come with me. And I was like, okay, I guess I'll just tag along. I'll shadow you for this. I'd never done that before. So it's kind of a random thing that my dad tried to do. And then my dad's flight gets canceled. My dad's coming from Indonesia at the time. So his flight gets canceled. And I'm like, oh shoot, I'm already at my connecting stop. I'm like, wherever, Kansas City. And what should I do? He's like, oh, just go do the meeting. And I'm like, I don't even know the context. I don't even know what you do for a living. How am I going to talk to this guy? He's like, don't worry, this guy's great. And I told him you'll be there. And he just said, come hang out with me. So I go to San Diego, I meet this guy, and the guy comes in as like a ball of energy. And he's got Neil Centurion. He comes in as this ball of energy, charisma. He's immediately cracking jokes. He's telling me a story. He walks in and he's late, like 25 minutes late. I'm just sitting in this room and he goes, he goes, ah, man, I'm sorry. I just got off the phone with whoever, Comcast. He's like, let me tell you one thing. You got a pen? Get out your pen. Write this down. And I'm like, I just met this guy. He hasn't even said hello yet. He doesn't even know my name. And I like go get my pen because like I'm the little bitch that I am. And he's like, um, he's like, write this down. If you have great customer service, you can run the world. You hear me? Run the world. And I was like, and so he's like this character and it turns out this guy had this crazy career where he, he built like skyscraper in San Diego. Cause he's like, oh, real estate's where I'm going to make my money. Then he's like, He got into Hollywood. He wrote two, like, you know, like scripts for films or something like that. He was a showrunner for, for, for a bit. And so he thought that's how we would make it. Then he started tech companies with the internet boom. And then he married the woman who started 1-800-Flowers. And he's like, just had this crazy career. He invested, he bumped into a guy in an elevator, invested in his company, and it ended up becoming like Chegg or something like that. Like it's a big multi-billion dollar thing. So he had this crazy, like, he's just wowing me with all this, like this, like afternoon, basically. He takes me to this restaurant. To go eat. They have a special table for him and the tablecloth is all made out of paper. It's a high-end restaurant, but his was made out of paper like a kid's table. And they had crayons and he would just draw diagrams and like cut deals at this table. And he never had to order. They would just bring out loads of food and then he'd walk away at the end like an Uber. He never had to pay. And I was like, I don't know who this guy is, but like, that's what I want to be in life. I want to be this ball of energy who's just cutting deals, drawing on tables and like, you know, has had 5 different arcs of his career in these different spaces. And he's still like, I don't know, this guy's like 65, 70 years old. He still seems to have all the energy in the world. So, and then I just like went back to school and like, but if I hadn't had that, I don't think I would have had this blueprint that like being an entrepreneur could be cool and it could have like more variety. And I didn't have to like choose one thing. I like, I just saw this one example for one day and it was like a dream basically. Then it was done. I never talked to this guy now. He's still there. He's still in San Diego and he's like guest teaches at some school there and He's got this mega mansion on the top of the hill, and that's still what he does.

That's awesome. That was a good story.

But oh, sorry, the book part on the way out, he's like, so I'm with this guy for 2.5 hours, and then I'm just like, whoa, I don't know what the hell I just saw. I'm 21 years old. I've never, I've never, like in college, you don't meet people like this. I didn't at least. So it was the first time I ever met somebody like dynamic like this and somebody who had made their own path and didn't just like follow their major into some career. And on the way out, he just shoves a book in my hand and it's his book and it's called I'm There for Your Baby. And if you want to read this guy's book, it never sold a lot of copies, I don't think. But he wrote a note to me in it, handed me this book, and then on my plane ride out of there, I sure enough read the book cover to cover. And I liked the guy. By the time I was done with the book, I loved the guy. And so I remember that because I was like, oh, I've always thought of books in one way as this I don't know, mass market. You're trying to become a bestseller or something like that. And then I realized a book is just a tool that like anybody can use. Like some people use their book to get public speaking gigs, but this guy used it for a different thing, which was he could turn a like it into a love it just by handing this book. It's like, cool, I met you for 2 hours or an hour. I'm not going to talk to you anymore, but this book will sell you on me and like what I'm all about through entertaining stories and whatever. And, and I was just remember thinking, oh, that's a great idea to do so that every person you meet for the rest of your life, you can convert them into being a believer and a buyer and a fan of what you do. And that's actually how I want to use my book when I write a book. I can't find this client info. Have you heard of HubSpot?

HubSpot is a CRM platform, so it shares its data across every application. Communication.

Every team can stay aligned. No out-of-sync spreadsheets or dueling databases.

HubSpot. Grow better. I did this, um, like personal values exercise like 6 months ago or so. And, uh, when I thought about what do I actually want, what do I actually like, why do I do business? It's I wanna meet interesting people. And one of the great things about being on Twitter or coming on this podcast is that I'll randomly bump into people in a coffee shop. So I'll be sitting there and some guy will walk up and say, "Hey, I heard you on My First Million. I want to tell you about my business." And I end up making all these new friends. So I've probably made 20 new friends from this podcast. I've had random lunches with people. Literally, I've been in line for lunch and someone's been like, "Hey, want to have lunch?" And I have. And so the next level of that is, yeah, a book. You get to exist in someone's brain.

That's a great question when you're in line for lunch. You can't say no.

Well, yeah.

They're like, "You're in line." I know you want to rush. Totally.

But it was great. The guy was super interesting. He had like an airplane leasing business. It was crazy. But I think a book, you get to exist in someone's brain for like 20, 25 hours. And it's exactly that, right? You can actually get someone to truly understand who you are. And then when you meet them, you don't have to do your preamble. You don't have to do your pitch. You don't have to do what that guy did with you. You don't have to sell. You can just be yourself and they already know the deal. And I think there's something really cool about that.

So speaking of meeting interesting people, let me ask you guys if you would do this. So I was talking to Nathan Barry the other the other day, Nathan Barry, you know, he owns ConvertKit or he owns the most, all of it. He's probably worth $200 or $300 million. He's worth a lot. And he told me how when he travels, sometimes he'll organize, like he'll stay, like if he wants to go somewhere for 7 days, he'll plan an 8th day that's dedicated to work. And what he'll do is he'll do like a 6-hour meeting where he'll let like 20 or 30 people all come and hang out with him, but he charges them. And it's almost like a very miniature conference. And I could, uh, maybe I'm butchering a little bit about what he does, but basically he's like, I got the inspiration because Basecamp, Jason Fried and those guys used to do these things where they would charge $200 to $2,000 and, um, you can come hang out at their office. And I thought, uh, you know, I should do this when I travel and it will pay for my trip. And also I can meet interesting people. And I thought about this and the cons are it could feel like sleazy and weird to like, well, I'm charging money for my time. But I think he actually said, Andrew, he went to one of your things and you gave the money away. I think, like, yeah. And I was like, yeah, that is the sleazy part. But it is kind of a cool way to like meet people that cross a certain threshold. And it could, if it could like pay for your trip. And even though it's like, well, I don't, I don't, I have enough money that I could pay for my trip. There's something about it that I find so intoxicating to do this. Have you ever thought about doing it? Sean, would you do this? Sean and Andrew? Yeah. What are you going to say?

I was going to say, I really struggle with this. So like you guys are, I think one of you guys is on Intro.

I'm on Intro because listen, I'm friends with the founder. Listen, listen. Uh, first of all, I don't even have any, I don't even think I have, well, I don't have that many dates available, but my friend started it and he was like, hey, use this. I was like, fine. I started using it. Then he puts my ad everywhere on Facebook. And so I only make like an hour or two available a month. And it's just crazy.

My friend's just a service that lets you meet Sam Parr. That's, I'm pretty sure that's what Intro It's based on the ads that I've seen. That's what intrapreneurs do.

Oh my God. They are killing me with all these ads.

Well, it's a terrible way to use your time. What we did, we did a charity ask me anything. So we were like, "Okay, anyone who pays, whatever you donate, we'll double it." And I think we suggested the donation or whatever, but with Nathan and about 20 other entrepreneurs, we did a Zoom, spent 2 or 3 hours answering all their questions. I think we raised like $50 grand for a charity, which was pretty cool. Um, but I really struggle with this kind of stuff because at the end of the day you're selling your hours and I don't want to be in that business. Um, but it's fun. It's a fun way to do it. And, but I feel like it compromises the, like, people expect value, right? So if you're on day 8 of your trip and you're exhausted, you know, have to dial it up like that guy that met you in San Diego. You have to be like histrionic. You have to wear a mask. You have to like, pump yourself up. And I find that one of the things I've realized is I'm very capable of doing that. I can be miserable and I can pump myself up like Tony Robbins style, jump on the trampoline and all that crap, but it makes me miserable. And so I just don't want to do that.

Would you do it, Sean?

I would not charge for that, mostly because if I'm doing that, it's because I want to meet interesting people. So I'd rather say it's filtered, Or I have the right to just stop talking to you or boot you out in the next 5— I can make these meetings 10 minutes. So Brad Feld did this. Brad Feld's a VC in Boulder. He's probably one of the main, most well-known venture capitalists in Boulder, Colorado. And he used to have this one day on his calendar every month called the random day or something like that. And he would just let you book a 15 or 20-minute meeting with him. He'd just sit in a coffee shop and he'd sit there for 4 or 5 hours and he'd just try to meet as many people as he could. And he had no filter there. He's like, you don't need a warm intro. You don't need this.

You don't need that.

And first, that was great branding for him. I'm like, I'm a man of the people. You know, it's like when Gary Vee does these TikToks, and it's like, it's just some, you know, somebody who comes up to him and they look like, you know, they're like haggard. And they're like, Gary, can I just get a minute of your time? He's like, of course, I'm anything for my, my fans. And he's like, Gary, you know, how do I— I don't have enough money for dinner. He's like, here's what you're gonna do. You're gonna take that guy's dinner and sell it. Now you got two dinners, give them back one and you got one for yourself. It's like, he gives them this pump-up thing and the guy's like, "Thank you so much." And they hug and they embrace. And I'm like, "Wow, I don't want to touch anyone who listens to the podcast." I just, here's a rule, we're not touching. Touching is not happening. That's just not a thing. But it gives a brand vibe of Gary's one of the people. He's a man of the fans. And so similarly, Brad would do this and I thought there was immense brand value for him doing this. And then the second thing was, I'm sure there is some— when I met him, I was like, "Why do you do these?" Because I went to one and he goes, Um, he goes, you know, you have to create a landing spot for luck. And other people call this a surface area for serendipity, but like you want to give in your schedule some place.

First of all, those are both of those phrases, Sean. Gold. A landing area for luck and surface area for serendipity. Sorry, go ahead. Those are both beautiful.

Yeah.

Future book titles. Uh, so, so basically you want to, you want to create like intentionally create space because the more successful you get, the busier you typically will get by default and the less space goes on your calendar. Buffett and others like, you know, Andrew, you do this too where you just carve out space. I'm gonna think, I'm gonna read, I'm gonna walk. I don't need to have meetings after meetings after meetings. 'Cause guess what? If I let that happen, that's exactly what's gonna happen to my calendar. And what this guy did I thought was interesting was cool. If I just stay in my bubble and I only admit people who on the surface like are, you know, worthy of my time or whatever. Then I'm just going to miss out on a whole bunch of other things. And so how do I carve out, you know, what's the 1% of my time or 2% of my time that I'm willing to allocate towards randomness, luck, serendipity, just so I can like have that in my, in my mix.

It's amazing how that goes away. Like I remember when people would email me early in my career, I would be so flattered. Like they'd write me like 4 paragraphs and I'd write them a really thoughtful response and get on the phone with them. And then, you know, you just get more and more of those and you waste your time. Like, they're only interesting maybe like 1 out of 5 times. The rest of the time you want to off yourself. And so I basically stopped. And then it was like, oh shit, how do I get that serendipity? And to be honest, going on here is a great form of serendipity because of those random meetings and introductions and stuff. But most of the time, if someone emails me, I honestly, I delete it unless it's like one line and super clear. If it's a pitch or anything, I just delete it.

I found my, my most Navalism, Naval thing that I can't— my original Naval quote where I realized the point of this podcast is not to be well known. The point of creating content is not to be well known, meaning known by a lot of people, but rather to be known well. So what's happening now is in my inbox or my DMs, people are sending me stuff that is so interesting to me, or they're making intros that are so on point. And the reason they can do that is because if they listen to the podcast, they know exactly the type of shit I'm into and that Sam's into. And so we get this amazing inflow of just dope stuff that we didn't have the eyes and ears out there to go see. And that's when you know it's working. For anyone out there who wants to create content, don't make your goal well known, make it known well, and you'll know it's working because you'll start getting more than you're being asked for in these emails or DMs. And Andrew, I'm sure you get the same, which is people send you either interesting companies or deals, or they want to come to work for you in this. They want to help you solve specific problems because they know you well. They know what you're, what you're interested in, what you're, what you're looking for more of.

Dude, I had a guy just recently send me— so he goes, hey, my website does this much revenue and this much profit. And he told me all about it and I didn't reply. And he goes, what, you don't believe me? And he sent me a Google Drive with his tax returns, like had his social and everything. And it was 100% his tax return. I mean, I guess it could have been Photoshopped, but it— and he goes— and then his reply was like, see, told you.

I didn't say anything.

Small boy stuff. That is absolutely small boy stuff.

The tax returns, it was like $17 million of income. And he, and he sent me multiple years, uh, and it was hilarious. It was one of the best things. And I was like, you know, instead of like, uh, Casey Neistat and Dave Portnoy used to do these awesome videos where they would unbox all the fan mail that they got, and it was actually really fun content. I'm like, we need to have like an unboxing our inbox.

No, no, we should unbox your tax returns. People just send us their tax returns and we open it up and we react. We create a YouTube reaction channel just to your income and your business, to your P&L.

Does that guy want to— does he want to sell or get you to invest or what was it?

He wants to be friends.

He just wanted to be friends. He just wanted to be friends.

You know, Joe Rogan has this like famous YouTube clip where he's read some quote from some guy, which is like most, someone famous, but it's like, most men lead lives of quiet despair or something like that. And he's like, it's so true. Most people walking around, they just have this sadness in them. And there's a version of that for rich people, which is if you are rich, but unacknowledged, there's something in you that just kills you. I mean, we get this a lot for the podcast. So much where people are just like, hey, I just need to like, It's like you go park at a mall or whatever, you're like, can you validate my parking? That's how I feel. It's like, can you validate my, my wealth? Can you validate my career? It's like, yep, here, let me give you the punch hole. Like, this is amazing. You're, you are way wealthier than me. You're way more successful than me. You're probably smarter than me. But they haven't, they don't have the platform or the audience where they get that sort of congratulatory thing. Like maybe the people in their life they can't brag to, they can't tell their employees how well they're doing. You know, there's no need to go do a press tour about it. So it's like, That would be uncomfortable. But so then they're just sort of like, damn, nobody, nobody, I won the game and nobody knows.

Dude, we've had so many people, Sean, who we've mentioned and they've reached out to me. And I noticed that, that just that mention, it's, they now view themselves as like a public figure. They start creating content and things like that. And I want to tell them like, hey, just so you know, you've already won. It's like, you're killing it.

They start doing, everybody's asking me about my skincare routine. And it's like, oh, it's like, you know, they get that little taste of that, that, that fame, that hit, those likes. And they're like, I guess I should abandon this working formula that's generating mounds of wealth in order to write some threads, baby. And they start writing tons of threads.

What's that? What's that quote? It's like, would you rather be the world's greatest lover and have nobody know, or be the world's worst lover, but have everyone think you're the world's greatest lover, right? There's so many of these, uh, world's greatest lovers walking around.

Dude, speaking of being a lover, Andrew, You have like a little bit of a 5 o'clock shadow right now and you've— your jaw is looking chiseled. You look— this is the best I've ever seen you look.

What's going on? Have you been getting some work done? What's going on here?

Yeah, extensive, uh, facial reconstruction. No, I've just been powerlifting for the last 6 or 8 months.

It's working. Look at these cheekbones.

They're coming through the Riverside to Sam right now. Anyone who powerlifts is just like automatically turns Sam on.

Yeah, you had me at squat.

I'm not the Sam Parr shirtless photos on Instagram level, but I'm getting there.

Okay, so that's another example. That's if you get there, let's say, let's say when you get there and you're just, you're so proud of yourself, but now nobody knows. Everyone still thinks you're just a normal looking dude, but now you know the truth. Are you going to get your parking validated?

Are you going to post something?

But maybe like, you know, you got to like, you know, do the fake, uh, fake like humble thing where it's like You know, I gotta be honest, I was so proud of myself. I was really depressed about my body and nobody talks about this, so that's why I'm coming forward with these selfies. Just, I needed to be vulnerable here, guys. Check this out.

Who's the, um, who's the guy? He was on Silicon Valley, the Indian guy, and he got jacked. What's his name? Kameel Nanjiani. The comedian. Yeah, like, like, think about that experience for him, right? Because he had the biggest version of that. Uh, yeah, I don't know. I've, I've done that. I've I personally have like progress photos and stuff and I showed my friends, but I would never, I don't think I would ever post.

I've seen them online.

I can't do it.

I think they look great. I've seen them.

Are you more or less ripped than Chamath, who's, I think you're, he's an investor in your thing, right? Do you guys exchange?

Yeah, I definitely am less, definitely less ripped than Chamath.

No, no, no, no, no, no. I don't think so. You guys are, you guys are, you guys are right around the same area. He's just dark, so, you know, darker always looks more cut, you know what I'm saying?

Yeah. My problem is I've got a hardcore farmer's tan, so my arms get dark and then my entire body is basically translucent. You can see my heart beating through my chest. So it's not the best for a six-pack. That's amazing.

Yeah. You're like, what white privilege? Have you ever seen a man's heart beat through his chest? So, All right, let's do some more. I wanted to say one thing real quick. You had said something that I thought was— I want to say this because this is one of the most interesting observations I had about my own investing misses that I made a firm note to change. So you talked about creating businesses off your P&L. So you look at your expenses and you say, oh, we spend money on SaaS fees. What if we could create a business? By the way, is the new one called Buyer or is it called something else now?

No, we actually started one called DealMaker. And because Buyer did software, we sold it to Ramp. They're doing that. We have to do something different. Right? So basically the story there was we, Chris and I, were maniacal about negotiation in the early days, right? When you're the owner of a business, say you save $30, that's $30 in your pocket directly. And what we noticed was as we, as we got bigger and bigger and bigger, we had managers and CEOs. Running the businesses, they're comp-based on hitting a very large number. And so $30 grand or $30 doesn't really matter anymore. But to us, the owners, that really matters. And so we were like, okay, how can we make this easy for the CEO? Because nobody likes the discomfort of negotiating.

I hate it.

And so the idea— it's very uncomfortable. I don't like it either. I know all the tricks. I've done it. Now I just don't enjoy doing it. But if I can outsource it to some scrappy person who loves to negotiate a car or a house or a lease or whatever it is. I'll do that all day long. And so we created this business called DealMaker, dealmaker.co. And instead of doing software, we're doing office leases, furniture, insurance, all the random stuff in your P&L. And basically you just CC them and they take a cut of whatever the savings are. And this is something I wanted myself because I was going, Oh my God. I had the experience of when you're rich or people know you're rich, they will rip you off if they can. So a recent example is I got Wi-Fi installed in my house and they had to wire the house and do some stuff. It was tens of thousands of dollars. And I was like, holy shit, it's too late now. I could have just had an Eero installed in a mesh network or whatever, but instead I did the rich fancy thing and got it all custom wired. Or another one is in our office, we got drapes and we got a quote and it was $20,000 for some white drapes. I looked at IKEA, we could buy them for like $2,000, right? So I'm just realizing that we have a target on our back. I think anyone who runs a business does, especially when times are good. And so I think having someone to negotiate on your behalf is a very good idea.

How did you, how much did you fund this business with? It looks cool. The site looks good.

Yeah, I think it may be like $50K. Like I said, we don't put large sums of money into this stuff. We basically find really scrappy operators where we can basically say, look, we've got all the back office, all the structuring legal, it's ready to go. We'll build the website for you. You just need to take it and run with it. And we go typically like 50/50 or 70/30 depending on the amount of capital we have to put into it.

Is it working?

Yeah, so far. I mean, I think it's profitable at this point. And you said it's pretty—

you said you just—

It doesn't need much to be profitable.

You just CC dealmakers, so you're like, when you're talking to your vendors or whatever, you just CC dealmaker in and it's like basically like, hey, you know, here's my brother who's going to beat you up.

It's like, think of it as like procurement department, right? So like if you go to Walmart, like we used to work with Walmart at Metalab and it would be like, okay, here, here's what we want. We'd say like, this is the number. And then they send you to procurement and procurement is a guy who's literally a professional negotiator who crushes you and they crush you in so many different ways, right? It's like, Your hourly rate is too high. Your payment terms, you know, you said 15 days, we want 45. And so it's just about getting the most.

In my head, I'm just imagining like a bunch of like young guys like, like shaking in their boots like, oh, we got to meet Mr. Brückjürgen. And he's like this scary guy. And you walk in and it's just this like dork with like a horrible like half beard with like mustard on his white shirt that's short sleeve and buttoned up like looking like Dwight. And he's just like the nerdiest guy ever. And he just like starts rubbing his nipples, like thinking about a good deal. Like, oh yeah, you guys probably read 10% Off.

There's a great, there's a great book called I Will Teach You to Be Rich by Ramit Sethi. And I read it like 15 years ago and he makes a really good point. He goes, look, you're not, you don't get rich by paying attention to like lattes and like building budgets and like not buying lunch out. You get rich by paying attention to these macro big things in your life. So for example, when you buy a house, there's a massive difference between getting a 3% interest rate and a 2% interest rate, but no one thinks like that. And so this is the stuff you want to outsource to someone else and have them do it. You know, you buy your car, you buy your house, you get an office lease, you buy $20,000 of furniture.

How are you actually pulling this off? Like how, how, what's the, what's the, what's the work behind the scenes to to do this deal?

It's literally an army of guys who love to negotiate and we train them up. We give them all the books that we read and we have a process and they get CC'd and they go for it. And they basically say, "Look, your first quote was X, we saved you Y, give us a cut of the savings and go for it." In some instances, they'll retain us. So for example, let's say there's a company and they're like, we want to do a super thorough review of everything, then, you know, they might pay a retainer or something. But usually it's just being CC'd.

My dad should work for you. My dad is incredible at this. He will like— but he's very unorthodox. He can't train this.

Well, it takes time. Here's the thing is like you and I, like if we were to— I remember I walked into a car dealership and I go to the guy and I say, I have 2 hours and if you can get me the car in 2 hours, I will just sign whatever you want. But I need it in 2 hours, right? That's the worst possible negotiating thing. But I value my time and I don't want to sign documents. I have a friend who will literally go to 5 of the same dealerships, gets quotes from all of them, name-drop them to one another, walk out 5 times, do like 10 test drives, show the guy how rich he is in a variety of ways to know so he knows he's serious. And then finally he'll save, you know, $10,000, right? I'm just too lazy. But there's other people that— where it's totally worth it. And the numbers are huge.

Picks up the phone. Oh yeah, Derek, I'll be there shortly. I'm just finishing up here. I don't think I'm getting what I want here, so I might go over there. Oh, you have it ready for— well, that's great. I'm just gonna hang out here for 10 more minutes in case something changes. You know, like my dude, my dad will be on the phone with some company, like, but he does it for petty shit. Like, he'll just try to get, like, you know, You know, like, you know, when you—

it's like, Dad, you can't negotiate with the grocery store.

Yeah, no, no, literally, he'll call like the airline and just be like, you know, why is it— why did you charge me for my seat? They're like, well, that's how planes work. And he's like— and then he'll be like, you know, I've been a customer for a long time. And they're like— and then he'll just pause. He'll just— most people will just bail because it's too awkward. He'll just sit in that shit. He'll just be like— and then they'll be like, oh, that's, you know, we've loved having you, sir. And he'll be like Long time. And then he's like, they're like, where are you going with this? This has nothing to do with the conversation about this. He'd be like, yeah, this is just very nasty behavior. And he's like, it's like, whoa, nasty behavior? What are you talking about? Like, nothing is happening. We just did the normal thing here. We just charged you for the product. And he's like, yeah, this is, it's just upsetting. And we're like, okay, well, sir, we gotta go now.

We need like a, I want to text folder of all these phrases.

Yeah, like, just, he always does that. Long time.

Like, you know, you know, Trump does this.

Trump will be like, you know, people are saying, people are saying it's great. They said it's great. You know, people are saying that. They're saying that. And he's just like, keeps going with this statement. That's my dad, dude.

Instead of—

well, so often, so often it's just silence. Just being silent. Saying, like you said, throwing out one of those open-ended statements. And then just staying silent and holding the discomfort. And then often they will start to, you know, give on the price or whatever. And you just realize like most people will just avoid social awkwardness.

Dude, you need— instead of dealmaker, you need to have like comp maker or salary maker. So many people, myself included, need this for salary. When I was negotiating my salary for HubSpot when we sold the company, they— I remember my wife was in the room, but she was like on the other side of the computer screen, so they I couldn't see. And they were like telling me a number and they told me a number and I was like, yeah, whatever, you know, whatever, whatever's cool. My wife was on the other end like, what the fuck? Shut up.

Don't say anything. It's all good.

During the—

yeah, I remember. That's actually, that's actually a really good business idea. Maybe we should add that on. Like a coach where it's like a coach. So it like, you know, you don't, cause it'd be weird if it was like a third party. Hey, I'm doing a comp review. This is Jerry from my procurement team.

Well, here's how you could—

but if you had that guy telling you like, do this, do this, do this.

Listen, here's why it could be cool is because I remember I got a speeding ticket recently during the pandemic in like rural Kansas when I was driving cross-country and they were doing Zoom things. So like Zoom, and I was like, oh, I'll fight the ticket because I actually think it's nonsense. And so I had a lawyer. I don't know if I'm breaking any laws here, but I had a friend lawyer and I would be like, hey, I'm going to put you on speakerphone so you can hear what they're saying and then just text me what you think I should say in court so I could fight this ticket and try to get off of it. And she was on the phone, like, listening to, like, all right, ask them this. And I asked them this. So then ask them this. And the lawyer or the, the, the judge was like, wow, you really know what you're talking about. I was like, oh yeah, you know, like, I just, I really didn't think I did anything wrong. And you really just need that for like when someone's just CC all emails, a part of the salary negotiation, negotiation, or have them there. Like, listening to the Zoom and like, all right, now say this, now say this. And then just give me half of the earnings that you, you just got gone up by.

When I was at Twitch, they were like, um, yeah, the salary, uh, is this. And I was like, oh, um, I just let them sit in it. And I was like, and they're like, you know, they were like, uh, sorry, did you say something? And I was like, uh, no, just lower than I thought. Um, and I was just like, I don't know, buying time. And they're like, well, you know, I was like, can you explain how the process works? I just Instead of saying, "I want more, here's a different number," I was like, "Can you explain how you guys get to a number like this? Where does this number come from?" And where do babies come from?

They're like, "Uh." They don't know.

And then they said the magic word. They're like, "We have these bands," which is like a band is code for a range, which is code for we're trying to see how much of a sucker you really are. Basically, I was like, "Oh, so you're telling me for my role, there is a specific minimum and a maximum band of compensation that I could get, and you're offering me anything anything but the absolute top of the band? Or hey, better yet, have you ever gone out of band and gone higher? What situations would cause that to occur? They're like, well, somebody needs to vouch for it. They have to go to bat. They have to write a memo. I'm like, cool.

All right.

Now I know what I'm going to go ask for. And I basically just worked through the system. But once you realize that these are all A, negotiable, and B, it's like playing a robot that can only make certain moves on the board. And you're like, oh, you can only go forward and backwards?

Oh, great.

So I'm just going to go around you over here because you're bound by these rules of like, this is how the process has to work. And, um, and so, you know, at most companies you can get a lot more than you're currently getting.

What have you guys ever like thought about this? When, like, you know, my wife works at a big company and she's been offered jobs at other big 10,000, 20,000 person companies, 100,000 person companies. And I'm like, Sarah, what would happen if you just told the interviewer like, hey, look, like, uh, Let's, let's screw this place a little. Like, just tell me the most amount that you can give me and let's like work things.

Yeah.

Like, no, I mean, not really, excuse me, but like, what, like what's stopping you? They're like, look, I don't give a fuck. It's not my money. Yeah. Let's just like, let's, let's, let's, let's rob this place if we can. So let's just like, I'm just going to tell you like why across the table.

Yeah. Write down a number here that you wouldn't like.

Why, why is this like? 100,000th person employee who has the power to allocate certain dollars. Like, they don't care, you know, it's not the company's money. And I've just— it's always shocked me that the culture is such that, like, they are actually being honest in many cases to the employer when they could be like, look, I like you, you like me. Here's the rules. I need you to tell me this and I can then give you this. You know what I mean? Like, what? They don't have an incentive.

They're not your friend.

They don't care.

Their incentive is to just do the base minimum, cover their ass. Like most people in big companies. Um, let's do, uh, let's do, can we do one other topic?

Yeah.

Andrew, pick the one that you had prepped that you're like, you'd feel like, ah man, we didn't get to that. So pick that one and let's do that.

Okay. Well, let me do one that's applicable. We were talking about winter coming and I had a story I wanted to tell. So one of the other things, obviously we're stress testing all the businesses, we're dialing in our P&Ls, we're pulling excess cash into head office, we're loading the elephant gun, so to say. We want to get ready for a big acquisition and winter. And two interesting things we're doing. One, this is very obvious. If you have debt, lock in, right? Even at a higher rate, I think a lot of people are doing this thing where they're going, Well, it was— interest rates were at 3%. I could have locked in then. Now they're at 5%. I don't want to lock in. And they're anchored to that 3% thing. To me, it's about certainty. I want to know that when I build a model, when I stress test the business, that I know that my interest is going to be at 5% or whatever, even if they go up or down or whatever. I just want that certainty. The other weird thing we're doing We've done this once before, is we're buying options on the stock market. And this is kind of speculative, but I look at it as an insurance policy. So here's an example of what we did in 2020. So we started freaking out about COVID We were a little bit early on it. Chris and I locked down kind of like late January or early February. And if you remember, Everyone was kind of saying like, oh, this might be a bit of a nothing burger up until March 1st or 2nd or 3rd, kind of in that zone. And so what we ended up doing is we're looking, we're doing these stress tests and we're looking across all of our businesses. And at the time, a lot of our revenue came from our agency businesses and we had these large Fortune 500 customers, but we're going, okay, what's the first thing all the Fortune 500s do? They pay everyone late. And so we're looking at, okay, we're going to get some late payments. That's going to cause cash flow issues. We might also have some of our startup clients go out of business and they may just not pay us. And so we started looking at what is the number there that we want to ensure. And it was like $5 or $10 million where we were like, okay, these are all companies that may just not pay us. We might lose that revenue. And if that's the case, we're going to have a bad year. We're not going to have liquidity. And so what we did is we basically said, okay, In late February, we said, okay, if this— if the S&P 500, the index of the 500 largest companies in America, goes down by 20%, we will get a big payout. And so we bought for $500,000 put options that were— went out about a year. So if any time in the next year, uh, the market dropped that much, we would get a large payout. And the idea is it's kind of like buying an insurance policy on your house.

Right?

You pay this premium, you put the money out, and you hope that you just pay that premium and nothing bad happens. But if your house burns down, they'll give you $5 million to rebuild it. And so what ended up happening is we bought these put options. They went from being worth $500,000 to $7 million all of a sudden. And Chris and I are like laughing our asses off. Never had, you know, never bought Put options, never been through this or whatever. So they go to $7 million and we're like, "Holy shit, this is amazing. Let's sell them." And so we sell them, we cash in, we take $7 million onto our balance sheet, and then we look at each other and we go, "Well, this could be the worst recession of all time. Are we the guys who just sold our insurance policy? Should we keep holding this? What if this is 1929 and The stock market's really going to go down 50%. And the whole point of this is to have this insurance policy and sleep well at night. Now we don't have it. And so we take all the money except for $500 grand. We, we took $500 grand out. We took all the money and we re-bet it and we lost everything because the Fed came in and the markets rebounded. Now there's two ways to look at that story. You know, one is we, we, we, uh, got hit with gambler's fallacy. You know, let's go in, we'll do one last roll at the roulette table. The way that I think about it is I go, I lost my premium, right? I paid for insurance and the bad thing didn't happen. Therefore, I didn't deserve to get the $7 million payout. And the fact that we sold it is just a, you know, that's— yeah, it sucks that we had that money in our bank account for 5 days or whatever, but it really is irrelevant. And so the way to think about this, let's say that you own a SaaS business and your entire net worth is in the SaaS business. And you currently, uh, you know, you've raised money at 20 times revenue or something. You might want to find a SaaS business that's publicly traded that is a comp to you. And you might want to buy out-of-the-money put options or buy a basket of those and basically say, if the market gets crushed, that's probably an indication that the larger economy got crushed too, or my part of the world got crushed and businesses like mine are doing badly. And so it's kind of an interesting way to buy an insurance policy. It is certainly a little bit gambly, right? But it is an interesting way to sleep at night.

Where'd you come up with the math of like, all right, $500K?

Well, you can model these out. There's a website called Options Profit Calculator, and you basically say this is the stock and it'll show you in a variety of scenarios. And so for example, on that one I just said, Okay. In previous recessions, a recession is defined as what? More than—

Like 4 quarters.

15% drawdown over 2 quarters or whatever. I just said, look, if that happens over the next year, I will get a payout. And I could look at the different payouts based on where it went.

Are you buying any real estate right now?

No, I hate real estate.

Are you, Shawn?

Buying real estate? No, not at the moment.

I, I hate real estate so much that I don't build equity in my own houses. So I do interest-only mortgages because I want everything in businesses, because businesses— a business can earn $1 million of revenue and then the next year do $100 million using creativity. There's no apartment building you can buy that'll do $1 million of revenue and do $100 million next year. It's just not—

how do you qualify for an interest-only loan? You just got to make a lot of money?

I think you can do it via most banks. It might be the sort of thing where you have to have some sort of collateral or other assets or be at a larger scale. Are you fixed or are you adjustable? Yeah, I'm fixed.

Yeah.

So then you got locked in at what rate? When it was back at 2.37?

I think I locked in at 5. I'm one of those people where I was like, you know, hey, let's lock in at 3%. Didn't do it. Let it go too long. Ended up locking at 5%. But it goes back to, I want to sleep at night. It's possible interest rates go back down to 2% and I feel like an idiot, but I want to sleep at night. I just want— if, if interest rates go to 8%, 10%, which is, you know, maybe not high probability, but it's certainly possible historically. I don't want to deal with that.

Sean, are you buying a house now?

No, I just rented this place. So it's like a 2-year, 3-year rental. Yeah, I like renting. I like renting the place I live.

Me too. I love it.

For multiple reasons. But basically, buying the house you own is not a great investment. There's no yield, right? You are the tenant. So it's not like— I think people conflate those two things. If you buy property that pays you, okay, that's an asset. If you buy property you live in and it costs you money, that's a liability in my opinion. So I think that's the first piece. Second piece is picking the place you like to live is not always the best investment. What are the odds that the best investment of a pretty significant amount of capital is the place my wife really likes the countertops? It's just not going to be the place. That's not where the value is. Trust me.

Yeah. You have people that put 50% or even 90% of their personal net worth into a single investment, which is a house. And then they go, oh, it, you know, doubled in value over 15 years. And you're going, yeah, if you just bought an ETF, you would've had the same result. And if you bought an individual stock, you probably could have done way, way better. So to me, it's like, if someone's completely— if they're not an investor at all, then sure, go buy a house all day, whatever. It's a reasonably okay investment. But if you're even remotely smart and you know how to read and you go and read investing books and stuff, I think it's crazy. I mean, I would, I would just rent a house all day and put everything into equities and businesses.

We're renting it too. I own a house in Austin because I wanted that to be my residence and whatever we did. And I actually rent that house out now when I'm not there. I would much rather in the future for like the next 10 years Sarah and I, even when we have kids, we're renting for sure. And I want to go a step further. I want to rent all my furniture too. So there's a company called Feather. Have you guys heard of Feather? You can rent furniture on that website, but it's only in certain cities. And I intend to rent a place and I'll, and I'll get a nice place and it'll cost me $10,000 to $15,000 a month. And then I'll spend another $2,000 to $3,000 a month and rent all my furniture. I want to own nothing.

I love it.

It's so much. I love it. It feels so much better not owning stuff. I was— I'm on my way back now to Austin, and I was in Brooklyn for 4 months and I rented a furnished place and it was sick. It made me so much happier.

I, I'm realizing like, so over the last couple of years, like I bought like a, I have a house at a lake locally. Uh, I've got a place in Vancouver. I've got a house here and then the stuff and the management, like just, I have to have a staff that now manage all the houses. Right. And I own them. I, you know, I do this interest only thing, but I do own them and I am responsible for them. And it's just constant stuff breaking, new furniture, hiring designers, doing renos, all this stuff. And so you realize pretty quickly, everyone thinks they want to have 10 palatial estates all over the world, but no, it becomes yet another business to manage, yet another P&L, yet another group of people who you have to give opportunity to and have HR around and everything. It's, uh, you know, don't cry any tears for me, but yeah, it's, it's really annoying.

Yeah. I think everybody, uh, ends up a prisoner of a prison of their own making. And so, you know, you want to design that prison to be— what are you going to be a prisoner to? Is it your stuff? Is it your properties? Right? Like if I bought a fancy car and I lived in San Francisco, I'd just be stressed all the time that it's going to get scratched or it's going to get broken into. And like, you know, I, it would net make me less happy and less free. And so it's like, where do I want to optimize for? Is more free and more happy. And so, cool, I need to do some things to make that happen. Maybe exercise is part of the prison I want to design. It's like, cool, I know that if I do this all the time and I make this a part of my routine and it's important to me and I don't miss it and I make time for it all the time, it costs me money and it's hard effort, but it has this payoff of how I get to feel at the end, how much more healthy I can be, how much more mobile I can be, et cetera, et cetera. And so I think it's not— people think you got to choose what you want or you got to choose what you want to do. I think it's also you got to choose the constraints you're going to put on your body and your time and yourself and your psyche because you will have some. And whether you chose them or not, that's up to you.

Totally. I mean, you look at any of these, there's all those sayings around if it floats or flies or other things, rent it. And I think that should be applied to most things, frankly. And it's just a matter of, can you get the things you want? For the issue for me is being in Canada in a small city, we don't have furniture rental. There's not a lot of great high-end rental homes and stuff, but I'd be all over that if I could.

Well, dude, thank you. Uh, this is awesome. I loved seeing you. I love, uh, seeing your face again.

It's not like being belly to belly. I'll tell you that much.

It's not like being belly to belly, but dude, his face Your face has become a better face in the last 6 months.

Your face is, is looking full, thick, tight, strong.

Thanks guys.

Yeah.

What's going on? You guys talked about, I know you did Camp MFM or whatever. Are you going to do more of that? I really regret not going to that.

You got the invite and you blew it, bro.

I know, I know. I hate basketball.

No one played, dude. It was like, like Sean was the best player there, which like, we, you know, we weren't, no one was that amazing. Yeah, no, Ben on the pod was like dunking on people. Uh, Nick Huber was great. Sean's really, really good. But besides that, we were all just like a bunch of morons.

Throw an event at something I suck at, right? Like, you know, Sam's Camp MFM is going to be like running the 200-meter sprint. It's like, oh, I just happen to be, you know, I have to be amazing at this.

Oh, you know, guys, there's a track down the street. Oh, look, a squat rack.

Andrew, what would be the version of that that you would do where it's like, it's all right, we, with the two staples are you're trying to have great, interesting people that are, you know, curated set of people coming. But the other is we're not just sitting in a room, you know, looking at a whiteboard or a presentation. It's not a conference. So it's like doing something that's a passion that we, that we like. And then the networking fills in the gaps in between that, right? Like the ins and outs, the bus ride there, the food, the whatever. But the focus is on some activity. What would yours be that you're really interested in doing? I don't—

Honestly, I'm not a big hobby person. I mean, like most entrepreneurs, I get obsessed with business and stuff, and it's been a real challenge for me to find those things. I do these forum groups where I've been in some of these groups for 10 years, 5 or 6 guys. We go into a room once a month, talk about everything that's going on in our business.

Who runs that?

I do. I used to be an EO and then I just started doing it myself. And we just did a forum retreat and we went to Whistler. So beautiful mountain. And we all went hiking. We'd go hiking all day, go do cold plunges, exercise during the day. So there's activities. And there's something about being in a group specifically with other dudes where you're sweating and your heart rate is going and you're talking about what's going on in life. It feels really good.

And then every day you would—

Did you do any wet towel ass whipping?

Actually, yes. Yes. Someone She did get ass whipped. We went to a spa and someone got ass whipped.

Yeah, I bet they did.

But we did this thing where we would do dinners and we'd have this pack of cards and we would just pull random cards and it'd be really fucked up questions like, what's a rude word your parents would use to describe you? Or how have you let someone down in life? And I just love that kind of stuff. Right? So for me, it's about How do you create things that facilitate deep, interesting conversations, ideally with people you have something in common with so there's a shared bond? But I mean, I'd be down.

Pull a card on top of your deck and you're like, "All right, guys, I have a question. Should we kiss right now?" Oh my God. The deck said it, not me. The deck said it.

Written in Sharpie.

That retreat sounds— that was too easy. Sorry, I'm working on my dad humor.

All right, I gotta go.

I'll see you guys.

All right, guys.