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Before we transition to the episode, I want to highlight the Founders Podcast, which is part of our Colossus Network. David Senra, who hosts Founders, has devoted his life to learning from history's greatest entrepreneurs, and every week he distills the lessons of a different founder. If you want an entry point, I highly recommend starting with episode 136 on Estee Lauder, or episode 288 on Ralph Lauren. I hosted David on Invest Like the Best last summer and it's hard not to walk away insanely energized after listening to any episode with him. You can find a link to founders and those episodes in the show notes of this conversation.

You can also search all past transcripts on our website, joincolossus.com. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like The Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.

Patrick O'Shaughnessy is the CEO and founding partner of Positive Sum and the CEO of O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum or O'Shaughnessy asset management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of positive some or O'Shaughnessy asset management may maintain positions in the securities discussed in this podcast.

My guest today is Jeremy Jafon. I spend all my time trying to find people who have some singularity to them, people who seem like they can do an N of 1 something. Having spent many days with Jeremy recently, he strikes me as 1 of those people. He was the first employee and general partner at private equity firm slash holding company tiny, which buys and holds internet and technology focused businesses. Part of that, he was on the founding team of media core, which was acquired by workday.

The focus of our discussion is about esoteric opportunities that exist in private markets, how misaligned incentives and coordination problems create special situations for people like Jeremy to invest in. The rest of the conversation is wide-ranging and covers everything from compensation advice to meeting your heroes. Please enjoy my discussion with Jeremy Jafon. All right, Jeremy, so we're gonna talk a ton about all sorts of different topics. You wrote an essay that I don't think you've published, but it's about the nature of a perfect business in your mind.

Can you describe some of the elements of what you would view to be like the perfect canonical business?

Yeah, the perfect business for me is getting paid a tremendous amount of money for your words, just your advice. I really do think the old school merchant banks and M&A boutiques like Lazard and Allen and Co. And some of these places are pretty close to the perfect business where someone has decided that your wisdom is so worthy that they're just gonna give you hundreds of millions of dollars for it. These businesses require no capital. They're hugely cashflow creative.

You can generally build equity by investing in the deals that you're advising on. And for the best ones, there's also this idea where the organizations are either selection effects or treatment effects. And so a selection effect would be Harvard or a modeling agency where most of the prestige comes from picking the people. Whereas the SEALs or something like that, to some extent will have a treatment effect. You become a different person by going through this program.

And I think the best organizations do both. By virtue of being selected by the company, it really helps you for your entire career. And it gives you something. Like I really admire certain organizations where you can just tell someone been at a consulting shop or something, or been at a really good bank and just the way they write emails or the way they think or whatever. And that's obviously double edged sword.

But I really like this idea of you can just tell the polish. And obviously same with military people. Maybe there's a path to becoming a principal. I don't actually think you need that necessarily. But You should be certainly be clear about it.

There's nothing worse than all these VCs that have never promoted from within to a partner, but then you ask associates and analysts there and they're like, oh, I'm gonna be a partner 1 day. And it's like, no, you're just totally wasting your time. I think that would be close to the perfect business because I guess what I'm after is leverage. And the idea of basically being able to be compensated super highly for your words is pretty close to just speaking money into existence, which I think is very close to the perfect business.

My friend Ali said to me recently that the best way to think about a great merchant bank is that you literally make things more valuable just by investing in them, basically is what you're saying. I have the same question about the perfect investment. I would love you to take on this because you're pretty unique in, I've talked to as many investors as anybody, And almost every investor will be focused on the asset or the thing that they're putting money into, whether that's equity or debt. So there's a million people that are incredibly smart from Buffet on down about the qualities of a business or the qualities even of a founder or the legal structure around something. I think you uniquely come at investing very often from the meta circumstances of the situation surrounding the asset and the deal and the incentive structures for all the stakeholders in a deal.

And so with that lens, I'd love you to describe your perfect investment, if you will. I don't

know if it's a reachable, but to me, the perfect investment would be 1 where you actually never have to talk to any of the people or know anything about the business. You can just understand the circumstances around it and the incentives of the various interested parties and feel out why this opportunity exists, why you can solve it, and then why you're getting paid for it without ever knowing anyone. I think a lot of these, especially in the private markets, are just coordination problems. You're basically coming in into a log jam and just unjamming it and you can get paid for that unjamming. When it comes to buying software businesses, it's amazing how many people would ask me about technical due diligence.

And it never crossed my mind. If this is a business that people are paying millions of dollars for. It clearly works. The software works. What do you need to diligence?

Obviously it's different in a hard tech company or something, but even then, if it works, it works. I think you can take all these signals. Do you really need to know that much about a product? It's serving a niche thing and people are paying millions of dollars for it and they don't leave or whatever, do you really need to know that much about buying a business if the guy is getting divorced or there's some tax law change or he has some other exogenous catalyst that you can just tell. I mean, this comes back to the people thing.

You sit down with them and it pains them to be selling the business. That's a great deal. I'm probably going to do that deal just from that fact alone. 1 of my favorite quotes that I think about probably every day is the Groucho Marx quote about, I don't want to be part of any club that'll have me as a member. People never think about this with investing.

It's like, why has this come to you? You better have a very good reason and no 1 ever has a good reason. If you believe markets are slightly efficient, then if it's landing on your doorstep, you're either the luckiest person in the world or everyone else has passed on it. And it's probably the latter, unless you have a very good explanation. And so I think I take comfort in, oh, this is a really messy situation and I totally understand why other people's incentive structures don't allow them to fix this problem and why I can uniquely.

And so that's why I think it's easy to make low risk investments if you like understand things that way. You have a very good explanation of, yeah, I got paid for this because I did these 3 or 4 things And there's these 5 different stakeholders and they all wanted these different things and I figured out how to solve it and it unlocked this log jam. I like things that are very explainable when it comes to investing at least.

So it was something like green blots. You can be a stock market genius, your favorite book on investing ever.

Yes, that is my favorite book on investing ever. The big thing that really turned a light bulb on for me in that was when Greenblatt would describe things like index or mutual fund has to dump this because they have some weird legal thing about what they can or cannot hold. Okay, so now I understand and I like that certainty. It's boring, I do view it as construction work. It's not glamorous, like macro or something, but it is very clear and understandable, and you can still make astonishingly good returns, because at the end of the day, they can be difficult problems to solve.

And even in the Greenblatt instance, you're probably 1 of 100 people who is actually reading the 150th page of the legal offering of the warrants offering or whatever, right? And so maybe that's your explanation for why you get paid, because you're the only guy who's gonna read 150 pages of a rights offering of a small cap. That's a good explanation. It goes to my other question. I always ask investors, what is their edge?

And I'm always shocked how few have a cogent answer. And maybe it's because people don't think about it. You can just say I'm smarter than everyone else. And that might be true. That could be your edge.

There's certainly cases of that, but you should have some reason why you think you can do better than everyone else. Even if it's just your cost of capital, like it can be anything, but most people cannot articulate why they're better than the next person, which I think is crazy in a business where you get paid for beating a benchmark.

You and I have talked a lot about how this special situation manifests in today's market environment. We're doing this in early summer of 2023. Maybe you can describe taking that philosophy and applying it to the current opportunity set and what you see, what gets you excited through the lens of solving coordination problems or undoing log jams in the market environment of summer 2023.

This one's great because it involves 2 parties that don't know anything about financial capital structures, which are founders and VCs. And so that presents a lot of opportunities. In this present day, you have all these companies that massively over-raised and are now realizing that even with a good viable business, The founder person is never going to make any money because the prep stack and because they just raised too much and You get this weird situation where VCs don't have any incentive to tell you to shut down. There are exceptions There are a handful of really great VCs, which is both economically and morally the right thing to do. But for the most part, a VC has no good reason to tell you to shut down because they're in the outlier business.

And a founder is going to just, first of all, just be terrified of telling their investors that They failed. Well, not even that they failed. That's the crazy thing about these. Maybe you have 10 million a year of revenue, but you're only going to grow 60% this year. And you raised.

Somehow that's bad.

Yeah. Cause you raised it 300 million or something. And you're going, oh man, am I going to have to do a down round? If I do a down round, then I'm really going to get drowned out on the prep stack. I'm never going to make a dollar here.

It's going to be another 5 years, but you don't want to go to your board and say, I want to give up on this company. I just realized I'm never going to make a dollar from it. And your board doesn't want to come to you and say that because then there's this boogeyman story of my VC told me to give up the coordination problem. And I've done this and we'll continue to do this, which is you can literally just talk to both of these people in private and then broker something together and they're both relieved. I mean, it's the best type of deal.

They're both relieved because the VC, it's just a pain in the ass. I talked to 1 large VC who was complaining about all the audit responsibilities of all these dead companies. And then you talk to the founder and the founder also wants out. It's like a bad relationship. Probably if you start thinking about breaking up, it's already over.

It's already

too late. Yeah.

But you're going to drag that out for another 2 years. And it's very nefarious for founders. Because you only get so many years really where you can take these shots. And if you're really dead set on trying to build a huge company, wasting 2 years of your mid or late twenties or something is a huge waste. And ironically, your VCs would probably be happier for you to give up and back you again, or keep the money or whatever.

And so that's a situation where you've got this asset, so a company that's doing $10 million a year, which is maybe, you know, if it's a SaaS business, maybe the best asset on the planet. If 1 person owned that, if you have a net negative churn on great multi-year enterprise contracts, It's the best asset that you could possibly own. It just compounds cash. But because of its weird financing situation, it's like a dead asset with these 2 parties that both want the same thing but won't talk to 1 another. And so that's like a classic example of a dislocation.

I don't really need to know anything about the company there to know that there's an interesting opportunity. You can go a level deeper and start thinking about the VC's economic incentive, which these are questions founders never ask. How big is the fund? When in the fund life cycle? Did they invest from?

Who else is in the fund? There's 1 case where business is doing like 15 million a year. And I get on the phone with their main board member and he was like, Oh yeah. Right. He's like, I think that was in the Uber fund.

We don't really care, you know? And it's just these crazy things that like, if these 2 people talk to 1 another, there'd be huge unlocks. And so, yeah, you'll get a situation where a VC is happy to give away basically a business that's making lots of money and a founder is happy to either run it profitably or take another shot on goal. And all of this can just be unlocked by having a little bit of knowledge and then solving these coordination problems.

A pro forma like example of the sort of transaction that could solve that specific long jet. And is this the same thing I've heard you talk about like ghost ship companies before? Is this basically the same concept?

Yeah, they call it ghost ship because everyone knows there's just no financial outcome that's gonna happen. And it's this weird thing because there's cash in the bank, you're making money, the team's happy, everything's going well. Still sailing along, but it's just you've screwed up, unfortunately, because you didn't really understand capital structures. It's funny, if you have top tier VCs, you actually get better deals because good VCs understand that returns are driven solely through power laws. And so anything that is not that 1 company in the fund, they actually don't care about.

All they care about is preserving their reputation. So I've seen recaps done for a million bucks. You can offer the founder 500 grand personally, and you can cram down the rest of the equity to 10 or 20%, and you can recap the business, or in a lot of cases, you can just cut costs, and then the business becomes very profitable and then it can run. And I mean the real kicker on these, most of the time growth will either increase or stay the same when you cut a ton of costs. A weird side effect of venture capital is that you never get to see the counterfactual on growth.

So a lot of times your company is growing for some reason, probably inherent to the product or something like that, but because you've taken all this venture capital, you have to spend it. You can't just leave it in your bank account. And so you'll hire a bunch of people or spend a bunch of money on dumb stuff and then you will falsely attribute that spending to the growth, but in fact it was not at all related. And what's funny about this is you can never run the counterfactual because of the venture capital dynamic and so it's really hard for people to believe. But I mean 1 thing that I ask founders, like if you take a founder out for a few beers and you're like, how many people could you cut from this business?

They generally know right away. Sometimes the founder's like, no 1. Everyone is essential and that's a really well run business but the majority of the time, yeah, well, we raised all this money so we tried to hire a big sales team and it's not really working but it's not going so badly that we have to cut it or whatever and we get to tell our board that we're doing something and so there's all these weird optimizations that can be had just by broaching these misaligned incentives.

I would love just to keep nailing the points. I just think it's a really interesting opportunity space right now, given market conditions with other examples, like categories of special types of situations in private markets that you've seen or done transactions in before, especially because of the environment that we find ourselves in today where cost of capital has gone up. I think there's probably more willingness and ability to do these special sorts of deals. Whereas in years past, you might say, ah, it's easy to raise money. I'll just keep going.

So maybe give us another couple examples of a classic special situations transaction that you've done in private markets. Robert Leonard

Some of these are so good, Red doesn't even talk about them because I know no one's doing them. An example is, anytime a large tech company makes an acquisition of another mid-sized company, There's almost always assets in there that need to get divested or the acquirer doesn't want. What's funny there and other misaligned incentives is the incentive of the corp dev or the acquirer is not at all related to maximizing price. What they want and what so many people want all the time in investing is just, they don't want to hassle. And fair enough, let's say a Fortune 500 tech company buys a company for $500 million and they want to divest a $50 million asset, does anyone get any credit for that $50 million sale?

No, it doesn't move the stock price. It doesn't help the CorpDev. No 1 gets anything for that. And so what's really wanted there is just make the poor CorpDev guy's life easier. And so those are great.

Another is sometimes startups have 2 product lines and one's working and 1 isn't. I've seen examples where a company is pivoted and you had a product that was kind of working, but maybe it wasn't working well enough to become a multi-billion dollar outcome and then you need to get rid of that asset. There's obviously a bunch of stuff in bankruptcies that can be great. I've seen situations where startups build marketing assets or basically like lead gen businesses that end up being better businesses than the main 1. And so when the main business goes under, you can buy those marketing assets or whatever.

There's all kinds of things and it's all just downstream of venture has outsized returns so that you can just be super wasteful. It makes more sense for every party economically to just throw it away than to do something diligent with it. And so we're at the best opportunity of all time right now to do that because of the amount of venture that's gone into the system. I think eventually for turns normalized, which I think they tend to do over a long stretches of time, the wasteful behavior will go away because it won't make any sense anymore.

It's a fascinating thing to think about all this stuff's under the rug, so to speak, because the pile of money is so big. I love the idea that it's actually the best funds of the best VCs where these opportunities are most present. I mean, interesting, weird twist on this all. Given all that, How did you build pipeline to get to see this stuff over your investing career, most of which was at Tiny? You're 1 of the few investors I've met that has been doing this style in private markets for a fairly long period of time.

So how did you build up a sourcing mechanism to be sure you saw this stuff? If some mid cap tech companies acquiring some private business, how are you in that flow? How did you work your way into that flow?

Well, tiny, I mean, in the early days, we were just very good at outreach. Andrew and Chris, the co-founders, had very good reputations, but we would just email people to say, hey, we'd use a product, use a lot of software in a day, and some amount of it will be venture funded, But the software that you use that isn't venture funded, it's probably just a small team who's bootstrapped and you can just email them and say, Hey, do you want to sell your company? We had to do that for the first few years. And then eventually we built up a reputation and it kind of flipped and we would get a lot of inbound and yeah, we would see a lot of this stuff at Tiny and a lot of it was just, which I love is 1 large investment bank sent us something and they were like, we could not think of anyone else to send this to because of a mix of how weird it was and its size. And I think that's great.

In retrospect, 1 of the very bullish signals at Tiny was when we started, people would ask us what we were buying, if they were assets. We would say, oh, we're buying Chrome plugins or Shopify apps or whatever themes. And people would ask, are those even assets? And I think that's really what you want. At least if you subscribe to the munger theory, which is that it's better to find your own lake than to try and be the best fisherman.

I think you get a reputation for it, but honestly, There's not a lot of people out there who can do this stuff because it's really weird and it requires very fast speed of execution, which requires really abnormal underwriting abilities or requirements. And you have to take weird risks on things that other firms can't or won't take risks on. A lot of company buying, at least in my experience, is not dissimilar from Craigslist. If you show up first with cash in hand, you get the deal, maybe if you're not the highest price. And so I think a lot of it is just being willing to go and do that and say, yeah, okay, we'll do this weird thing.

Very Buffett-esque, right, where you would hear examples of him writing extremely large, increasingly large checks over his career in very short periods of time, over the weekend or something.

And that's what inspired us. We couldn't believe that we had tried to sell, in my case, a business to a public company and Chris Sanders case to private equity. And we couldn't believe that it was 6 to 9 months, steak dinners, back slapping terms, all this stuff. And we look at Buffett who could buy a $30 billion airplane parts manufacturer in an hour. And we were like, hold on, this company is a Stripe account and a website.

It's not complicated. Surely someone out there can do it in less than 6 months. And you can. That's testament to tiny successes that you clearly can, but I think a lot of that just exists for incentives and busy work and stuff.

What have you seen as the biggest mistakes in buying companies, whether it's been your own mistakes or ones that you've observed in others?

The biggest mistake is just ignoring your gut, which is trite, and I hate to say it because it's not that interesting, but it is the absolute biggest mistake. Every bad deal I've ever done or seen someone ever done in terms of buying a private business, the first 2 minutes with meeting the owner, the principal, the seller, you could have saved yourself. Because if you're not doing 9 months of diligence, you're basically just diligencing the principal or the seller and saying, can I trust this person? Is this person trying to screw me? Because if they are, it's pretty easy.

Because we're not gonna deploy Bain on you. And so you probably can get stuff past us. It would be seeing if a person is trustworthy and then understanding why are they selling the business. Because you're buying from the ultimate insider who's decided this is the exact moment to divest from the asset. So that's already a completely bearish signal.

You're already at such a disadvantage. And so you really have to work to overcome and understand, okay, Why is this still a good deal despite that? And so I think a lot of new entrants to the space, they get some prospectus in their inbox and they're like, oh, this is amazing. Maybe the person who's run this business for 30 years has decided that now is a very good time to sell the business. Maybe you're not, it's not just your lucky day.

That's the most basic there's tactical stuff, but it's really all downstream of why is this business being sold? And is this person just a trustworthy person? Or do I understand that their story makes sense? Does it all add up? What if you

were to flip it away from the buy side, which is where you've always been to the sell side and explain the things that you've seen sellers do the most poorly. Maybe that functions as like advice, like don't do this if you're out there listening and you're trying to sell a business.

Oh God. I remember the startup that I was at prior to Tiny, we got bought by Workday. And it was some 30-year killer from Morgan Stanley who had just come on, and we were just these doofus Canadians. The Sun Tzu thing, like the battles over before it even started. And I think It's classic, this is not novel, but it's the most important transaction of your life.

Probably you've never done it. Maybe, you know, someone else who have themselves done it once. And you're up against someone who that's all they do all day, every day. And so It's very difficult. I think the best thing you can do is talk to a lot of buyers.

Maybe try and get an understanding for how it works for the buyer and what they're getting out of it. It'd be very strange. Sometimes you'd put an offer on a business and the seller would come back and say, I got this other offer that's a lot more. It's not magic how that other offer happens. Okay, you can take that, but let me at least explain to you how they're levering up the business to give you that offer.

And maybe you're okay with that, fine. All the time I tell people, congratulations, Microsoft has decided that it's strategically important for them, so they're gonna give you 40 times revenue. Take that deal. But you gotta at least understand why and how. And so I was always amazed how much the seller had no idea what the buyer was getting or how they get paid back or how they make money.

And I don't think it's super hard to understand. Certainly if you're in a position where you've built big business that you're selling, you're more than capable of understanding this stuff in an afternoon. And it's really worth doing it just to get a sense of what is the other side getting here.

So if we go back to the speed and simplicity that sounds like you've always valued in the investing process, what got refined over time about the underwriting process? In what way was the hundredth thing you looked at, the process itself, I mean, for the hundred thing that you've looked at, most different from the first thing that you looked at.

I think a lot of investing is pattern recognition. It's nice because compound interest dovetails well with pattern recognition. So I think part of it is you just see what matters and what doesn't. A first time buyer will always care about things that just don't matter at all. I think a lot of that comes from just reps, but I think the other thing that I really noticed is when I started, None of us had any finance or investing background.

We were just fans of Buffet and Munger and read all the books. And so I think there's an air of insecurity that comes from that, which leads to asking a lot of complicated jargoning questions. So in the first 4 or 5 years of doing this, I would ask a lot of very complex questions, which in retrospect I think were mostly about trying to telegraph to the seller that I knew what I was doing.

What's an example?

Well, we used to make DCFs just so we could all feel like we made a DCF. Check

that box.

Yeah, well it wasn't even that, It was more that we thought, well, geez, everyone else does this, so we better make sure we do it. Now, the questions that I'll ask a seller are, what does this business do? Why do people buy this business and not the other business? How do you make money? How did this start?

How did you get here? You make $20 million a year from a Chrome plugin. How the hell did that happen? Just understanding that. And I'll see new analysts who don't really understand what the business does, but they don't ever want to say, what does your business do?

Because they're worried they're gonna look unprepared or whatever. And I think that tracks because fundamentally, the more quantitative the analysis is, the more of a commodity it is. And so what really gives you an edge, in my opinion, is experience on the qualitative. It's going to be that very simple line of questioning that actually gives you an advantage. And it's really the sign of an amateur to be really caught up in why did the margin change from this quarter to that quarter?

Because they think that, oh, if you can just understand all there is to know about this business, then you can have an edge on it. Which ironically, I think, makes you miss the main thing. And so it's just asking really simple questions like, why is the product good? All these very basic things. And that allows you to move really fast.

A great investment should just smack you in the face. Probably the best thing we ever took from Charlie was the too hard box. A good investment is just something should be really easy to sell to the team. You should be able to pitch it in a few sentences. It just makes sense.

It's hard. It's really hard to do this. We'd catch ourselves all the time. We'd be on week 3 of debating this company. Ah, should we buy this?

The best thing we could do is go, we've been debating this for 3 weeks, ergo we should not buy it. It's not obvious, it doesn't smack us in the face. And this comes back to incentives again, which is you have to have the ability, incentive wise, to be able to say no. If you're being forced to deploy capital or whatever, you trick yourself into doing these deals. But the good ones, you're just like, yep, I get it.

Let's do it. This makes a lot of sense. I think part of that is just having the abundance mindset of being like, if things are too hard, just let them go. It's fine.

In the spirit of simplicity, then how would you layer on the quantitative as it relates to expected rate of return? Because 1 of the things I think about a lot is, okay, we have proxies for rough expected equity returns. Obviously with fixed income, you know what the base case is in terms of your return. Therefore only do something if it's quite significant. The hurdle rate is way higher than what seems available through your best alternative, which is go to Vanguard and open up a simple brokerage account and stash your money there.

Been a very compelling thing to do with your money for most people. So how would you think about minimum rates of return or hurdle rates or basic multiples on capital or IRR requirements for the investments that you would make understanding that you were trying to approach this with a simple mindset?

I used to get asked this question a lot. My answer was always, is it roughly as good or better as the last deal? That was our entire hurdle underwriting. If it was worse, then we'd go, ah, we can do a better deal than this. And if it was better, then we'd get excited about it.

This is something that Chris Andrew came up with. You always want your deal to be the last investment you ever do. Very often we'd buy a company and we'd be like, alright, we can just hang it up now because this company's gonna take us through to retirement. And so you don't really think about benchmarks and returns and stuff when you're thinking in that mode. Because there is no better asset than a great business that has operating leverage and pricing power.

And if you got that, you just have a machine that prints money. And if it has a moat, then you have a machine that prints money for a long time. And so obviously that's gonna be way better than the stock market or whatever. And in terms of risk, we were probably just too unsophisticated to think about risk or certainly I was risk. And this is just another monger line, but I think it's true.

It's just loss of capital. And so if you're not going to lose your money, then it's not risky. You want a simplistic, that's really simplistic. I think it's served us well.

If you think about the bridge between everything you just said, which is basically get a great deal on a really good enduring business that you understand that doesn't take 3 weeks of debate up against the earlier discussion we had on, okay, there's this really unusual, special, timely situation of incentives that are out of whack and there's an opportunity. I think you read the Greenblatt book, if I remember it correctly, the holding period on lots of those trades would be short. Maybe measured in months or years, certainly not in decades. So are those 2 things different in your mind or is the special situation just a unique opportunity to get an especially good deal on an enduring business?

It just comes back to being lazy and not doing hard things, which is I want every business to be the last business I ever buy. So if it's not going to be, it has to be so smack you in the face good that I feel compelled to get off my ass and do it. We bought lots of cigar butts. I would continue to do those, but they have to be so good that it's, do you want to make millions and millions of dollars for very little work? Okay, sure.

Another favorite question from managers is how long have you gone without deploying money? The best I've ever heard is 6 years.

Yeah, you and I heard that once together.

Tiny did 2 years, which was incredibly hard. I can't fathom 6 years. I mean, 6 years of doing nothing. You literally just do nothing.

I think Buffett went that long once too.

Yeah, Buffett and some other folks I think have done that, but it's so difficult. I find you don't really need to think about all this stuff if your default frame is just not to do anything, you have to be compelled out of your seat. Because if you are, then you're going to have this visceral hurdle rate, which is, is this worth my time? And if you're excited about it, then you do it. And if you're not, you don't.

And I find that you can really avoid doing bad deals that way.

It actually brings to mind this notion of, I think it's your 1 question, does this energize me or drain me? Talk about that in as many ways as you can, including maybe for investing.

To go back to underwriting, we hired, I don't know, dozens and dozens of CEOs. And really the main thing that mattered the most was when you leave the conversation, do you feel energized or not? Because everything else is downstream of that. If you hire someone that drains you, even if they're really good, you're not going to interact with them, you're not going to have a good relationship. It's just not going to work.

It's 1 of those situations where you have to be like brutally realistic with yourself. You can't be like, oh, I wish I was the sort of person that liked this person because they're really good. But it's like, yeah, you're not. So even if they would be a good fit, it's not gonna work for you. And that applies to investments too.

I think good investments get you really excited. We would go long stretches. Sometimes we'd do no deals or 1 deal or whatever. A good investment, we would suddenly start moving extremely quickly and get really excited and go from working far less than 8 hours a day to working

14, 15, 16

hours a day. And because it was just like this great thing that you had to do and then going back to just waiting around.

Why do you think so many people spend so much of their time on things that they don't like doing?

I think this is the single most important question in the world probably because I think it's extremely puzzling that a world where a lot of people can cover their bases in terms of food and shelter, they still spend the grand majority of their life doing things that they don't like doing. I think it's a deep and troubling puzzle that I don't really have the answer to. I think a lot of it comes back to not really understanding what your true desires are and having fear around losing things, being stronger than desiring what you actually want. I basically think most people wish that they like things that they don't actually like. For example, even in my own case, I think a lot of people wish they wanted to make more money than they thought they actually did or they wanted status more or it was important to them where they live or what clothes they wear or whatever.

And I think a lot of people don't actually want those things that much, but they feel like they should, or they're very scared of the consequences of acting like someone who doesn't. And then they really get into this mess. But I mean, yeah, it's a real puzzle. People with tons of options will spend their whole life working jobs they hate It's really strange and it's really tragic and it's really bad for the world because you're not gonna do great work. I Once was talking to like a therapist performance coach who?

Would tell people what he thought their true calling was. I had had a few highly accomplished people tell me that it was the most devastating thing they'd ever done in their life. I was puzzled by that. His name was Jack Skeen, and I asked him, why do people describe this as devastating? And he goes, well, if I tell someone who's a very successful investor that they need to be a third grade teacher, do you think that would be devastating if it weren't true?

Well, no, of course not. You'd just think you wasted your time and money. It's devastating because you know on some level it is true, but you know that becoming a third grade teacher now means you no longer live in Tribeca, you don't have the same friends, you don't have the same apartment, and all that is terrifying to you. So the fear of loss, there's some great tragic loss to the world about you not being that thing that you feel called to. And so yeah, I think it's a really difficult puzzle and it really just comes back to most people don't really know what they want or are in denial about what they ultimately want.

How far down that path do you feel personally? Do you feel like you really know what you want and have set your life up accordingly?

I feel like I've made a lot of progress. What's led me here to this conversation is I just, I'm a big sabbatical fan. You're probably getting a theme throughout the podcast of just generally not doing anything. I'm a big sabbatical fan. I've taken multi-year sabbaticals before.

I'm on month 6 of 1 right now. And I think that almost everyone does not spend enough time thinking about how they want to spend their time. A lot of this comes from just do things, just execute. And I think that's really important. And I'm certainly weak in the other direction, but thinking very deliberately about what you want to do and how.

I think it's very underrated and society makes it difficult. You're very low status when you're not doing anything and there can be financial constraints or whatever. We've been talking about different things that we're interested in and things that we want to build in the future and things like that. And that's really come as a result of just taking a year off, or taking months off in this case, and just letting the world soak in and come to see what gives you energy, what's exciting, what's not. And I think the only way that I've found to be able to do that is yes, a lot of introspection, but also just sitting back and letting things come to you and see what feels right.

Because I've certainly had no shortage of opportunities that are rationally interesting, but they just don't. Energetically not. Yeah, they don't really get you out of your seat. And so I think it's something that more people should do and it's not that difficult, all things considered, especially if you have a low burn rate. And it's really worth it because it's trite, but the low status things become high status.

And people I know who are working on the most interesting things just wandered off in a weird direction. But it's painful, it's a very painful process. I think you have to realize a lot of things about yourself that you're not so motivated by this or you're not the person you thought you were. And maybe you won't have the life that you thought you wanted. If they really viscerally embody those, those are really painful and hard to deal with.

Maybe say a click more about what that means for the notions of laziness and the quality bar for what you'll do. I'm curious how you react to the word laziness, but also just the notion of people settling much earlier than you think they should. Is that the right main conclusion that it relates to how long have you not done a deal for? It seems like the common theme here is the ability to set a crazy high quality bar and not change it.

There's a couple of good heuristics here that have been helpful. 1 is a question from our friend David Senra which is what could you not be paid a billion dollars to stop doing? I think there's a lot of people who would very happily take a large check to never do what they do again. But generally there's something for everyone. I mean, for me, it's figuring out people.

I'm super curious. I think I'm an incredibly curious person. And the curiosity mostly manifests through people. And I really like to meet and try and understand the world through talking to different people. I really don't think I would take a check to stop doing that because I sincerely don't know what would get me out of bed in the morning.

But there's a lot of other things that I would happily take a check not to do. And it's not lazy. Lazy is the wrong word. I think the classic case here that I like to point to is Andre Agassi versus Novak Djokovic. I was really struck when I read Agassi's biography that he's basically this miserable guy who hates tennis.

That opening chapter in that book is amazing.

It's insane, and then the pinnacle of his career, he starts smoking meth. It's nuts. Then you hear from Djokovic, who's going to be 1 of the greatest of all time, if not the greatest of all time, or Federer for that matter. And they're both just, yeah, like really like playing tennis. It's super fun.

Djokovic has this line that is seared in my brain, which is, I just like hitting the tennis ball. And I think that there's something so funny and kind of tragic there because in a more just universe, some would say that it should make sense that if you kill yourself for the work, you become the best, but that's not actually the case. For the ones who it's easy for, they do the very best work and become the greatest. And so I think it's really a win-win Pareto improvement, but it's really difficult. I think the reason you see it in sports, by the way, is because sports is 1 of the very few things that we test on children super early.

So I think if we tested way more things on children, you would find this in all areas of life. But because sports are a thing that young children do, it's much easier for those who do find their fit in sports to get it early and push it hard. Whereas say that you're a great investment banker, a lot of things are going to have to go right for you to even start investment banking to find out if you like it. But I imagine if you gave a lot of toddlers spreadsheets, the same number who are incredible or prodigious at tennis would be incredible and prodigious at spreadsheets and they should probably just jump right into banking or something like that, but we just don't do that. I think everyone has something they're not lazy about, but it's hard to find that.

Laziness, like depression, like all these other things, I really do think is a deep indicator from within you that you're not doing something right with your own life and you should heed these warnings and listen to them and not try and push them away.

I just had Kevin Kelly, the founder of Wired and just an amazing guy in a lot of respects, speaking of lines seared onto one's brain, His line that the reward for good work is more work is my favorite shibboleth of all time. If you say that to somebody and they start nodding, that's the kind of person I want to hang out with because they've solved the problem you just described. What would you do if the only reward was getting to do more of that thing? What is that for you? And almost no 1 has a professional answer to that.

And I'm curious if you think there's ways of nudging oneself in the right direction, other than taking a sabbatical and just not putting pressure on yourself to find it.

Another cut at that same thing is, as you get closer to doing the work that you're called to, you get less envious of people or rather the things that make you envious are fewer. It's a very common thing that I see of top school, super ambitious kids to have to put down everything around them as bad to justify what they're doing and I think that's really a terrible way to live and what you see with someone who's really found their calling is they're just not envious And I can still tell it exists for me. An example is if I see an NFL quarterback, I'm not envious of him. It's not like, oh, like, you know, that could have been me or even worse. I'm not going, oh, well, you know, he sucks.

He's late in the draft or whatever. It just doesn't even cross my mind. I don't even think about the quarterback. Good for him, great. Still, if some 20-year-old sells their company for $600 million, I still get all those thoughts about, oh, you didn't own very much of it or it was a fake company or whatever.

And that's how you can tell that you're still not really in your zone, per se, because I think people who are truly locked in are just like, great, that's not what I wanna do, but good for you. I think it's probably possible to get to a place where everyone is quarterbacks, and you're always like, oh, that's cool, but I don't wanna be that, so I'm doing what I like, Good for you. I think that's very possible, but it's really difficult.

You think about, let's say hiring a CEO, which is something you did a lot. Where you buy businesses, you said earlier that sometimes businesses are just such a reflection of the founder, which means accession's hard period in any business, certainly in investing. It's extremely hard, maybe even harder, but it's hard in business to change from 1 King to an extra 1 queen to the next, what did you learn about? That very nuts and bolts thing that you had to do, I don't know how many times you did it, but I think you did it a lot at Tiny where you'd buy a business and install a new CEO.

I think a lot of these debates around talent and hard work and all these kinds of things, there are people talking past 1 another because I think there are companies that need the best in the world, but by definition, almost every company does not need the best in the world, any layer. What you need is someone who has that specific skillset. Andrew's insight, which is correct and worked brilliantly, is you just find someone who's done it before at a bigger scale, and you get them to do it again. And that works great. And it's so anathema to the Valley philosophy around it, which I'm also very sympathetic to.

It reminds me of manager selection. It's like you either get top tier, or you're unable to get top tier and you've got to bet on emerging. That would be the whole Stanford, spot talent, young thing. And that works too. And I think there's a real skill set there.

But if you can get just the person who's done it before, then great. I think people really romanticize business, especially recently in the culture, for being a lot more difficult than it is. I used to always harass my computer science friends that they're just bricklayers. Yes, a small smidgen of them are doing difficult technological work, but generally no, you're basically a construction worker, which is nothing wrong with that, but don't kid yourself. You're just building things that have already been built before and there's like a known way and there's codes and infrastructure and blueprints and you'd follow and implement those things.

And so you don't need to get too romantic about it. Again, it's always different for outliers, but for the median business, I don't think it's some great intellectual edge or some world-class talent or whatever is required. I think it's just solving problems reliably and diligently.

So then why, Like if I add a bunch of this up, which I'll describe as really good perspective returns in simple businesses that you can understand with relatively low risk that can be run by somebody who's just got the experience that you're not betting on potential. Add all that up and you just wonder why is that opportunity persist? Again, thinking about markets as like mostly efficient or competition coming to bid down returns when something like what I just described as possible, why will this kind of opportunity continue to persist if it all stacks up that nicely?

Because it's really hard. It's just really hard. And part of the difficulty is how simple it is. It's boring. Every value investor gets to some point in their career where they think, I should be like Buffett and buy an insurance company.

And they've all done it, and none of them have made it work. And you know why? It's because the guy who runs Berkshire Insurance is a genius, prodigy, and it's just that simple. It's 1 of the most, if not the only, like reliably profitable insurance operations in history. And so yeah, it is simple.

Buy an insurance company and use the float. But it's hard because you need to find a guy who's really good at insurance. And that's exactly the same with all this. It's all simple. There's no tricks.

It's just really difficult. And to go back to the desire, most people don't want that. If the difficulty is being really bored all the time or doing the same thing over and over and over or whatever, most people do not want that. They actually would rather not be bored or not do the same thing over and over than want the riches, which comes back to the crisis of desire. You think you want the riches, but only contingent on a bunch of other things.

And that's what makes Buffett and Munger and people like that unique, is they really love doing that. I think it's just hard. It's hard to do for psychological reasons. I really like the saying, the only enduring edge is the psychological edge, because human nature has yet to really change. And I think that's entirely right.

It's just attrition, or just being willing to be low status, or be weird, or set up incentive structures in such a long-term way that you can actually operate differently. But in exchange for doing that, you're gonna look really strange or not make as much money in the short term or whatever. It's all pretty simple, but it's difficult.

What tactically then would you say about doing the, let's take the CEO thing, well, I'm especially interested in like negotiation and sourcing. So I believe that every 1 of these steps that I just described is hard and your hit rate's low. You're going to have to look at a lot of things to do 1. Sometimes it might take 6 years, but you know, between 1 and the next. So Tactically, what did you learn about sourcing and negotiating with, let's say CEOs, or you can say business sellers, but the sourcing and negotiation are things that I'm really interested in.

The tricks you picked up along the way. Sourcing is an interesting question. We were like doggedly anti-recruiter for a long time because we tried a bunch of

them and they were all terrible. But then we learned that actually Buffett found Ajit Jain, the guy who runs the insurance company through a recruiter. Just like anything, you can find good recruiters. Obviously having a large social presence makes it really easy. So Twitter accounts and audiences remain incredibly underrated and underpriced.

And it's pretty straightforward. If you have a good deal, you can find capital. If you have a good opportunity, people will pick up the phone. And so I actually don't find sourcing to be that difficult, especially with this framework of, what's a company that's done this exact thing before and let's go talk to someone there. So that would be on the sourcing piece.

On the negotiation piece, there's lots of tactical tricks. I think generally the biggest thing with negotiation is getting out of your own head. Most people just negotiate against themselves, whether verbally, I mean most people negotiate themselves verbally or mentally, where I could never offer that, I could never say this, or they don't think outside of the box. There are no terms really that you can't bend or change or whatever. And so I think it's really just about very rarely will people get an offer and actually be like, I'm so insulted, I'm never talking to you again.

Like doesn't really happen. And so I think a lot of it's just coming down to just being able to make the offer that other people don't or can't. And that's not to say that you always need to be cheap. You can also make the offer on the upside in ways that are weird. A Classic scenario is a business owner who is selling his business and he's got different offers and we found out that he's really into Ferraris.

It was basically implied that he's going to sell his business for 30, $40 million. So it's obviously not a problem of affording it. But what we realized was that like his wife is not going to let him buy a Ferrari or zone South. Isn't going to let him buy a Ferrari or it's uncouth in his neighborhood or whatever in the yellow. I $25 million and A488.

Why not? There's no rules against that. And so these are the kinds of things with negotiating where you can just get really creative as long as you're willing to just be a little weird and just be a little vulnerable. And then the other thing is, it comes back to patience again. Very often you make an offer and someone goes for the other offer and you know there's something wrong with it.

Like this would happen all the time at Tiny. We'd make an offer that wasn't the highest offer. They'd go with the highest offer and I would very glibly say, I'll see you in 6 months and they would never believe me. And 80% of the time they'd come back and they'd realize that actually money isn't the most important thing in a transaction where you have a lot of counterparty risk. Actually you want a person who can actually get a deal done.

And I don't blame them. I think that's something you have to see for yourself. I don't really think you can educate someone into that. It's like saying money doesn't buy you happiness. No 1 has ever not tried to accrue money after hearing that.

But just the confidence of like, okay, we know what we're selling. We're pretty sure that you're gonna see the value in it eventually, and we'll be here. And that's a really great negotiating position as well.

I think you and I share a deep interest in people and what makes them tick. And we both really enjoy and have talked a lot about fun and simple categorizations for people and you've turned me on to the simplest version of that, which we'll call binaries. They're this or they're that 1 or 0. And I'd love for you to explain 345 of these that you've used before to categorize people. I just think they're all so interesting.

And probably the 1 that resonates the most with me that you've talked to me about is this notion of whether or not someone is before or after their personal fall. Explain what that is, how you came on the idea, and why it's a powerful way to understand someone's situation in life.

Pre and post fall is really, I guess, a perversion of a Christian idea, which is, Has someone really been brought to their knees by life? You can see it immediately and I find it's entirely uncorrelated to who they are or what they grew up with or what they do in life or whatever. It just seems to be random and you can just see it in someone's eyes whether they've really been humbled deeply by life or they haven't. And the reason that I find it useful is it gives you a sense of the capacity that that person has for suffering or pain. I find it to be a very good indicator of if something bad happens to this person, how are they going to react?

An extreme example would be someone with multiple combat deployment. Probably not going to get too disturbed by something going wrong. Whereas maybe someone who's never had anything go wrong in their life, it's really going to disrupt them.

Is there a difference between hardship and a fall? It seems like everyone's had some form. Obviously, it's a gradient, but everyone's had hardship. Is this just saying hardcore hardship, or is there something more truly binary about this concept for you?

I use the word fall because it's capitulation. So it's actually not really related to how hard the thing is. You could maybe go through an extreme hardship and not be beaten down. But I literally think of it as like, maybe even literally been brought to your knees and just this moment of life is out of my control to some regard. It's more about the reaction, what you come to recognize is true about the nature of reality from that than what the actual thing is.

What is the fastest way to tell if someone is pre or post fall? I've heard you say you can see in their face.

This might be a weird answer, but I just think you can see in someone's eyes right away. You can just tell. Maybe it's the loss of innocence or something, like just how much have you seen? And I actually think it probably gets worse the more you ask someone about it, because then there's this weird thing about wanting to perform or say, oh, that was really hard or whatever. It's just a sense.

Is this useful? I'll give you some examples. Would you rather be business partners or an investor in somebody who is post-fall versus pre-fall? Does it matter in that tangible context?

Well, I know plenty of very successful people who are pre-fall. And so I think it'd be a mistake to say that you wouldn't want to partner invest in those people. But I do think it's useful in the sense that there's a little bit of a ticking time bomb. If something is going to befall that person, they might react in unpredictable ways. And I think you see that all the time.

There's tons of data around investors and divorces and personal circumstances for CEOs and stuff. And I think that's in the tales, that's where it becomes more relevant.

How about for you personally, maybe describe the experience of going through a fall?

For me, it was just, I got super depressed. I was chronically depressed for a while. And the real moment was like when I really started scaring myself. And I think that's that level of maybe I'm not really in control here. And I think now I just have this feeling after that, having come through that, that it's like, I can handle that.

Nothing's really going to phase me that much. Like, I think it's a sense of being brought to your limits in some sense, and coming back from that. It converges into another dichotomy that I like, which is easy or hard to kill. I don't think they're synonymous, but I think there is some similarity between being like post-fall and being hard to kill, which is just another 1 that is not necessarily related. None of these are related to background or life circumstance or anything, it's just inherent attributes.

I think hard to kill is just someone who's above all just has a certain sense of will and is just gonna be difficult. And someone who's easy to kill I think is someone who's very fragile and doesn't take much to go wrong for them to think to really go catastrophically.

Does that 1 extend beyond the individual to group settings or business settings or something like that? Or does it just come back to the leader being easier hard to kill?

Yes, and no I mean, I think every group is basically just made in the image of its founder and so it come back to the founder I would be very confident that a hard-to-kill founder would create a hard-to-kill organization even if the founder stepped away from the business.

Can you describe that picture you sent me of Goldman Sachs during Hurricane Sandy?

My favorite business picture is there's just this picture of the bottom of Manhattan during Hurricane Sandy at night and all the buildings I think everything below the park lost power, but there's this 1 building that's totally lit up and it's Goldman and they just built their building with generators and stuff. It's amazing that they built the building, you know, however long before and we're like, we're not going down like Goldman Sachs does not die. And I think that's probably some kind of deep entrenched thing in their DNA. You would ask, you can see other banks in that picture. Why weren't they built with generators?

What culture went into 1 bank doing that and the other is not doing that.

How do you underwrite something like this? I assume you would think the hard to kill thing is valuable in the investing context. As you've looked at a gazillion opportunities, companies, people, how have you used this binary, if at all, as a investing filter?

Maybe the best way to describe it is, does this person make me sleep easy at night? So there's a real distinction between, say you're like investing in a company with a CEO or you're hiring a CEO for a business. There is a distinction between skills and sleeping easy at night. I've had plenty of situations where maybe there was someone more skilled, but someone else just makes you feel like you can rest easy. And I think that's part of this hard to kill.

They're just going to handle it. They're going to figure it out. They're used to things going wrong. They're not going to freak out. There's just a calmness.

So I think it's really about downside protection more than anything in an investing context.

Is this directly comparable to Paul Graham's notion of being relentlessly resourceful, Or is it different?

Yeah, I would describe maybe relentlessly resourceful, to my understanding, is more about being proactive. And this is more like the reactive frame. I think really what that means is just a tremendous amount of will or desire. And I think that this is maybe the flip side of having the will to succeed versus the will not to die, which I think are like closely related, but are not the same thing.

You talk about the next binary, which is, I don't know what you want to call it, like brute force versus cleverness or repetitions versus efficiency or something like that?

Yeah, I mean this 1 I think you see everywhere, which is there's people out there who see linear progressions and just get excited. If I apply more effort to this input, then I know I'm gonna get more output than anyone else. So they'll look at like a competitive situation or something and get really excited about it because they know that as long as they can work harder than everyone else they're gonna have, it's like a very sure thing that they're gonna have a higher level of success. Whereas the clever person or the wits person is all about waiting around and waiting for the non-competitive thing, seeing the non-obvious thing and then striking. And they're very different.

And I think you can see this all the time. And I think generally most investors are more on the clever side of things and most operators are more on the kind of the rep side of things, but obviously they cross over and at the top people are generally both. But yeah, I would describe it as does the idea of having to outwork everyone excite you or fill you with dread. And I think for half the people, they love that. Arnold Schwarzenegger is a classic example of a guy who's just thrilled to be able to outwork people.

And then for the other half, it's terrifying because it's just going to require so much effort and there's not a clear edge or whatever. And another way that I like to ask this in interview questions is, you're standing outside of a really popular nightclub in whatever global city, and how do you get in? There's a wide variety of ways. You can bribe the bouncer, you can make friends with a bunch of girls online, you can sneak in the side door. I would, the day before, I would find a mutual friend with the owner or the investor of the club and meet them for coffee.

That's how I would do it because that's what's most comfortable to me. But I think it's a really clean way of understanding how people think about problems and also what they're averse to and what they're really attracted to in terms of challenges.

What other favorite interview questions do you have that are somewhat universal?

My absolute favorite interview question is just asking people what they want over and over and over until they break down. It's probably the most reliable way to actually figure out is this person, if you're truly trying to put the right person in the right job, and it's different if you're trying to sell them or whatever, but if you're just trying to get a really good fit, I would be suspicious of anyone who isn't vice driven at some level. And so you want to find out like, what are you after? Are you after money? It's amazing how many investors you'll interview who will not admit to being money driven, which like clearly they are.

Unless you're the investor who really just likes the puzzle solving, you could also be a professional Sudoku player or something. And you just happen to think that options trading is more interesting or something, those do exist. But even then, if you really just puzzles, you should probably just be in the academy. I always find it deeply suspicious when you're interviewing, like, you know, especially for someone who's doing like quality of business analysis or something, And you ask them, what do you like? Why do you want to do this?

Over and over and over. And at some point they don't just say, well, I want to make a lot of money. Well, if you're a good investor, you're going to make a lot of money. So what's going on there? And I think that's a hugely powerful question.

And most people don't even know the answer. So it can be this fun co-discovery thing that you can go on.

Do you think that the best investors ever get post money as a motivation pretty fast though, like pretty clear that Buffett's of the world or not, maybe to some degree they view money as the scoreboard or returns as the scoreboard on their puzzle solving ability or something. But that seems like maybe the not healthiest motivation over the long term as you think about evaluating an investor, which I know you've done a bunch. How do you parse that?

No, I think they like the money Because I think the ones who don't like the money disappear and right off into the sunset. And there's lots of those guys, but you don't hear about them because they disappear. I think Buffett loves the money. He doesn't love spending it. Just think about Buffett famously never sold a share of Berkshire.

That's insane. Everyone's like, Oh, I want to be the next Buffett. And it's like, okay, so you want to make a lot of money, most of which will come in your extreme old age, and then you never want to spend any of it. That's crazy. Buffett has clearly found the right thing for him that he loves, but that's really unique and strange.

I think everyone's pretty money motivated, whether it's as a score or as a means to an end. I think the ones who are means to an end will just quit.

Another binary that is totally off the wall is this notion of guy versus boy. What do you mean by this dichotomy? Not so much a binary, it's 2 different paths.

I realized a while ago that a lot of my friends that I'd really break out career trajectories, they basically became the boy for like billionaire. I make vague like Roman illusion here, which is You're not really, I guess, normally a chief of staff, but generally it's more than that. It's some deep mentor thing. The way it usually goes is you find your way into 1 of these guys' networks, and they basically do make a deal with you where it's like, you just be my assistant for 2 years, and then you have all my resources and backing. And it's actually very similar to knights and feudalism or something like that.

It's kind of whose banner are you gonna fly under? I noticed a strange phenomenon where like a lot of my friends who couldn't afford business class plane tickets had flown private a bunch because they're in the court of the king and they just move around in this convoy. And I think it's like a really great career path. It might be like the only good job worth taking out of college if you want to be entrepreneurial. That's the boy.

The boy is weird because on 1 hand, he is this lowly person, but on the other hand, he's held in a high regard in the organization. Whereas the guy, the billionaire, will also have a guy who is number 2. And that's very different. Like the number 2 is extremely important, but the number 2, there's this weird dynamic where like it's understood that the number 2, that is his station in life. Maybe he's rich and makes a lot of money or whatever, but he is going to be that number 2 forever.

And the boy is this person that is, it's almost an omission from the billionaire or whatever saying like, maybe you can be like me. And so like, maybe you're the next me. And I just think it's a interesting dichotomy that also a lot of people confuse because I also see a lot of people, classic mistake is you want to be like someone. So you go work for them, which is classic mistake. And it's always wrong that you have to say, would this person at my age be working for someone else?

And the answer is generally no, because 1 like sets you on this path to be an entrepreneur or whatever, and the other sets you on this path to be like a number 2. And I don't think people think very clearly about that.

Is it fair to distill these down to 1 is convexity and 1 is concavity or something, not to get overly nerdy about it, but it seems like the payoff curve.

Yeah, I think you're exactly right about that. Cause there's way less stability in 1 too. And I've seen lots of boys flame out as well.

That 1 doubles as quasi career advice. There's another career advice 1 you have getting away from the binaries now, which is stay off of the org chart. Is that different than be a boy?

Yeah, so I've given this advice to a lot of people now and it's worked really well, so I'm pretty confident in it. This is only Machiavellian advice, which is if you want to like really succeed relentlessly at an organization, and this probably like applies to smaller, basically organizations where you're within arm's reach of the principal. You have to stay off the org chart. Whatever you do, stay off the org chart because there will always be a temptation of the principal to make you report to someone and you cannot do that. And if you do get forced to report to someone, then you always want to report to 2 or more people.

Because the thing is, you always want to be, the way that you can get ahead in these organizations, especially if say you're younger, you're under-credentialed or whatever, relative to other people, is you want no 1 to really know what you're doing, but they all know that you're very favored by the principal. So you're this guy that is kept around and everyone knows that the principal likes you, but no 1 really knows what you do, no one's entirely clear on who you work for, and you gotta fight. It is the nature of any bureaucracy to try and-

Suck you into the org chart.

Suck you into the org chart, make you report to someone, do something like that, and you really gotta fight. But that's the way in which you can get ahead, because I think what people really failed to understand is that all that matters is whether the decision maker likes you in a company. Everything else is completely unrelated. And you can see this because people who do good work get fired and people that don't do good work, but are liked don't. So if you're looking to get ahead and curry favor in an organization, yes, stay off the org chart or report to multiple people.

It's funny how often there'll be things, maybe you're outranked at the company, but you get invited on the principal's plane, or you get invited to the birthday party, or whatever, and all these things. You wanna be known as this untouchable person just through soft power. There's huge alpha in this because it's not at all how most people think about organizations, but it's a way that I've pretty reliably seen very young people rise very quickly at places.

You said earlier that audience is underpriced or social graph or something is underpriced. Maybe just say more about what you mean there.

Just having an audience is incredibly underpriced. I mean, you know this better than anyone. I am always shocked by the serendipity of what happens online. And my friend David Prell's been beating me over the head on this for years, and I should've listened to him earlier. I think the thing that I really didn't understand is you don't need to have a very big audience.

So quality and quantity really apply for audiences. And I cannot believe the people that you meet. I have this line, posting is the last great American meritocracy. The American dream lives in posting. And I think that's true, I really do.

I think the last true and total meritocracy, you can post your way into any room in the world. If your takes are interesting, and people think what you have to say is compelling. You can be an anonymous account, I mean you've had anonymous accounts on the show before, and you can just go anywhere and you really don't need anything other than a smartphone. And so I think It's underrated from a social mobility point of view. I think it's underrated from a commerce point of view.

Social presence was a huge factor in building Tiny, and that became quite a big business. I think we're going to see this interesting trend where like right now, maybe the way you monetize an audience, you sell 30% of your audience a $10 t-shirt. I think now we're moving into a stage where maybe you sell 5% something for $100. I don't see why it wouldn't move towards an area where you just sell 1 person in your audience something for $100 million. And I think that could totally happen.

And I think we'll kind of come to see that even in private equity and things. There will be a hundred million dollar plus deals that are just through social audiences because some business owner likes you and has heard you talk over and over and will sell you their business in a way that allows you to make a ton of money and then you don't have to sell anything to anyone else in the audience. The distribution is incredibly underrated. The serendipity of it, I think, is really underrated and still fairly unrecognized. And it's because the monetization is still very unsophisticated.

Podcasts will not monetize off ad reads in the future. It's very much the celebrity holding a Coca-Cola from 40 years ago. The way that it will happen and we're already seeing is that Companies will have, in the same way that they'd have a technical co-founder, they'll have an audience co-founder, and all that person will do is organically sell that product or service to their audience over the long term in an authentic way. The company really has to be intertwined with the creator or the person with the audience, that's gonna be how people buy things. I mean, especially for commodity products, which most products are, including most investing is a commodity.

It's just selling money. And so in any situation where it's a commodity, you're gonna go with the person that you have a slight affinity for. And the way in which we build real affinity with people is long-form content or repeated exposure through social. And so I think those things are super underrated. And it's still funny that it's still in the zone where like amongst the high status, it's still pretty low status.

To have a Twitter account or a podcast or whatever. And I mean, it's even funny with you, the amount of prestige and notoriety that you get from the show, I think would still really surprise people who probably have deep in their brain somewhere a negative view of podcasting and podcasters. And I'm always really excited by those disjoints where like it actually is getting you, it is the future. And that generally just means that you're like in the future on something. Everything will catch up to this and it will become normal and high status and everyone will do it.

But right now it's this weird disjoint thing where like you get access to the best people in the world and it provides real alpha and large opportunities but people still think it's kind of weird that you're a podcaster. I know someone who has a very successful podcast who like their spouse doesn't want to talk about the fact that they're a podcaster. Even though they get paid a ton of money, they're incredibly influential and prestigious, and that's gotta be a huge opportunity at any time you get some weird disconnect like that.

What else is significantly underpriced, do you think, in the world today?

Lots of things. Having money is underpriced. I've come to see this firsthand. I think People who say that money only solves a very specific set of problems or whatever have just not been around people who can use money creatively to solve problems. Like yes, of course it doesn't really solve your like psychic or spiritual issues, but it can help a lot in ways that are very underrated.

I think people are just really cagey about this, and so they don't really appreciate it. But it's astonishing. It's never direct. Being able to donate to people's foundations and then getting access to the smartest thinkers or going on marriage retreats or marriage counseling that's with the best person in the world. There's a lot of things available to those with money.

And in America, especially, everything is for sale. I actually think it's 1 of the great merits of America, which is that if you have enough money, for the most part, you're welcome in. And that is in contrast to somewhere like Canada or England or whatever where there's like old families and class and things that matter more. I think the fact that everything's for sale is pretty.

America is coin operated.

Super coin operated And I think that's amazing because at least you can do something about it. And then probably the other thing is nice real estate boats, all that kind of stuff. Again, human nature hasn't changed. It's like people who deny that advertising works. It's like, well, it obviously works on everyone.

Otherwise it wouldn't be this huge. So many people are like, ads don't work on me. It's like, well yeah, of course they work. What are you talking about? Like the next time you go buy a soft drink, like try and explain to me how you choose 1 over the other.

If someone brings me on their plane or like has me to their big house or whatever. That works. That totally works. And so those things become very useful. You can see very quickly how there's a shock and awe there that works really well, and how those seemingly exorbitant or gauche assets can become quite like a creative quickly.

I think that's totally real.

What do you think is the most overpriced, probably a better term right now?

I don't know if it's the most overpriced, but venture capital always makes me scratch my head because I haven't seen any good explanation or data for that matter for why the amount of exceptional companies is going to increase. That are created per year is going to increase over time. And I would totally change my mind on this, but as far as I know, there isn't. And so if that's the case, then it's basically just this cage match to get into these few assets. If you're good at that or you're willing or happy to play that game, then great.

But I think that's not how most people look at it. And I don't know, it just seems like there is seemingly a finite amount of good companies. And so I'm very sympathetic to venture investors who really have a cynical understanding of, it's all about just getting in these deals. And it's not about investing or spotting things or whatever. It's just about selling your money for a little bit cheaper or a little bit better than the next guy to get into the handful of deals.

And so I'm always puzzled about that. I think probably holding companies are about to get very overrated. It's very popular when we started doing it at tiny, everyone looked at us like we were so weird. Obviously Constellation was the big first 1 to do it, but it was still very low status and strange when we did it. And now I literally talk to 2 or 3 people a week who want to start profitable holding companies.

I think it's the rolling fund of higher rate era. Even very liquid founders want to buy these cash flowing assets. And I just think that's very strange because it doesn't really even scratch the itch of like a good investor. A good investor is after superior returns. There's something just very odd about indexing your own abilities, the holding company about saying, Oh, I'm just going to like crew all These mediocre assets that'll like sum up to some cashflow amount.

I just think that's strange. Also owning businesses is not that exciting. And again, the same problem there. There's a fixed amount. Constellation literally has all of them in 1 Excel spreadsheet.

There's a fixed amount of these companies. And so the prices have gone up and it's just strange. So I'm always skeptical of these weird kids playing soccer, swarming around these little weird pockets of alternative assets. Probably the stuff that's actually interesting is stuff that no one's talking about. Trading electricity futures or giving loans to charter schools, weird stuff like that.

All of a sudden HVAC becomes really popular or airplane leasing got really popular for a while. People love the contrarian thing too. Peter Thiel has a great line about how the trade of the 2010s was just buying fang. If you wanted to be the best performing hedge fund manager in the world or whatever, you just hold fang and that's it. Something like an 8X or something like that over that period, but no 1 did that because it's boring and you don't get paid for that.

And so people don't actually want best returns. They want to feel clever and do some weird little thing that makes them feel interesting or different or something. But sometimes you just gotta do the obvious thing and just be really strong on it. I always admire those managers who have been paid 2 and 20 for like 40 years to just own Berkshire. I kind of think that's awesome because it's- They were right.

Yeah, they were right and they were providing this service. The service that they were providing was the LP does not have the personal confidence to own Berkshire on their own. So they actually need to pay a huge premium for someone else to give them the confidence to own Berkshire, and it's just like a tax that they pay for not having the conviction to do it themselves. And I think that's great. That's solving problems for people, so God bless them.

I think 1 of the legitimate criticisms of maybe podcast or just posting in general is that it's very easy to grow an audience on the back of what is or feels like advice. It's very easy also to spend a lot of time optimizing, preparing, learning. It feels like a universal good. Like yeah, you can't have enough learning, you can't have enough preparation, can't have enough knowledge, but I think you make a good point in some of the conversations we've had that maybe that's the wrong way to approach some of these things. And so I'd love you to talk through that criticism of this cult of learning, so to speak.

Well, first of all, on advice, I think the only honest thing that you can say about advice is there is no general advice. I think giving general advice is a complete charlatan move, is just terrible. When you give advice, you are just extrapolating some general rule from your own experiences, which is like asking, create some general rule about the world from your own life. That's kind of what you're asking with advice. That's a problem.

Like if anything, you should just ask people what they did and then maybe ask them to explain what they were thinking at the time. Then you can do your own inference if you want. A second thing with advice is all advice cancels out. So you can find counter examples to every single piece of advice. Someone's done something, someone's been very successful doing the opposite.

So that's another knock against advice. And then the third problem with advice is that it's fundamentally unserious. So the only real sincere and serious advice asking is a very tactical and specific question. If someone reaches out to you and says, I don't know what the podcast example would be, but for an investment it would be like, I have this company doing this transaction between these 2 states, I know you've done this before, what is the right way to think about tax planning here? That's like a useful advice question.

Most advice questions, they're like, how do I become an investor or whatever. They're just fundamentally unserious questions that what you're asking for is give me something that I can go, oh, okay, that'll make me feel good for a second, that I can just go back to doing whatever I was doing. And that's all productivity advice. Like there's a great little parable about a 12 year old comes up to Mozart and asks him how do I start writing symphonies? And Mozart goes, well go to music college and work through it and study the greats and then you can write a symphony.

And the 12 year old goes, yeah, but you were writing symphonies when you were 12. And Mozart says, why didn't go around asking people how to write symphonies? And I think that's so profoundly true that really if you catch yourself asking these, like how do I start a company or something, you know you're not serious. You're just procrastinating. You just wanna consume information that feels productive or useful.

Advice is just such a racket for that reason. And it's addictive, I mean, don't get me wrong. I've read tons of self-help books. I've read lots of business books. I've consumed hundreds of hours of podcasts.

It's a really compelling sham because it makes you feel productive and it does the classic shell game, which is it takes 1 thing that you can justify as feeling productive, but it's actually just entertainment. Coats entertainment in this educational or productive sense. And then yeah, the preparation point is in the same vein. Like there's this really weird hyper fixation on routines and performance and things. And I think these are really weird things to think about in the abstract and I think it's indicative of just a general very low lack of conviction that we all have.

So it's this idea of I actually don't know what I want to do with my life or my day so I'm gonna optimize my performance abstractly. Maybe if I wake up at 5am and I do all this stuff, then I will set the stage to perform at my best for this mystical X that I'm going to figure out. It's useful if you're like going full tilt at a business and you're like, how do I be less tired? Fine, then go learn about sleep optimizing or something. But it's really weird to optimize your sleep first.

And it's tragic because it feels like, especially, I don't know, amongst my peers, there's this big tendency of Everyone is sharpening their sword for the battle that's never gonna come. Yeah, I'm gonna improve my performance, I'm gonna be ready to perform. When it comes, when it happens, I'm gonna be ready, but the thing never comes. And so I just think it's this really nefarious way of diluting yourself and wasting your time, and I'm just as guilty of this as anyone, but I think you just gotta figure out what you like and do it, and then backfill specific problems.

You said that you've done the million self-help books, I guess me too, because I'm just curious about all things and that no one's more interested in anything than themselves, I guess. But there is 1 thing that you and I have discussed that you've taken away from 1 of those explorations that I think is incredibly powerful, which is this notion of the 1 call that everyone needs to make. Can you describe what that is and how you discovered that idea and put it in practice.

Yeah, I got this from doing the landmark forum and the idea, which is on the theme of extremely simple but very hard, is that if you tell anyone there's 1 call they should make, everyone immediately knows what that call is. And people will go 40, 50 years without ever making it. And sometimes the call, 5 minutes, 10 minutes, and everyone knows. If you're hearing this, and it's that thing that you immediately thought of and then like felt bad about feeling about it or like tried to push out of your head. That's the call is.

And doing that has massive returns. I had to do it in the landmark form because it requires altered setting to be able to coach yourself to do it.

There's this corollary question, which is what's not being said, which I think is actually quite productive in businesses too. If you just once a week or something sat down and were really honest with yourself about like, what am I not saying and to whom, and then just go say it. You talked earlier about the service you were providing being unclogging log jams or solving coordination problems. Do you think that that is like the single question that is most useful for doing that across the board?

Yeah, But you have to be good at it. Think about it like a relationship. In abstract, it's always better to have the hard conversation. But if you execute the hard conversation poorly, it can make things worse. So yes, but you got to have some finesse to being able to actually do that and then resolve something from it.

You were saying earlier that maybe the software business model with the multi-year high net dollar retention or more than a hundred percent net dollar retention, like enterprise contracts, like the best asset to own in the world. And obviously the world has funded a lot of these things. But then on the other hand, I think you're quite skeptical that most of them should be venture funded or funded in the way that's become very popular. So how do you reconcile those 2 things? You have a fairly negative view of like venture funded venture equity funded growth for software businesses or software businesses that aren't already profitable.

So talk about having looked at God knows how many of these things over the last 10 years, the major things you've learned about the funding type and source and the quality of the business.

Venture capitalists started to fund high capex businesses with very low probability of success, that if they did succeed would have humongous outcomes. And your Average software company does not hit any of those marks. And so I think if you're gonna raise venture, you should really have a very good reason. There are clearly businesses out there that are perfectly designed for venture capital. But Most people I think raise venture because of 1 of 2 reasons, at least initially.

1 is because they don't know what else to do and it's the default path for starting a business. The other is it's just easier. So most businesses you could bootstrap the business by selling a customer and getting them to prepay. Basically every business you can do that in. And even the best venture funded founders I know have done that.

But that's hard and it's easy to go get a couple million bucks and then you get an office, you pay yourself a salary and it's just easier. And to be honest, I don't really have any problem with that. Raising a few million dollars, especially from non-institutional, I wouldn't even consider that venture funding. It's some kind of weird hybrid thing. But once you start going institutional, that's when you really can't backtrack.

And that's when I think people make a lot of mistakes. I really admire the businesses that bootstrap for a long time and then do a mega round like Elassian or GitHub or something. I just think you should be very intentional about it. If you're like, you know, We've scaled this thing and we really have this burning need for $20 million. And if we had $20 million, we could do this specific thing and it would really help our business.

Great. You should raise venture. But most people don't have that. They're on the treadmill. Obviously their investors want to put more money into the company.

And so I think that it's just become this weird default path when it's actually this very niche product that serves a very specific form of business. I always find it funny that people don't abuse convertible notes or safes more. There's a classic example of this in the valley of 1 company that did actually do a convertible note and then they just returned the money. And then the company went on to be a billion dollar business and the founder owned the whole thing and he didn't do anything illegal. He made everyone really angry because he violated a huge taboo.

But if I recall, he was a foreign guy and I think he didn't know or didn't care about the cultural norms and he just read the contract to the letter and took it as a loan and gave the money back and never hit any of the conversion clauses and got the business off the ground. And I'm surprised people don't do that more, honestly, because that's often what you need. If you do need venture at all, you need 1 or 2000000 dollars to get you a couple of years and then you're off to the races. But yeah, I think it's just 1 of these very default things. It's easy to do.

You get prestige for it. Obviously you can talk about how much money you've raised as a proxy for success and all this stuff. But I also don't think founders really understand the cost of raising venture if you don't have to. It can really hurt you financially and lifestyle wise. And it's funny too because really the companies that venture capitalists want to fund are also ones that should exclusively only take venture.

Like the huge $10 million outcomes are generally not ones that could have got off the ground without capital. And so I actually think the incentives are fairly aligned, but there's just a lot of capital to deploy and people see it as default path.

You mentioned the word taboo there, not returning capital in the safe or something. Are there other taboos in business or investing that you think are interesting?

Running really high margin businesses are taboo because I think there's a sense that distributing capital signals something negative about the nature of your business or like makes it a lifestyle business or something. And so I think a lot of people really are reticent to take a lot of money out of their business. Even if it can't, sometimes businesses are growing and are great businesses, but they just don't need capital reinvestment. So I think that is 1 very strong feature of a holding company, is there's always someone going, hey, that's not the best use of that capital should go over here. It's amazing.

I've seen VC back founders go on to do bootstrap businesses or whatever, and the dividend check is amazing. It's this novel concept and it's cool. We've talked a lot about the difference in successful bootstrap founders versus successful venture founders. And there's something about having a lot of cash flow that's really underrated.

You said that the more general the advice, the more useless it tends to be. What about meeting your heroes, having mentors like this whole category of thing, I think is something you've thought a lot about. What have you learned meeting, I think you have, been lucky to meet some of your heroes? What has that process been like? How would you suggest that people think about mentorship heroes and so on?

Like advice in disguise or something.

Every living hero, mentor or person I've looked up to, I've met and in some cases built a relationship with, which is crazy, but I would also say that it's more doable than you think. It's interesting this mentorship thing. I think mentorship is another thing that only people who don't have mentors talk about mentorship as such. I've never once referred to someone as a mentor, but I have plenty of older people who give me great advice. But again, that advice is either I'm either asking very specific advice to someone.

You can totally give advice to someone about a specific situation that you know well. I mean, that's very useful. And then in terms of meeting them, I think in person is really important because you just pick up on all these things. Kanye West has a great quote that everything is the same. He is referring to music being the same as fashion.

But I think that every decision someone makes about everything tells you basically just as much as any other decision. So I love to meet people. I love to meet people in their homes. I love to go and just see how they live and stuff. And I think you learn all kinds of soft, nuanced things that are really useful and interesting.

And some business people that I really look up to. I've talked to for hours, but I've never once talked to you about business. But I think I've learned a ton about business because you just learn about the world. And so, yeah, I think exposure is really useful and important and exposing yourself to people and their situations and stuff, you learn a ton from. You should always be asking your friends, what should I do?

They gotta know you, it just can't be general.

You think the Beatles are especially good role models?

I just still think it's amazing. It was a 5 year run, 2 albums a year, and that was it. Most artists today put out an album every 2 or 3 years, just as a phenomenon. Maybe The Beatles as musicians are not underrated, But as earthly phenomenon is very underrated, this idea that you could just in this 5 year run, basically go on a perfect streak, permanently change things, and then that's that. These amazing little bursts.

There's really something to be said about just doing something really well for a short period of time, accomplishing something, and then that's that, you've changed it. There's also lots to learn from the Beatles. They were all better together than they were individually, and there's just something about just what can happen when you get the right mixture of people doing the right thing. I also think it's really underrated that they basically change genres every album. I think that also never happens.

I think there's really a lot to be studied there, even though it's already been studied a ton. Just hanging it up on top, that's also hugely important. Way more people should do that. I think the Beatles would be significantly diminished if they were still touring.

Yeah, it's like Seinfeld did when he was offered whatever insane contract.

Yeah, and I think he cited the Beatles as his example, his role model there. Yeah. There's an inhuman quality to walking away on top as well. It's probably very difficult to do. I'm not sure that I will be able to do it if I get to that situation.

1 thing that's interesting is that most of the time you've spent professionally was operating out of a Canadian company, Canadian by background. What are the most notable differences between the business environment in Canada and the US that you've observed, having been in both?

Yeah, so it's really interesting. I'm from Victoria, which is beneath the American border. It's next to Seattle, and Canada is a very American place for the most part. And so I didn't actually think there was gonna be that big of a difference. And I spent a lot of time in San Francisco and I've lived in New York for a long time.

It is really shocking though, there is a certain optimism amongst Americans that is totally unmatched. And I think the rest of the world, Canada being this weird split between Commonwealth and European thinking and then American thinking, I think American thinking does have this incredibly unbridled optimism that leads to just this generosity, growing the pie abundance mindset that you just do not get anywhere else. My experience in Canada is very much that everyone feels like they got theirs and it was really hard to get and they're really scared of losing it. And I think that's probably also the case in Europe as well. I'm always pleased to see all the dumb frauds or stupid companies or whatever that happened in America, because that's like the flip side of the American optimism.

It's this blase. Yeah, let's do it. It's going to work out. Yeah. People are way more generous with equity.

Lack of fraud would be a bad sign because it means you're not.

Yeah. I mean, there's a classic cliche and I'll give the PSA that I always give. If you're a Canadian, raise money in America. Do not fall for the trap of raising from Canadians and Canada has gotten better. It's not as good as I would have hoped given the Shopify and the large outcomes that have been there.

There's the old thing of in Canada, you raise money from a bunch of people who ask why you aren't profitable as a startup and England is the same. And there's a great story about the founder of DeepMind talking about how no 1 in Europe would have funded DeepMind and he had to seek out Peter Thiel. I'm surprised by how much of a cultural difference there is and I think Americans take it for granted. It's always very funny to hear Americans talk about how they're going to lose immigrants to other places or whatever, it's not even close. There's nowhere that even comes close.

And I think these are deep cultural things that if you've never been in another culture, even as Canada, which is by far the most similar country, it's very hard to notice, but it is this real optimism of let's try it out.

What have you learned from, and my sense is that you love investing, you're gonna keep doing it. Are there other paths or people that you've learned from that you admire, whether it's someone you met, as you described earlier, or just models of the world that you think are good to have in your mind as you figure out what you want to do?

For me, I'm always interested in the point of maximum leverage. I mean, what got me involved in investing was at the startup that I was at, worked hard on it for 4 plus years, and then the guy who put 25 grand in in the first week made more money than I did. You know, it was quite a lesson to learn as a 19 year old. I was like, oh, okay, like, I guess it is capitalism, not laborism. I guess I get that now.

And that was very interesting, because I was like, okay, that's unintuitive to me. That is not how I imagined this would all work. And so I think you can just scale the leverage points like that infinitely. I'm very interested in these people, we've described it like the guy who finds the guy who finds the guy. If you get tired of picking companies, you can pick a person to pick the companies.

Call me a big Archimedes fan or something, but I find something very elegant about minimum effort for maximum return. And I think picking managers is really up there. It's its own art. It's kind of like pre-seed investing. It's kind of like stock picking.

It's this weird mix. It's kind of a dark art. It reminds me of venture capital 15 plus years ago where there's a very small group of people. The market rates are terrible. It's this very obscure arcane thing.

It's fairly unoriginal. It's just like venture capital. You spin out of a huge hedge fund as a wealthy PM when you're in your 40s or 50s and then you get funded. And venture capital used to be like, you know, a suit and a tie business plan spinning out of Fairchild or wherever and I think there's a lot of interesting stuff to be done there and it's a very fun challenge. And I think equally as rewarding as being a pre-seed investor or maybe more because I think the capacity, I always think like 1 way of looking at venture is whether you're counterfactually useful.

Would the company exist if it weren't for you? And I think generally the answer is no, but I think there's more opportunity for the counterfactual to be different in manager selection because it's such an esoteric dark art. Also just anything that's an esoteric dark art I'm drawn to.

What views do you have that you think would make the most people scratch their head or even get angry?

I think that there's a lot of alpha in looking at things that society says doesn't matter, and it's not to say that these things are actually that important. In fact, they might not even be that important, but because they're so doggedly looked at as you cannot look at this, it's not important, I think there's alpha there. I'd encourage you the next time you're at a dinner, ask who there is firstborn amongst their siblings. If you want to look up US presidents in eye color relative to general population, It's not what you would think. Height matters a lot.

There's all these things about people. Theodore Adorno has this great line in 1 of the intros to his books where he says, every sentence in his writing is equidistant from the point. Every sentence is just as important. To the point about how every choice someone makes is reflective of their life philosophy, everything about someone tells you something, even these inherited attributes. And so I think the fact that it's basically you have to stick your head in the sand about it now means that there's alpha there.

Do I think it's incredibly important and make or break? Obviously not. I mean any population difference is not applicable to any 1 individual, but I do think these things are interesting. To pay attention to that thing, I think, can tell you all sorts of things and allows you to get a better sense of someone. You just have to be really open-minded because where you start to get in trouble is where you look at any of it as good or bad.

You want to keep your ethical judgments really limited and most things you just look at as truly neutral. And I think that allows you to be far more open to looking at these odd signs so you can notice that everyone's the firstborn child and not immediately jumped firstborn child or better or something. It's just something that you notice, the way that you notice a flower or a tree or something.

What eye color is more popular or dominant?

Blue is hugely overrepresented in US Presidents.

What is resentment as the core basis for long partnerships?

This is something that I learned from Chris and Andrew who have been in business together 15 years, have a very successful partnership. And the thing that they attribute it to principally is never allowing any form of resentment to creep in against the other person. And I think it's just profoundly right. It can be the smallest thing. Never uncovering an expense for the other person or accepting gifts or anything.

I think any little thing that can get into a relationship where, hey I did this for you, and you didn't do this for me. I think that really starts to erode things. And so as I've been thinking about what to do next, I've been spending a lot of time talking with people about partnering on things. And I think what's most important to me is really going into something with no resentment, which doesn't mean things have to be like equal or whatever. It's just, there's really gotta be no ill will.

And I think this is important in deals too. You don't want to pull 1 over on the other person at all. You want everything to be really upfront because that little resentment, I think it festers and grows. And I think people don't really think about that. I think people will ink a lot of deals, especially with co-founders or whatever, where they kind of agree to it and it works good enough, but they both don't feel a hundred percent perfect about it.

And it's because they're shying away from a very uncomfortable conversation, which is totally natural, everyone does that. But I think that's a real death knell. As part of like the last 6 months, I've just talked to tons of co-founders separately and asked them about 1 another. And 1 in 10 are like, yeah, he's the best, couldn't have done it without him, no regrets. But all the others, the most common answer is, gave him way too much equity, it was important in the beginning, but now he doesn't do anything.

And they'll say that about 1 another. And it's amazing how much there's resentment between them, especially around equity or whatever. And I think that's amazing. I think it's a Paul Graham thing, but the suicide versus homicide for why startups die is very real. And we've certainly been on the other side of resolving co-founder conflicts and buying co-founders out.

And it's very common that 2 co-founders will come to an investor and be like, we want to get rid of the third person. And that can be very expensive. They're good deals to do, but they can be very expensive to their co-founders. And those are probably all just hard conversations that they've been avoiding, or some original founding sin that they didn't really get out of the way.

Jeremy, this has been so much fun. So many different ideas and places that we took the conversation. I really appreciate your time. I think you know my traditional closing question. What's the kindest thing that anyone's ever done for you?

Been very fortunate ton of people have taken unreasonable bets on me at a very young age with very little experience So it's hard to pick 1. But the 1 that comes to mind is Had a teacher in high school named Paul who taught me history and philosophy When I graduated he gave me a book He gave me this book called On Liberty by John Stuart Mill. It had a note written in it, and he basically said, this book is going to be very important for you, and I really hope you take it to heart. In high school I was working at the startup full time, but I was also very interested in philosophy and the academy and writing and literature and all this stuff. And I couldn't really figure out why, and I had to read on Liberty a bunch.

And I think what he was getting at was that couple chapters in there where Mill basically argues that the reason classical liberalism is so important is because you need to just have people doing weird things and just being themselves, and that's how progress is made. And you actually need to set that up structurally such that it's allowed and a society can tolerate having a lot of uncorrelated weird people around, which is actually really hard to do. Like it's hard to have social cohesion when you have weirdos running around. And I think that what he was saying was just that it's really important. I can see the struggle in you between business and the arts basically and if you're gonna do business don't get lost in chasing money or status or vanity or whatever and do it for intellectual or inherently satisfying reasons.

Don't forget about the other stuff. Society is going to be better off if you do everything that interests you. And even if it means you're a worse investor, but you're like a more interesting, unique person, not only will that be better for you, it's also necessary for society. And I take that to heart a lot because I think it's easy to just be like this pre-ascribed thing and be good at it and that'll be good, but no, actually We need people who are just 1 of 1 doing weird stuff. That's what moves us forward.

I could use that book after high school. Great closing message. Thanks again so much for your time. If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning.

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