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

🎧 20VC x Tim Ferriss — Full Episode Timeline 00:00 – "How Do You Stay True to Yourself When You Have to Perform for the World?" 06:00 – "Why Tim Ferriss Refused to Go All-In on YouTube" 09:00 – "You Don't Need 10 Million Fans—You Need 1,000 True Believers." 12:00 – "The Internet Is Not a Relevance Machine—It's a Sensationalism Machine." 15:00 – "Money Fixes Money Problems—And Nothing Else." 22:30 – "When Did Tim Ferriss Feel Completely Lost?" 27:00 – "The Million-Dollar Mistake That Still Haunts Tim Ferriss." 36:00 – "Why Tim Ferriss Never Raised a Fund—Even Though He Could Have." 45:00 – "The Truth About Uber, Duolingo, and the Power of Relationship Investing." 54:00 – "Why Tim Ferriss Stopped Angel Investing at His Peak." 1:04:00 – "The Podcast That Changed Everything." 1:15:00 – "The Real Cost of Love: Is Efficiency Killing Connection?" 1:31:00 – "What Tim Ferriss Has Changed His Mind About Most." 1:36:00 – "Erections Matter."

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is 20 VC with me, Harry Stebbings, and this episode was about 10 years in the making. No one actually knows this, but I started podcasting because I fell in love with Tim Ferriss's podcast 10 years ago. I remember listening to it for the first time, and I actually used his episode with Ed Cook to study for exams at school before I dropped out. He has been an idol inspiration, mentor to me for many years. I'm so thrilled that we were able to do this show today. It's one of the most thoughtful and reflective that we've done. I'd love your feedback. Let me know what you think. Harry at 20vc.com. But before we dive into the show today, SecureFrame empowers businesses to build

• 0:41Harry Stebbings?

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• 1:25Harry Stebbings?

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• 2:10Harry Stebbings?

  Team, just send it over to [email protected]. Okay, HMC fuels the growth. Acuity Scheduling ensures our time stays on track. This show is brought to you by Acuity Scheduling, the flexible scheduling software that helps you focus on what matters most. Growing your business with Acuity, you can manage your calendar, you can accept secure payments, offer clients a seamless booking experience that reflects your brand. I've been using my complimentary subscription and it's been a game changer for staying organized and saving time. I especially love online booking. Clients can book, reschedule or cancel anytime and the booking page looks fully branded with my logo and colors. The calendar management tools let me set buffer times and sync with other calendars, so I never feel overbooked.

• 2:55Harry Stebbings?

  And with secure payments, I can collect deposits or full payments upfront through Stripe or PayPal, making the process smooth and professional. Head over to acuity scheduling.com/20vc for a free trial. And when you're ready to launch, use the offer code 20vc20 to save 20% off your first Acuity Scheduling subscription. You have now arrived at your destination. Tim, I'm so excited for this dude. As I said, I literally have my podcast because of you. I have the name because of you. I probably wanted to make this happen for 10 years. So thank you so much for doing this with me, man.

• 3:31Speaker 01

  I'm thrilled to be here and congrats on the success. You've had some amazing interviews, so well done.

• 3:36Harry Stebbings?

  That is very, very good. It's amazing how far a British accent goes. Really, really, you have the intellect and I have the accent. And I think it really elevates mine, just they think you're so smart in the US.

• 3:48Speaker 01

  It does equalize things out. I remember back in the day, and he's actually a pretty clever guy, but people would say Lennox Lewis is a phenomenal boxer. He is 10 times smarter than any other boxer. And I would say, I think it's because you're American and he has a British accent. There is a certain inflation that seems to happen. But congratulations, well done. Either way, by hook or crook, you have created a very, very prominent, very compelling show. So nicely done.

• 4:17Harry Stebbings?

  That's very, very kind of you. You said that I could just take this in any way that I wanted. I find it difficult when you have a public persona to actually separate who you are from the showman. You know, you've got to be on show when you're doing podcasts, when you're speaking, and I really struggle with that. How do you think about retaining your true self when you also have to be a showman?

• 4:40Speaker 01

  Well, I have thought about this very consistently since the early days because you have to be careful which mask or masks you wear because you can become the mask very easily. And I think that's never been more true than now. That's the first warning, I would say. Another is that if you simply respond to your audience by doing more of what they respond most strongly to, you will end up exaggerating tenfold all of your most extreme behaviors and views. And over time, what does that mean? You will become the embodiment of those things, even when you're off camera, off mic.

• 5:20Speaker 01

  And to try to counteract some of those, I have done certain things. For instance, you probably have noticed, I'm sure a lot of people have noticed, I have not fully embraced video. I have not gone into full production television studio land. I have not tried to spend a lot of time on algorithms on YouTube as a driver of growth. And part of that is because I think video puts all of those inclinations and all of those risks on steroids. It also happens to obliterate your privacy just through giving you broader facial recognition in the world. And as I start looking towards future chapters with parenting and kids and so on, I want less and less of that.

• 6:05Harry Stebbings?

  How do you think about balancing then? Reach and impact. Me as a kid, changed my life listening to your show. I mean, genuinely, and I might have never heard it had it not been for algorithms pushing it and distribution channels pushing it. If you don't do video, do you worry a lot about missing out on reach?

• 6:23Speaker 01

  I don't because I've seen how much you can do with very little. And what I mean by that is if you are very, very focused in a number of ways, there are different ways to be focused in, for instance, let's just say podcasting, although it's basically become television shows. But let's flashback to 2014 when I started my podcast. Do you remember how you found the show? It probably would not have been, it wouldn't have been YouTube. I did, it was Apple Podcasts, top of the charts. Exactly. So it would have been in the charts or it would have been direct promotion by Apple or something like that, for instance, most likely, or a friend.

• 7:05Speaker 01

  I firmly, and maybe this is just old fashioned, maybe this is extinct, but I don't think so. I think it's going to be more and more relevant. 1,000 True Fans by Kevin Kelly. If you could only pick 1,000, who would those 1,000 be? And if you pick very wisely, right? Maybe those 1,000, I'm just choosing some options arbitrarily. Maybe those 1,000 are the leading tastemakers in the furry community who go to conventions and you're making outfits on Etsy. Maybe it is, I chose a weird one on purpose. Otherwise, it could be the 1,000 people who are return attendees to TED.

• 7:43Speaker 01

  Could be the 1,000 most influential, let's just say, creators who have participated in the Olympics or at national championship level sports in half a dozen sports. Okay. Why are these so specific? And they sound so maybe constrained. My experience is if you put in the forethought to choose those 1,000 people, even if you reach 10 million or 100 million, you will be able to create highly, highly leveraged content, ideally that also checks the box of being true to yourself in the sense of following your own curiosity. And when you do that, let me just give a concrete example.

• 8:26Speaker 01

  When I launched The 4-Hour Work Week, it's very tempting to try to write a book for everyone, to appeal to as many people as possible. To have the widest top of the funnel imaginable. But in the case of the four hour work week, I wrote that book as if I were writing it as an email to two friends, two very specific friends with two very specific sets of challenges and problems and hopes. I marketed that to tech savvy males, let's just say between the ages of 20 and 35 in San Francisco first, then New York City, then it hopped to the same demographic in Chicago and LA and so on.

• 9:05Speaker 01

  Then it hopped to females in roughly those same kind of psychographics and then it spread everywhere. So by choosing the right starting point, the ripple effect naturally extended out to ultimately millions upon millions of people. So I really feel like you can go big by putting in the forethought to go surgically small. I also remember a conversation I had very early on the podcast with Andrew Zimmern, who is a very well-known TV host, chef, crazy compelling, wild story of being, I think he was a heroin addict at one point, homeless and has just created an empire for himself now.

• 9:48Speaker 01

  And on his first episode of his first television show, someone gave him the advice and he gave me the advice in that conversation. He said, be very careful who you pretend to be on episode one, because if that goes well, you're going to have to be that person forever, or you're going to feel like you have to be that person forever. Last thing I'll say, because this is turning into a monologue, is I will routinely put out things that are right in the bullseye of my interests or weirdness or quirkiness or goofiness that will in some way split my audience. And it's not for controversy, it's to cull the herd of fair weather fans who might shape me in a direction I don't want to be shaped otherwise.

• 10:33Speaker 01

  So I will deliberately kind of routinely get rid of like 10% of my audience by just being unapologetically brazen.

• 10:43Speaker 01

  Myself showcasing the things that I would not be inclined to showcase otherwise. And I find that at least for me, that has helped to keep off camera, off mic Tim and on camera, on mic Tim, I think the same. I really don't think there's a discrepancy. If there is, it's very, very minor.

• 11:05Harry Stebbings?

  Listen, you said about a monologue. I could turn this into a therapy session with you like the OG. But I think we constantly debate between, you know, doing the like the Steven Bartlett, do you want a bigger penis visual? Like, you know, it is not like clicking yes, like, you know, versus like Venture 101 with Kevin Rose. And my point being, I love Kevin, you love Kevin. But I'm just saying, like, it's very easy to go down the sensationalist because we're in a relevance machine. Algorithms drive discovery.

• 11:36Speaker 01

  It's not a relevance machine. It's a Sensationalism machine. You have to be very careful. And that's, that's a conversation I have with my team constantly also, because to their credit, they want to grow different channels. The fastest way to do that, the easiest way to do that, I shouldn't say it's easy because it's actually very complicated, especially when you have to bob and weave and play the cat and mouse game with the algorithm, which I have no interest in, for them to get pulled into lots of big red arrows, lots of crazy clickbait titles, even if it's one incremental kind of 2% shift at a time.

• 12:18Speaker 01

  Before you know it, you're there and you see these numbers and you get really intoxicated. But also, I think, and this applies to startups, it applies to investing, separating key metrics from vanity metrics is really important, right? And I'll give an example of that. Views, likes, all this stuff. If your business is predicated on CPMs from ad dollars from YouTube, okay, maybe that is a real metric. Otherwise, let's just say my newsletter is the most important thing. And I would argue that it is actually one of the most high leverage things. On clips matter? Well, that's a good question. What are the drivers to the newsletter? Well, maybe it's the podcast and the blog. Okay. Do clips drive to either of those?

• 13:04Speaker 01

  I've had clips, shorts that have exceeded 100 million views. The branding of the show is there. It's clearly an interview on my podcast. There's a link to the full episode and the impact on the long form episode has been imperceptible. You look at the downloads and there is sweet fuck all, zero impact. So I think it's also just worth noting these, the, the teams and the platforms, you know, the teams behind the platforms are very smart. They're very well funded. They have data scientists and teams of many others whose sole objective is to keep using the product as consistently as possible, both as a creator and as a user.

• 13:49Speaker 01

  You can be swayed to adopting the metrics they want you to adopt very easily, but a lot of them don't matter if you actually drill down and look at the fundamentals of your business. If, if the business matters, if you're just doing it for love of the game, then hey, knock yourself out. No problem. But I just constantly return to the why, why, why, why, why? Why are we doing this? Let's take that answer. Well, why that? Why does that matter? Okay. Then the next one, well, so what? Why does that matter? And when you drill down, you might realize I am sleepwalking through this. Some digital snake charmer of a platform is just pulling me through this. And I've spent the last six months building something that doesn't actually serve my interests.

• 14:32Harry Stebbings?

  Can I ask you a very direct one? When did you feel most lost? It could be as a podcast, but also just personally, when you were focused on the wrong metrics that didn't matter?

• 14:43Speaker 01

  That's a very good question. I think of myself as hopefully a teacher more than anything else. I mean, I wanted to be a ninth grade teacher for a long time when I was younger because I went in a good direction due to some mentorship at that point. A lot of my friends went in a bad direction, end up ODing and going to jail and so on. But fundamentally, I think I've kept my Eye on the ball with that specifically. In terms of the wrong metrics, I think if I had to pick one, there would be the overweighting of quote unquote productivity overall. Right? Kind of like productivity is the cure all. And then secondly, I think that money in general has its place.

• 15:26Speaker 01

  It's a currency that you can trade for other things or that you can use as a pacifier for psychological reassurance. Just, but by and large, money fixes money problems and it doesn't fix a lot of other types of problems that people expect it will. So there does, I think, come a point, unless you ask the why, why, why? Where you can steer yourself in the wrong direction. For instance, and this might be controversial. I don't think it is, but if we take the purpose of investing as improving your quality of life or the quality of life of your family. Right? If we put aside the whole like legacy, have an impact on the world,

• 16:11Speaker 01

  all this stuff after I die, or if I'm going to do this, giving pledge, blah, blah, blah. If we just put that aside, because I'm actually skeptical of quite a bit of that. Then if you make any investments that keep you up at night, that cause you to be distracted from your family, those are bad investments, even if they're returning record setting compounded annual growth rates. So I think I have fallen prey to that perhaps a couple of times because I'm competitive. I like measuring things. If there is a scoreboard of some type, I'm drawn to it like a moth to a flame. But you can play the wrong game. So before the question of how do I win this game? First is to be aware of the games you're playing. What are you already playing?

• 16:56Speaker 01

  And if you have food, shelter and a few other things, trust me, you're playing a bunch of games. So just being aware of the games and then it's game selection before asking the question, how do I win this game? And I slip, I'm certainly not impeccable with that. But if I have followed the wrong metrics, I would say probably just overall some type of productivity or a growth metric, even if it impacts the business, which then comes back to the why build the business? Well, if it's a business, presumably it's generating revenue and profit. And maybe you don't need more Skittles. Maybe you've eaten all the Skittles you need to eat.

• 17:33Harry Stebbings?

  I want to unpack this. What do you do today that is less efficient than an alternative, but you choose to do it all the same?

• 17:41Speaker 01

  Well, there are activities writ large that have nothing to do with, I suppose, any way I've conceived of productivity. I mean, I read a lot more poetry now and fiction. I never read fiction for decades. If I can just make it up, why would I read it? I needed things that I can use. So I read lots of fiction. I think you can actually absorb and remember truths from fiction much more effectively than you can from nonfiction oftentimes. Poetry, painting, digital painting on an iPad, things like this. So activities overall that I put into my life to remind me that racing to the finish

• 18:23Speaker 01

  line doesn't really help you because there's always more work. The work is never done. I think 4,000 Weeks by Oliver Berkman is an incredibly good read, just to realize fixing your gait on the hamster wheel does not actually lead you anywhere particularly interesting, which is not to say that being in the game is not interesting. Like, if you want to build a business and do all this stuff, it's awesome. Like, I still do plenty of things. But I also find it helpful to use something like the Way app or anything else to meditate 10 minutes once or twice a day, just to prove to myself, if you chill out for 10 minutes twice a day, you feel better and guess what? The world doesn't

• 19:07Speaker 01

  end. And the stuff you're doing, a lot of it, even though it's meaningful to the business or whatever, whatever, like a long term, or if you zoom out to 30,000 feet, it doesn't really matter that much. It's not worth getting run ragged about. So I will say that I'm sure, and I've had plenty of coffee, so that might explain the word per minute rate right now. But people might say, well, that's easy for you to say, right? You've hit escape velocity. You've had this, that, and the other thing succeed. So it's easy for you to be like, yeah, now I can chill out. And I think there's some truth to that, right? You have to be very careful when you're interviewing and when I'm interviewing folks to Are the habits that they're talking about post-success or pre-success?

• 19:49Speaker 01

  I will say, if I could give any advice to myself of 10, 15 years ago, it would have been, start meditating now. There are a few pieces of advice I would give, but absolutely, probably with something like transcendental meditation or something like the Way app that's kind of programmatic, meditate twice a day. Prove to yourself that praying at the ends is actually not the way to be most competitive and most effective.

• 20:18Harry Stebbings?

  Tim, when did you make your first real money?

• 20:21Speaker 01

  I would say, well, I made my first real money with my very, very first company. I mean, the first money that made me realize, oh, wow, I can do what I want to do, was through the sports nutrition company way back in the day, the company that I started at Brainquicken back in the day. The one that in a lot of ways was the experience that formed the Petri dish for the four hour work week, right? There was more in that book, of course, but it was that experience of automating and outsourcing and delegating and kind of systems thinking that led to the point where I was like, oh, all of these things that I wanted to do or that I thought I wanted to do, I can play around with, like, I can do these things.

• 21:06Harry Stebbings?

  Did you have a number, like, when I was starting, I was like, if I have $10 million, that's like as much as I'll ever need. Did you have like a number, most entrepreneurs?

• 21:14Speaker 01

  In the beginning, it was, I think it was probably just some nice, clean arbitrary number, like a million dollars. I also had goals which were sexy and very useful at the time. I think it's useful to have these very precise goals. I wanted to make as much per month as I was previously making per year. So at my startup job at a college in Silicon Valley, shortly thereafter, keep in mind, this was 2000. The company imploded, everybody got fired, and I started my own company. I was like, you know what? I really want to aim for this, what I considered almost absurd goal, which was making As much per month profit as I was making gross per year.

• 21:58Speaker 01

  And that just seemed like it would solve almost everything.

• 22:02Harry Stebbings?

  You said there are lots of problems that money doesn't fix that people think it maybe does. What does money not fix that people think it does?

• 22:09Speaker 01

  Oh, just sit in a room of a couple, a handful of wealthy people and just listen to what they complain about. All of those things, or give them a few drinks and listen to their laments and insecurities and any of the battles they or their spouses have with depression, anxiety, insecurities that well up and cause all sorts of interpersonal conflict, interpersonal communication and honing EQ into something that allows you to have more harmony instead of disharmony.

• 22:40Harry Stebbings?

  I would say when I look at my friends who are billionaires, money does more to damage EQ than improve it.

• 22:47Speaker 01

  Yeah, you know, I was, I was tempted to, to add that and you're right. Money is like alcohol or power. It is an amplifier. So if you have insecurities, oftentimes money will amplify those. If you're hyper vigilant, as I am, from a lot of childhood experiences and other things, maybe it's just out of the box. Money's going to make you extra, extra hyper vigilant and in my case, just slow to trust. If you are a micro asshole and you get a lot of money, you're going to be a mega asshole. The good news is also if, if you are inclined to be generous and you get a lot of money, you're probably going to be super generous. So there are some upsides, but it's not selective. Maybe it's like psychedelics also.

• 23:30Speaker 01

  It's a non-specific amplifier. So the good and the bad are both going to get amplified. There is that. I just, I hesitate sometimes to bring it up because it's like, you know, cry me a river. America weeps for the sorrows of the billionaires, you know? But it's true. It's true. So something to be aware of. Now, if you told me that, would I have listened to all these warnings? I would have been like, yeah, that's cute. I'll worry about it when I get there. And I, I don't think that's necessarily a bad approach to take because here's one. I think that the transient depression of People who are still chasing the phantom of riches is in some ways different from the depression

• 24:11Speaker 01

  of those who catch the rabbit on the greyhound track and have actually hit the number. And I'll explain why, because I've experienced both. When you have depression, anxiety, fill in the blank, but you have this big number in mind or this goal in mind, you can hold on to the hope that once you have that, these things disappear. You no longer have to worry about them. When you get it and you realize that more likely than not, that is not the case, then you can feel hopeless, then you can really feel lost. And I think that is part of the reason why so many people who have wealth, and it's not everybody to be clear, but so many people who have wealth actually click down

• 24:56Speaker 01

  into some lower levels of sort of existential distress. Good news is I think there are ways to kind of hedge that and contend with it. Step number one is realizing money solves money problems.

• 25:09Harry Stebbings?

  Did you find it changed your relationships? Friends maybe listen to you more, your voice is a bigger voice in a family. People don't argue with you as much.

• 25:19Speaker 01

  Yeah, I mean, the family stuff, I have, didn't grow up with a lot of money and money was always the, if we only had more money. And money doesn't grow on trees. You gotta have money to make money. These types of cliched expressions were something that I was steeped in. So given that, you would imagine the same people saying those things take me more seriously now that I've done well professionally. As far as my friends, my closest friends are generally my oldest friends. So I just had a gathering of six to eight of my closest friends. They came in from all over the place.

• 25:59Speaker 01

  And these are people who will always tell me that my baby's ugly if need be. They will take the piss constantly. These are people I've known for 30 plus years, 20 plus years. My closest friends have not changed. What I will say is when you have more public visibility, the volume of people who are going to be very eager to blow smoke up your ass with some ulterior motive is going to go up dramatically. So there was a period of adjustment for sure after the first book hit and then stayed on the New York Times list for four and a half years or whatever it was, where I was very vulnerable because I had not experienced that. So if I got

• 26:42Speaker 01

  an email or a phone call from hotshot agent at XYZ Talent Agency in LA and they said, "We want to do this with you and A, B, and C mega-stars are very interested and we want to make this happen. We think it can happen quickly." I would take that at face value. And lo and behold, total horseshit, 99.9% of the time. So you develop a water feel for, I suppose, that type of nonsense or someone who's a more kind of dangerous player where they're really angling for something nefarious. You just develop a better spider sense for all of that.

• 27:21Speaker 01

  But my actual core friends have not changed. In the same way that I've tried to pay very close attention to not wearing masks, I don't want to become. I've really paid attention to those friend groups.

• 27:35Harry Stebbings?

  Tim, when you look at writing, you look at podcasting, you look at angel investing, and you look at wealth today, how does it distribute amongst them? Is one 10, another 10, and one 80?

• 27:47Speaker 01

  I would say like maybe it's 70% angel investing, could be 80, 20% podcast, 10% books. Then there's a bunch of other stuff that might be 5%. So I know the numbers don't add up perfectly, but making money in books is like making money streaming music on Spotify. It's a tough model to make work. All five books have been number one New York Times and/or Wall Street Journal. And in the nonfiction world, I mean, I've done about as well as books can do. There are other books that have done better, certainly. But it's in the top 1%, maybe 1% of 1%. And nonetheless, on an annual basis and on

• 28:31Speaker 01

  an ongoing basis, the podcast is much larger. I expect that to change. I think the podcast world is going to get much more challenging, particularly with some of the decisions that I made. But fortunately, coming back to making the audience as wide as possible, I've maintained a very tight focus. The types of interviews I have, I don't dumb down. So my audience tends to be very well educated, very high household income. And as a result, I can command and deliver on premium, very premium CPM. So I positioned myself as ultra-premium very deliberately. And that, I think, gives me more insurance against the red ocean that podcasting will

• 29:13Speaker 01

  continue to become. But the downward pressure is real. The race to the bottom dynamics are real. So Which book made the most money? Probably The Four Hour Work Week. But the success of the books, for instance, I mean, Four Hour Body did and continues to do. I mean, The Four Hour Body, a lot of what was written about in that book is getting a second wind and a third wind every year for the last few years, because a lot of the scientific publications are just supporting what was in it. And a lot of what was in there was already based on various publications and case studies in the literature. So it wasn't just pulled out of my ass. But The Four Hour Body, and this had

• 29:56Speaker 01

  nothing to do with me, went completely viral on TikTok last year. It just exploded again. This book was published in 2010. Why? There was this guy, he's actually very well known. He just interviewed Joe Rogan on his podcast. It was very, very good conversation, actually, Gary Brekka. And Gary Brekka had a short video talking about 30-30-30 rule, which alluded to a number of things in The Four Hour Body. He mentioned the book by name at the end of it, and it just went completely ballistic. Now, did that drive sales? Because we said about the 100 million in views on the clips. It did drive sales. It did drive sales. So there are exceptions. I'm not saying that social media can't drive

• 30:37Speaker 01

  sales. I'm just saying be very skeptical if you assume that to be the case. Don't assume transference. Prove transference, right? And in this case, it absolutely happened because the numbers went nuts. And the publisher was like, hey, we're about to run out of stock. What the hell is going on? I had no idea. But one of my researchers did some homework and quickly found Gary Brekka. And we're like, oh, okay. That's the only thing we can find that has any plausible explanatory power.

• 31:07Harry Stebbings?

  Which book did the worst? And on reflection, can you see why it did the worst?

• 31:12Speaker 01

  Yeah, I would say, I mean, the book that did the worst is a delta between, let's just say, expectations and reality. I think happiness, broadly speaking, and I'm not the first person to say this, or contentment is expectation minus reality. So you can play with that equation a couple of different ways. Like I asked this, I'll answer your question on the book in a second. But I was talking to this Danish friend of mine, because the Danes, Costa Rica, Singapore, and I'm skeptical of these polls, but are rated as some of the happiest places in the world. And there are these speculations around the reasons, right? Costa Rica, the social fabric, social interactions, Singapore, safety net, health

• 31:56Speaker 01

  insurance, everything else you can imagine. I wouldn't say health insurance, just health system, blah, blah, blah, blah, blah, kind of predictability. And I asked my Danish friend, why the Danes seem so happy? Why did 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, four hour 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, learn to shoot three pointers, do anything very, very, very quickly? And that book did not do nearly as well as

• 32:38Speaker 01

  I would have hoped. It 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 Four 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. Uh oh, Amazon's going to be competing

• 33:21Speaker 01

  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. So The Wall Street Journal, at the time, was a compiled list.

• 34:05Speaker 01

  It was based off of Nielsen BookScan. 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

• 34:46Speaker 01

  through Indies, if you only have sales through something like Amazon, which was the case for The Four Hour Chef, 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. I 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.

• 35:29Speaker 01

  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 Work Week became successful, when I was invited to do all these speaking gigs. The advice that I was given was presentations more often fail from too much information, not too little information.

• 36:09Speaker 01

  I think that was perhaps a core weakness of The Four Hour Chef. It just tried to do too much. The book itself was 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.

• 36:34Harry Stebbings?

  The biggest reason CEOs are unhappy is because they attach the happiness that they have to the performance of their company. I 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?

• 36:56Speaker 01

  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.

• 37:17Speaker 01

  But I will say that I do think about identity diversification for this reason. And 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.

• 38:00Speaker 01

  I 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. If 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.

• 38:45Speaker 01

  You have, just like in a portfolio, and I'm not, we had 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 and saying, what the fuck? There's a huge dislocation between, I just got punished, right? Like, I feel like this was punitive, getting put in this place on this list. Like, yeah, that's annoying. It's very annoying.

• 39:20Harry Stebbings?

  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 you, I 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.

• 39:47Speaker 01

  Yeah, favorite investing lesson.

• 39:49Harry Stebbings?

  Or story of how it happened.

• 39:52Speaker 01

  Yeah, let me just, let me just give briefly part of the origin story. And I think that explains it. Yeah, cause I've had some, 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 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 happened. 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.

• 40:31Speaker 01

  And then it becomes this phenomenon where it's getting like parodied in TV shows and mentioned in pop culture. Even last, yeah, 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 Edge Xiao, 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,

• 41:14Speaker 01

  we ended up having breakfast together. We would have breakfasts 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, 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.

• 41:37Speaker 01

  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 and he would later start floodgate and become a very, very successful venture capitalist, which he still is. 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

• 42:22Speaker 01

  was I recognized there was a risk of me pigeonholing myself or getting pigeonholed as a business author, 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. You 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 5K, 10K, and just help

• 43:04Speaker 01

  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. What do you think? To his credit, I owe him a lot of gratitude. He 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?

• 43:47Speaker 01

  How do I think about should I get into portfolio construction and this and read? What was this zero gravity about 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. But 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 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.

• 44:26Speaker 01

  When this thing came up with Mike Maples, I thought, well, why don't I take what I would have spent on tuition? 120K for two years, something like that. And 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.

• 45:11Speaker 01

  But that is what kicked off the angel investing. What was the biggest mistake you made, 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. I'm like, oh my God, what am I going to do here? I no longer have the bankroll to.

• 45:57Speaker 01

  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. All 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.

• 46:40Speaker 01

  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 because I have 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. Okay. Seems like a sad story. Wow, wow, wow. 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.

• 47:24Speaker 01

  And I think all of those advisors had been advisors to StumbleUpon. 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. They 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

• 48:07Speaker 01

  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 right a 10x, 100x, 1000x or whatever.

• 48:21Harry Stebbings?

  Was Uber the best investment you've made?

• 48:24Speaker 01

  Uber 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 would have been, that was a $150 million mistake or whatever. But I also went back and at the very beginning of COVID, because I was tracking COVID starting in like December or early January, something like that. When Shopify got crushed and went down to like, I'm making this up, but 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. I love the company. I'm still super bullish on those guys.

• 49:07Speaker 01

  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. But knowing what I know now, do I wish I had held it?

• 49:51Speaker 01

  Yeah, of course I wish I'd held it. That's true for a bunch of companies.

• 49:54Harry Stebbings?

  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?

• 50:00Speaker 01

  Yeah, Duolingo I held on to because I tried 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. I 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.

• 50:41Harry Stebbings?

  When did you sell Facebook?

• 50:43Speaker 01

  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 100X. Oops. 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,

• 51:24Speaker 01

  at least I have no fucking idea. So here's the thing, like now my policy is just let almost everything ride. If they go public, if they go to zero, they go to zero. If they don't go to zero, they might go to 100X. So just like assume you do not know and just hold on to them. But that's the luxury of having enough cushion now. Back in the day, I think a lot of these decisions were the right decisions, given at least the information I had.

• 51:46Harry Stebbings?

  Tim, why did you not raise a fund? Like podcasters can raise huge amounts of money and enjoy management fees.

• 51:53Speaker 01

  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? I mean, that's just not how you make the math really amazing. You know, you do a 30 or 75 million dollar fund, then you double or triple that. And then you raise another one and another one, and then you have overlapping funds and hallelujah,

• 52:38Speaker 01

  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. You 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, 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.

• 53:22Speaker 01

  And frankly, I'm not convinced that with larger dollar amounts, this is, 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.

• 53:33Harry Stebbings?

  That I agree, what my advice to you would have been, had we 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.

• 53:49Speaker 01

  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, you know, he used to be the godfather of Silicon Valley. And he was in every deal, right? And 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.

• 54:31Speaker 01

  And that allowed me to go hunting more effectively. Does that make sense?

• 54:37Harry Stebbings?

  You get the report card and then you're double down on three that you thought were really interesting.

• 54:41Speaker 01

  I would double down or I'd be like, oh, wow, that's a really interesting sector. Let me go look at that. That and 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 that stuff was super, super helpful.

• 55:01Harry Stebbings?

  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.

• 55:10Speaker 01

  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. And 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 would 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 homerun. 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.

• 55:41Harry Stebbings?

  Which hurts the most?

• 55:43Speaker 01

  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. This is one where I'm like, ah, 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 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 raised any money. That idea was new to them. They weren't sure they wanted to raise any money.

• 56:22Speaker 01

  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. What 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, like the, the, the deck is stacked in their favor. And it was a, it was, there was a feeling to it, but that, that's pretty much limited to like D to C stuff, I would say. Whenever I stray outside of stuff I could use myself, would want to use myself,

• 57:06Speaker 01

  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. But 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, 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

• 57:46Speaker 01

  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. And I'm not sure I would have time to do that if I were doing dozens of them. But you're, you're right. I did stop around 2015. I stopped Angel Investing completely for a couple of years.

• 58:09Harry Stebbings?

  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 and 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.

• 58:39Speaker 01

  Yeah, 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 have 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. And 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

• 59:24Speaker 01

  in those. I love that. Like Chris Sacca's first fund.

• 59:28Harry Stebbings?

  I was listening here in Sacca, Sacca.

• 59:31Speaker 01

  Yeah, that would be, I mean, that's the most absurd example, right? Because he put, I think, 500K into Uber's Series A 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. There 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 in 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

• 1:00:14Speaker 01

  quite a bit later, and hedge funds and private equity were much, much, much, much later. They weren't even aware of these deals. Then 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 we're getting

• 1:00:49Speaker 01

  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. It seems like I'm just going to get diluted out of existence and blah, blah, blah, blah, blah. And 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 it, 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.

• 1:01:32Speaker 01

  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. Fickle, 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.

• 1:02:16Speaker 01

  And at the time, in 2012, I interviewed a bunch of my friends and also cold emailed a bunch of people. Podcasts, that 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 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 Work Week, that was blogs, right? For, 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.

• 1:02:59Speaker 01

  I made any use of email, which is funny because I was collecting emails starting in 2017 from 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'd 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 till quite a bit later, but the podcast had its 1,000 true fans from the beginning. Because of the blog.

• 1:03:32Harry Stebbings?

  Was there a guest which blew it up? So like for me, it was Ariel Zuckerberg in the early days. I think the Zuckerberg name really helped. But that really instantiated us. Was there one episode where I went, I remember when you did Tony Robbins shows, they were mega.

• 1:03:47Speaker 01

  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? And he's just like enveloped my whole head in his catcher's mitt. I think that's the first Instagram post I ever put up. 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

• 1:04:31Speaker 01

  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 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. That just wasn't really a thing.

• 1:05:09Speaker 01

  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,

• 1:05:54Speaker 01

  but also for me, where I was like, oh, I think there's really something here. If 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 in. I should do a follow-on investment on my podcasting. Did you ever do shows where you thought that'd hit MAGA and they didn't hit? Yeah, I have. I don't think I'm gonna 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.

• 1:06:32Speaker 01

  And I'll usually beg off and say there was an audio problem of some type and I really, really, like, my name in Chinese is Fei Ting Chang or Fei Yu Shang, but it means basically like fei, 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 10, 30%. So I've gotten to the point where that almost never, ever happens. I would say out of 800-plus episodes, there are

• 1:07:06Speaker 01

  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 or both happened. Number 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're interview 10 on a crammed radio satellite tour type day, you're fucked. It's not going to be a good interview.

• 1:07:50Harry Stebbings?

  Tim, you mentioned earlier you were 48. Do you want to be a papa?

• 1:07:54Speaker 01

  Yeah, oh yeah. Yeah, yeah, yeah. That's the, that's, that's the chapter. That's the, I think that's the next big chapter for sure.

• 1:08:01Harry Stebbings?

  Do you prioritize that today?

• 1:08:03Speaker 01

  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, 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 are five, six years in length and I'm still friends with those women. I mean, it is entirely doable, right? To have kids. I do have some fear around the permanence of it, right?

• 1:08:49Speaker 01

  Because I look at all of my friends who have been married, divorced, married again. 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.

• 1:09:12Harry Stebbings?

  Is love not the ultimate sacrifice to your truly efficient mind? Being 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.

• 1:09:26Speaker 01

  I mean, 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.

• 1:09:47Harry Stebbings?

  What do you think you look for in a partner that is non-typical compared to what other people would look for?

• 1:09:52Speaker 01

  I think what I look for that may not be something people immediately pay attention to is someone who is good at de-escalating conflict. I think that is just so, so important. Someone who's a clean fighter, because you're gonna have fights. Of course, you're gonna have fights. So with any significant other, that's gonna be the place. So someone who's a clean fighter, is good at de-escalating conflict, someone who can apologize, and this applies to, of course, myself as well. Those, I think, are... they're really important. You asked for maybe non-obvious, but those are things I look for. Ideally, someone also who's very good at recognizing what's inside or outside of control, which is why travel's

• 1:10:36Speaker 01

  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?

• 1:10:42Harry Stebbings?

  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.

• 1:10:50Speaker 01

  There are a couple of things, right? 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 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. That 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...

• 1:11:35Speaker 01

  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" is 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 and I'm going to prove that I am right. Like, usually that's what it means. As Terry, Terry Real is a very famous couples therapist.

• 1:12:13Speaker 01

  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 level. So like, that's going nowhere. That's just gonna 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. And 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.

• 1:12:53Speaker 01

  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. I 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 type of circumstances, you need tools.

• 1:13:38Speaker 01

  And I think those tools and those communication strategies do 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.

• 1:13:52Harry Stebbings?

  Do you think you should go to sleep angry?

• 1:13:54Speaker 01

  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. What 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.

• 1:14:39Speaker 01

  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. My 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've definitely gotten better.

• 1:15:21Harry Stebbings?

  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.

• 1:15:35Speaker 01

  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 12-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.

• 1:16:20Speaker 01

  So it has like 300 million-plus social views of gameplay already, after pretty much no time at all. So we've playtested the hell out 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 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?

• 1:17:04Speaker 01

  1 in 25 American families or individuals have an in-person social activity planned for any given weekend. And 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 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,

• 1:17:49Speaker 01

  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. When you talk to, whether it's people who are striving for success or people who have 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?

• 1:18:30Speaker 01

  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

• 1:19:15Speaker 01

  on games, but on everything, huge payoff. Just, I can't even put a number on that, along with the team. But Alan and I have become very close. So from a relationship payoff perspective, 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 US 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.

• 1:19:59Speaker 01

  So understanding like the political game. 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? I'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, the marketing has to be the product itself. People have to want to talk about it. We'll see.

• 1:20:44Speaker 01

  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.

• 1:20:54Harry Stebbings?

  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.

• 1:21:02Speaker 01

  Yeah, it's, it's a bit of a WTF move. And it's, 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.

• 1:21:14Harry Stebbings?

  Oh, my God, I totally agree.

• 1:21:15Speaker 01

  Yeah, and you can get, and you, and you can also like the podcast, the podcast for the first 50 episodes. I mean, it's a super part-time endeavor.

• 1:21:24Harry Stebbings?

  That's why I advocate for 996. You're gonna hate this, but I didn't say 996 in a Chinese routine and I'm getting killed for this right now. 9am to 9pm, six days a week.

• 1:21:33Speaker 01

  Yeah, that's, yeah, that's, that's.

• 1:21:37Harry Stebbings?

  My question is, why are people working part-time? You've 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.

• 1:21:46Speaker 01

  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.

• 1:22:18Harry Stebbings?

  I was chatting to Brian Johnson the other day and he was telling me about the duration of his erections. And I said, you should feel, you should steal Tim's title like I did. Just do the four-hour erection. Not bad. It probably clicked, wouldn't it, Tim?

• 1:22:30Speaker 01

  Yeah.

• 1:22:31Harry Stebbings?

  Click, yeah, sure.

• 1:22:33Speaker 01

  I mean, the trade off is you may need to go to go to bed after 8pm to make good use of those erections. It depends on how much, how many lunchtime nookie sessions you can have.

• 1:22:43Harry Stebbings?

  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 your routine.

• 1:22:48Speaker 01

  Yeah.

• 1:22:49Harry Stebbings?

  Doing red light therapy for my penis at that time.

• 1:22:54Speaker 01

  Brian, Brian's run a lot of interesting experiments. If if somebody wants to, I interviewed him on the brain tree stuff before the transformation into into don't die. So if you want a before and after.

• 1:23:05Harry Stebbings?

  Do you believe that he's doing this out of like genuine passion for it? Or is it customer acquisition for blueprint and for the company that is built behind it?

• 1:23:14Speaker 01

  I 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 think 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 thing.

• 1:23:56Harry Stebbings?

  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 with Jack and Rose.

• 1:24:10Speaker 01

  And and just because I don't want to feel like, you know, we're throwing him under the bus. It's like.

• 1:24:17Harry Stebbings?

  We're giving him credit on a large platform that he has massive erections. What, how is this throwing him under the bus?

• 1:24:22Speaker 01

  It's not throwing him under the bus, but it's, you know, like erections do matter, just to be clear. And and heuristic for a lot of male health is, I owe this to Kelly Starrett, who's a very famous PT and performance coach, but boner, no boner. Like in the morning, does it happen or doesn't it? Does it not happen? Like, that is actually like a good leading indicator for a lot of things.

• 1:24:45Harry Stebbings?

  My God, I so want to do 20 VC with Tim Ferriss, erections matter.

• 1:24:52Harry Stebbings?

  Your team is just like, what the fuck?

• 1:24:55Speaker 01

  I mean, yeah, big red arrow on the thumbnail,

• 1:24:59Speaker 01

  pointing to the microphone in front of me. Yeah.

• 1:25:01Harry Stebbings?

  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?

• 1:25:08Speaker 01

  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. And this is not tinfoil hat wearing territory. I mean, I really feel like minimizing microplastic exposure is a good investment. So this, this Rhonda Patrick talks a lot about this from a credible perspective, but like not putting teabags in hot water. Any of the disposable to go cups in most places outside of maybe blue bottle coffee,

• 1:25:52Speaker 01

  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.

• 1:26:04Harry Stebbings?

  What was the one person you'd most like to have dinner with? Dead or alive, and what would you ask them?

• 1:26:10Speaker 01

  It would probably be someone dead. I can't, I can't hone down to one, but let's just say Richard Feynman, 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 did you feel about that? What were you saying to yourself when that happened or before that conversation? The inner monologue piece is effectively self coaching. I find that type of question really fruitful. So I would, 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.

• 1:26:46Harry Stebbings?

  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?

• 1:26:56Speaker 01

  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. But 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

• 1:27:39Speaker 01

  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, alright, 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. I'm just going to copy that. But they don't talk about their

• 1:28:22Speaker 01

  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.

• 1:28:45Harry Stebbings?

  Tim, as I said at the beginning, I wouldn't actually have my business without you. Wouldn't have my funds without you. It would be entirely differently named, which probably wouldn't have been successful. I 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.

• 1:29:00Speaker 01

  Oh, thanks, Harry.

• 1:29:02Harry Stebbings?

  I really appreciate you and everything that I've learned because I wouldn't have my life without it.

• 1:29:08Harry Stebbings?

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• 1:29:52Harry Stebbings?

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