The Exchanges

Q 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?

A 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. 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 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.

AI assessment note: “to try to counteract some of those, I have done certain things.”

Q 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?

A 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. 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 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.

AI assessment note: “To try to counteract some of those, I have done certain things.”

Q 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?

A 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, 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 was 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. 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 varia…

AI assessment note: “I don't think it's impossible, but When you put that much time into something”

Q I want to do a quick fire with you. What is a piece of advice you gave in your thirties that you wouldn't give today?

A 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, 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 tea bags in hot water, any of the disposable to go cups in most places outside of maybe blue bottle coffee, which uses a sugar cane 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.

AI assessment note: “Any advice or videos that I put together involving high heat... I would rescind”

Q 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?

A Yeah, Duolingo I held on to 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, who do I think I am? Like, 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, that was another mega massive mistake. I mean, God knows how much money that would be worth.

AI assessment note: “Yeah, Duolingo I held on to because I try to learn from my past mistakes”

Q 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?

A 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, 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 was 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. 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 varia…

AI assessment note: “I don't think it's impossible, but When you put that much time into something”

Q I want to do a quick fire with you. What is a piece of advice you gave in your thirties that you wouldn't give today?

A 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, 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 tea bags in hot water, any of the disposable to go cups in most places outside of maybe blue bottle coffee, which uses a sugar cane 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.

AI assessment note: “Any advice or videos that I put together involving high heat and eating things out of plastic”

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

A I 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. Cause 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 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 look for. Ideally, 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?

AI assessment note: “someone who is good at deescalating conflict.”

Q Do you think you should go to sleep angry?

A 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. 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 tryin…

AI assessment note: “For me, I would say the answer is yes, you can go to sleep angry.”

Q 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.

A 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, 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 thirty-plus years, twenty-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 hits 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 an email or a phone call from hotshot agent at XYZ talent agency and L.A., and they said, we want to do this with you, and A, B, and C megastars are very interested, and …

AI assessment note: “My closest friends have not changed.”

Q Do you think you should go to sleep angry?

A 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. 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 tryin…

AI assessment note: “For me, I would say the answer is yes, you can go to sleep angry.”

Q Tim, when did you make your first real money?

A 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 Brain Quicken back in the day. The one that, in a lot of ways, was the experience that formed the 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.

AI assessment note: “I made my first real money with my very, very first company.”

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

A I 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. Cause 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 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 look for. Ideally, 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?

AI assessment note: “someone who is good at deescalating conflict. I think that is just so, so important.”

Q What was the biggest mistake you made, do you think?

A 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 a 120 K for two years. I go in, I think one of my earliest investments, I was like, I'm putting in 50 K. 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 a 50 K almost immediately goes to zero. I'm like, oh my God, what am I going to do here? I, 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 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. Alright, 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 …

AI assessment note: “Biggest mistake was I didn't realize in the early stages just how effective certain founders”

Q 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.

A 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, 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 thirty-plus years, twenty-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 hits 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 an email or a phone call from hotshot agent at XYZ talent agency and L.A., and they said, we want to do this with you, and A, B, and C megastars are very interested, and …

AI assessment note: “My closest friends have not changed.”

Q What was the biggest mistake you made, do you think?

A 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 a 120 K for two years. I go in, I think one of my earliest investments, I was like, I'm putting in 50 K. 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 a 50 K almost immediately goes to zero. I'm like, oh my God, what am I going to do here? I, 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 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. Alright, 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 …

AI assessment note: “Biggest mistake was I didn't realize in the early stages just how effective certain founders”

Q Was it a mega hit from the first episode?

A 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 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. 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.

AI assessment note: “I wouldn't say it was a mega hit.”

Q 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?

A Yeah, Duolingo I held on to 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, who do I think I am? Like, 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, that was another mega massive mistake. I mean, God knows how much money that would be worth.

AI assessment note: “Yeah, Duolingo I held on to because I try to learn from my past mistakes”

Q Tim, when did you make your first real money?

A 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 Brain Quicken back in the day. The one that, in a lot of ways, was the experience that formed the 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.

AI assessment note: “I made my first real money with my very, very first company.”

Q Was it a mega hit from the first episode?

A 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 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. 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.

AI assessment note: “I wouldn't say it was a mega hit.”

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

A Yeah, I would say, I mean, the book that did the worst as 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. Um, like I asked this, I'll, 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 interaction, Singapore, Safety net, health insurance, everything else you can imagine. I wouldn't say health insurance, just health system, blah, blah, blah, blah, blah. Kind of predictability. And then I asked my Danish friend why the Danes seemed 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, four hour body, and then the four hour chef was 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 no…

AI assessment note: “in the case of the four hour chef, so the four hour chef had the biggest delta”

Q Tim, 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 matrix that didn't matter?

A That's a very good question. I think of myself as a 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 overweighing 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. 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, all this stuff after I die, or if I'm gonna do this giving pledge, blah, blah, blah. If we just put that a…

AI assessment note: “there would be the overweighing of quote unquote productivity overall.”

Q Did you ever do shows where you thought that hit mega and they didn't hit?

A Yeah, I have. I don't think I'm going to name names because that's just not how I, I operate, but yeah. 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, I was just like, not good enough. 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, is Fei Tingcheng, or Fei Yucheng, but it means basically, like, Fei, Ferris, very honest, because I was so blunt in all my Chinese classes, so I, 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.

AI assessment note: “Yeah, I have. I don't think I'm going to name names”

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

A Yeah, I would say, I mean, the book that did the worst as 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. Um, like I asked this, I'll, 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 interaction, Singapore, Safety net, health insurance, everything else you can imagine. I wouldn't say health insurance, just health system, blah, blah, blah, blah, blah. Kind of predictability. And then I asked my Danish friend why the Danes seemed 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, four hour body, and then the four hour chef was 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 no…

AI assessment note: “the four hour chef had the biggest delta, right?”

Q 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.

A 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 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.

AI assessment note: “I'd have to go back and look. I mean, the most common way”

Q Did you ever do shows where you thought that hit mega and they didn't hit?

A Yeah, I have. I don't think I'm going to name names because that's just not how I, I operate, but yeah. 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, I was just like, not good enough. 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, is Fei Tingcheng, or Fei Yucheng, but it means basically, like, Fei, Ferris, very honest, because I was so blunt in all my Chinese classes, so I, 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.

AI assessment note: “Yeah, I have. I don't think I'm going to name names”

Q 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.

A 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 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.

AI assessment note: “I'd have to go back and look. I mean, the most common way”

Q Tim, 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 matrix that didn't matter?

A That's a very good question. I think of myself as a 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 overweighing 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. 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, all this stuff after I die, or if I'm gonna do this giving pledge, blah, blah, blah. If we just put that a…

AI assessment note: “if I had to pick one, there would be the overweighing of quote unquote productivity”