Tim Ferriss: Why You Should Stop Over-Optimizing Your Life

By the way, this episode, where's the camera? This episode's not for you. This episode's for me. I've been listening to this guy for a long time. I read his books. I used to gift, your book was one of the most gifted books I had for like a long time, maybe the first 10 years of my career. Thank you. And I would say, "I'm giving you the 4-hour fever." They're like, "It's called The 4-Hour Workweek." I said, "You're gonna read this and then for 4 hours you're gonna question everything in your life. I call that the 4-hour fever. It's normal, don't worry. Call a doctor if it lasts beyond 4 hours." And so today I have like a bunch of things that I think maybe the audience wants to know. Honestly, I don't give a shit. I just wanted to ask you the questions that I want to know.

I think that's the key to a good podcast.

Exactly. So one of the things I wanted to know is you talked about this space where you're like, I'm thinking about what's next. I've been there. I sold my company. What's next? I have a lot of friends that are there right now. Yeah. And what's the What's the approach? Because it can be paralyzing to have 1,000 options.

Yeah.

Especially when you have a track record. You have a track record of success now that almost adds some difficulty to the, to the, to the answer of what's next because it's got to be good. It can't be, it can't be something tiny, right? How does Tim Ferriss approach the what's next question?

Yeah, I think it can be tiny in a sense, right? I mean, let's just— I'll answer your question, but let's just note that the podcast started as I'm going to try to do 6 episodes. That's tiny.

So did this podcast, by the way. This is a tiny side thing.

So I think that, to quote Seth Godin, who is really wise beyond even what people would expect, and he walks the walk, he's a real operator who has authored a contrarian— that's not contrarian, it's an unorthodox life for himself. And I have a lot of respect for Seth. And he said, big things, the big dreams, changing the world, those are easy to hide behind. He's like, but doing the smallest thing possible, the next action, you can't hide behind that, right? It's, it's a, it's a pass/fail.

Say that again. So big dreams are easy to hide behind.

Yeah, but when you make something small, next, next episode, right? If you don't do 6 episodes, you fail to do 6 episodes. But it's like, I'm going to change the world and do this and blah blah blah. Great. But like, you know, not to, not to like quote everybody in the world, but like kind of David Allen GTD style, like, okay, great, what's the next physical action, right? Okay, now you have a report card, right, that I can give you because you've just made yourself accountable to me in a way to like do this thing that is very discreet. And so this— I, I don't underestimate the small things. I think the big visions can be helpful at times, and I could give examples of that where it's been helpful for me. But to answer your question, in terms of choosing the next thing, I'll say upfront, I don't know what my next thing is right now.

But how do you approach that? How do you approach figuring that out?

Well, there, yeah, there are a few ways. So the first is I make, I suppose, a menu of things I would like to try.

Okay.

Which is often a thing, a list of things I would like to learn. Like, I just returned from 3 days overseas with a game designer prototyping games.

Nice.

And board games or?

Yeah. Yeah, sweet.

And That's something I'm trying, right? We'll see. And the— there's a lot that goes into even choosing the things on that list.

But, and do you have a box on the menu, like the part of the menu where it's like, and we have like sea urchin? That's, you know, do you have the weird box where you're like, let me think of some non-obvious—

oh, I try to do weird stuff, right? No, no, because there's tons of stuff that I could do that would be straightforward or predictable or reliably profitable. That's the That's the most seductive, right? And I'm not saying they're bad options, but like, I could make a course. Yeah, I could. I'm sure— I know I could execute that and make it do really well, right? I know that. I know I could potentially create some type of membership platform or mastermind or something like that, and I think I would enjoy some of these things, right? However, Let me come back to the criteria. So whether I'm coming up with my list, I go for weird. If there's something weird, that is a huge plus, kind of, yeah, that's like a turbo boost for inclusion, right? You're not bending to the social expectations or norms, right? Those are the weird things. That's why they seem weird. And chances are, if those end up on your list, either they're easier for you than they are for other people or you're going to have the enthusiasm and therefore endurance to do it longer, harder, more intensely with greater purpose than other people. Those are all huge competitive advantages. Not that this— not that all of life is a competition, but to stand out in a crowd, right? You need—

the weird ones are like the immigrants. It's like, you got here. If you made it here, you already have shown some amount of— there must be some strength that got you onto this list. Oh, totally. Because you had a negative filter associated with it.

Yeah. Yeah. Or you just come from better, like, more resilient or risk-taking genetic stock. Like, yeah, if I could invest in like first or second generation immigrants, if I could just choose a— if I could only choose certain filters, that would be very high.

I've said that. I've been like, I love Mormons.

I love—

if you're from the Ukraine, I'm listening. If your name is Dimitri, love it. Tell me more. What, what's your idea? Come closer.

Yeah. So, so the, the, the short synopsis of how I choose projects is I look for projects that can be successes even for me long-term, even if they fail short-term. What that means is projects where by any external measurement or perception they can be a failure. However, in the process of pursuing those things, I develop or deepen relationships, or develop or deepen skills that are durable, right? And those— when even if it's something like that, those snowball, right? right? Because if I do like 5, 4 projects, they all fail, but I am developing relationships with the type of people I want to develop relationships with, I'm developing new skills, and then I start to bridge all those things and I'm paying attention, I'm taking good notes, my experience is eventually you win, right? Whatever that happens to mean. That's kind of it, honestly. Outside of that, I would say these days, some getting, getting old as fuck and all that, is energy and energy out. Like, does this— do I have more energy doing this, or do I have substantially less?

Right.

And that's a product also not just of what you're doing, where you are, who you're interacting with. I pay attention to that stuff because I could do something that people might see as frivolous— archery or something. I could pick a whole ton of them that seem like wastes of time But that's like plugging my iPhone into the wall. It's like, oh, now I have 100% charge instead of 20% charge. There's a lot more that I can do with this phone.

Right.

And just because I plugged it into the charger in the circus funhouse doesn't mean I have to use it for the circus funhouse.

Right.

You get to transfer it to other things. So that's, that's also something as a fundamental currency that I pay a lot of attention to. Right.

I'll tell you two related things on that. Last night I was at dinner with, I think, a mutual friend, Joe Gebbia, founder of Airbnb. And he was saying, he's like, "Oh, what are you in town for?" I was like, "I'm doing a couple podcasts." And we were talking about it. He's like, "Okay, so what's like a win? You know, like why do you do that? You fly into town, you leave your kids, you make an effort. What are you looking for out of these?" I said, "Well, I just wanna leave with more energy than I came." And really I want the guest to feel that way too. Like at the end of the day, like what is the only way I can guarantee a success out of this is if you walk outta here feeling energized rather than drained from this conversation. And if that's a, so I've been using that heuristic and it's so powerful to use the kind of like, where's my energy after activity and how am I leaving the people around me also? You want it to be mutually beneficial in that way. The second thing he said was that I thought you'd find interesting. I was like, we were going through this exercise I do called the Perfect Tuesday. So I was like, life is not really about these peak experiences. Like, yes, those like going and seeing, like there's the total eclipse happening. Go and see this total eclipse. Apparently it's like a totally emotional experience if you're there. I think it's happening in Dallas this weekend or whatever. There are those moments, but they're few and far between. Most of your life is just like Tuesdays, just normal Tuesdays over and over again. And so put a lot of effort into thinking like, what's a dream average day for me? And then try to live that dream. And so we were talking about it and I asked him, I said, like, how close are you to your perfect Tuesday? He's got all the resources in the world, right? Sold Airbnb. They went public. It's a super success. And one of the things he said, he goes, that's a great question. I go to the gym for my physical, my— to get my— like to physically fulfill myself. And then I work, which is great. And I feel productive and useful to the world. And I have my family. Family, which is love. He's like, but I don't really make time for creativity anymore. He's like, he's a designer by trade, and he's like, I need like a creative gym. He's like, I feel like if I, if I sat down and I started sketching, it'd almost feel like I'm wasting time. Like, it's like, what am I doing here? I found that really interesting, and I feel like you do a good job of kind of making time for the things even if they're not societal norms for what people do.

I try. Yeah, I try to do it for sure.

Do you have your version of a creative gym?

Yeah, I mean, I was like playing the drums earlier today. So from a like financial perspective, that could be wasted time. But the financial stuff, and we can talk about it, it's very useful for certain things. I mean, money only has a certain utility. It's kind of like, yeah, you can eat until you're full and then you can eat until you're stuffed and then you can eat until you're sick. But like, at what point do you stop eating? Like, there's a point beyond which food ceases to serve any positive function, right? And then like things in excess kind of become their opposite. So you have to be very careful with money and other things, you know, alcohol, power, fame. They, they can distort a lot of things.

How do you keep that in check? It's hard to keep some of those things in check.

I mean, I just know too many rich people now to think that money fixes the inner game or the most problematic kind of psychological challenges that people have. It doesn't at all. It can fix a lot, like money can fix money problems, right? But that's just one category, right, of issue. And yeah, and it's incredibly useful as a vehicle for other things, uh, but I find a lot of folks very uncreative about how they use money. So I do, I would say, make time for the creative gym, more so in the last handful of years. But time with concept artists doing concept pushes, building fictional worlds, playing the drums earlier today. Had an art teacher, Stan Prokopenko, who runs proko.com. Amazing teacher. Came out and we worked on a whole bunch of different aspects of drawing and live charcoal sketching and shading and so on. One could make the argument that isn't entirely off base that must be nice. Great. You have all this time. You can kind of do what you want to do. But I will say also that when I have been at levels of peak performance professionally, I usually have a creative outlet of some type. It may not take the form of charcoal, right, drawing— that's a bit on the nose as far as creativity goes— but like jiu-jitsu is creative, right? It's like going to the jiu-jitsu gym and learning how to operate in that free-flowing environment. That's very creative, right? So if, if you're working on anything that requires a level of extreme present state awareness and improvisation and experimentation, like you're in the creativity game, right? So there are a lot of ways to do that.

I got a book recommendation from you.

Oh yeah, I haven't seen this book. This is a few decades.

Yeah, I've never even heard of this book.

It's an old book.

This book is called Toughness Training for Sports, and it's by Jim Lauer. Do you remember anything from this book? You probably read this a long time ago.

I mean, I read that when I was probably 15 or 16, and I do remember that there is an inventory, there's an assessment in there. It's 2 or 3 pages long and you're intended to give that to your coaches, peers, teachers, people around you effectively for like a 3— what I would call now a 360 review of different factors that affect mental toughness. Yeah. And I did that when I was 15 or 16.

So this one, right?

Oh, there you go. Yeah, there we go. So the Competitive Adjective Profile. Yeah. So there's, there's, I found this book incredibly helpful and later had Jim Lehrer on the podcast, did some training with him and a, and a tennis pro with tennis. And having that 360 review from a mental toughness perspective was incredibly helpful to me. It provided me with a level of awareness that I couldn't have developed on my own.

Right. And one of the things it talks about is basically, if you haven't read the book, it's like there's talent you're born with, there's skills which everybody else understands, you practice, and then there's performance.

Yep.

And there's a gap between talent and skill. That gap is called practice. There's a gap between skills and performance. And that's basically your toughness training. It's the, and he calls it, I think, the ideal performance state. And it's like, if you ever played sports, you know this, which is like some games you're off. Oh, I just wasn't fully locked in. I was, I just wasn't, I didn't play up to my potential. So like what causes that versus those days when you get in flow state or you're just totally dialed in and you kick butt out there and it's like, well, that's because you were in your ideal performance state. This is not just for sports, obviously. Like this can be for, you know, how you show up as a dad at home. It could be show up for work. It could be for this podcast. How do I show up in my ideal performance state? Do you do things to be in your kind of ideal performance state?

I do. I do. I would say that also, just to highlight a few other things in here, I haven't looked at this in a very long time, 20-plus years, but it discusses at length stress and recovery and deloading phases and periodization. And awareness. And there are all of these different checklists and assessments, different assessments that you might use after a given training session, and stress evaluations and so on, all of which helped me to become more aware of cause and effect in what I was doing. So I had a, I had a fantastic— I mean, my best season by far after reading this book. And there are other factors that played into it.

Hey, real quick, you know, one of the cool parts about we're doing is that people have reached out and told me that they've built actual million-dollar businesses, made their first million off an idea they heard on the show. That is crazy. That's wild. That's why we wanna do the show and we wanna see more of that. One of the questions we get asked over and over again is, is there some kind of idea database or spreadsheet where we list out all the different business ideas that we've talked about? Well, the answer is finally yes. The fine folks at HubSpot have dug through the archive and pulled out 50+ business ideas and put them into a business idea database. It's totally free. You can click the link in the description below. And get the database for you. All right, now back to the show.

In terms of ideal performance states, I've become less focused on optimization overall, I would say, just because so much of it just does not fucking matter at all. And the amount of breaking news—

Tim Ferriss optimization.

Yeah, I mean, there's a place for it.

Who needs it?

There's a place for it. There's a place for it. But it's like, are you taking a taxi from the start to the finish line of a marathon because it's efficient? I mean, like, yeah, speed reading poetry. It's like there's a, I suppose, a cult of optimization that is appealing on a lot of levels, but it ends up being a hammer looking for nails and it gets applied to everything. And I think that that misses the forest for the trees sometimes. And I've been guilty of that for sure. So, but in terms of optimization, I would say that let's take today as an example. So I had a great day today. Today was pretty uncrowded. I had a few team calls, meaning employee calls, earlier today. Typically those are on Tuesday, but it got shifted forward because I was traveling yesterday. Beautiful day outside here in Austin, which helps, of course. Went for a walk, got a cold brew coffee, had a phone call with a friend, came back, did a bit of work, knocked off a few emails or a couple of pending angel investments and deals of that type, and I had to get back to some lawyers and so on. That took 15, 20 minutes. Printed out some documents to prepare for a podcast that I recorded earlier today and then did a 7-minute— I guess it was about a 7-minute cold plunge at 40 degrees, which is pretty chilly.

That'll wake you up. 7 minutes continuous?

Yeah. That's solid. That'll wake you up. And I use that in part because I knew that we would be recording this late and I didn't want to consume too much caffeine early in the day. And then consume way too much caffeine throughout the day and end up not being able to sleep since we're recording this at night. And also then had a little bit of titration with like a light green tea before recording my own podcast after walking a bit, had some synthetic ketones. So beta-hydroxybutyrate, which does help cognitive performance quite a bit. So it can act as a stand-in for me for more caffeine. So it's a blended— let's just say like tail end of the cold brew, green tea about 30 minutes prior, and then also the synthetic ketones about 30 minutes prior. And light meals, so very light meals. If I have a lot of mental lifting to do, then I generally eat pretty lightly, mostly protein, a little bit of fat, small amount of carbohydrate. And here we are, that's the day, right? I got a great night's sleep last night, which isn't always the case, but was the case last night. And for me, that is an optimized day. There's not a lot crammed into it. I'm not executing this sophisticated time management Tetris to be as efficient as possible, but I'm keeping the main thing the main thing. Like the main things were Team one-on-one calls, being physiologically and just literally, I guess, prepared in terms of documentation research for podcasts that I recorded, and then being in a good state for having this conversation. That's it, right? It's like you don't have to do a lot every day.

Yeah, I think that's effect versus efficiency, right?

Effectiveness over efficiency.

Efficiency would be more like maximum output per unit of time regardless on what the output is directed towards. Is that right?

Yeah, yeah. It's— if you think of effectiveness as what you do, effect— efficiency is how you do any given thing. But doing something really well doesn't make it important.

So yeah, I'm a Tony Robbins guy. He calls it, uh, majoring in minor things.

Yeah, majoring in minor things, not a great way to go.

Yeah.

And I also fritter away time and lose days to bullshit, or I don't sleep well, and then I'm grumpy, and I have too much caffeine, and I have a shitty night's sleep. Like, I, I suffer from all that stuff. Yeah, human. I make mistakes. But if you're thinking about projects as experiments, using the criteria that I laid out before, and you're doing your best— you're gonna falter, you're gonna make mistakes— but to keep the main thing the main thing, and you have a good rationale for why that main thing is the main thing, over time you tend to you tend to perform pretty well and just ship a lot more than most people. Even if you go a month without doing anything, right? If you get fuck all done for a month, sometimes that happens to me, but I try. I would almost rather do that. And I guess my version of doing fuck all might not look like fuck all, but I would rather do that than rush into committing to something that doesn't meet my criteria because I'm uncomfortable not being busy.

Right.

Because that's how you end up overcommitting to things that longitudinally eat up years.

You said you're comfortable not being busy.

Yeah.

Yeah, that's a big one.

Yeah. Just, I mean, like The best way to get what the outcome of busyness should be, which is, right, like big effects of some type, or it could just be more joy, whatever, is not by engaging in nonstop action. All right. It's by, in a sense, it's similar to my startup investing. It's like having very tight parameters, a lot of constraints, and not breaking your rules, right? It's like the equivalent of like blowing your bankroll in poker or blackjack or in startup investing would be you have no, you have no real thinking around portfolio constructions. You don't have enough positive constraints, so you get overenthused about a ton of things. You put out all these bets too quickly and then you lose all your money. Or you just can't play the game very long because you were never playing the long game to begin with. And in life, like, that bankrolls your time, and, uh, that's non-renewable. You can always make more money.

I've heard you say something like, uh, people who are on 24/7, or they're just like hustle, hustle, hustle, grind, grind, grind, uh, you, you're like, that's actually a dangerous form of laziness.

Yeah, uh, indiscriminate action.

Indiscriminate action is a form of laziness.

Yeah.

When people are like, I need to do X and then like, first I'm going to do research or make a long list. It's like, that's fancy procrastination. Like, yeah, shouldn't you just— you don't need a list of 100 prospects. Just call one. Let's start with that.

Yeah. Yeah. And we all have our favorite pet forms of procrastination. Like reading is one of mine, right? I have to be very cautious about reading. Love reading. And no one's going to say you should stop reading.

Yeah.

They'll be like, oh, so diligent, doing so much homework.

So sophisticated he is.

So sophisticated.

I want to ask you about your book thing in a second, but before we do that, teach— you said teaching. Teach me about the art of podcasting. You've been doing this for 10 years now.

Yeah.

You've done many a high-stakes interview, whether it's pick your favorite famous person or pick a person you admire. What can you teach me about the first 5 minutes of a podcast?

First 5 minutes?

Maybe 5 seconds. I don't know.

Yeah.

The beginning of a podcast.

Yeah. I mean, the most important 5 minutes are the conversation I have before I start recording with someone.

Okay.

So that would be putting them at ease to the extent possible. Right. My job is to make you look as good as possible. Every guest has final cut.

Mm-hmm.

So let it all hang out and we can cut whatever you want to cut. You'll get a transcript. Nothing's going to get published before you give it the okay.

Put the walls down a little bit.

Yeah, put the walls down. General housekeeping so they don't get distracted. Like if you need to take a water break, bathroom break, pause, stop, you want to start a story over again, that's all totally fine. I'll keep an eye out for things that I think we might want to cut, like if you accidentally mention your kids' names or something like that. So like, oh, this guy's A, done it a lot, B, is actually looking out for me, C, has actually sat in my seat, interviewee seat, a lot. And I always ask, and like nobody, almost nobody asks this, it's such an easy layup in terms of differentiating yourself. Ask interviewees what a success would be like. What would you look back at this? I asked my interviewee this morning about this. I said, 6 months from now, you look back and you say, I'm so glad I did that. Why? Like, what does success look like? And even if they don't have an answer, they're so unaccustomed to being asked anything like that. They're like, huh?

And it's like being a good boyfriend. It's like, he cares. It doesn't even matter if he brought me the water. It doesn't even— I could have got the water myself. But the fact that he did, he's thinking about me. Who cares?

Yeah. So I would say that that pre-record conversation is something I don't see very often. Like when I get—

I didn't do it today.

Well, yeah, I mean, and sometimes that's fine, right? It's like I'm comfortable in this environment, right? And we've had contact before. Yeah, but it's not always going to be the case. It could also be the case that somebody is very experienced but they're rushed, right? They got in like an argument with their husband or wife the night before, and their publicist is frazzled and off their meds or whatever, and they're just running from thing to thing to thing. And then boom, they get plopped in front of a mic, or they get plopped in front of a computer, and they're like, okay, go. Yeah, you're talking to this guy named Tim. Okay, you need to give them an on-ramp if you can to decompress a little bit from that experience. It doesn't always work, But it's, it's worth the investment in my experience. So that's even if I have to give up 5, 10 minutes of the interview, right? Let's just say they have a hard stop at 90 minutes or 60 minutes. I will still give up that time. So that's, that's one. In the first 5 minutes, I would say it depends a lot on the, the profile of the person. And I don't mean fame. I mean, have they been interviewed 1,000 times? In a case where someone's been interviewed 1,000 times, I want to ask them a question that shows I've done an inordinate amount of research. Right. So I'll ask them something that, for instance, I'll very frequently dig up like a deep cut.

I've noticed you do this.

Yeah. Third grade teacher or a mentor that helped them when they were at one school, when they were transitioning from one place to another. That got mentioned in passing in a profile in The New Yorker 8 years ago. I'm like, who was so-and-so?

Right?

Tell me about so-and-so. And they're like, huh, okay. And that can get them off of autopilot. Whether someone's been interviewed a lot or very little, I will often ask them beforehand because there's a lot of prep that goes into it. If there are any greatest hits stories, I'm like, what are stories people respond really well to that stick with them, that people have brought up with you a year later, 2 years later? And they could be an academic, right? Academics talk to people, right? Just not necessarily Tony Robbins or Edward Norton, but they're in front of people. So they'll— they should have probably some examples or anecdotes or studies, things that really stick with people. Okay, great. And I will then figure out a question or a cue, or I might even ask them to suggest one to prompt talking about that. And I will lead with that for two reasons. First is that I'm starting with something that my audience is likely to resonate with. Number two, I'm giving them a win, right? Fastball. I'm giving them a win upfront, and that is helpful oftentimes when someone doesn't know where the conversation is going to go. To that point, I always try to tell people where I am likely to start. And that's part of the pre-conversation. I'll say, I'm thinking about starting with this, right? Because I don't want to cause anyone to stumble out of the gate or for us to get caught on our heels. This is probably where I'm going to start. Do you think that's a decent place to start? And if they're like, well, I don't know, it's like some random thing I read on the internet that isn't true. I want to know that before we start. And if they're like, oh yeah, yeah, that'll work great. Now I've planted that seed. Their brain's working on that while we're doing the housekeeping, while we're talking about everything else. And then we start and it's usually pretty smooth, at least, you know, running out of the blocks. So those would be a few things that come to mind for the first 5 minutes.

That's a great answer. Very helpful to me because we usually do the show. It's me and Sam.

Yeah.

And it's— that's the core of the show is me and Sam hanging out and our dynamic is very simple. It's, dude, have you seen this? It's like a random show. Like you do the random show. We do our— it's— that's very much like the core of our show. And we usually, if we have guests on, it's because we want them to do that with us.

Yeah.

But then occasionally there's guests where actually it's us scratching our own itch. I want, I really want to meet this person. I want to get to what they're really like and I want to ask them the questions that I don't feel like I've heard from them in the same way that like some people say you should write the book you, you wish you could just read. You wish you could read it. If somebody else had written it, you wouldn't write the book. That's the way I feel about when I do an interview like this. It's like, what is the question that I haven't heard in addition to the greatest hits, because you want to, you know, explore those a little bit together as well.

And it also depends on what you mean by good podcast, right? So there's good for you or me personally, and then there is good for the audience, whatever the audience is, right? Depending on the show. And I've gone back and forth on that, right? So sometimes I'll do a show for the audience every once in a while, right? I'll have a couple of Scooby Snacks for myself. But I'll do something that is really for the audience. That is a risky approach.

Seems safer, but it's actually probably riskier.

You can get shaped by your audience and then become a bit of a, like, domesticated oxen getting driven by what you perceive to be the preferences of your audience. But I have the Henry Ford maxim in mind, which is— and I'm paraphrasing here— but effectively, people don't really know what they want or need. Which includes you and me, by the way. But for that reason, rather than playing the speculation game, follow your own interest. And the risk there is that you end up playing inside baseball and really doing something that is not necessarily transferable to your audience. As far as I'm concerned, and maybe I just have the luxury of being a relatively early mover in podcasting, but if your goal is to do this for hundreds and hundreds and hundreds of episodes, or that's not the goal at all, but if you're, if goal is to continue to— continuing to have this amazing, ridiculous job, which is just absurd, like this is a job, then you got to play the long game. And part of the long game is, right, it's like training and recovery. So if you need to take a couple episodes as recovery that are purely self-interested, just for you, that's what you do. And I don't have any compunction about that. And the personal is the most universal also. So if depends on your audience size, of course, but with, with the size of my audience, if something is bothering me, if something is really piquing my curiosity, if something's in my head at night and just won't go away, chances are there are at least, I don't know, a few thousand, a few tens of thousands of people who have the same thing going on, right?

I heard this great quote from my buddy, uh, how much has the world benefited that Tim Ferriss decided not to just keep selling supplements and to do like to do other things. Like what would the world have been like had that not happened? I think that's a, that's a great compliment.

Yeah, very huge compliment. Very kind.

If you go from selling supplements, which makes a lot of money, it's like a very clear, direct payoff and you could do good at it to being an author, that's like, you know, not usually a good, it's not usually an upward career move, let's say. So why'd you do it?

Well, there are a few things I would say. So the first is that I didn't end up selling the supplement company until 2009. So whenever possible, I have things running in parallel. I do not view myself as a risk taker. Like, if anything, I would be a producer— risk reducer, like risk mitigator, for sure. Like, I'm very good at capping downside risk. And in this particular case, I already knew that from, uh, From a— from an intellectual perspective, that sounds too pompous, but I'm struggling to find a better modifier. Let me put it a different way. My learning curve with the sports nutrition supplement world had flattened largely. I understood the basic mechanics. I understood distribution. It wasn't that interesting to me. And it was also an industry that was and still is marred by a lot of bad behavior, right? And unbelievable tactics, and in some cases just outright deception. I mean, legal and illegal, that I, I really struggled being associated with. And if we really flash back and look at what I thought I might end up doing as an adult, I always wanted to be a teacher, in part because I had these amazing teachers that had a huge impact on my life. Kind of saved my life in a bunch of ways. I think I could have gone in a really bad set of directions, and they helped prevent that. So I thought, when I get enough experience in life, which is not now at that age, 29, but eventually it'd be really nice to be a teacher and have that kind of impact. So I thought 9th or 10th grade teacher. Still haven't done that. I mean, I've done some volunteer teaching, but I had been going back, I want to say since 2003, to Princeton to teach this guest lecture. Right. I was invited to come back and speak.

I've tried to find these online many times, by the way.

They're not online.

I wish you had uploaded them.

Yeah, they're not online. I don't think I recorded them. I might have recorded one or two. I'm not sure. But if I could find them, I'd be curious to see them. I'm sure I would.

Well, I'm sure the book kind of grew out of that, right? Like you basically represent your lifestyle.

Yeah. The notes from that, because every time I spoke, it was twice a year. Ed Shao, the professor, high-tech entrepreneurship, invited me back. Because I had the harebrained idea of doing everything bootstrapped and all the other guest speakers had these venture-backed companies and some of them were huge. I was small fries by comparison, but I was doing it my way. I was taking a different approach. So I came back and twice a year, a lot happened in my life at that point. I mean, it was trench warfare dog years, right? It's like if you ask anyone who's had the manic depressive experience of being involved with crypto, it's like, yeah, what does the last year felt like? And they're like, 17 years.

Yeah, exactly.

And it's similar, I think, when you're running a company in the early stages. It's like, you know, 2 months ago is like a lifetime.

It's like Obama when he left office.

Yeah, yeah, went from black to gray hair. Yeah, exactly. I mean, look at me, right? No hair. So, uh, I would say that that desire to teach and the, the positive feedback, really positive feedback I got from workshopping the lessons and principles and so on in this class led me to conclude a few things. Number 1, I really enjoyed teaching. Number 2, teaching in that format in front of 20, 30, 40 students didn't scale. Now, I think scale can be a dirty word and dangerous and overly seductive for a lot of folks, but it, it wasn't going to enable me to reach a lot of people. And then I was done from an identity perspective with the supplements. So looking for something new, and I had an author friend of mine— this is a shortened story that could be really long— but effectively say, you should write a book, and start introducing me to agents and editors, even though I didn't want that, right? Right. I was just looking for feedback, and suddenly I had all these intros, and so I was like, ah, okay, well, let me start having these conversations. I'd also at that point returned from a year and a half, or about a year and a half of this global walkabout, which I chronicle some of in the book, right? Argentina and this, that, and the other thing. And I came back and I was like, okay, what next? Right? I'm not motivated to really go into hypergrowth mode with this company. This isn't going to be my thing for 10 years, 20 years. So what next? And that coincided with these intros. You know, the book was eventually accepted and there was an offer made, but a lot went into it, right? 20-some-odd, 26, 29 rejections from publishers and so on. But I knew the material worked, right? I had the confidence because I'd workshopped it. I knew—

With a live crowd, which is huge.

Over and over and over and over again. I knew it worked. Right. And I frankly love experiments. That's the way I model my whole life. So I viewed the book as an experiment. I was like, at the very least, it's like an MBA. It's like, all right, it's like a, a break from whatever I was doing that looks acceptable, like on a resume slash like career trajectories. It's like, all right, let me try it.

And it's a great mask for unemployed, right? No, it's great. I'm writing a book.

Great.

I'm getting an MBA.

Yeah, great mask for unemployed. And, and then everything went bananas.

Uh, well, you did the podcast that way too, right? Experiment. You were like, I'm gonna record— I forgot what— 6 episodes. And like, you, you built yourself a golden bridge if you wanted to retreat. You're like, hey, I'm going to try this. I'll do 6. It's either going to be a wonderful 6-episode series or it's going to be the next thing. But like, I'm going to just portion off this experiment versus making a huge commitment.

Yeah, give yourself a grace flexin'. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a grace flexin', right? It's so simple, but it's such a psychological— it's such a strong form of psychological leverage that I think very few people use, right? They're like, my next thing is this. And I'm like, oh, totally.

I felt that before. I felt that pressure to have an answer.

Yeah.

I want to ask you about a different— a couple of your, like, principle— core principles that I have found very useful, and I want you to unpack them. One is the Law of Category. Can you explain what is the Law of Category and maybe how you used it?

Sure. The Law of Category is, is taken directly from a book called The 22 Immutable Laws of Marketing. The law of category in brief is a description of the power of creating new categories. So rather than trying to be the best in a crowded category, trying to be the only in a new category. That's where Amstel Light comes in, right? The, the first light imported beer. Okay, there you go. Or in the US, let's just say low-cost airlines, Southwest. Right? And there are a million examples that you could find. The, the law of category is also, I would say, an encapsulation of something that might be called the Blue Ocean Strategy versus the Red Ocean Strategy. So there's a book called The Blue Ocean Strategy I would also recommend that people read in combination with this chapter from The 22 Immutable Laws of Marketing, the law of category. I think I put it in either Tools of Titans or Tribe Mentors. I liked it that much. I went to— I went through all the brain damage of getting permissions to include it. And they— those two pair well with an article you can find for free. You can read it in 15 minutes called 1,000 True Fans by Kevin Kelly on kk.org. You can find that. And they're all driving at the same thing. Which is positioning and differentiation and trying to figure out how you can be the first something. Now, some— sometimes that turns into a bunch of hand-wavy smoke and mirrors nonsense like we did, like we discussed earlier. But at least as an exercise, it's, it's worth considering because, for instance, one of the questions I was going to ask you, which you can, you can answer, or we can just use it as a sample question, was when a diehard fan of your show is talking to someone who does not know the show, how would you ideally like them to describe the show, right? And that is a question of positioning, because branding, it gets turned into this huge process with flowcharts and tons of agencies and companies and this and that. And sure, I'm sure there are people who are very sophisticated with their approach, but at the end of the day, for me Brand is what people consistently associate X with. X could be you, X could be the show, right? How do they describe it?

Right.

That's it. That's your brand. I mean, just like a brand, like, where does the term brand come from? Like brand on cattle, right? So from that perspective, I think it's very useful when you're considering doing a new project. It's not how can I be the best competing in the same way against people doing the same thing? That is not the frame. And even if you end up emulating other people or borrowing best practices, I think it makes sense to start with examining the Law of Category and thinking about Blue Ocean approaches. Which is why, for instance, with my podcast, we're now at the 10th anniversary, and I don't, I don't really see a viable path forward for me that is heavily video-focused, even though I think there are going to be some significant taxes to pay for that. Podcasts have a huge discoverability problem.

Yes.

And a huge long-term, uh, surfaceability problem. And YouTube offers a solution in the form of— what is it— the second largest English language search engine in the world, right? And I understand why it makes sense for a lot of people to harness that as one engine for growth. Makes a lot of sense. But it's crowded. It's really crowded. By anyone's definition, it would be a red ocean, and it's definitely going to get redder. And for that reason, maybe I make the decision in 6 months, you know what, fuck it, I'm gonna go whole hog, let's see what happens.

Right, right.

But I don't have, I don't have a really high degree of enthusiasm for that right now, and enthusiasm is important, right? Which means I'm not gonna have the endurance compared to someone like Chris, right, right, uh, Williamson. If people are like, who is this Chris? And furthermore, I feel life, the threads of life pulling me in other directions. So doing it half-assed would be the worst thing I could do. Like doing it 6 out of 10 would consume resources and not be particularly effective.

Right.

So I'm trying to decide if I want to take a barbell approach with podcasting on some level, which I've experimented with.

Explain that. What's the barbell approach?

Barbell approach could be applied. I mean, this is a term I'm borrowing. I don't know if he originated it from—

Taleb?

Yeah. Nassim Taleb, when he talks about investing. Right? Like super risky stuff and then really boring— let's just say fixed income or S&P 500 or something, right? Like super boring stuff and really risky stuff where you have a capped downside but potentially huge upside. In his set of games, it would probably be some type of like black swan option, right, position. And then nothing in between. That's it, right? And you could apply that to exercise, you could apply that to many different things. As I'm applying it, I would say within the format of podcasting, you would have no video whatsoever. That would be on one end of the spectrum. And I've done that. I've experimented with walk and talks where I have a headset on and I'm recording with someone and we're talking and getting exercise and it's great. I feel better because I'm not sitting down for 3 or 4 hours or whatever the, the amount of time might be. And I love it. I love doing it. So I think that there's a possibility doing that with a lot of enthusiasm and joy and curiosity, I might be able to make up for the lack of video with those elements. And I would probably do higher frequency also, right, because of that. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like, we'll have a nice video set up tomorrow and I have effectively a studio. It's no wraparound immersive Avatar LED screen, but it is, it's a nice studio setup.

It's what used to be considered really nice.

It's what you tell—

yeah, we saw the craziness.

Yeah, yeah, I wouldn't call it cinematic, but it's high quality video, right? And probably shy away from stuff in between and We'll see. We'll see.

This barbell principle applies to so much, right? Investing. You talking about it with a project, how I could approach a project. We, me and Ben, have been talking a lot about how we do this with our network. It's like, man, we're meeting so many people, but like death by a thousand Zoom calls. Like, I just, I'm not going to do it.

Yeah.

So what am I going to do, not talk to these people? Like, no. And so we decided there's a barbell approach, like a bunch of random texts where there's no obligation for either side to reply. It's just like, hey, thinking about you, or hey, check this out. That's it. Quick text, spend a half day or full day together. I'll fly to you. Let's have a good time. And we started doing this and oh my God, it's like, yeah, I feel like I've cracked the cheat code of the relationship building that, that, that was otherwise felt very draining and overwhelming.

Yeah, the, the barbell approach can be applied to a lot. I apply it all over the place. Another example would be, say, speaking engagements, where I very rarely do speaking engagements, but it. It's either free, where I would maybe even pay to be in front of the audience because the event and the audience is so interesting. Could also be a pro bono thing, or ultra premium, ultra premium, high, high watermark. Like, what— whatever company or organization paid me the most I've ever been paid, that's my new minimum, right? Like, whoever is going to meet or exceed that, that's it. And I will do probably 2 to 6 engagements a year. That's it.

You did this early on. I remember you had like your blog, or I think it was just blog days, and you did— you were like, everything's free, I'm gonna give everything away for free. I'm not gonna be a kind of online course slinger like most people who, once you get a little bit of following, it's like, hey, would you like half a million bucks? Would you like a million dollars? You could just sell this course. And then you, you were like, I'm either gonna be all free or I'm gonna be ultra premium. And I remember you did this like What's it called?

The, uh, opening the kimono.

The kimono. Yeah, open the kimono. It's like a $10,000 thing, but like a lot of us were happy. You'd be happy to pay that because it's like, oh man, I've gotten so much free value and I have the means. And you're like, cool, I only need a small number of people, which might make it a more enjoyable event for me. Was that the kind of calculus there?

Yeah, it's free. It's free or ultra premium generally. I mean, that's how I try to approach things. Also because ultra premium gives you a lot more margin for error, so you can afford to experiment, right? So it's, it's a virtuous set of conditions that you can set in the beginning, and it also poses a creative problem that I enjoy. Like, setting the price— I set the price before I figured out the content of the— I was like, all right, let me figure out the price and then I want to figure out— and it was, it wasn't just $10,000, it was like $10,000 if you apply and are accepted in the first like 6 hours or something. And then it got more expensive. Then it went to like $12,500, then it went to $15,000. And then my creative challenge was, okay, how do I make this event— it's a 2 or 3 day event— and I was done more than a decade ago. It was a long time ago. I've only done that one event as far as paid events goes, right? And I was like, how do I make this event worth that amount of money? Like, how do I exceed the cost of this event in the first 2 hours of the event, and then the rest is just gravy?

Powerful question. That's a great question. Yeah.

And that was, that was the challenge. And part of the answer was I'm going to give people my actual book proposals for the first 2 books that lay out everything, like the marketing plans, all the nitty-gritty, the sales pitch, and all sorts of details. Because people were there for, I guess, what we would call now content marketing, right? Right. They wanted to know how to launch books. They wanted to know how I had launched these books. I was like, okay, let me just skip the, skip the conceptual overlay. I'm just going to show you exactly what I did.

Open the kimono.

Boom. Opening the kimono. And And then I did, I did an exercise. This was also to answer that question. Very simple, where we had something like 120 people. I mean, we had tons of people apply and we were trying to vet for assholes to omit them, right? So we had questions that were bear traps for assholes. Well, we wanted to make sure— I have an audience, I have a very enthusiastic audience, and The last thing I would want is someone to take out a second mortgage or max out their credit cards to come to some event. Right. So first off, it was like wire transfers only. We're not accepting credit cards. Right. And I had— I had— but it's going to sound weird, but like a warning slash lecture in text, which is like, I do not want you to go into debt for this. Right. This has to represent I can't remember what the percentage was, but like no more than X percent of your current savings, right? Excluding your retirement accounts.

And you gave him a stern talking to.

Yeah. And so I had, I had a couple of questions about finances, right? Because I really didn't want to have the guilt on my conscience of knowing that somebody after the fact, you knowing after the fact that somebody went into the red or put themselves into a really compromised position to come to this event. And I do have fans who would do that. I remember one guy in response to one of the finance questions, he said, well, I appreciate you being my financial nanny, but if you want to— and if you want to come onto the tarmac to look at my jet when I come, you're welcome to. And I was like, and you're out. Yeah, thanks for that. You have done exactly—

that's the financial qualifier. Yeah, but you failed the second test.

I was like, you, you fell into the exact bear trap that I was setting for you. Thank you for disqualifying yourself. We do not need you in a small event. Financial Nanny is good though.

I like that. Maybe it's a good service we can have for people.

So clever. Yeah, financialnanny.com. So we had something like, let's call it 100 people. We had 100 people in the room and there was an attendee book with very short bios, maybe not even bios. And I think there were bios for everybody. And we had every single person stand up in the room and I was like, this is going to take a little time, but like Bear with me, folks. I think this could be interesting. And I'd never done this before, so I didn't know how it was going to turn out. I said, everybody's going to stand up, they're going to say their name, they're going to have a brag, which is give them permission.

Yeah.

Like, don't give me some fluffy bullshit humble thing. Right, right. This is not the time or the place. Don't be like, yeah, I write books sometimes, and it's like a 10 times New York Times bestselling author. Like, don't pull that stuff. Get up. Up, brag. I'm giving you permission. I'm actually giving you a requirement. Then you have an ask, make an ask of the audience. And then you have a give. It's like something that you're really good at, or it could be anything. So get up and it's like a brag and ask, a give. And I was like, everyone else is active this whole time. You are listening and you're writing this stuff down. If somebody has an ask that you can help with with, write their name down. And if there's a give that you want to discuss with someone, write their name down. And just doing those few things, the proposals and then everybody standing up, and like by the end of that day people are like, okay, this is already 10x, right, what I spent. This is amazing. And then it was just gravy from there.

Yeah, I think the easy thing to gloss over in that's cool. It's like cool story, obviously. But the takeaway for me and for anybody listening is that, that question of, or the technique of, first I'm gonna set the price, then I will ask myself how I can overdeliver on that value, or deliver in the first 2 hours where that was a no-brainer transaction for them to do. That question led you to such a different result than if you had just said, what event should I do? Yeah, average question. Common question. And I feel like you have a lot of these powerful questions. And you've said something that questions are like a pickaxe for the brain. It's how you dig the gold out of the brain. And I love that metaphor. I've, I'm a collector of questions. I got a swipe file of like 100 questions, mostly not interview, people think it's interview questions. I don't know. These are questions that I need to ask myself to get my brain to ask a better question, get a better answer. One of my other favorites of yours is, What would this look like if it was easy? Mm-hmm. Used it today for this interview. I was like, oh, great. I gotta do a great interview today. All right. Oh man, this could be difficult. There's so much content. What would this look like if it was easy? Mm-hmm.

And so what was your answer?

What would it look like if this was easy is me being genuinely enthusiastic and excited to meet you, you feeling that from me, and you walking outta here being like, oh, I actually had an interesting conversation. He didn't just ask me 10 questions, but maybe Sean said 2 or 3 interesting things that got me, got me like, 'cause I know like, what does Tim want out of an experience? If he learns something, it's probably a good experience. Or if he heard 1 or 2 provocative things that he might think about later, that's like a useful use of an hour for you. And so I thought, well, I'm good at that. So let me just like not withhold those, which would be common in a podcast where I'm only gonna ask you questions. I'll mute myself to make sure that you're at the time. But in this case, given that you have a platform, you've been so vocal in the past, I thought, oh, maybe I'll let myself do that because I think if I give Tim one or two nuggets that are interesting, he'll walk out of here feeling like it's a great experience.

Yeah, totally. So what other— what other questions do you have on that list that you use a lot that maybe I haven't heard?

Okay, I'll give you a couple of them. Am I leaning in to my absolute strengths and unfair advantage as much as I could be? And what this really is, is I call it the theoretical max. I had a friend who had an app one time, and his developer, his product managers were saying like, oh, the response rate on our push notifications is like 10%. And he's like, guys, if we just got that to 15%, then like the rest of our funnel looks great. And they're like, ah, we tried a bunch of A/B tests, didn't work. He goes, go in there right now and just write, your Uber is arriving. And this app was not Uber. And they sent it out and like 50% of people opened it. He goes, that's now the theoretical max. Don't ever do that again. But like, Don't give me the BS that like, because before that they were like, people don't have them on, people just got, people are too numb, there's too many apps, too many notifications. They had all kinds of stories. Yeah. And he's like, actually, let me just torch that BS real quick. And so the theoretical max question is basically, we, am I leaning into my superpower or my unfair advantage to its theoretical max? And so like, I'd ask you that, like, what is your unfair advantage?

I ask that question of myself a lot. I try to edge into it a few different ways. I'll ask friends of mine, when have you seen me at my best? That's one. Or what do you see me do that is easier for me than for other people?

Right.

Uh, I think my unfair advantage is at this point I have a lot just in terms of audience and platform and so on. But if we're talking about just what I can take with me, right, what I can walk out of here with, I would say it is an ability to ask unusual questions, also ask the dumb questions. When I'm trying to learn something from someone, from a book, from a video, it doesn't matter. I'm always asking these questions, these various questions, and then I can take whatever I learn. And I suppose I could try to deconstruct this, but I consider myself a fast learner at this point. And if I can get to point X in 6 months, which is going to be usually pretty, pretty good, sometimes super impressive, sometimes not, depends on the thing. But overall, on average, I'm going to learn things very quickly because I have a method at this point. I can— if it takes me 6 months to get to point X, I can get almost anyone to that same point in 3 months or less because I realize I also had so many false starts and I tried so many things that didn't quite work. I tried a lot of things that were common that turns out should be removed from the learning process entirely. I'd say those, those are what come to mind.

Yeah. My first reaction, if I was Tim Ferriss, what would I say? I think my first reaction would be I can get— first it was I can get any guest on my podcast really that I want. Every guest is within reach. And you said, well, that doesn't really need to be about the podcast necessarily. Yeah. Anybody I want to talk to is within reach.

Yeah, that's interesting.

That's not true for most people. And even if you are booking tons of guests or you're meeting cool people, like, you probably aren't at the theoretical max. You're not at the 'your Uber is arriving' level of like leaning into that superpower. For good reason.

Your mom is dead text message. Theoretical max.

Exactly. And so, but then even further is not only can you get in touch with them, okay, that's easy, but You can go in and you can get people to open up the kimono because your reputation is, I'm Tim Ferriss. I learn things. I've interviewed people. I deconstruct the things that they're great at. I ask them questions. People will come to you in an interview ready to open up the kimono.

Yeah, totally.

So that's interesting. Another interesting thing is like you said you went to go visit the game designer in Europe for 3 days. That's cool. That's kind of like throwing your weight around into your unfair advantages. Like you could probably pick up the phone and if somebody is the best game designer in the world, they would be honored to say that, Tim Ferriss wants to come and learn my stuff from me. Fantastic. Please. I'll block out 3 days. That's cool. And how many more times could you do that? So I would start to have a little bit of a brainstorm around that. There's another question I find really, really valuable, and that is, what is— what is the silly story I'm telling myself? And it immediately puts you on the defensive because you're like, why would I tell myself a silly story? But we all are constantly. Telling yourself silly stories. Why we can't do this, why that's gonna be hard, why that's not gonna work for me, why that will take forever, why this person is not responding to my thing. It's because of A, B, C, D. No, actually it's probably not, right? And so identifying the silly stories, it's like, I'm a Harry Potter guy. I don't know if you read Harry Potter, but like there's the—

I like Harry Potter.

The Boggart, right? The thing that will present itself as the thing you fear. And the way to get rid of it is the spell is ridiculous. You make it, you basically, If you're scared of spiders, you put the spider on skates and then it can't walk and then it actually becomes funny instead of scary. The same thing can be done with what are the silly stories in my life? As soon as you start to point them out, it's typically things that you've made real. But when you, when you sit down and you interrogate that, that story, turns out it was just as fictional as like an easily replaceable story that might be, might be better for you. And so, yeah, that's one that I ask quite often because it's the one that I hate. It's the question that I hate, that like, yeah, that's the one I need.

Yeah, yeah. I suppose if, if I could choose one question, the only question I could ask, it'd probably be some version of that. Yeah.

Do you have it in mind what it would be, or no?

Uh, no, I mean, we're just, we're constantly— I mean, the, my favorite answer to the question that I ask most guests at some point, what would you put on a billboard? Favorite answer I've ever had was from a hospice care physician named B.J. Miller, who's helped thousands of people to die and help them to die.

Help them.

So he didn't— yeah, he didn't euthanize them, but he's midwifing them through the transition to death if they have terminal cancer or something like that. And his answer, he actually confessed to me, he got from a bumper sticker somewhere. But the— his answer answer was, don't believe everything you think. That's it. Don't believe everything that you think. And, you know, having some method for cross-examining those beliefs, right, these thoughts we take to be true, is, is really, really critical. So that's a good one. Yeah, I like that.

I want to leave with one thing, which is Naval. You're friends with Naval. He's a fascinating guy to me. Never met him in person, only chatted online and whatnot. Really respect the guy, really admire a lot of things about him. Do you have any stories about Naval? Anything that you noticed early on or a moment you observed kind of like the wisdom or the sort of the insightfulness that he has?

Naval's one of my favorite people. He's very, very smart and hilarious and does not suffer fools gladly at all. Which I like. You don't have to guess what Naval is thinking, which I deeply appreciate. And the first thing that came to mind is probably not the kind of example that you would expect, but it's actually the first time I met Naval. So the first time I met Naval, I went into a coffee shop in the Mission in San Francisco, and I ordered a coffee, and I'm waiting at the counter, and there's this very attractive, uh, girl standing next to me, and She's very friendly and smiles, and I start talking to her, and I'm kind of chatting her up, you know, hitting on her, hoping to ask her for her number and take her out. And who knows, you know, maybe dinner, maybe drink, who knows. And then I see Naval walk up with this huge grin on his face, and he's like, I see you met my girlfriend. And I was like, oh, Tim. And he's like, Naval. And he just had this huge grin on his face. Was just like, wow, what a good way to address it. Like, totally calm. And then we, we, then we started talking and like, and we hit it off. And that was probably, God knows when that was, I don't know, 2008 or something.

Yeah, you're like a man crush, actually, move out of the way.

Yeah, face palm. Yeah. And, and, uh, and that was it. I, I, I just, I admire Naval for his ability to speak truth and ask uncomfortable questions. And he doesn't go out of his way to be rude, but he's, he's, he's, I think, less inclined. He is less inclined to the type of people pleasing that I'd say many people are predisposed to, myself included. Like, there are definitely times when I'm maybe too polite or tell white lies to make people feel good or whatever, like normal human social lubrication, right? Nothing major. But it's like if, you know, if my girlfriend's put on a few pounds, she's like, do I look fat? I'm like, no, you know, like, I'm not going to say, yeah, you look really fat. Not to say that Naval would say that, but he's, he's direct in a way that cuts through the noise and is very refreshing to me.

Have you been able to pick up or learn anything from him in terms of whether it's, you know, tactical stuff on the investing side or—

Tons of stuff on the investing side. I mean, I think the site was way back in the day Venture Hacks.

Oh yeah.

That he and Nivi co-authored. And I mean, that was basically the kind of Wikipedia Bible of angel investing and advising for, for an inside game on venture capital. I mean, Naval is Jedi level when it comes to early-stage investing, very technical. He just ends up in every deal you would ever want to be in. It's like, you know, the sort of, you know, Pinky and the Brain meets like Forrest Gump meets, you know, Siddhartha. You're just like, how is he in every cap table? Right. He's, he's incredibly skilled as an angel investor. Uh, yeah, we don't even have enough time. It can be hours and hours and hours of conversation to even begin to describe what I've learned from him there. And he's very curious, he's very interested, and it's not at all limited to business. So if it's, you know, David Deutsch or other thinkers, he introduces me to a lot of eclectic thinkers from different disciplines. And his, his exploration is certainly not limited, as it is with a lot of people, to say the sport of business or finance or investing. A lot of people are one-trick ponies that way. He is not a one-trick pony. So I, I admire that as well.

I have a funny Naval story, which is I have a buddy who was doing some— like when Facebook launched its platform My buddy made an app and it was like one of the silly apps. I don't remember back then. It was like people throwing sheep at each other and stuff like that. He was doing one of the like silly apps, but it was clear that, oh, Facebook platform, that's like an opportunity. And so smart Silicon Valley people were interested. My friend's sitting in Georgia and Naval's in San Francisco and he gets an email from Naval. Basically, he found the Contact Us page or whatever and was like, hey, I'd love to meet with you sometime, you know, talk about your app. I'm a venture capitalist here in San Francisco. So friend doesn't know who Naval is, doesn't know what venture capital is, but it's like, okay, sounds interesting. He's like, oh, you know, like, sure, I mean, I'm open to that. Next email is a plane ticket. Like, here's a plane ticket, goes out tomorrow. So friend's like, okay, gets on a plane, flies out here, meets Naval, meets him in his office. Naval asked him, he's like, he asked me questions for like 30 minutes. And he's like, I had no idea what the right answer should have been, but I'm saying whatever's my honest answers. Naval was like, hold on, goes into the other room, comes back, has printed out like a term sheet and says like, here, uh, you know, I'll give you whatever, half a million bucks or something, whatever it is, like some amount of money for, you know, some percentage of your company. And my friend who's like 23 or something like that is just like, I don't know who this Indian guy is. I don't know what the deal, I don't know any of the words on this page. My app is stupid. I don't know why he wants to invest in it. Uh, I don't really understand this. So he's like, uh, I just don't feel comfortable right now. And he's like, and Naval at the time was like, you know, he's very He's like, I think Facebook is gonna be, you know, huge. I think it's gonna be the platform where you do lots of things. You're not just gonna talk to friends on there. You're gonna be able to do XYZ. That's my thesis. That's why I want to invest in this. Because my friend was like, honestly, this is kind of a stupid idea. Why you— but why? There's not a business. And so he gave him that pitch. My friend was like, wow, that sounds awesome. I didn't realize all that. I had stumbled into this goldmine potentially. So he's like, listen, man, I just— I don't understand what this thing is. I just need to think about it. And I was like, no problem. And so he's like, I go. And then by the way, that same week he meets Keifer Boy, Max Levchin, a bunch of other people who are also giving him the same pitch but in different flavors. Like Keifer Boy was like, you should come work for us. He's like, I don't want a job. He's like, see all those people right there? All those programmers, they're gonna put you out of business. Like, you know, tomorrow. And he was like, this is a stupid app. It's not a business to do it. It wastes your time doing this.

You're gonna put me out of business. That isn't a business.

I live in my mom's bedroom. Like, what are you talking about? And so then I, he said, he goes, you know, the great thing about Naval though is that He's like, like 15 years later now, my friend's very, very successful tech entrepreneur. He's like, I actually dug up that old term sheet. He's like, it was so fair. He's like, he could have taken advantage of me and I didn't know anything. And he's like, it was incredibly founder-friendly and fair. And he's like, that told me a lot about Naval that at that time when a lot of people were in the heat of the moment about this kind of gold rush in that Facebook app days, and I was clearly a novice, he, he operated with very high integrity. And I thought that said a lot about him.

Yeah, that matches with my experience. I've always seen that in Naval. Yeah, for sure.

Right on. Well, Tim, thanks for doing this, man. I really, really appreciate it.

Yeah, my pleasure, man. Thanks for taking the time.

Mission accomplished, I hope.