This episode features Tim Ferriss discussing his approach to life, productivity, and decision-making. He emphasizes the importance of avoiding over-optimization, focusing on small, consistent actions, and maintaining a “theoretical max” performance state without falling into the trap of constant, unsustainable hustle.
Topics: Productivity, Decision Making, Entrepreneurship, Mental Toughness, Personal Development, Life Philosophy
The Four-Hour Fever [00:00]
Sam Parr: By the way, this episode, where’s the camera? This is, this episode is not for you. This episode is for me. I’ve been listening to this guy for a long time. I’ve read his books. I, I used to gift your, your book was one of the most gifted books I had for like a long time, maybe the first 10 years of my, my career. And I would say, you’re about to, I’m giving you the four-hour fever. Like, it’s called the four-hour work week. I said, you’re going to read this and then for four hours you’re going to question everything in your life. I call that the four-hour fever. It’s normal, don’t worry. Call a doctor if it lasts beyond four hours.
The Key to a Good Podcast [00:35]
Sam Parr: 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.
Tim Ferriss: I think that’s the key to a good podcast.
Sam Parr: Exactly. So, um, 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 in that spot. Yeah. And how what’s the what’s the approach? Because it can be paralyzing to have a thousand options.
Tim Ferriss: Yeah.
Sam Parr: 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. Can’t be can’t be something tiny, right? How does Tim Ferriss approach the what’s next question?
Tim Ferriss: 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 six episodes. That’s tiny. So did this podcast, by the way. This is a this is a tiny.
Sam Parr: Right. So I think that.
Tim Ferriss: So I think that it’s a quote, uh, Seth Godin, who is really wise beyond even what people would expect. I mean, 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 you know, 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.
Tim Ferriss: Yeah, but when you make something small, do six episodes. Right. If you don’t do six episodes, you failed to do six episodes. But if it’s like, I’m going to change the world and do this and blah, blah, blah.
The Next Physical Action [02:16]
Sam Parr: 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.
Tim Ferriss: Okay. Now you have a report card 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 discrete. 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 a next thing, I’ll say up front, I don’t know what my next thing is right now.
Sam Parr: But how do you approach that? How do you approach figuring it out?
Tim Ferriss: 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 three 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.
The “Weird” Box [03:26]
Sam Parr: 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.
Tim Ferriss: 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. Um, and I’m not saying they’re bad options, but like, I could make a course. Yeah. I could I’m sure I I know I could execute that and make it do really well. Right. I I know that. Uh 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. Um, however, let me come back to the criteria. So whether I’m coming 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 to be 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, 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. 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 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 snowball. Something like that. Those snowball. Right. Right? Because if I do like four 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 I could pick a whole ton of them that seem like waste 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.
The “Perfect Tuesday” [12:21]
Sam Parr: I’ll take you two related things on that. Last night I was at dinner with I think a mutual friend, Joe Gebbia. Yeah, yeah. Founder of Airbnb. And he was saying, he’s like, oh, what are you doing for? I was like, I’m doing a couple of podcasts. And we were talking about it. He’s like, okay, so what’s like what’s like a win, you know, like why why do you do that? You fly to town, you leave your kids, you you make an effort. What are you looking for out of these? And I said, well, I just want to 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 out of here feeling energized rather than the drain from this conversation. And if that’s I’ve been using that heuristic and it’s so powerful to use the kind of like, where is my energy after activity and how am I leaving the people around me also is it 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, um, we’re 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. Are they went public? It’s 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, which is love. He’s like, but I don’t really make time for creativity anymore. He’s like, I’m he’s a designer by by trade. And he’s like, I need like a creative gym. He’s like, I I feel like if I if I sat down and I started sketching, it would 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.
Tim Ferriss: I try. Yeah, I try to do it for sure. Do you have your version of a creative gym?
Sam Parr: Yeah, I mean, I was like playing the drums earlier today. So from a like financial perspective, that could be a waste of time. But the financial stuff, 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 is 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? Because it’s it’s hard to keep some of those things in check.
Tim Ferriss: 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 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. Uh so I 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, uh Stan Prokopenko, uh 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. Sure is. 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 drawing. That’s a bit on the nose as far as creativity goes. But like jujitsu is creative. Right. It’s like going to the jujitsu 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. You got a book recommendation from you. Oh, yeah. I haven’t seen that. This book is a few decades. Yeah. I never even heard of this book. It’s an old book. This book is called uh Toughness Training for Sports and it’s by Jim Loehr. Um do you remember anything from this book? You probably read this a long time ago.
Tim Ferriss: 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 two or three pages long and you’re intended to give that to your coaches, peers, teachers, people around you, effectively for like a three 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 Loehr 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 it provided me with a level of awareness that I I 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 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 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?
Tim Ferriss: 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 were other factors that played into it. Hey, real quick, you know, one of the cool parts about what 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 want to do the show. And we want to 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 plus 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.
Optimization vs. Effectiveness [15:11]
Tim Ferriss: In terms of ideal performance states, I 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 the 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 there’s a 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’m 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. Uh 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, 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 seven minute, I guess it was about a seven minute cold plunge at 40 degrees, which is pretty chilly. That’ll wake you up. Seven minutes continuous? Yeah. That’s solid. And 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 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 it 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 and 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 is what you do, 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 measuring in minor things. Yeah, measuring 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 going to falter, you’re going to 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 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 over committing to things that longitudinally eat up years. Because you’re comfortable not being busy. Yeah, that’s a big one. Yeah, just I mean the like the best way to get what the outcome of busyness should be, which is, right? Like big effects of some time, or it could just be more joy, whatever, is is not by engaging in non-stop action. All right? It’s by in a sense, it’s similar to my my my start of investing. It’s like having very tight 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 have you don’t have enough positive constraints. So you get over enthused 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 bankroll is your time. Mm. 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 you’re like, that’s actually a dangerous form of laziness. Yeah. Yeah, indiscriminate action. Indiscriminate action. It’s 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 uh 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 our 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. They’re like, oh, so diligent, doing so much homework. But So sophisticated he is. Yeah, so sophisticated. Um, I want to ask you about your book thing in a second, but before we do that, teach you said teaching. Teach me uh 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 big person you admire. What can you teach me about the first five minutes of a podcast? First five minutes. Maybe five seconds. I don’t know. Yeah. The beginning of a podcast. Yeah, I mean, the most important five minutes are the conversation that 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. Mhm. 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 they’re like, oh, this guy’s A, done it a lot, B, is actually looking out for me. Mhm. C, has actually sat in my seat, interviewee seat a lot. And I always ask and like nobody, almost nobody asks this. It’s uh it’s such an easy layup in terms of differentiating yourself. Ask interviewees what what a success would be. Like what would you look at back at this? I asked my inter the interviewee this this morning about this. I said, six months from now you look back and you say, I’m so glad I did that. Mhm. 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. 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. He cares. Yeah. Yeah. So there I would say that that pre-record conversation is something I don’t see very often. Mhm. Right? Like when I get I didn’t do it today. Well, yeah, I mean, and and 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 the case that somebody’s 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. 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. And the first five 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 a thousand times? In a case where someone’s been interviewed a thousand 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. Like a third grade teacher or a mentor that helped them when they were at one school when they were transitioning from one place to another. They got mentioned in passing in a profile in the New Yorker eight years ago. I’ll be 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, like there’s a lot of prep that goes into it. Uh if there are any greatest hits stories. I mean like what are stories people respond really well to that stick with them that people have brought up with you a year later, two years later. And they could be an academic, right? Academics talk to people. They’re 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 up front. And that is helpful often times 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 if 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 five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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 ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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 texts. Spend a half day or full day together. I’m 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 would 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’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 two to six engagements a year, that’s it. You 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 going to give everything away for free. I’m not going to be a kind of online course slinger like most people who once you get a little bit of a 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 going to be all free or I’m going to be ultra premium. And I remember you did this like, what’s it called? The uh opening the kimono. The kimono. Yeah. I opened the kimono. It was 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 was it wasn’t just 10,000. It was like 10,000 if you apply and are accepted in the first like six hours or something. And then it got more expensive. Then it went to like 1250, then it went to 15,000. And then my creative challenge was, okay, how do I make this event, so a two or three 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 two hours of the event? Mhm. 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. Yeah. 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 inter- people think it’s interview questions. No, no, 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? Mhm. Used it today for this interview. I was like, oh, I Great, I got to 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? 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 out of here being like, oh, I actually had an interesting conversation. He didn’t just ask me 10 questions, but maybe Sean said two or three interesting things that got me got me like, because I know like what does Tim want out of a out of an experience? If he learns something, it’s probably a good experience. Yeah. Or if he heard one or two provocative things that he might think about later, that’s like a 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 going to ask you questions. I’ll mute myself to make sure that you have that 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 are the what what other questions do you have on that list that you use a lot that maybe I haven’t heard? Uh 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, as I call it, the theoretical max. I had a friend who had an app one time and his developer, his product manager was saying like, oh, the 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, uh we we tried a bunch of AB test, didn’t work. He goes, go in there right now and just write, your Uber is arriving. And they’re this app was not Uber. And they sent it out and like 50% of people open. 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 time on, people just got people are too numb, there’s too many apps, too many notifications. They had all kinds of stories. Yeah, 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 in to my superpower or my unfair advantage to its theoretical max? And so like I 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 six 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 six months to get to point X, I can get almost anyone to that same point in three months or less. Mhm. Because I realize I I I 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 for the first five minutes. It’s a great answer. Very helpful to me. Because we usually do the show, it’s me and Sam. Yeah. And it’s so that’s the core of the show is me and Sam hanging out. And our dynamic is very simple. It’s uh 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 a scratching our own itch. I want I really want to meet this person. I want to get to know 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. 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’s good for the audience, whatever the audience is, right? Depending on the show. And uh 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 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. Mhm. 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 an 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 your 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 it depends on your audience size, of course, but with with the size of my audience, if something is bothering me, if something is really peaking my curiosity, if something’s in my head at night and just won’t go away, chances are they’re 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 It’s very kind. It’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? Uh but there 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 risk producer. Risk producer, like risk mitigator, for sure. Like I’m very good at capping downside risk. And in this particular case, I already knew that from a 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 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 flashback 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, ninth 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 were presenting your lifestyle. Yeah, the notes from that because every time I spoke, it was twice a year, Ed Schow, the professor, high-tech entrepreneurship invited me back because I had the hairbrained 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, what is 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, two months ago, it’s like a lifetime ago. It’s like Obama when he left office. It’s like, went from black to gray hair. Yeah, exactly. Four years. 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 one, I really enjoy teaching. Number two, teaching in that format in front of 20, 30, 40 students didn’t scale. And 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 Nice. 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 a, yeah, 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. And 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 With a live crowd, which is huge. Over and over and over and over again. I knew it worked. Right. And I I frankly love experiments. That’s the way I 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 like career trajectories. It’s like, all right, let me try it. And It’s a great mask for unemployed. Right. It’s like, I’m writing a book. Great. I’m getting an MBA. Yeah. Great mask for unemployed. And and then everything went bananas. Well, you did the podcast that way too, right? Experiment. You were like, I’m going to record, I forgot what it Six episodes and like you 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 six. It’s either going to be a wonderful six 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 Yeah, give yourself a graceful exit. I mean, framing it for yourself, but also to other people. Whatever you do as an experiment gives you a graceful exit. 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’ve found very useful. And I want you to unpack them. One is the law of category. Mhm. 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. Like 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 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 of 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 smoking 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 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 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, where 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 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 six months. You know what? Fuck it. I’m going to 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. I’m which means I’m not going to have the endurance compared to someone like Chris, right? Uh Williamson, if people are like, who is this Chris? And 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 six 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 in this case? A barbell approach could be applied. I mean, this is a a term I I’m borrowing. I don’t know if he originated it from yeah, Nassim Taleb when he talks about investing, right? Like super risky stuff and then really boring, let’s just say fixed income, 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 position, right? 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 with in 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 three or four 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 because of that. Right. And then on the opposite end of the spectrum, I might actually, for instance, tomorrow, like we’ll have a nice video setup tomorrow. And I have effectively a studio. It’s no wrap-around immersive avatar LED screen, but it is it’s a nice studio setup. It’s what used to be considered really nice until we saw the craziness. Yeah. Yeah. It’s 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. I’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 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