Asking Billionaire Investor - Andrew Wilkinson - How To Prepare For The Economic Collapse

Summary

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Podcast Summary: "Asking Billionaire Investor - Andrew Wilkinson - How To Prepare For The Economic Collapse"

My First Million – October 6, 2022 | Host: Hubspot Media
Guests: Sam Parr, Shaan Puri, Andrew Wilkinson (Founder of Tiny)

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Overview

This episode features recurring favorite guest Andrew Wilkinson, the entrepreneur behind Tiny—a holding company sometimes called “the Warren Buffett of Internet businesses.” Sam and Shaan dig deep with Andrew on how he’s preparing for "economic winter," discuss practical moves he’s making with his investments, new business ventures born from stress-testing his own portfolio, and broader economic and lifestyle philosophies. The talk is wide-ranging, candid, tactical, and sprinkled with irreverent humor.

Main Theme:
How to proactively prepare, both personally and as a business owner, for an economic downturn. Plus: behind-the-scenes looks at Andrew’s portfolio risk management, new business launches during a recession, and why he lives as a renter even though he could buy nearly anything he wanted.

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Key Discussion Points & Insights

1. Economic “Winter” Preparation

• Only the Paranoid Survive ([09:20])

  • Andrew stresses that no one truly knows what happens next—a recession could be looming, but nimble players will benefit.
  • "There's this great quote by Andy Grove, only the paranoid survive...none of us know what's going to happen. We could have a rebound." — Andrew Wilkinson [09:20]

• Stress Testing Businesses ([11:22])

  • Andrew runs severe financial stress tests: models outcomes if revenue drops 20%, 50%, 70%, or if customers delay payments by months.
  • "Are you able to lay people off? Are you stuck in long term contracts and leases? Do you have a lot of debt that you can't pay?" — Andrew Wilkinson [11:31]

• Strategic Conservatism, Not Panic ([14:41])

  • While opportunities arise during recessions, Andrew is focusing on conservative, low-risk ventures, not wild bets.
  • Investment fund is pivoting to focus on secondary and minority buyouts, structured deals, and companies that are "default alive" (i.e., won't die if they can't raise new funding).
  • "I want to be investing in businesses where if they can't raise the next round, they're not going out of business." — Andrew Wilkinson [14:41]

2. Personal Portfolio Strategy

• Mostly Cash & T-Bills ([16:33], [17:59])

  • Andrew is holding a large percentage of his personal portfolio in cash and treasury bills, awaiting opportunities (“waiting for winter”).
  • Holds Pershing Square Holdings as only stock — chosen for its deep discount to net asset value and unique interest rate swap exposure.

• Avoiding the Index Fund Route ([17:59])

  • "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." — Sam Parr [17:59]
  • "Yeah." — Andrew Wilkinson [18:09]

• Separation of Business and Personal Net Worth ([18:39])

  • Stays 90% invested in Tiny, but keeps personal liquidity as a “freedom fund” in case everything else fails.

3. Investing Philosophies and Market Observations

• Understanding “Mr. Market” & Price Volatility ([20:42], [21:40])

  • Andrew cites Warren Buffett’s teacher, Benjamin Graham, on tuning out market mood swings; the price of a business on any given day is largely irrelevant to its intrinsic value.
  • "The stock market is like this moody person. It goes up and down...if you know what your business is worth, it's irrelevant what the stock market says it's worth." — Andrew Wilkinson [20:42]

• Caution Against Anchor Bias in Venture Valuations ([25:33])

  • Warns that what looks like a “deal” now may actually just be a reset to long-term averages; many startups are still overpriced without clear exit paths.

• Poker vs. Roulette ([28:08])

  • Andrew prefers deals where he can know and tilt the odds (poker), not random moonshots (roulette).
  • "Are you playing roulette or are you playing poker? I play poker. I want to play with very good odds in my favor." — Andrew Wilkinson [28:08]

4. Incubating New Businesses from P&L Expenses

• Procurement As a Service: Dealmaker ([54:36])

  • Andrew creates businesses by identifying major expense lines across his portfolio and building solutions to turn those cost centers into revenue generators. E.g., Dealmaker Co negotiates better terms for contracts, leases, etc., often getting a share of any savings.
  • Low capital required, quick to profitability.
  • "We basically find really scrappy operators where we can say, look, we’ll build the website, you just need to take it and run with it." — Andrew Wilkinson [57:19]

• Negotiation Aversion ([55:04], [58:57])

  • Most CEOs/managers hate negotiating, which inspired the business.
  • "Nobody likes the discomfort of negotiation. I hate 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, I’ll do that all day long." — Andrew Wilkinson [55:04]

5. Unfiltered Advice on Home Ownership

• Why Rent, Don’t Buy (Even if You’re Rich) ([73:39], [75:09])
  • Andrew prefers interest-only mortgages; even with means to purchase, he’d rather allocate capital to businesses for greater flexibility and higher returns.
  • Both he and Shaan confirm they rent their homes, finding it offers more freedom and—counterintuitively—a better life, as property management quickly turns into a major time sink.
  • "I hate real estate so much that I don’t build equity in my own houses. I do interest-only mortgages because I want everything in businesses." — Andrew Wilkinson [73:39]
  • "Buying the house you live in is not a great investment. You're the tenant... Picking the place you like to live is not always the best investment." — Shaan Puri [75:10]

6. Community, Networking, and Luck Surface Area

• “Landing Spots for Luck” & Surface Area for Serendipity ([42:41], [47:29])

  • Conversations about the value of making time to meet random people. Increasing serendipity is framed as a key entrepreneurial strategy.
  • "You have to create a landing spot for luck. Other people call this a surface area for serendipity." — Shaan Puri [46:32]

• Known Well > Well Known ([48:09])

  • Shaan’s maxim: the point of content isn’t fame, but to be deeply understood by your target audience—leading to high-quality inbound.
  • "The point is not to be well known, but to be known well." — Shaan Puri [48:09]

7. “Butterfly Effect” Moments & Book Writing

• The Influence of Random Encounters ([35:00])

  • All share stories of small, chance events or meetings that powerfully altered their trajectories.

• Andrew's Book Announcement ([34:12])

  • Andrew is working on a book about his journey and insights from building Tiny.
  • "I'm working on a book, actually...about the story of building our business." — Andrew Wilkinson [34:12]

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Notable Quotes & Memorable Moments

• On the emotional rollercoaster of net worth ("yokel" story):
  "These yokels will yell numbers at you. You don't have to sell... At the end of the day, these values fluctuate constantly. But we don't feel that, because you don't see a ticker." — Andrew Wilkinson [21:40]

• On accidentally validating the rich:
  "If you are rich but unacknowledged, there's something in you that just kills you...can you validate my wealth? Like, this is amazing. You're way wealthier than me...But they haven't—they don't have the platform or the audience." — Shaan Puri [50:28]

• On optimizing for life freedom, not more stuff:
  "Everyone thinks they want to have, you know, 10 palatial estates all over the world—but no, like, it becomes yet another business to manage...It’s really annoying." — Andrew Wilkinson [77:24]

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Timestamps for Key Segments

• 00:00–09:01: Andrew’s current investing posture; intro banter.
• 09:01–14:41: How Andrew is preparing for an economic winter; stress testing.
• 14:41–16:25: New, conservative approach to angel investing and venture.
• 16:25–19:39: Andrew’s personal portfolio allocations; why mostly cash and Pershing Square Holdings.
• 20:19–23:26: Handling the emotional whiplash of paper net worth swings.
• 25:33–29:47: Debating current venture valuations and real business value.
• 35:00–41:31: Butterfly effect moments; how small encounters or books change lives.
• 54:36–62:43: Building Dealmaker (procurement service); negotiation tactics.
• 73:39–79:53: Real estate rants; why both Andrew and Shaan choose to rent.
• 81:33–83:16: Andrew’s approach to networking, entrepreneur forums, and creating bonding experiences.

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Tone, Style, and Vibe

• Playful, self-deprecating humor; willingness to “pull back the curtain” on both wins and failures.
• No-nonsense, actionable advice—baked inside friendly banter and real-world stories.
• Plenty of asides, jokes, and friendly roasts, especially about looks, fame, and “belly-to-belly” meetings.
• Candid acknowledgment of emotional and psychological aspects of wealth, risk, and entrepreneurship.

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Conclusion

A deep-dive into the practical and psychological strategies for recession-proofing your business and personal finances, this episode gives listeners an actionable “crash course” on stress testing, opportunity spotting, and contrarian thinking from one of the internet's most successful company-buyers. Andrew’s blend of dry humor, real-world tactics, and meta-level philosophy is both entertaining and directly applicable in uncertain economic times.

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End of Summary

Transcript

[Andrew Wilkinson]

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.

[Sam Parr]

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.

[Sean Gold]

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 dribble, they own Aeropress, basically. He buys and sells biz, buys and sells businesses of total value. Maybe over a billion dollars at this point. Definitely over a hundred million in revenue. 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. 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 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 how, what moves he's making or has made in order to prepare for, like, you know, what's going on in the economy, so what he's doing in his business, what he's investing and 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. 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, 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.

[Sam Parr]

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

[Sean Gold]

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.

[Sam Parr]

Where'd you go?

[Sean Gold]

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 has to stop five times. Basically every 90 minutes. I had to stop for 30 minutes. It was awful.

[Sam Parr]

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

[Sean Gold]

No, nothing. Not fast. Two kids in the back and a bunch of, you know, snacks like this. 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, I. Apparently this isn't what most Teslas would be like, but the Tesla I had rented, you know, was, 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 yeah, I had the opposite effect.

[Andrew Wilkinson]

You know what's interesting is like, I bought a Tesla like maybe eight or nine 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, 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.

[Sam Parr]

Yeah, they've done such a good job of rebranding fake leather to vegan interior. And 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.

[Andrew Wilkinson]

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, 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, 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, that takes you from A to B. And Then you know, does it work with your iPhone or your Android? And if you look at the Tesla interface, it's like really bad. You can't sync your maps up on the screen or anything like that. It's not great.

[Sam Parr]

So Sean, you're not getting one.

[Sean Gold]

Actually I still probably will get one, but yeah, I gotta like do research and shit now. Like I joined the subreddit for Tesla. 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 in the subreddit alone there's 2 million members. 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 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 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 backseat and you open up the trunk of it, it would turn it into like a sleeper van. And 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 seven figures on just, just as 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 five 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, A B, R, P. And it's like the number one ranked thing. The interface looks like it's, you know, from the 90s and 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, 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. 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. This is like, there's the same opportunity with Tesla and other products like that.

[Sam Parr]

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

[Sean Gold]

So we should reintroduce Andrew. So Andrew Wilkins is back. Definitely the number one guest of the pod, both in our hearts and the fans hearts. I don't know why we don't schedule more of these because we should. But 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 a day, let's do this. And so he's back. He's the founder CEO 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. Do you still listen to the pod regularly? I know you used to listen to the sauna at night.

[Andrew Wilkinson]

Yeah, all the time. I take little breaks because I get too pumped up sometimes when I listen in the sauna.

[Sean Gold]

That's a nice way.

[Andrew Wilkinson]

I listen in the shower of the sauna usually.

[Sam Parr]

All right.

[Sean Gold]

If that lasts for more than four hours.

[Andrew Wilkinson]

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

[Sean Gold]

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

[Andrew Wilkinson]

That would be ideal.

[Sean Gold]

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

[Sam Parr]

Yeah. So you got, you have a bunch of good shit. 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. I want to talk about the anonymized workers. So you like, you've been hiring some anonymous folks and then you also have like five or six companies that you've started and we're going to 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 going to 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.

[Sean Gold]

Yeah, let's start with winter. So Andrew, maybe tee it off, which is, I think there is a consensus now that like we're 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, what you, what your view is of the market and then what are you doing to prepare for that situation.

[Andrew Wilkinson]

Yeah, so I mean there's this great quote by Andy Grove, only the paranoid survive. So ultimately like none of us know what's going to happen, right. Like we could have a rebound. I was super terrified. Like 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 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 over engineer 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 and, and 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. You can't do that because you're, you're a liquid 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, you know, I've been thinking a lot about this over the last couple months. And generally we operate quite conservatively. Our goal is like, you know, 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 ahead office. But there's a couple specific things that we're doing that I figured I'd share that could be useful.

[Sean Gold]

So number one, 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?

[Andrew Wilkinson]

Okay, so you would say, okay, what happens if revenue drops 50% in this business? Right. 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? These that you can't pay? You know, you're really modeling out. Like 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 going to 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 two or three months? Do you have enough money in the, in the bank? Do you have credit lines, et cetera? So I think, you know, it's really wise to kind of do that shadow boxing and imagine a bunch of nightmare scenarios so that you can sleep at night.

[Sean Gold]

Great.

[Sam Parr]

What is.

[Sean Gold]

Yeah, go ahead.

[Sam Parr]

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

[Andrew Wilkinson]

Yeah. Okay, so I'll talk a little bit about like what we're specifically doing. Um, so everyone always says, you know, the best companies get started by 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 Angelus 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, 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. And then the other one is structured deals. So, for example, saying to someone, look, I'll give you a $5 million valuation, but I want a guaranteed 15% return in the case of liquidation or 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, the other thing with Venture is like, we've realized too, we can do venture internally by incubating businesses with low downside. So, for example, like turning our P and L expenses into businesses in and of themselves. So, so, for example, we want better procurement internally. We want to negotiate rates and get our P and 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.

[Sam Parr]

We just talked all about that the other day.

[Sean Gold]

What was your take, Sam?

[Sam Parr]

On what?

[Sean Gold]

On what he just said.

[Sam Parr]

I think it's.

[Sean Gold]

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

[Sam Parr]

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 of the salaries and however much it's going to 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?

[Andrew Wilkinson]

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 negotiation service for software that we launched two 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 two or three 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.

[Sam Parr]

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.

[Andrew Wilkinson]

So basically it's cash. So I have treasury bills 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.

[Sean Gold]

But that's by design.

[Andrew Wilkinson]

Highly.

[Sean Gold]

Most of these don't. Most of these kind of like holding company types trade at a discount anyways.

[Andrew Wilkinson]

Not to this degree. Right at the end of the day for the type of fund it is. Well, I think there's a variety of different reasons. I mean, it's illiquid. It's traded in Europe. It's run by Bill Ackman who has had a few blowups and people associate him with blowups. If you actually look at his record, he's killed it. The other thing I like about that business, by the way, is that they own a very large position in interest rate swaptions. So 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 four weeks, it's barely moved while the larger market has gone down significantly. But anyway, 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.

[Sam Parr]

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.

[Andrew Wilkinson]

Yeah.

[Sean Gold]

And that's wild.

[Andrew Wilkinson]

What do you do?

[Sean Gold]

I guess, where's your main focus with your balance sheet? Like 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, in their business. And then their personal kind of checking accounts, savings accounts and stock trading accounts are much smaller in comparison.

[Andrew Wilkinson]

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 can retire and be free and have enough money to do stuff. So it's a little bit more conventional. But 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.

[Sam Parr]

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 Squares?

[Andrew Wilkinson]

Pershing Square, I think it's 50, 50 right now.

[Sam Parr]

And one thing that I've been following basically like two years ago so. Or a year ago, you own or co you're, you're a major or. I actually don't know what your percentage is. I think it's in the, the annual report. But you own WE Commerce, 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 dollars 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. What is it today?

[Andrew Wilkinson]

I think it's like 80 million or something. Let me.

[Sam Parr]

So how does 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. How's, like, what's it feel like? What's it. What. 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?

[Andrew Wilkinson]

So I think if I was just like a pure. One of the interesting phenomenons 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?

[Sam Parr]

Well, and you're.

[Sean Gold]

You're.

[Sam Parr]

Personally, you're fine. Like, you've got liquidity and you've all these other things going on. But like, I imagine.

[Andrew Wilkinson]

Let me put it. 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 $1 million 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. But 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 have been worth next to nothing. And then there are other times where it would be worth crazy numbers. Right. And at the end of the day, you know your business, you know what it's worth.

[Sean Gold]

Yeah. Dharmesh said this thing, he goes, valuation oscillates around value. And I just had this image. 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 is created in most businesses. And. 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 and the valuation of a business. And that's, I think, what you're. What you're talking about.

[Andrew Wilkinson]

Totally.

[Sam Parr]

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

[Sean Gold]

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 two years, really.

[Sam Parr]

Because with your personal money.

[Sean Gold]

Well, though the fun money, but I'm the steward of that capital. Right. And it's. And 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 this amazing thing has happened, which is that all the founders have just read Bad News for, like, six months straight. And this has done two things. One, a bunch of, like, nuts, 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. So the same deal you could get for 10 million, you're now getting for 4 or 5 million. Right? 20 million you're now getting for 10 million. But the reality is that that same business was going to exit seven to 10 years from now, where 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 seven 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 kind of down cycle of the market looks like over this year, next year, whatever, however long it looks.

[Andrew Wilkinson]

My worry is anchor bias, right? If you think about it, everyone was saying venture valuations were crazy in 2019. Let's say the average seed, 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, you know, as a, as a cash flow, real world investor, it just looks insane. The only way to get your money back is to have a massive exit.

[Sean Gold]

That's always. So that's always been true for venture. Right. Venture. 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.

[Sam Parr]

And Andrew, on this pod, 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 have known that this company was going to be as big as it was, and I wish I would have pounced it 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 going to look back and there's a chance that it's going to say, I really just screwed that up. Like, that was 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. And I didn't go harder on that and I missed that opportunity. And so right now I am wondering, you know, I. About eight months ago, Sean and I were like, dude, we're never going to 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?

[Andrew Wilkinson]

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? Are you playing roulette or are you playing poker? I play poker. Right. 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 two or three years, maybe five 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 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.

[Sam Parr]

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 are good examples of this?

[Andrew Wilkinson]

Well, there's one really weird one. Bridge based dot com. I started playing bridge like five years ago and it's kind of like chess dot com there's always nerds that play. The website isn't particularly good, but I was quite impressed by, you know, all the numbers behind it. I think it ended up selling to someone else. We [e-mail] 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, you know, 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 like a nerdy cohort of people that have a dedicated place where they all gather.

[Sam Parr]

How much you think Bridgebase.com sold for? I'm looking at it now. It looks like it has like, I don't know 8 million monthly unique visitors. It's a. It's pretty huge.

[Sean Gold]

Yeah, I think my mom uses this, um, by the way, that little kiss and tell line. I have this sheet on my phone where I just save little throwaway lines that, like, I call them get out of jail free phrases. Or it's basically like, how do you use a phrase in certain 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 like, no damage done. Versus there were many other things that he could have said in response that just would have been sort of awkward. And another one, my uncle told me this once. He goes, he was trying to do this deal and it wasn't really working. And we all kind of felt like, I feel like this deal is doable, but we're just not there yet. And maybe we just need to. If you just wanted to dine this guy a little bit, 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 got to meet someone belly to belly if you're really ever going to do a deal with them. And, like, whether it happens or not, you never regret meeting another man. Belly to belly. The guy laughs. 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 belly if they wanted to, if they ever want to do it.

[Sam Parr]

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

[Sean Gold]

Like, you use one all the time. Like, don't, don't piss on my leg and tell me it's raining. You know, like, 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, ambiguity versus just speaking so fucking like. Because 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 useful things they've taught. And one of the things he teaches in there is he goes. What does he call it? Like, he's like, transition. He has this long list of, like, transition phrases. And it's like. Or like, he calls it, like, 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, like, aggressive and upfront, but also it's hard to be like, you know, small talk, small talk, small talk. So, anywho, do you want to do that? You know, like, would you like to buy my product? And it's like, oh, damn. Like, you know, 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 sign. 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.

[Sam Parr]

Dude, Belly to Belly is a good one.

[Sean Gold]

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

[Sam Parr]

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

[Andrew Wilkinson]

Yeah, I'm working on a book, actually.

[Sean Gold]

What?

[Sam Parr]

Really? On what?

[Andrew Wilkinson]

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

[Sam Parr]

What's it going to be called?

[Andrew Wilkinson]

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

[Sean Gold]

Story that will give you. So somebody, when you tweeted out you're coming on, you're like, oh, what should we talk about? There's a bunch of questions, bunch of good ones, honestly. But one that stood out to me was this guy goes, give us. Can you guys each tell us, like, an example of a butterfly effect moment in your life, meaning a chance encounter you had with somebody or somebody or something that, like, just, like, 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 senior in college. And he said, come with me. And I was like, okay, I guess, like, 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. Like, I'm like, wherever, Kansas City. And like, should I. What should I do? He's like, oh, just go do the meeting. And I'm like, I don't even know the context. Like, I don't even know what you.

[Andrew Wilkinson]

Do for a living.

[Sean Gold]

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 Centuria. 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, 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 haven't even said hello yet. He doesn't know my name. And I like, go get my pen. Because, like, the little bitch that I am. And he's like, 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 because he's like, oh, real estate's where I'm gonna 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 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 his company and it ended up becoming like Chegg or something like that, like this big multi billion dollar thing. So he had this crazy, like, he's just wowing me with 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 didn't, 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, drawn on tables and like, you know, has had five 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. 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.

[Sam Parr]

That's awesome. I love. That was a good story.

[Sean Gold]

But. Oh, sorry, the book part. On the way out, he's like, so I'm with this guy for two and a half 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's 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 right 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, like, I don't know, mass market. You're trying to become a best seller 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 two 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 I 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.

[Andrew Wilkinson]

I can't.

[Sean Gold]

Find this client info.

[Sam Parr]

Have you heard of HubSpot? HubSpot is a CRM platform, so it shares its data across every application.

[Sean Gold]

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

[Andrew Wilkinson]

HubSpot grow better. I did this like personal values exercise like six months ago or so. And when I thought about what do I actually want, what do I actually like, why do I do business? It's I want to 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 like 20 new friends from this podcast. I've had random lunches with people. Literally, like, 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, like a book, you get.

[Sean Gold]

To exist when you're in line for lunch. You can't say no. Well, yeah, they're like, I know you.

[Andrew Wilkinson]

Want to rush or totally. But it was great. The guy was super interesting. He had like an airplane leasing business. It was, it was crazy.

[Sam Parr]

But.

[Andrew Wilkinson]

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.

[Sam Parr]

So speaking of meeting interesting people, let me ask you guys if you would do this. So I was talking to Nathan Bar Day, Nathan Barry. You know, he owns ConvertKit or he owns the most all of it. He's probably worth two 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 seven days, he'll plan an eighth day that's dedicated to work. And what he'll do is he'll do like a six hour meeting where he'll let, like, 20 or 30 people all come and hang out with them, but he charges them, and it's almost like a very miniature conference. And I could 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 you can come hang out at their office. And I thought, 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 can pay for my trip, there's something about it that I find so intoxicating to do this. Have you ever thought about, would you do this, Sean and Andrew? Yeah. What were you going to say?

[Andrew Wilkinson]

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

[Sam Parr]

I'm on Intro because, listen, I'm friends.

[Sean Gold]

With a founder on Intro.

[Sam Parr]

Listen, listen. 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's like, hey, use this. I was like, fine. I started using it. Then he puts my ad everywhere on. On Facebook. And so I only make, like, an hour or two available a month. And it's just crazy.

[Sean Gold]

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

[Sam Parr]

Oh, my God, they are killing me with all these ads.

[Andrew Wilkinson]

Well, it's a terrible way to use your time, right? Like, what we did, we did a. A charity Ask me anything. So we were like, okay, anyone who pays whatever you donate will double it. And I think we, like, suggested the donation or whatever, but with Nathan and about 20 other entrepreneurs, we did, like, a Zoom. Spent two or three hours answering all their Questions? I think we raised like 50 grand for a charity, which was pretty cool, but I really struggle with this kind of stuff because the end of the day you're selling your hours and I don't want to be in that business. 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 eight of your trip and you're exhausted, you now 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. Like, I can, I can be miserable and I can pump myself up like Tony Robbins style, like jump on the trampoline and all that crap, but it makes me miserable. And so I just don't want to do that.

[Sam Parr]

Would you do it, Sean?

[Sean Gold]

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 like the next five. Like, I can make these meetings 10 minutes, right? So Brad Feld did this in. Bradfield's a VC in Boulder. He's probably like 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 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 four or five hours. And he just tried 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 tick tocks 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, 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, he said, 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 him back one, and you got one for yourself. It's like, he gives him this, like, 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. You know, it's like, here's a rule. We're not touching. Touching is not happening. You know, like, that's just not a thing. But he does it gives a brand vibe of, like, Gary's one of the people. He's a man, 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, 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 someplace.

[Sam Parr]

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

[Sean Gold]

Yeah. Future book titles. 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, buffet and others like, you know, Andrew, you do this too, where you just carve out space. I'm going to think I'm going to read, I'm going to walk. I don't need to have meetings after meetings after meetings, because guess what? If I let that happen, that's exactly what's going to 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?

[Andrew Wilkinson]

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 four paragraphs. 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 one out of five times, and 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.

[Sean Gold]

I found my most navalism naval thing that I came my original naval quote where I realized the point of this podcast is not to be well known. 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, like, 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. Like, 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 like, people send you either interesting companies or deals or they want to come, you know, 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.

[Sam Parr]

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 head, his social and everything. And it was 100% his tax return. I mean, I guess it could have been photoshopped, but. And he goes. And then his reply was like, see?

[Andrew Wilkinson]

Told you.

[Sean Gold]

I didn't say it was small boy stuff.

[Andrew Wilkinson]

That is.

[Sean Gold]

That is absolutely small boy stuff.

[Sam Parr]

The tax returns, it was like $17 million of income. And, And. And he sent me multiple years. And it was hilarious. It was one of the best things. And I was like, you know, instead of like, 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.

[Andrew Wilkinson]

No, no. You know what I mean?

[Sean Gold]

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 in your business, to.

[Andrew Wilkinson]

Your p. L. Does that guy want to. Does he want to sell or get you to invest or what was it?

[Sean Gold]

Wants to be friends?

[Sam Parr]

He was just. Wanted to be friends. He just wanted to be friends.

[Sean Gold]

You know, Joe Rogan. Joe Rogan has this, like, famous YouTube clip where he' read some quote from some guy, which is like most. Someone famous, but it's like, most men lead lives of, you know, quiet despair or something like that. And he's like, so true. You know, most people walking around, they just have this, this. 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.

[Sam Parr]

For the podcast so much, where people.

[Sean Gold]

Are just like, hey, I just need to like. 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.

[Sam Parr]

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.

[Sean Gold]

And they start doing everybody's asking me about my skincare routine. And it's like, you know, they get that little taste 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.

[Andrew Wilkinson]

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 world's greatest lovers walking around, dude.

[Sam Parr]

Speaking of being a lover, Andrew, you have like a little bit of a five o' clock shadow right now and you've your jaws looking chiseled. You look. This is the best I've ever seen you look.

[Sean Gold]

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

[Andrew Wilkinson]

Yeah, extensive facial reconstruction? No, I've just been powerlifting for the last six or eight months.

[Sam Parr]

It's working.

[Sean Gold]

They're coming through the riverside to Sam right now. Anyone who power lifts is just like automatically turn Sam on.

[Sam Parr]

Yeah, you had me.

[Andrew Wilkinson]

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

[Sean Gold]

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, fake, like humble thing where it's like, you know, I gotta be honest, I.

[Andrew Wilkinson]

Was so proud of myself.

[Sean Gold]

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.

[Andrew Wilkinson]

Who's the, who's the guy? He was on Silicon Valley, the Indian guy, and he got jacked Kumail Nanjani, the comedian. Yeah. Like. Like, think about that experience for him. Right. Because he had the biggest version of that. 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.

[Sam Parr]

I've seen them online.

[Andrew Wilkinson]

I can't do it.

[Sam Parr]

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

[Sean Gold]

Are you more or less less ripped than Chamath? Who's. I think you're. He's an investor in your thing. Right. Do you guys exchange? You know.

[Andrew Wilkinson]

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

[Sam Parr]

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

[Andrew Wilkinson]

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.

[Sean Gold]

Yeah. You're like, what, white privilege? Have you ever seen a man's heart beating through stress?

[Andrew Wilkinson]

So.

[Sean Gold]

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 and 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?

[Andrew Wilkinson]

No, we actually started one 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, you save 30 bucks. That's 30 bucks 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, their comp based on hitting a very large number. And so, you know, 30 grand or 30 bucks 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 negotiation. I hate it. And so the idea, it's very uncomfortable. I don't like it either. Right. 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 like office leases, furniture, insurance, like all the random stuff in your PNL and basically just CC them and they take a cut of whatever the savings are. And I just, this is thing I wanted myself because I was going to. Oh my God. Like I had the experience of, you know, when you're, when you're rich or people know you're rich, they will rip you off if they can, right? 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 like an EERO installed in a mesh network or whatever, but instead I did like the, you know, rich fancy thing and got it all custom wired. Right. 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.

[Sam Parr]

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

[Andrew Wilkinson]

Yeah, I think it may be like 50k. Like, 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.

[Sam Parr]

Is it working?

[Andrew Wilkinson]

Yeah, so far. I mean, I think it's profitable at this point. It doesn't need much to be profitable.

[Sean Gold]

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

[Andrew Wilkinson]

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, 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.

[Sam Parr]

In my head, I'm just imagining like a bunch of like, young guys, like, like shaking in their boots, like, oh, we gotta meet Mr. Brickier. 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 button 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, 10% off.

[Andrew Wilkinson]

There's a great. There's a great book called I Will Teach youh 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. But how does this business buy $20,000 of furniture?

[Sam Parr]

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?

[Andrew Wilkinson]

It's literally an army of guys who love to negotiate. And we train them up. We, you know, we give them all the books that we read and we have a process and, you know, they get cc'd and they go for it and they basically say, look, you know, your first quote was, X, we saved you. Y, give us a cut of the savings And. And go for it. In some instances, they'll retain us. So, like, 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.

[Sean Gold]

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.

[Andrew Wilkinson]

It takes time. Here's the thing is, like, you and I, like, if we go to. I remember I walked into a car dealership and I go to the guy and I say, I have two hours. And if you can get me the car in two hours, I will just sign whatever you want. But I need it in two 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 five of the same dealerships, gets quotes from all them, name drop them to one another, walk out five 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's. 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.

[Sean Gold]

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 going to hang out here for 10 more minutes in case something changes. Like, might do. 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.

[Sam Parr]

It's like, dad, you can't negotiate with the grocery store.

[Andrew Wilkinson]

Yeah.

[Sean Gold]

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, 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. 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, 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, you know, 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 then they're like, okay, well sir, we gotta go now.

[Sam Parr]

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

[Sean Gold]

Long time.

[Sam Parr]

You know, Trump does this.

[Sean Gold]

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 as my dad, dude.

[Sam Parr]

Instead of.

[Andrew Wilkinson]

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.

[Sam Parr]

Dude, you need, instead of deal maker, you need to have like comp maker or salary maker. So many people myself include news 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 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. Shut up. Don't say things.

[Sean Gold]

It's all good. During.

[Andrew Wilkinson]

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

[Sam Parr]

Well, here, here's how you get.

[Andrew Wilkinson]

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

[Sam Parr]

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 do say in court so I could fight this ticket and try to get off of it. And she was on the phone, like, listening, like, all right, ask them this. And I asked them this and then ask them this. And the lawyer or the.

[Andrew Wilkinson]

The.

[Sam Parr]

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, part of the salary, negotiate negotiation, or have them there, like, listening to the zoom, 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.

[Sean Gold]

When I was at Twitch, they were like, yeah, the salary is this. And I was like, oh, I just let him sit in it. And I was like. And they're like, you know, they were like, sorry, did you say something? And I was like, no, just lower than I thought. 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. So 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? And they're like, they don't know. And then they're like. And then they said the magic word. They're like, we have these bands, which is like. A band is like code for, like, a range, which is code for like, 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 any. 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. Like, 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, like there's actually. It's like playing A, like a robot, you know, like that can only make certain moves on the board and you're like, oh, you can only go forward and backwards.

[Andrew Wilkinson]

Oh, great.

[Sean Gold]

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

[Andrew Wilkinson]

What?

[Sam Parr]

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, 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, worthy. Yeah, like, no, I mean, not really screws, but like, what, like, what's stopping. They're like, look, I don't give a. 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 gonna tell you why across the table.

[Andrew Wilkinson]

Yeah.

[Sean Gold]

Write down a number here that you wouldn't forgive me.

[Sam Parr]

Why is this like, hundred thousandth 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. Has 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, and I.

[Sean Gold]

Can'T believe they're not your friend. They don't, they don't care. Their incentive is to just do the. The base minimum, cover their ass like most people in big companies. Let's do, 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.

[Andrew Wilkinson]

Okay, well, let me do one that's applicable. We were talking about winter coming and I had a story I wanted to tell you. So one of the other things, you know, obviously we're like, you know, stress testing all the businesses. We're dialing in our panels, we're pulling excess cash into head office. We're, you know, loading the elephant gun. So to say we want to get ready for a big acquisition and winter and to. To like, kind of interesting things, we're doing one. You know, this is very obvious. If you have debt, you know, lock in, right. Even at a higher rate. I think a lot of people are doing this thing where they're going to. 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 kind of 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 kind of weird thing we're doing, we've done this once before, is we're buying options on the stock market. So this is. 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're 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 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 were 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 insure? And it was like 5 or 10 million bucks where we were like, okay, these are all companies that may just not pay us. We might, you know, 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 and P500, 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 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 a 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, right? 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 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. One is we 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. 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 five 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, 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 that.

[Sam Parr]

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

[Andrew Wilkinson]

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, in that one I just said, okay, in previous recessions, you know, a recession is defined as what, you know, more than like 4/4, 15% drawdown over 2/4 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.

[Sam Parr]

Are you buying any real estate right now?

[Andrew Wilkinson]

No, I hate real estate.

[Sam Parr]

Are you, Sean, buying real estate?

[Sean Gold]

No, not at the moment.

[Andrew Wilkinson]

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 a million dollars of revenue and then the next year do a hundred million dollars using creativity. There's no apartment building you can buy that'll do a million dollars of revenue and do $100 million next year. It's just not.

[Sam Parr]

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

[Andrew Wilkinson]

I think you can do it via most banks. Generally 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.

[Sean Gold]

Are you fixed or are you fixed?

[Andrew Wilkinson]

But effectively, yeah, I'm fixed.

[Sean Gold]

Yeah. So then you got locked in at what rate? When it was back at 2, 3.

[Andrew Wilkinson]

I think I locked in at 5. Right. I'm one of those people where I was like, you know, hey, let's lock in at three. 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.

[Sam Parr]

Sean, are you buying a house now?

[Sean Gold]

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

[Sam Parr]

Me too.

[Sean Gold]

I love it for multiple reasons. But, like, basically buying your. Buying the house you own is not a great investment. Doesn't. There's no yield. Right. You're. You are the tenant. So. So it's not like. I think people conflate those two things. Like, 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. My opinion. So. So I think that's the. The first piece. Second piece is picking the place you like to live is not always the best investment. Like, what are the odds that the best investment of a pretty significant amount of capital is the place? My wife really likes the countertops. Like, it's just like, it's not going to be the place. Like, that's not where the value is.

[Andrew Wilkinson]

Trust me. Yeah, you have people, people that put like 50 or even 90% of their personal net worth into a single investment, which is a house, and then they go, oh, it doubled in value over 15 years. And you're going, yeah, if you just bought an etf, you would have 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.

[Sam Parr]

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 they'll cost me 10 to 15 grand a month and then I'll spend another two to $3,000 a month and rent all my furniture. I want to own nothing. It's so much, 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 four months and I rented a furnished place and it was sick. It made me so much happier.

[Andrew Wilkinson]

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. 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, you know, stuff. Breaking new furniture, hiring designers, doing Renault, all this stuff. And so you realize pretty quickly, like everyone thinks they want to have, you know, 10 palatial estates all over the world, but no, like you're running it becomes yet another business to manage, yet another P and L, yet another group of people who you have to give opportunity to and have HR around and everything. It's, it's, you know, don't cry any tears for me. But yeah, it's, it's really annoying.

[Sean Gold]

Yeah. I think everybody 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, 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, you know, cool. I need to do some things to make that happen. Like maybe exercise is part of the prison I want to design. Right. 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 like, hard. 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 like, 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, like, you know, 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, like, whether you chose them or not, that's up to you.

[Andrew Wilkinson]

Totally. I mean, you look at like any of these, there's all those sayings around if it floats or flies or other things, you know, 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.

[Sam Parr]

Well, dude, thank you. This is awesome. I loved seeing you. I love seeing your face again.

[Sean Gold]

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

[Sam Parr]

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

[Sean Gold]

Yeah, you're looking full, thick, tight, strong.

[Andrew Wilkinson]

Thanks, guys. Yeah. What's going on? You. You guys talked about. I know you did camp MFM or whatever. Are you gonna do more of that? Not going to.

[Sam Parr]

You got the invite. You blew it, bro.

[Andrew Wilkinson]

I know, I know. I hate basketball.

[Sam Parr]

No one played, dude. It was like, like Sean was the best player there, which, like, we, you know, we weren't.

[Sean Gold]

No, no one was that amazing right now.

[Sam Parr]

Yeah, no. Ben on the POD was like dunking on people. Nick Huber was great. Sean's really, really good. But besides that, we were all just like a bunch of morons.

[Sean Gold]

Throw an event at something I suck at.

[Andrew Wilkinson]

Right?

[Sean Gold]

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.

[Andrew Wilkinson]

Be.

[Sean Gold]

Amazing at this.

[Sam Parr]

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

[Sean Gold]

Andrew, what would be the version of that that you would do where it's like, it's all right. 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, like, the focus is on some activity. What would yours be that you're, like, really interested in doing?

[Andrew Wilkinson]

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

[Sam Parr]

Who runs out?

[Andrew Wilkinson]

We do. 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, you know, 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. That feels really good.

[Sam Parr]

Towel ass whipping?

[Andrew Wilkinson]

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

[Sam Parr]

Yeah, I bet they did.

[Andrew Wilkinson]

But. But we. We did this thing where we. We would, like, do dinners and we'd have this pack of cards, and we would just pull random cards and be really up. Questions like, what's a. What's a rude word your parents would use to describe you? Or like, 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.

[Sam Parr]

Pull a card on top of your deck, and you're like, all right, guys.

[Andrew Wilkinson]

I have a question.

[Sam Parr]

Should we kiss right now? Oh, my God. The deck said it, not me. The deck said it.

[Andrew Wilkinson]

Written instructions. Happy?

[Sam Parr]

That retreat sounds. That was too easy. Sorry, I'm working on my dad humor. All right, I gotta go see.

[Sean Gold]

All right.

[Sam Parr]

Guys.

[Sean Gold]

All right. This episode is brought to you by Mercury. They are the finance platform of Choice for over 200,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of. And then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder. It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to actually fix it himself. And really, any type of entrepreneur you are, let's say you're an agency. Well, one of the things every agency has to do is be able to send invoices easily, create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside market. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show. For more information, check out mercury.com Mercury is a financial technology company, not a bank check. Show notes for details.