20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable

31:59I wouldn't say health insurance, just health system, blah, blah, blah, blah, blah, blah. Kind of predictability. And I asked my Danish friend why the Danes seem so happy. Why'd they rank so highly? And he said, low expectations, low expectations. But in the case of the four hour chef, so the four hour chef had the biggest Delta, right? Because I was coming off of the four hour work week for our body. And then the four hour chef is actually a book on accelerated learning. Like the whole book is about skill acquisition. How do you learn languages, just learn to shoot three pointers, do anything very, very, very quickly.

32:35And that book did not do nearly as well as I would have hoped. It's still sold hundreds of thousands of copies in the first handful of months. But the reasons that I can try to point to, there are some that are, that are, I think pretty much certainties. The first is that The 4-Hour Chef was the first major book announced and launched by Amazon Publishing. And Amazon Publishing was this huge brouhaha. It was announced in the New York Times. And it meant that Amazon was going to be acquiring authors, paying them just like publishers would. And this freaked everybody out in the publishing world.

33:19Uh-oh, Amazon's going to be competing directly against us? What does this mean? What is this? There was blowback, which I expected, but the degree of the blowback, I did not expect. I thought that Barnes and Noble might boycott it or all titles from Amazon publishing, which they did. I did not expect the big box retailers to do the same. I did not expect the pretty much full-blown fatwa from traditional media that ensued. As a result, the book got really hamstrung from the outset. And what a lot of people don't realize is at least at the time, well, this is still true for the New York times, but some lists are what I would consider true bestseller lists.

34:02So the wall street journal at the time was a compiled list. It was based off of Nielsen book scan. There were others as well that followed this format. That meant that what you see is what you get more or less the New York times list, which is still even more so maybe The Crown Jewel is really an editor's choice list. It's a black box. Nobody knows how it's put together. And some people think it's based on a handful of indie stores that they favor based on the events they announce, plus certain retail outlets, plus online. But if you don't have a spectrum of sources, meaning if you don't have sales through the Barnes and Noble, You don't have sales through Indies.

34:47If you only have sales through something like Amazon, which was the case for the four hour chef, you get fucked. I mean, look, it's still not bad, but I hit number, I think it was number four on the New York times instead of number one. But if you looked at the Nielsen book scan, it definitely should have been number one. I was, I put so much into that book. That was very, very, very, very hard. Now there was a silver lining on that burnout and that disappointment that we can talk about. Namely, the podcast wouldn't have happened if all that hadn't happened. But the other reason I think the book was difficult was entirely my fault.

35:21I tried to do too much in one book. And I think the title was very confusing. The subtitle made it clear, but the four hour chef, and just to explain it real quickly, I was using cooking, which I had attempted and failed multiple times as a journey through exploring all of these learning techniques and spent time with many of the best chefs in the world and went all over the place, learned to hunt, learned to forge, all this craziness. But I think the book tried to do too much. That is perhaps ironic because I was given the advice early on after the four-hour workweek became successful when I was invited to do all these speaking gigs.

36:01The advice that I was given was presentations more often fail from too much information, not too little information. I think that was perhaps a core weakness of The 4-Hour Chef. It just tried to do too much. The book itself is coherent. If you read the book, it makes sense. But the messaging, the promo, the why this book, what is this book, was muddy. And I think those are the two reasons, at least I can point to, why that book did not hit the expectations that I had for it. The biggest reason CEOs are unhappy is because they attach the happiness that they have to the performance of their company.

36:40I am inherently aligned to the numbers that I have that matter to me. If they're down, I'm fucking depressed. My mom's like, oh shit, bad days. When you say that number four and you were very down and depressed, is it impossible to make that detachment? And how do you think about that? I don't think it's impossible. But when you put that much time into something and the external validation is limited to a handful of scoreboards, if you're competitive enough and driven enough to get something like that done in the first place, I think it's very unlikely you'll be completely unaffected. but I will say that I do think about identity diversification for this reason.

37:24And what I mean by that is having at least two or three pursuits at the same time. And this is not being distracted. I'll explain what I mean by that. So for instance, when I was working on the four hour work week, I was training really seriously in jujitsu at the time. This is a long time ago. I no longer do that. Gentle art turns out not always to be super gentle. So I've acquired quite a few. I'm getting surgery on my elbow in two weeks because of an injury I had 20 years ago, but I was doing jujitsu really seriously at the time. There were a few other interests that I was pursuing in off hours.

38:00I also keep in mind, still had, I still had brain quickens. So there was also the company that meant that if the company, let's say just had a hard month or a hard quarter, because who knows, right? Something completely out of your control happens. A distributor goes out of business, whatever. If I was making progress in jujitsu, that was a psychological safety net. My self-worth is not pinned to one variable that can be affected by a lot of things outside of my control. And similarly with other books, maybe it's rock climbing, right? Where you have a rating system, you're making progress and you're climbing, great.

38:36If you have a great week in the gym, even if there is a tough week of writing where you're not hitting your word count goals or whatever, you have that offset. You have just like in a portfolio, and I'm not the way of luck, I'm not saying you want to maximally diversify all the time, right? It's a tough way to build wealth at least quickly. But that identity diversification is something that I've thought about and paid a lot of attention to for a couple of decades now. But does that mean I'm immune to looking at the core numbers through Nielsen BookScan and saying, what the fuck? There's a huge dislocation between, I just got punished, right?

39:15Like I feel like this was punitive getting put in this place on this list. Like, yeah, that's annoying. It's very annoying. Before you mentioned it leads to the podcast, before we discuss the podcast, I'm always like, you know, I've been a huge fan of yours for years and the angel portfolio is nuts. It's Duolingo, it's Uber, it's Shopify, it's Facebook. It's insane. And honestly, it's not discussed much, which I find strange. Can you talk to me about your favorite investing lesson on getting into one of those? I want to leave it open to you. Yeah, favorite investing lesson. Or story of how it happened.

39:51Yeah, let me just give briefly part of the origin story. And I think that explains it. Yeah, because I've had some pretty good luck, you know, and I'm not going to be one of those guys who's like, ah, it's all luck. I don't think it's all luck, but it's definitely a component for sure. So the way that the angel investing started is totally related to the identity of diversification stuff. So the first book hits, right? And there was a lot of serendipity, but there's a lot of engineering behind why that happens. And so the book hits, meaning it hits the New York Times list, then it creeps up, boom, it's number one, then it just sticks there.

40:31And then it becomes this phenomenon where it's getting like parodied in TV shows and mentioned in pop culture. Even last year, last year in one of the teaser trailers for Wolverine Deadpool, the four hour work week was mentioned, right? It's like become this thing in the zeitgeist. And a friend of mine who I had met through an entrepreneurship class I took in college, high tech entrepreneurship taught by Ed Schau, who's this amazing, amazing figure. His son-in-law, Mike Maples Jr. was one of the guest speakers. So I got to know him and we kind of intermittently kept in touch. And when I moved to Silicon Valley, five or six or whatever years later, the book hits, we ended up having breakfast together.

41:17We would have breakfast every once in a while or brunch at Hobie's way back in the day. I don't know if deals still get done there, but it was kind of like Bucks in Woodside, where for a while, it's like, oh, wow. Yeah, if you walk in at any given time, there are a bunch of VCs and entrepreneurs sitting at tables getting deals done. so I'd sit there with Mike and my recollection is I don't think is Mike wanted to get into better shape and I was doing all of the self-experimentation and all of the training and all of the combing through research that later would make its way into the four-hour body so I was helping Mike get into better shape and the trade was at these breakfasts I would ask him to tell me about the deals he was doing as an angel investor because he had this incredible track record as an angel investor.

42:05And he would later start floodgate and become a very, very successful venture capitalist, which he still is. And so we're talking about these, talking about these, he would want to ask me about the PR and marketing strategies for the four hour work week as well. So we just sit there and spitball stuff. The reason I was asking about the angel investing was I recognized there was a risk of me pigeonholing myself or getting pigeonholed as a business author, right? A self-help business author. And I recognized that was a risk. If I stayed in that lane too long, solely in that lane, I would be afraid to step outside of that.

42:44You see this happen all over the place. People kind of get trapped or they feel like they're trapped in one lane. I was also just fascinated by the world of investing. Eventually I was like, Mike, is there any chance I could co-invest with you and just put in a small check, something, you know, 5K, 10K, and just help these startups with go-to-market plans, marketing, PR, anything. I can be the most valuable, cheapest labor on their cap table. That was kind of the pitch. I was like, I'll take very little equity and put in way too much work. I was like, what do you think? Like to his credit, I owe him a lot of gratitude.

43:25He was like, yeah, sure. Like, let me try to pitch it. And that's how it started. But the mental heuristic, which comes back to the lesson, right? Or story around startup investing. And this is also how I pick almost all the projects I get involved with was once I was in, it seemed like I was going to angel invest. I was like, okay, well, how should I think about this? Right? How do I think about, should I get into portfolio construction and this and read? what was it? Zero gravity book on venture capital. And should I do it the same way as a venture capitalist? Short answer. No, you should not playing with your own money and playing with other people's money and getting management fees is a totally different thing.

44:02But I decided because I had fantasized about going to Stanford business school for ages, I was very unhappy at Princeton. That's where I went as an undergrad. I felt like I made a big mistake. I had a lot of dark chapters there. Did not like it. And I was like, fuck Stanford was the other one I wanted to go to, but I got in early at Princeton. It was like an exploding offer. So I kept fantasizing about going to Stanford business school, but for a bunch of reasons, I decided not to do it. When this thing came up with Mike Maples, I thought, well, why don't I take what I would have spent on tuition, 120 K for two years, something like that.

44:35And that would have been sunk cost. I pay out of pocket. And what's the hope with business school, what you learn and the connections you make, make it worth it that you spent all this money on tuition. So for me, I was like, all right, let me commit to putting 120K into startups. My assumption is like the tuition that's gone. I'm never making that back. I am going to optimize for building relationships, developing skills and knowledge, and hopefully developing a reputation of some type. That's it. Those are the three that I get. And that's what I did for the next two years and made a bunch of mistakes.

45:11But that is what kicked off the angel investing. What was the biggest mistake you made, do you think? Biggest mistake was I didn't realize in the early stages just how effective certain founders can be with a reality distortion field in pitch meetings. So I got really excited and my allocation was fucking terrible. It was outsized, right? So I have 120K for two years. I go in. I think one of my earliest investments, I was like, I'm putting in 50K. And Mike was like, you sure you want to do that? And I was like, oh man, yeah, yeah, this is really incredible. No, I just, I see the upside potential, put in 50K, almost immediately goes to zero.

45:52I'm like, oh my God, what am I going to do here? I no longer have the bankroll to sustain a string of bad luck, right? If I were playing blackjack and backing an MIT team, I just screwed up on my staking. the silver lining on that is I had to figure out how to extend my runway. So I talked to a couple of people who were doing advising and I figured out how to begin stepping into advising. And ultimately with Shopify becoming an advisor when they had whatever it was, 10 or 12 employees, and then becoming an advisor at Uber. Actually, the Uber story is very instructive. Uber happened because I was introduced to Garrett Camp because somebody thought we would just get along.

46:35All right. So then Garrett Camp is working on StumbleUpon, which delivered a lot of traffic around the web back in the day. People might not remember. I became an advisor to StumbleUpon and Garrett and I worked really well together. I really liked Garrett. We're still friends, still close and busted my ass on StumbleUpon, right? I was able to add value outside of an incredibly popular blog at the time. So we could do all sorts of experimentation, worked a ton on the product, blah, blah, blah. Didn't work out, right? That was a zero for me, for me personally, as an advisor. So I put a lot of time in it, didn't work out.

47:07Okay. Seems like a sad story. Wah, wah, wah. Well, what happens a few years later, Garrett's like, Hey, I have an idea. I want to bounce off of you. And we meet up looking at these kinds of sketches. We're trading emails and that becomes Uber cab LLC. And I become one of the first three advisors. And I think all of those advisors had been advisors to stumble upon. So if you're looking at it from the relationship and skill development perspective, because those will transcend any given single project, even if it fails, and a lot of those projects are going to fail. My assumption is those, those just compound over time.

47:43They snowball over time. It's very hard to fail long-term. If you budget, you have to budget your money and time appropriately. But I just, I love that example because it's not the only example that I can point to for that kind of thing. It's like, I get involved with a startup. It fails. I put in tons of time, but what happens, right? Later on that founder introduces me to someone else who's a founder because I was a good advisor, just a good asset, good friend, reliable, able to help with dark periods, whatever. And then that becomes a 10X, 100X, 1000X or whatever. Was Uber the best investment you've made?

48:23Uber was the biggest outcome for sure. Shopify could have been just as big, but I sold a lot of my Shopify as soon as lockup expired because I had no experience with public markets. Yeah, you're holding your face. I mean, that was$150 million mistake or whatever. But But I also went back and at the very beginning of COVID, because I was tracking COVID starting in like December or early January or something like that, when Shopify got crushed and went down to like, I'm making this up, it's something like$200 a share or something. I bought a bunch of Shopify. So I actually was able to reclaim a bunch of that, which felt really good because I love those guys.

49:05I love the company. I'm still super bullish on those guys. Anyway, the reason I try not to judge myself too harshly on that is at the time that that happened, the money involved, even though I can look back and say, Jesus, I made such a huge mistake, that money felt life changing. Seven figures. And it was life changing, at least psychologically, but even monetarily. It's like if I didn't know what the future held, who knows what any of these startups are going to do. To that extent, it was the right decision. If I'm looking at it like a poker player, with the data I had, with the circumstances, with the bankroll and everything considered, it was a very reasonable decision to make to sell.

49:48But knowing what I know now, do I wish I had held it? Yeah, of course I wish I had held it. That's true for a bunch of companies. By the way, the hardest question in investing is not only when to get in, but also when to get out. Did you hold on to Duo? Yeah. Duolingo. I held on to it because I try to learn from my past mistakes and I realized very quickly, like, do I want to compete against the citadels of the world and those people in public markets? Like, what do, who do I think I am? I'm bringing a butter knife to a gunfight here. I do not consider myself a good public markets investor, but you can use that.

50:20I just realized I can't predict at all what's going to happen. It's like I was early, I was pre-IPO on Twitter and kind of sold that at the perfect time, accidentally. And then was reasonably early on Facebook. And I sold that way too early. That was another mega massive mistake. I mean, God knows how much money that would be worth. When did you sell Facebook? I can't remember. I mean, it was not that long after IPO. Maybe it was, I don't know, six, 12 months. I can't remember exactly. but huge mistake in quotation marks. But there are examples, even with secondary transactions where it's like, okay, I sold a bunch on the secondary market with a given startup, and then it goes on to a hundred X.

51:05Oops. But then there are other examples where it's like, I put in many years of advising. I sell half of it on secondary and get at least some return on investment. And then the startup goes to zero, right? So you just don't know. I think it's important to recognize that in so many of these circumstances, at least I have no fucking idea. So here's the thing. Like now my policy is just let almost everything ride. Like if they go public, if they go to zero, they go to zero. If they don't go to zero, they might go to a hundred X. So just like assume you do not know and just hold onto them. But that's the luxury of having enough cushion.

51:40Now back in the day, I think a lot of these decisions were the right decisions given at least the information I had. Tim, why did you not raise a fund? Like podcasters can raise huge amounts of money and enjoy management fees. Yeah, well, there are a few reasons for that. So the first is I think asset accumulation and really good investing are sometimes at odds from a, I wouldn't want to have a misalignment of incentives. I just, I'm so hyper aware of incentives and how they drive behavior. And the scenario I could see playing out is that sure, raise a small fund. Nobody raises a first small fund intending to stay with small funds, right?

52:23I mean, that's just not how you make the math really amazing. You have the, you know, you do a 30 or$75 million fund, then you double or triple that. And then you raise another one and another one, and then you have overlapping funds and hallelujah, right? Things get super, super interesting. and I was aware of that. I'm very impatient. I'm very, very impatient. And so as some of my friends put it, and these are VCs, they're like, Tim, you would hate this job. And I'm like, why would I hate this job? And they're like, because you have to go like, go to these meetings. You have to like handhold some of your LPs.

52:56You have to like go on the road show and talk to this person who's actually not that smart, but you kind of have to get on bended knee and laugh at their jokes and do this and this. They're like, you would fucking hate this job. And these are, close friends, right? They're not, and I'm not saying every VC feels this way, but when they described like the actual ins and outs, I was like, yeah, you're right. I would hate that. And so that's another reason. And frankly, I'm not convinced that with larger dollar amounts, this is maybe another very big reason. I'm not convinced that with larger dollar amounts, I would be able to do what I do with smaller dollar amounts.

53:33That I agree. And what my advice to you would have been, if we've been friends, then we've been, hey, stay with the 50k checks. You can afford to hold them for longer and you can afford to write more 50k checks and you can you could get into any deal with the 50 to 100k check size. But then you stopped angel investing. Yeah, I mean, I guess if I were to do a fund, I'd probably take the oh, I'll give you another fun bit of intel that I don't think I've talked about publicly. So I was going to say I'd probably take the SV angel approach from back in the day. Ron Conway, He used to be the godfather of Silicon Valley and he was in every deal.

54:06And it was like small checks, which is how I ended up also actually doing pretty well on a lot of things I didn't even know I was in. But the reason I invested 25 or 50K, whatever it was, in SV Angel and their approach, I mean, it ended up being pretty smart on a lot of levels, was because I got a report card on pretty much everything in the Valley regularly. and that allowed me to go hunting more effectively. Does that make sense? And so what, so you get the report card and then you're double down on three that you thought were really interesting. I would double down or I'd be like, oh wow, that's a really interesting sector.

54:44Let me go look at that. That end just for the education also to see what was moving and what wasn't moving was really interesting. How many got kind of overfunded in a sense and then went to zero or got marked down. Like all of that stuff was super, super helpful. What was your biggest miss? You've been in those incredible companies from very early on. What was the miss where you were in the room, you didn't do it and you're like, oh, oh, there's so many, there's so many. I mean, I'd have to go back and look. I mean, the most common way that I have missed great deals is I just have like too many email or too many inbound.

55:22And I mentioned not being terribly patient, which I'm not proud of, by the way, there are a lot of downsides to that, but I just have too much email. And I would be like, yeah, you know what? Sounds amazing. I just don't have time to dig into this right now. Like, I really hope it's a home run. I'll be cheering from the sidelines. Boom. And then I look back a year later and I'm like, Oh my God, this company's worth a billion dollars. Which hurts the most? The ones that hurt the most are the ones that I sold early, frankly, because I was like a hand, you know, a bird in the hand. But actually this is a great one.

55:51This is one where I'm like, Oh, maybe I should have been a little. So one password, love those guys, love the product. And before they had raised any money whatsoever, I met with them when I, maybe they came out just to me. Maybe they came out for other reasons. I can't remember, but to Silicon Valley, took them out to like a gun range to shoot and just had a bunch of fun with the guys and was talking to them about possibly becoming an advisor, but they hadn't of raised any money. That idea was new to them. They weren't sure they wanted to raise any money. And then I saw the news of these funding rounds later and I was like, Oh God, I feel like I was 90 % of the way to possibly doing a deal.

56:32What a bummer. Cause with products like that, there's like a physiological quickening that I feel, and it sounds very unsophisticated, but with a lot of these startups that ended up working, I feel like I kind of knew. I was just like, yeah, I mean, the deck is stacked in their favor and there was a feeling to it. But that's pretty much limited to D2C stuff, I would say. Whenever I stray outside of stuff I could use myself, would want to use myself, could promote to my audience, whenever I stray outside of that, I get my face ripped off. I mean, almost always, there are a few exceptions that keep me going back to stuff I shouldn't touch.

57:16But whenever I write bigger checks, right, which is tempting when you have more assets under management, personal or otherwise, you're like, well, to move the needle, let's write bigger checks. oof man not a great idea but so the one argument to have maybe a family office would be so that i could do 50k checks into a lot of stuff and just not deal with any of the brain damage of the paperwork and admin and i have people who help with a lot of that kind of stuff now but i'm not sure that would work though because the spray and pray thing it can work But the reality is when I'm putting in these 50K checks, I actually do a lot of diligence and like dig into it and use the product.

57:58And I'm not sure I would have time to do that if I were doing dozens of them. But you're right. I did stop around 2015. I stopped angel investing completely for a couple of years. If I was you, I'd do a$25 million fund one. I'd call it the four hour fund. I'd hire two super ambitious, energetic young associates to run around the valley with Tim Ferriss t-shirts on and do 50K checks. I'm going to do 50k, 100k checks till the cows come home. It was saying, hey, if you're a breakout, Tim will meet you and Tim will perform for you. And then you double down with massive SPVs, 10, 20, 30, 40 million deal by deal carry on the BCD where you'll make some serious fucking cheddar.

58:39Yeah, it's not a bad idea. I've thought about like the SPV approach for doubling down doing follow-ons is very interesting. I've thought about it, right? Because I've done very well investing in SPVs that have launched through funds that I've invested in. Maybe this won't surprise folks, but my favorite fund approach, because generally I don't like investing in funds. It's like they last too long. The capital calls are unpredictable. So there've been multiple cases where it's like, I don't get a capital call for two years. And then a bunch of funds come in and it like totally fucks up all my financial planning.

59:13And I'm like, oh Jesus, now I have to like sell something to deal with this. I generally don't like funds, but if it's somebody very, very aggressive and very smart, who's been an operator who has a first fund. Oh man, do I love investing in those? I love that. Like Chris Saka's first fund. I was busy hearing Saka, Saka. Yeah, that would be, I mean, that's the most absurd example, right? Cause he put, I think 500 K into Uber's series or something like that. He's a great investor. So the reason I stopped angel investing was in 2015, there was a bunch of money coming in from all sorts of places.

59:47There was a lot of capital coming in from China, like a lot of lead investors I'd never heard of. The other thing that was happening over that period of time and the preceding, let's just say three or four years on mass was that when I started circa 2008, you had a handful of people called super angels who are like very, very, very active angels, sometimes writing slightly larger checks. Mike Maples would have been one of those. There were a bunch of other examples. Then you had VCs, which came in quite a bit later and hedge funds and private equity were much, much, much, much later. They weren't even aware of these deals.

1:00:22Then around 2015, a lot of the VCs started coming downstream or upstream as it were, choose your metaphor. And they were hunting in the same ponds that the angels were. And before you know it, then you have like Tiger Global and all sorts of other folks who are also beginning to come further down, further down in valuation. The valuations were getting really, for me, I considered it kind of bloated. The terms were getting super weird. I was like, wait a second, this seems very unfavorable to investors. And there are all these restrictions. And it seems like I'm just going to get diluted out of existence and blah, blah, blah, blah, blah.

1:01:06and I was like, you know what? This is like, I keep using card game examples. I don't actually play cards. I don't, I don't bet on that kind of thing. But if you read bringing down the house, or I guess the movie that was made from a 21, it would be like, just from a strategic perspective, going from single deck blackjack to like five deck blackjack. Like you got a big problem here and like, maybe you can make it work, but counting cards is going to be pretty tough. It just makes the game so much, so much harder. And I was like, you know what? in addition to this, I'm dealing with a lot of fair weather entrepreneurs and investors who I don't really like.

1:01:42Fickle, difficult, titled. I was like, I don't really like this new group of a lot of these folks. And so I was like, fuck it. I'm going to take a break because I'm easily replaceable. If I'm just a source of capital, I want to do things that I feel like I am uniquely suited to do. So I stopped in 2015, which also allowed me to double and triple down on the podcast, which was born of the burnout of the four hour chef. Why? Because I tried to experiment with one or two different promotional channels or platforms that are increasing in importance, but undervalued. And at the time in 2012, I interviewed a bunch of my friends and also cold emailed a bunch of people podcasts.

1:02:25That was the answer. There are these things called podcasts. Most people don't pay attention to them, but it seems like they are in sharp ascension and And things like television, daytime TV are in sharp decline in terms of conversion to sales. And I was like, okay, I'm going to look at podcasts. For the four-hour workweek, that was blogs, right? Every book has its example. Was it a mega hit from the first episode? I wouldn't say it was a mega hit. I had the benefit of a built-in audience from the blog. In 2012, still, the blog was very, very, very popular. This was before I made any use of email, which is funny because I was collecting email starting in 2017.

1:03:04from fourhourworkweek.com and never emailed anybody. I was like, I get too many email. I don't want to get more email. I assume other people don't either. So I'm just not going to email these people. I had like, when I finally went into, I think it was constant contact at the time. I was like, holy shit, I have 300 ,000 email addresses or whatever it was. So I wasn't, I didn't use email until quite a bit later, but the podcast had its 1000 true fans from the beginning because of the blog. Was there a guest which blew it up? So like for me, it was like Ariel Zuckerberg in the early days. I think the Zuckerberg name really helped, but that really instantiated us.

1:03:41Was there one episode where it went, I remember when you did Tony Robbins shows, they were mega. Tony Robbins was big, but there were a few that predated Tony. And actually my first, I think my first Instagram post of all time, because I'm really hesitant to incorporate any addictive social platforms into my life. And I haven't had any social media on my phone for two or three years at least. But my first Instagram post of all time, I think is Tony Robbins palming my face. So I was like, I was just like, Tony, you have the biggest hands I've ever seen in my life. I was like, can we do a photo of you palming my face?

1:04:15And she just like enveloped my whole head in his catcher's mitt. I think that's the first Instagram post I ever put but Tony Robbins was a big deal also for me because I was inspired in many ways to brainstorm and start my own company listening to Personal Power 2 on used cassette tapes that I bought at a used bookstore which I listened to in my piece of shit hand-me-down minivan from my mom driving to and from work where I would commute from this tiny apartment in Mountain View right across the street from a jack-in-the-box to San Jose so I felt a debt of gratitude to him still do but But the two episodes that come to mind, I would say were Arnold Schwarzenegger and Jamie Foxx, because it was early enough in the game that A-tier celebrities were not really on podcasts.

1:05:06That just wasn't really a thing. And when I had those two on, led to a lot of promotion on Apple. Keeping in mind also, at that time, the promise and premise of the show, which is interviewing world-class performers to deconstruct how they do what they do, like tools, routines, habits, favorite books, et cetera. That was novel. Now it's not novel. There are 700 shows on YouTube that do roughly the same thing, maybe in a different way, but at the time it was novel. So it was a special place for people who are looking for that. And when I got those two, which took a long time to book, like a year, year and a half, I mean, it took a long time to get those guys that I feel like not only for my audience, not only for the platforms who are like, holy shit, but also for me where I was like, oh, I think there's really something here.

1:05:58If these folks can be on and have a great time and be willing to be on a second time because of the first experience, like, holy shit. Like, I feel like this is something I should double. And I should do a follow on investment on my podcasting. Did you ever do shows where you thought that hit mega and they didn't hit? Yeah, I have. I don't think I'm going to name names because that's just not how I operate. But absolutely. I mean, there have been some very well-known folks who have been on and I haven't published the episodes because they're not that was just like not good enough. And I'll usually beg off and say there was an audio problem of some type.

1:06:35And I really, really like my name in Chinese is is feiting or feiyu shang. but it means basically like Ferris very honest because I was so blunt in all my Chinese classes so I really don't like even white lies but in the case of something like that I'll be like yeah there was an audio problem sorry man we're honest so we don't release three out of ten 30 percent so I've gotten to the point where that almost never ever happens I would say out of 800 plus episodes there are half a dozen or fewer that would fit the category I'm describing it's because I got intoxicated by a name and one of two things are both happened.

1:07:16Number one, I didn't look at long-term interview footage of them. I just did text research and then they didn't perform or more commonly, they could do a great job, but they just didn't take it seriously or were not playing the game. They weren't returning serves, right? And you can have the best person in the world. If they don't want to be there, if they just got forced to do it by their publicist and you interview 10 on a crammed radio satellite tour type day, you're fucked. It's not going to be a good interview. Tim, you mentioned earlier you were 48. Do you want to be a papa? Yeah. Oh, yeah.

1:07:55Yeah. Yeah. Yeah. That's the, that's, that's the chapter. That's the, I think that's the next big chapter for sure. Do you prioritize that today? Yeah, I do. I mean, you know, haven't had any kids that I'm aware of. I like practicing. Practicing's great. But yes, it is a priority. I do prioritize relationships and looking for the lovely woman who will be my life partner. And I've had some very long relationships. It's not like I have trouble with that. I think I have excellent taste in women and my past relationships have been great. They just haven't ended up with kids for one reason or another, but you know, I've had two relationships that were five, six years in length, and I'm still friends with those women.

1:08:40I mean, it is entirely doable, right. To have kids. I do have some fear around the permanence of it, right. Because I look at all of my friends who have been married, divorced, married again, And at least in the US, it's like the stats aren't great. So I think part of the calculus is, is it worth it even if you end up co-parenting with this person after you separate? I think if you choose wisely and you don't delude yourself, I think the answer is yes. At least certainly that's what I've heard from most of my friends who end up in that position. Is love not the ultimate sacrifice to your truly efficient mind?

1:09:16Being you sleep worse with someone in the bed with you, of course you do whatever anyone says. You have to give up huge amounts of time you're less efficient i mean the the effective efficient stuff i think can be a smokescreen for avoiding a lot of the difficult introspection required to handle the non-money problems so i don't worry about love being inefficient like human relationships are messy and difficult and we are not purely rational actors which is why efficient market theory is so funny to me sometimes what do you think you look for in a partner that is non-typical compared to what other people would that fool.

1:09:52I think what I look for that may not be something people immediately pay attention to is someone who is good at deescalating conflict. I think that is just so, so important. Someone who's a clean fighter, because you're going to have fights. Of course, you're going to have fights. So with any significant other, that's going to be the place. So someone who's a clean fighter is good at deescalating conflict. Someone who can apologize. And this applies to, of course, myself as well. Those I think are, they're really important. You asked, you asked for maybe non obvious, but those are, those are things I, I, I look for.

1:10:30Ideally someone also who's very good at recognizing what's inside or outside of control, which is why travel is so helpful. Like taking a long trip with someone, it's like, what happens when the luggage gets lost? What happens when the waiter's really difficult? What did you learn about yourself from the two longer but failed relationships? I think you often learn a lot about yourself from ones that didn't go to plan there are a couple things right i i grew up in a household where i would say tone wasn't great lots of yelling and kind of harsh tones and i would say patience matters right i talked about my general kind of impatient wiring which i mean i have some very funny stories about even when i was very young right like being in a restaurant when i'm like six or seven and getting fed up with not having an empty water glass and just walking into the kitchen and like finding a pitcher of water and coming back out, stuff like that.

1:11:23That doesn't work super well. I would say in interpersonal dealings, especially when there's any tension. So learning even temporary, like just acceptance and letting stuff kind of blow over you instead of having to react to it, right? Acceptance over understanding, like forget about understanding. Understanding is so overrated. That doesn't mean you can't inquire and ask about someone's experience, how it made them feel. All of that is important, but seeking to quote unquote, understand a super overstated, I think like what, what does done look like when you understand X, right? Usually what it means for type a males understand is let's debate objective reality.

1:12:05And I'm going to prove that I am right. Like usually that's what it means. And like, as Terry, Terry real is a very famous couples therapist. He has some excellent books and his position, which I think is true is that objective reality has no place in intimate relationships. Like if you're like, Hey, you yelled at the waiter. And then she's like, no, I didn't yell. And you're like, no, I hired an audiologist sitting right next to us. And based on the accepted standards for decibel levels, like that's going nowhere. Like that's just going to be, you're lighting your own hair on fire. Yeah. I think that those are a few things that I've picked up over time.

1:12:40And I would say furthermore, that romantic love, like troubadour type love is relatively new as a basis for partnership. This isn't something that has existed throughout all the ages. The idea of like love being the basis and soulmate connection being the basis for lifelong partnership is relatively new on the scale of, let's just call it human history and evolution. So, which is not to devalue any of that. It's just to say, it's not enough. I would say also living as a couple, raising kids by yourselves outside of some extended community, et cetera, also very new, relatively speaking. So I don't think that men and women are meant to be together all the time.

1:13:26I really don't think that's meant to be. So if you're going to one way or another choose that or be forced societally into those types of circumstances, you need tools. And I think those tools and those communication strategies did not come naturally. You're not just born with those. You need to learn them through modeling or you have to study them and you have to practice them. And I'm just saying that might sound really clinical, but I think it's true. Do you think you should go to sleep angry? this there's like a religious divide on this stuff for me i would say the answer is yes you can go to sleep angry because what the alternative often means is having a heated conversation right before bed that may or may not get resolved usually it's not going to get resolved and then i'm just more dysregulated and i can't get to sleep and then i'm exhausted the next day And I'm going to be even less resourced to resolve the stuff that's going on.

1:14:24What I think can work, at least for me, is I'll say, hey, look, neither of us is super well resourced for this right now. I recognize this is hard. We'll figure it out. Let's talk about it tomorrow, like after lunch, when I've gone through all this stuff and we'll have a chance to cool down. I like having a partner also who can just recognize like, hey, we don't we do not have what it takes right now to figure this out. So let's calm the fuck down and we'll come back to it tomorrow. or whenever, but just having a time to reconvene so that a partner, right? If you might have an avoidant tendency from an attachment perspective, which I think I probably do.

1:15:00My mom is that way, super conflict avoidant, that the other person knows you're actually going to come back and have that reconnection. And look, I'm not saying I'm a black belt in relationships, but I have learned a lot and I'm good at practicing things. I am good at trying very, very, very methodically to get better at things so i i've definitely gotten better you mentioned it was a priority final one before we do a quick fire if we think about moving metrics that matter and priorities coyote the card game talk to me about why you thought that was important to do and why you wanted to do it so much yeah so for people who are like what the hell are they talking about so every couple of years i like to do something that's off menu to see what doors it opens what i learn because i've never done much long-term career planning really it's kind of six to twelve month projects let's go 100 in and i assume the doors that open the things that appear are things i can't predict and they'll be more interesting than anything i could have planned with any degree of certainty so coyote is a casual card game did it in collaboration with some friends at exploding kittens which is an awesome game design studio and as we're talking whenever this comes out, it will have launched in Amazon, Walmart, Target, like 8 ,000 plus locations and got to do my pitch.

1:16:20So it has like 300 million plus social views of gameplay already after pretty, pretty much no time at all. So, uh, we've play tested the hell of it. Feel really good about it. Like the prospects are good. The reason I did it, I'd say probably threefold. one is that i mentioned this gathering of friends that i have every year how deeply meaningful that is for us to have this offline analog interpersonal connecting it feeds us for the rest of the year and if you look at the stats and there's a great piece that came out in the atlantic not too long ago i think it's i think it's just called americans need to party more but i'm sure it could be applied to many other countries where the statistics are roughly as follows right one in 25 american families or individuals have a in-person social activity planned for any given weekend.

1:17:12And if you look at the decline for certain age brackets, it's like 70 % down over the last 10 years. And I see that kind of screen time, digital malaise, induced loneliness, apathy, et cetera, in my audience. So I wanted to create something that is a light lift that encourages is offline, non-screen human interaction, which is what we are evolved for. We are not evolved for fixating at 18 inches all day long at all. Secondly, games have just been part of my life, which I let atrophy for a long time, but I grew up just feeling like I was saved and fueled by Dungeons and Dragons and others. I still have all of my modules and everything from when I was a kid.

1:18:00When you talk to, whether it's people who are striving for success or people who have quote quote unquote, achieved success. If they do therapy, if they have a psychedelic experience, the thing that comes back all the time is like, I need more play. And unless they're really diligent about asking, what's the next step? What is the next concrete action? What I put on the calendar that just gets lost in the hustle of autopilot or doing whatever business gear you're accustomed to. So that's another reason why I was like, you know what I am going to spend, it turns out two years in total trying to create the best game possible that's easy fast hilarious just to play with friends after dinner or family or whatever so what is your metric for success with it they're different metrics i would say the most important one is this sounds maybe squishy but it's not when you start to actually practice it the relationship side like alan lee the co-founder of exploding kittens worked on the first xbox halo has created entire genres of games absolute polymath genius has created not just one but many many hit tabletop games along with his team to work with him and to deepen our friendship and have a chance to just spitball not just on games but on everything huge payoff just i i can't even put a number on on that along with the team but alan and i have become very close so from a relationship payoff perspective like like i've already more than broken even with that in terms of learnings and skills right learning how a lot of the behind the scenes machinery works for the biggest retailers in the country if not the world walmart target right 90 of the u.s is within 10 or 15 minutes of a walmart location right as an example i'm sure target has similar numbers the scope and scale is nuts it's easy to forget about how much of the US economy food security is dependent on these retailers.

1:19:59So understanding like the political gamesmanship and everything that goes into getting something at mass retail is super valuable. And then look, would I love to have this game be the number one selling game at Walmart, Target, Amazon, everywhere simultaneously? Yes. Like that, that is in my mind. It's a little hard to figure out exactly where to aim with that because so much of the data is proprietary. That's a bit of a bummer minus Amazon, which you can watch publicly. But first and foremost, the marketing has to be the product itself. Like when people are like, how did you launch your book?

1:20:34I'm like, is your book done? They're like, yeah, my book's done. I'm like, it's too late for us to have a conversation. Like the marketing has to be the product itself. People have to want to talk about it. We'll see. It's my first time selling something that's$9.99 and really small. So it's fun to promote something that is not a 600 page homework assignment to see what that looks like. I remember seeing the first trailer probably a month or so ago now. I'm just going, I have to know why Tim's doing this. Yeah, it's a bit of a WTF move. And it's worth pointing out too. It's like you can do a lot in the evenings and weekends if you want to get something running in parallel.

1:21:13all oh my god i totally agree yeah and you can get and you and you can also like the podcast the podcast for the first 50 episodes i mean super part-time endeavor that's why i advocate for 996 you're gonna hate this but i didn't say 996 in chinese routine and i'm getting killed for this right now 9 a.m to 9 p.m six days a week yeah yeah that's yeah that's that's my my question is why people working part-time you got sunday off i haven't had a sunday off in years people just don't want to work hard today tim this is the problem and look people misunderstand you know the four-hour work week because it's about maximizing per hour output if you want to work four days a week four hours a week four nanoseconds or 400 hours a week i know the math doesn't work but that's fine as long as you're really thinking about the sort of archimedes lever approach to doing things and you can actually get a lot done in very concentrated periods of time if you step back and really aim for high leverage stuff and ask a lot of questions so the point being i was shouting to brian johnson the other day and he was telling me about the duration of his erections and i said you should steal you just steal tim's title like i did just do the four hour erection not that it probably clicked wouldn't you tell me yeah yeah sure i mean And the trade-off is you may need to go to bed after 8 p.m.

1:22:36to make good use of those erections. It depends on how many lunchtime nookie sessions you can have. No, no, no, no. You don't do that because that's too much energy at lunchtime, Tim. No, no, that doesn't fit in the routine. Yeah, yeah. Doing red light therapy for my penis at that time. Brian's run a lot of interesting experiments. If somebody wants to, I interviewed him on the Braintree stuff before the transformation into Don't Die. So if you want a before and after. Do you believe that he's doing this out of like genuine passion for it or is it a customer acquisition for Blueprint and for the company that is built behind it?

1:23:14I don't know. I think, I don't think they're necessarily mutually exclusive. I mean, he's definitely interested in building a company. maybe some of the attacks on various things were basically just setting the stage for launching products and customer acquisition but i think he's i also feel like he's sincere in a lot of the experimentation and the pursuit of longevity and health span i like i feel like he's my impression is that that he's sincere but those are not mutually exclusive and we're talking about incentives like can incentives steer and impact other areas absolutely so who knows but have you interviewed him on your show or not yet or i guess maybe it's not a thematic no i have he told me about his erections and i said dude you could watch titanic in that time like seriously and he now uses that in all of his talks and so i feel incredibly proud to have inspired him yeah i mean and and just because i i i don't want to feel like you know we're throwing him under the bus it's like we're giving him credit on a large platform that he has massive erections what how is this throwing him under the bus no it's not throwing him under the bus but it's you know like erections do matter just to be clear and and a heuristic for a lot of male health is uh i owe this to kelly starrett who's a very famous pt and performance coach but boner no boner when like in the morning.

1:24:38Does it happen or does it not happen? That is actually a good leading indicator for a lot of things. My God, I so want to do 20 VC with Tim Ferriss, Erections, Matt.

1:24:52Your team are just like, what the fuck? I mean, yeah, big red arrow on the thumbnail pointing to the microphone in front of me. I want to do a quick fire with you. What is a piece of advice you gave in your 30s that you wouldn't give today? I would probably just add some asterisks to a few things like what gets measured gets managed. I measure what matters, but not everything that matters is easy or even possible to measure. And you can lead yourself astray by trying to do that. So I would add that any advice or videos that I put together involving high heat and eating things out of plastic or drinking things out of plastic, I would rescind.

1:25:30And this is not tinfoil hat wearing territory. I mean, I really feel like minimizing microplastic exposure is a good investment. So this Rhonda Patrick talks a lot about this from a credible perspective, but like not putting tea bags in hot water, any of the disposable to go cups in most places outside of maybe blue bottle coffee, which uses sugarcane coating, I believe. So you're putting hot water, hot coffee, hot matcha, whatever in that you are consuming lots of microplastics. that's that's one that comes to mind what's the one person you'd most like to have dinner with dead or alive and what would you ask them it would probably be someone dead i i can't i can't hone down to one but let's just say richard feyman ben franklin or seneca the younger and i imagine they're kind of blowhards they're all going to talk a lot but i would interject and ask like what did you learn from that like how do you feel about that what were you saying to yourself when that happened or before that conversation.

1:26:31The inner monologue piece is effectively self-coaching. I find that type of question really fruitful. So I would probably just, I'm sure they would all run long and over talk and I would get annoyed. But I'd say those three come to mind. Tim, how has your style of interviewing changed? You're one of the greatest interviewers. How has your style changed over the, whatever it is, 850 now, close to? Yeah, something like that. I would say that I still try to deliver on the promise of the show, right? Which is kind of practical, tactical strategies, tools, frameworks, whatever that you can use from these people, whether it's a Seinfeld or an unknown Japanese knife maker, something like that.

1:27:14But the older I get, the more I have realized that the emotional terrain matters, right? The inner game, not just from a mental performance perspective, but from an emotional navigation regulation perspective, from a mental health perspective, I've asked more questions about those facets in my interviews, because I don't think that you can separate any of these things. They're all integrally interconnected, just like mind-body, that's a false dichotomy. like cartesian duality doesn't make any sense if you just look at any modern biology and understanding of for instance psychiatric conditions so i've tried to make the interviews useful but more holistically useful because it's also easy to emulate or copy someone without realizing the hidden costs of what makes them so good at x right you could be like all right I'm making this up just because it's an easy one, but like killer finance person X, they wrote this book on how they do what they do.

1:28:20I'm just going to copy that, but they don't talk about their three divorces. They don't talk about their battle with alcoholism. They don't talk about all of these things that may be independent. Maybe they're on separate tracks, but maybe they're actually a direct side effect of the things you're about to copy. So I really try to flesh some of these things out. So if people are going to emulate these folks, they get a more complete picture. Tim, as I said at the beginning, I wouldn't actually have my business without you. I wouldn't have my funds without you. It would be entirely differently named, which probably wouldn't have been successful.

1:28:53I probably wouldn't have started a podcast. So of all the guests I've ever had on, I probably owe the biggest debt of gratitude to you. So thank you. Oh, thanks, Harry. I really appreciate you and everything that I've learned because I wouldn't have my life without it. But before we leave you today, SecureFrame empowers businesses to build trust with customers by simplifying information security and compliance through AI and automation. Thousands of fast-growing businesses, including NASDAQ, AngelList, Doodle, and Coda, trust SecureFrame to expedite their compliance journey for global security and privacy standards, such as SOC 2 and ISO 27001, CMMC, NIST standards, and more.

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