The Exchanges

Q pounding, and I really didn't expect it. I feel like this should be old hat for me right now, but I still feel a little insecure at times. I still feel like I don't have it. I told you via email when I invited you on here, you look like Mr. Confidence to me. You never seem to break a sweat. Is there anything that makes you shake your confidence?

A Oh, absolutely. I think that, uh, as one example, for instance, before I do any type of public speaking, I still feel like I'm going to vomit, and I pace like a caged animal before every speaking engagement. Um, but I feel like I would have to worry more if I weren't nervous before events like that, and it made me feel better to know that even Dean Martin used to vomit before every performance. Mike Tyson felt very similarly, and I think that Uh, we can delve into confidence, but I think that as Custom Auto, Tyson's trainer, would say, it's, it's not that the hero and the coward feel different. They feel the same way. It's, it's how they respond to that feeling that makes them different. Uh, so I, I, I have self-doubt. I have, ah, crises of meaning all the time, ah, and I think it's, it's important for people who only see the highlight reel, like maybe they only watch some of my presentations, or they see, you know, the Tim Ferriss highlight reel, to realize that it, it, it is a roller coaster, and those, there are those ups and downs, and that's just part of the ride that you sign up for in a lot of ways.

AI assessment note: “before I do any type of public speaking, I still feel like I'm going to vomit”

Q ah, of Dropbox. Is gonna be coming on here. Um, I wanna, I'm wondering from you, how do you learn from these extraordinary entrepreneurs? I wanna try to bring back some of your way of breaking down with they, with what successful people do. I wanna bring that to my interviews so that I can pull out ideas from my audience that they can use the way that you might.

A Yeah, I, I have a set of questions that I tend to ask, and they include, you know, what, what is the biggest mistake that novices make, the biggest waste of times, a waste of time that you see entrepreneurs making in, in the beginning, or it doesn't have to be entrepreneurs, but novices in any field, could be bobsledding, could be anything. Um, secondly, if you were to start over again, what would you do, what would you do differently? Uh, if you had to choose one or two people to emulate, who would they be and why? Uh, if you had, say, four to eight weeks to train me for fill in the blank, huge audacious goal, raising ten million dollars in funding, building a hundred million dollar company, whatever it might be, uh, how would you prepare me? I understand it's impossible, but if you had, you know, ten million dollars of your own money on the line, how would you train me? If you had to. Uh, and there's a set of questions like that, many of which seem absurd, uh, like the, you know, how would you train someone for an ultramarathon in eight weeks type of question, uh, that turn out to be possible if you force someone, uh, to answer the question. They have no option but to try to make that work. And, um, that, that's generally how I approach it. And, uh, If you had to choose, say, two or three resources, whether that be a book, a series of lectures, a blog to help someone self-stu…

AI assessment note: “I have a set of questions that I tend to ask, and they include”

Q a mutual friend of ours, Ryan Holiday. He said, Tim Ferriss used to talk to, ah, Tucker, Max, and Ryan before they, ah, before he made it, and you'd ask all these great questions, and they wanted to help you out, thinking, you know what, we're gonna help this guy get started. And I always wondered, what was it that you said that made them want to help you out?

A Oh, that's a great question. I'd say, number one, I did my homework. So I, I knew that Tucker, for instance, had done some Brazilian Jiu Jitsu. I had background and was current, was then training in Brazilian Jiu Jitsu. So I viewed that as a way to differentiate myself, especially at a place like South by Southwest Interactive. Uh, secondly, I didn't try to impress, I didn't try to impress him. I said, look, this is totally out of left field. You have no idea who I am. But I know you've done A, B, C, D, and E. You know, I'd love to buy you a drink and just ask you three or four questions. I'm not going to, like, pick your brain for an hour. I know you don't want that, but I have a couple of really specific questions. You know, in exchange, maybe I can do blah, you know. But gave them an easy out, I think, is another thing. And, you know, I was, I was really, uh, identifying with what Seth said about Rarely rewarding persistence, because then you're just asking for more of that sort of slamming a head against the wall behavior, even if you say no. Um, but, uh, you, you tend to get more bites with a softer cell, so I always give them an easy way out. I'm like, hey, look, if you don't have time, it's no problem at all, but, you know, this is one of three sessions I wanted to come to. I'm happy to, you know, maybe I can help you with this, this, and this. I have literally two or th…

AI assessment note: “number one, I did my homework... secondly, I didn't try to impress him.”

Q avoiding it in the future so that I don't make the same mistake, and if it ever comes up again, I know how to deal with it. Do you have an example of a time where you just lost it, where you said, I can't regain, I can't make this work, and as a result, maybe you had to sit back afterwards and figure out what not to do again?

A Oh, all the time. I, I mean, even this past year, ah, it was very difficult for me because I decided to take a break from writing books, so that identity of author kind of went away, or I didn't associate with. And I experimented with television, and, ah, you know, all the episodes of the Tim Ferriss experiment are coming out at the end of May on iTunes, sort of house of cards style. But I'm not sure if I want to continue doing TV, so I thought that was going to be my new identity, and that's kind of gone, ah, maybe. And, ah, simultaneously, as much as I enjoy angel investing and, and being involved with startups like Uber and Evernote and Twitter, whatever, I don't want to be a full-time VC, so I had this, this crisis, ah, this existential dilemma, ah, that really shook me pretty hard to my core, and I think that when that happens to me, my first default, and I think a lot of this comes from competitive athletics a long time ago, um, athletics were mandatory every season at the high school I went to, Is that, uh, the easiest way for me to work on my inner game when I start getting monkey mind is to work on my, my outer game, if that makes sense. So like, embrace motion, go to the, go for a long hike, go to the gym, have some type of metric, whether that's, Uh, stroke count in the pool, whether that's time in the mile, whether that's pounds in the deadlift, so that you don't ha…

AI assessment note: “I had this, this crisis, ah, this existential dilemma, ah, that really shook me”

Q out of seven days, maybe four out of seven days, and I, I find that I minimize the importance of it when work comes into play because I prioritize work. Isn't that the better way to do things? To, if thing, if life, if work isn't working out, to focus more on that and then to take away from the running or swimming or the external benefit, the external activities?

A Well, I think it, it depends on how you're looking at your schedule. So you can look at your schedule as a finite pie of discrete elements, and you have to allocate one that is separate from another, but in my experience at least, the easiest way to Address, say, depression. It is diet, as well as exercise. There's, there's a very interesting book called Spark about this entire, this exact topic, and the best way to improve cognitive performance is to improve physical performance, because of course the brain is an organ like any other. So I find that The most important time to exercise is when you feel like you have no time to exercise. And I remember something that Russell Simmons said, ah, to me once, which was, ah, if you don't have time to meditate for 30 minutes, you need to meditate for three hours. And I think that that, that sense of time scarcity Is often an indicator of exactly what we should make time for. Easier said than done, but this is something you constantly have to practice. It's a habit. Uh, and I think that, uh, it's not as though you make the decision once and you're done. It's like, oh, ok, I understand what a good diet looks like, now I don't have to ever think about diet again. That's not how it works, but When you develop a habit and say, ah, consume 30 grams of protein within 30 minutes of waking up for two weeks, that will become your new default. An…

AI assessment note: “The most important time to exercise is when you feel like you have no time”

Q him. I wonder, when you come up with ideas like this, how do you document them and remember them? These ideas come to me. I recognize that I should be going to someone else and asking for, ah, an introduction. I write them down, maybe in an Evernote or in a Google Doc, and then I forget to go back and use them. How do you keep track of this?

A It's a consistent issue. I mean, I have, this is, this is one of, you know, 50 notebooks that I have, and I also use Evernote and so on. Uh, I will calendar them and set reminders. Uh, so typically when I start my day and I have a morning ritual, because I think that it's important to have ritual and routine to keep away fear, uncertainty, and doubt. So in terms of maintaining confidence, I think a big part of that is conserving your decision making only for the things that matter. Like you shouldn't have to wake up and decide, spend 10 minutes figuring out what to have for breakfast. That's a waste of your bandwidth. Uh, where I was going with that is I'll, I'll make a list of sort of three things that I'm grateful for What I want to be, sort of the characteristics I want to have that day. Uh, you know, this day will be great or exceptional if I do the following three things. And then at the end of the day, I'll do another, uh, three items of, like, amazing things that happened that day. And it might sound cheesy and new agey or whatever. I find it extremely, number one, therapeutic, and number two, Uh, calming, and, uh, efficient. Very effective. So, for all those reasons, uh, I really like to scope it out and just write down two or three things, and very often, if it's one of those high-level things, that is a force multiplier, like, I want to, uh, Completely, let's say, lau…

AI assessment note: “I will calendar them and set reminders. Uh, so typically when I start my day”