Foto: Author, podcast host, and tech investor Tim Ferriss. source Sarah Jacobs/Business Insider

Tim Ferriss first found fame in 2007 with the massive bestseller “The 4-Hour Workweek.”

His interview podcast, “The Tim Ferriss Show,” has been downloaded more than 200 million times.

His newest book, “Tribe of Mentors,” is a collection of advice he gathered from some of the world’s most successful people.

Ferriss explained how this year was a time of introspection and learning.

Tim Ferriss first found fame with his 2007 book “The 4-Hour Workweek.” After taking a break from writing, in 2012, he became an accidental podcast star with “The Tim Ferriss Show,” which has surpassed 200 million downloads. He’s an investor and self-described human guinea pig. He sat down for an interview with Business Insider senior reporter Richard Feloni for our podcast, “Success! How I Did It.”

This past year hasn’t been typical for him. He celebrated the 10th anniversary of “The 4-Hour Workweek” and then decided to leave his successful “4-Hour” brand behind him. He’s out with a new book, “Tribe of Mentors,” in which he collects advice from 140 successful people, a project that was as much for him as it was for his audience. Ferriss has spent the last year thinking a lot about his own life. He lost some friends, he got a lot of attention for talking about his struggle with depression in a viral TED Talk, and he turned 40.

On this episode of “Success! How I Did It,” Ferriss spoke with Richard Feloni about all of that and more, including how wrestling shaped his childhood, the original title of “The 4-Hour Workweek,” and why he hopes no one considers him a role model.

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The following is a transcript, which has been lightly edited for clarity.

A year of reflection

Foto: Ferriss has used the past year to reconsider what he wants from both his personal and professional lives. source Andrew “Drew” Kelly

Tim Ferriss: Turning 40 didn’t, as a number, scare me, or throw me off, at all. I’m very comfortable being 40. But as a thought exercise, you know, I asked myself, “If this is the halfway point, if we’re just looking at the actuarial tables, it’s like, all right, if I’m at 50%, right, I’m halfway through this race called life, and when I hit the finish line, you’re dead at 80, how might I want to rethink trajectory? How might I want to rethink over-planning versus under-planning? Even though I’m trying to improve my relationships with others, are they dependent on my relationship with myself? If so, how should I even conceptualize improving that, right? If it’s never been part of my repertoire?

And all these questions sort of came to the surface, and, rather than try and go at it on my own, which has been my predisposition and my reflex for decades, I figured, why don’t I just take these questions and, given the reach of the podcasts and books and everything else at this point, why don’t I just reach out to 130 or 140 people and ask them all the same questions? People who are the best at what they do, in many, many dozens of different fields – and then just try to borrow? Why not do this the potentially easier way?

Rich Feloni: It seems an extension of what you’ve done that past 10 years. Even beginning with “The 4-Hour Workweek,” which is dabbling in a bunch of different things and seeing what works and then sharing that with an audience.

Ferriss: Yeah, it’s exactly the same. I mean, really I view my job more almost as a field biologist or anthropologist, where I’m collecting practices. I’m collecting techniques. Then testing them on myself, and if I can replicate results, and then share those with, say, six to 12 friends, and they’re able to replicate results, then fantastic, off to thousands or millions of people it goes.

Laying the foundation in childhood

Foto: Ferriss developed his love of learning and experimenting as a boy growing up on Long Island. source Courtesy of Tim Ferriss

Feloni: And did this constant love of learning anything and everything, did it start as a kid?

Ferriss: Yeah. My parents did a great job of raising me and my brother. Very supportive parents. Did not have a lot of money, and the one exception they made: “We always have a budget for books. So if you want to get a book, we will figure out a way to get the book.” So what does that do to a child brain? It makes you excited to figure out ways to get books. And so we became fascinated at a very early age with books.

And I remember to this day this book called “Fishes of the World,” I think it was, that I carried with me. This huge hardcover – I mean I was a little runt, I was a really small kid growing up, and it was this gigantic hardcover, beautifully illustrated book on marine biology, and I took it with me to school every day, because the playground was not a safe place for me. I was born premature, I was really small and got my ass kicked mercilessly up until about sixth grade. So I wouldn’t go out to the playground. That was a danger zone. I would stay by the classroom and kind of sit on the step leading out to the playground, and I would read this book.

Feloni: Was being a small kid and someone picked on for his size – was that an impetus for getting involved in body experiments? As you say, you’re a human guinea pig. Is that when it started?

Ferriss: It wasn’t a deliberate decision to become Captain America or anything. I was really small and had a lot of health issues growing up. I mean, not compared to some people certainly, but I had a number full-body blood transfusions when I was kid. Premature, so I can actually – this is audio, most likely, so people can’t see it – if you look here, Rich, on my wrist, it looks like a cigarette burn, and that’s actually from being intubated. And then I have another one under my left lung, where my lung collapsed, where my blood was being oxygenated.

Nonetheless, so all of these various issues, and to make my parents’ lives more difficult, really hyperactive. And some other mothers told my mom, “You should put him into something called ‘kiddie wrestling,’ because that’ll drain his batteries, and then when he gets home he’ll just fall asleep.”

Wrestling is unique among sports because it’s weight-class-based. So you could have the puny runt from Class A competing against the puny runt from Class B. So it’s a situation which one of the puny runts can actually win at something. And my mom inserted me into kiddie wrestling, and I took to it, and that became my sport, until the very end of high school effectively. But the confidence built on the wrestling mat as a puny, little – God knows, like 40-pound kid – is where a lot of it started.

Feloni: I’ve heard you downplay your time in high school, like your time as a student and all of that. But you ended up at Princeton, which doesn’t happen by accident.

Ferriss: Yeah. My brother and I were always told, maybe not in these words, but if you get really good grades, you can do whatever you want in life. In effect, that’s your ticket.

And I transferred from a high school on Long Island to a high school in New Hampshire, which was a much better school called St. Paul’s. Very well known – it’s one of the older boarding schools in the US.

Feloni: “Dead Poets Society” type of thing?

Ferris: Very – feels like “Dead Poets Society.” So you’d have seated meals, seated dinners a few nights a week, with suit and tie, and classes six days a week, chapel almost every day of the week, mandatory sports. And I was encouraged to go there – or to at least leave high school on Long Island – by teachers who could see me getting complacent. Like “All right, you think you’re pretty good because you’re a big fish in a small pond, but you should go somewhere else.” Number one.

And then one of my friends – just one of my classmates, because very few people left where I grew up in Long Island, or relatively few people – and one of my friends had gone to a boarding school and came back and effectively was, like, “I’ve seen the promised land – you need to get the hell out of here,” and so I was able to get support from my grandparents, and kind of extended family, got a few small scholarships, and go to St. Paul’s. And St. Paul’s really set the stage for everything else and really opened the door, or even the possibility, of even thinking about applying to a place like Princeton.

Finding himself in his 20s

Foto: At Princeton, Ferriss struggled with depression. He also tried to open a gym chain in Taiwan. source Tim Ferriss/Flickr

Feloni: At Princeton you studied East Asian studies, and you took a break as well.

Ferriss: I took a year away from school, which was in the middle of my senior year. It was a very, very, dark, dark, dark time for me, due to a bunch of – just a conflagration of all sorts of heavy things hitting me at the same time.

And that is when I came close to sort of the precipice of total self-destruction. I don’t want to belabor it here, because I’ve spoken about it at TED and people can certainly just search “Tim Ferriss suicide TED” and it’ll pop right up.

During that time, I saw my classmates competing, because that’s what they were good at. I mean, you take kids who go to a school like Princeton, they’re used to competing, and they’re used to being No. 1, so if something seems coveted, they will compete for it, whether or not they really want that thing. And in this case, the thing would be, say, a job at McKinsey or a job at Goldman Sachs.

And everyone was competing for these, and I ended realizing very clearly I did not want to do either of those things. And I felt very lost. So during that year I tried all sorts of things. I spent six months in China, mainland China, and then went to Taiwan, and just fell in love with Taiwan. So I had this dream of opening a gym chain in Taiwan and went pretty far down the line of trying to figure out all the details, this that and the other thing, meeting with gym owners throughout Taiwan, and ultimately you had to interact with, like, paying, in some cases, protection money and so on, to Triads, and organized crime, and it just got so involved, it was, like, “You know what, this is just a little bit above my pay grade – don’t think I can handle this.” So came back, ultimately rejoined school, and graduated a year later. Most of my friends had already graduated. I walked away with an illustrious degree in East Asian studies.

Feloni: And the foundation of your career over the past 10 years was “The 4-Hour Workweek.” And key to that coming together was your experience with BrainQuicken, the first company that you started. And so, it’s a young guy, and he’s selling supplements out of his house. That sounds a little sketchy.

Ferriss: OK, all right – what’s your question?

Feloni: I’ve seen you refer to it as, like, you jokingly refer to yourself as a drug dealer or something.

Ferriss: In fairness, I was actually neuroscience before East Asian Studies and had some of the wherewithal to determine what might make a good product, because as someone making 40,000 pretax in Silicon Valley, in those days, with roommates, and a hand-me-down minivan, did not have a whole lot of disposable income, but nonetheless was spending an absurdly high percentage of my take-home income on sports nutrition.

I was, like, “All right, I have some ideas of the pain points and needs of this market, and know what I would want to create if I had the budget for myself,” and, which would in effect be what we ended up labeling a “neural accelerator.” BrainQuicken was a real learning-on-the-job MBA. I mean, it was very, very difficult.

Achieving unexpected success and creating a brand

Foto: Ferriss gave his first TED Talk in 2008, not long after “The 4-Hour Workweek” made him a celebrity. source TED

Feloni: So “The 4-Hour Workweek” comes out in 2007. It seemed like no one really expected that to be success, including yourself, right? Like, a massive success.

Ferriss: Nobody expected it. I mean, I had an initial print run of 10,000 copies, which isn’t even partial national distribution. So for those who don’t know, the premise of “The 4-Hour Workweek” – which, by the way, was initially titled “Drug Dealing for Fun and Profit” – is a collection of tactics and tools and case studies of people who have designed ideal lifestyles for themselves by thinking about this nonrenewable resource of time and how they want to spend their day-to-day, week-to-week, and then reverse-engineering that by building a business, a cash flow, or a career that allows for remote work and so on. So that’s “The 4-Hour Workweek” and those are the basics, but nobody expected it to do anything.

Feloni: Yeah, and it led to this “4-Hour” brand essentially.

Ferriss: Yeah.

Feloni: “The 4-Hour Body,” “The 4-Hour Chef.”

Ferriss: Very accidental, but yeah.

Feloni: And I’ve seen you lately kind of be self-deprecating about it, like, “Oh, this makes me sound like an infomercial guy or something.” Do you actually regret the title?

Ferriss: No, no.

Feloni: Would you have changed it?

Ferriss: No, no, no. Definitely not. No, I don’t regret it at all, but, you know, there comes a point where all good things must come to an end. And in the beginning, you want to be pigeon-holed, in a sense, you want to be clearly defined in the very beginning. But past that point, and I did. You want to diversify your identity so you don’t become a parrot who regurgitates the same party lines over and over again.

So in the beginning, “4-Hour” this, “4-Hour” that, fantastic. But right after “The 4-Hour Workweek,” I was heavily advised by many people that I should do “The 3-Hour Workweek” or “The 4-Hour Workweek Revisited” or something along those lines.

I felt, if I didn’t do something that was a complete left turn in a different field, I would forever be thought of as “The 4-Hour Workweek” business guy. Which is why I took the same approach and applied it to physical performance and sort of physical manipulation. And then with “Tools of Titans” retired the jersey of “4-Hour.” And you know, who knows? Maybe it comes back at some point, but probably not.

Living the Silicon Valley investor life

Foto: Ferriss at Burning Man, a favorite bizarro retreat for the tech set. source Garrett Camp via Tim Ferriss/Flickr

Feloni: At what point did investing enter the picture? You had a public post that you essentially retired from it in 2015, but you had deals that – most any one of them – people would kill for. Uber, Facebook, Twitter.

Ferriss: Yeah.

Feloni: How did those happen?

Ferriss: Yeah, I’ve had a fortunate run. So in the case of angel investing, in 2007, “4-Hour Workweek” pops and suddenly it’s a No. 1 New York Times bestseller and so on. I’m not so naive to think that I can just put lightning in a bottle and do that over and over and over and over again. I thought to myself, “Well, if this is really my moment, like the opportunity window, what might I do with this?” And around the same time, I was having lunches with Mike Maples.

Feloni: And Mike Maples is?

Ferriss: So Mike Maples, at the time, was a very successful angel investor, meaning he invested his own money in generally small-ish checks into very, very early-stage embryonic startups. He’s now a founding partner of Floodgate, which is a successful venture-capital firm. And at the time, we would meet up for lunch or brunch at a place called Hobee’s in the Bay Area, and we would very frequently talk about launch strategy or PR angles that his startups could use. In return, I would ask him about deal structure, about company selection. “Why did you choose this company instead of A, B, or C companies? What are the most important points in deal negotiation for, say, a seed round of financing?”

And over the span of a few months of asking him these questions, I had decided that, rather than go to Stanford Business School, what if I took $120,000 of my money, which I would have spent on Stanford Business School for two years at the time and instead created a real-world MBA for myself where I create the “Tim Ferriss Fund,” in quotation marks, and invest $120,000 in startups over two years with the expectation that I’m going to lose all of that money. In other words, every startup will fail, but the relationships developed – that I develop and the skills that I develop, the knowledge that I acquire, will, and so forth and so on, will more than make up for that over time.

So I asked Mike if I could co-invest with him in a few deals and that’s how it started.

Feloni: You had a good run.

Ferriss: I had a good run. The first one was not a good run. The first investment I made – I won’t mention the name. But I invested – now keep in mind, I’m looking at 120K over two years, right? So the first investment, I want to say I put in – it’s so stupid – I put in 50K in the very first investment, because I got so excited. This is one of the risks of being an angel investor who’s a former entrepreneur, is you can sometimes get very easily excited. And Mike says – I remember Mike saying to me, “Don’t you think 50K might be a little aggressive?” – given that my allocation for the year is supposed to be 60. And I was, like, “Oh man, but no, based on your description, based on this, this, and this, no, I’m so bullish,” and it promptly just went sideways and became walking dead.

Over time, as I started to learn, “All right, well now that I’ve overspent my budget, I need to figure out also how to become an adviser.” And an adviser, for those who don’t know, really just means that I am acting as a consigliere or consultant slash adviser, and instead of getting paid in cash, I get paid in equity. I get paid in a portion of the company over time. And so that – that then led to some very good decisions, and I had very lucky timing also. Because, say, 2008, 2009, there was less capital in the startup game, and that allowed me to invest in some great companies, and, like you mentioned, some of them – I mean, the Facebooks and Twitters and being an early adviser to Uber and then later Ali Baba, and I was the first adviser to Shopify, which had eight employees at the time and now has 2,500 to 3,000, and is a publicly traded company, and so on and so forth. So ultimately, the portfolio ended up being, I want to say, 60 or 70 companies, currently.

A new chapter as a podcast star

Foto: Ferriss had a chance to interview Arnold Schwarzenegger for his hugely successful podcast. source The Tim Ferriss Show

Feloni: So, Tim, you’ve had a few books at this point, but whenever I mention your name to someone now, what typically comes up is the podcast, and this is something that you started a few years ago. The way you put it, it almost seems like it came up as a lark type of thing.

Ferriss: Oh, it did. It’s not just the way I put it – it totally was, dude. It totally did.

Feloni: How did that happen?

Ferriss: Well, after “The 4-Hour Chef,” which was a very complex book, I was very burned out and wanted to take a break from anything that was writing-focused. And I was interviewed at the time on Joe Rogan’s show, Marc Maron’s “WTF,” “Nerdist” with Chris Hardwick, which has since exploded into its own industry unto itself, and I really enjoyed it. I really enjoyed it because I could be myself. I could curse if it came out, from Long Island and all, and there was very little censuring. A and B, the format was long enough that I could get into the details, I could dig into the nuances, and I didn’t have to try to encapsulate everything about a 600-page book into 20 seconds of scripted time when the person I’m talking to is reading a teleprompter over my shoulder.

And in those interviews I had so much fun, No. 1, and then, No. 2, they moved a lot of books. I was blown away by how many books these podcasts moved. It just completely made my jaw drop compared to a lot of other media.

And I committed to six episodes to start. I felt like that would give me a certain critical mass, where I could develop new skills, maybe remove a few verbal ticks and decide and assess fairly whether I enjoyed it or not. So I committed to six episodes. First one was a softball with my buddy Kevin Rose. Didn’t even have a name for the podcast at that point, and we got – or I got, I should say; I’m trying to use the royal “we,” but it was me – I got sloppy drunk because I was nervous, I was really nervous to interview one of my best friends, partially because he was busting my balls the whole time, and after six episodes I decided to keep doing it. I was having a lot of fun. And now, 300 episodes or so later, I’m still going and it’s become, like you mentioned, what almost anyone who comes up to me in the street mentions.

Feloni: I’ve noticed in your podcasts, it seems to be a common thing that you interview people across all kinds of industries. You even have some maybe experimental episodes where you’re talking about things like your morning routine or things like that. When I look at the past 10 years or so of your career, it seems that you – this a common theme – that you jump around among things. Do you get bored with stuff easily?

Ferriss: Oh, I would say I get bored with things easily, but the jumping around is also a protective mechanism. So much like, I had mentioned diversifying my identity with content by going from “4-Hour Workweek” to “4-Hour Body,” even though I’m still … I still had interest in business stuff, but I wanted to establish the precedent of me exploring different subject areas with the same framework. The insertion of experimental episodes into the podcast, say, the “drunk dial” episode, would be a good example. So I decide, all right, what would this look like if it were easy? Well, I would put out a note on social. I’d say, “Hey, guys, fill out this Google form, give me your phone number or Skype handle, and I’m just going to sit down with some gin and soda and I’m going to start drinking and then I’m going to call the first 15 people or 20 people and you can ask me anything you want, and that’s going to be a podcast episode.” So it self-selects for an audience who’s up for that type of experimentation.

What it means to be Tim Ferriss

Foto: Ferriss learns anything and everything, getting people from the top of their fields to teach him. Here he is learning to drive a rally car. source “The Tim Ferriss Experiment”

Feloni: I’ve heard you call yourself a dilettante before. Someone –

Ferriss: Yeah.

Feloni: Dabbling in a bunch of different things. And what is it that you specialize in?

Ferriss: I specialize in pattern recognition and accelerated learning. So taking a subject that seems very complex or that can be presented in a very complex way, and distilling it down into the fewest number of moving pieces that really matter. So the 20% that gets you 80% of the results that you want. And then imparting that to other people.

Feloni: So with that perspective, you’ve built up a good amount of success over the past 10 years, but something that I find interesting about you is that, more so than a lot of even entrepreneurs in tech, that you’re really open about your failures, whether that was being turned down by publishers or your TV show being dropped or just a wide variety of things. Is that deliberate on your part? Is that as much for you as it is for your audience?

Ferriss: It’s very deliberate. I don’t know if it’s “for me” because it’s painful.

Feloni: Well, maybe coming to terms with the pain?

Ferriss: No, no, I mean it’s not really a cathartic exercise for me – I suppose it has that effect – but I talk about my failures because I think it’s dishonest to only talk about your successes. It’s so critical that people realize mistakes are part of the game. Unforced errors are part of the game and as soon as that becomes the norm or the expectation, people can persist when they inevitably flub or drop the ball. I’ve had a bunch of what people would consider failures, in TV, in books, in any domain that I’ve participated in, I’ve made huge mistakes, massive errors of judgment. And nonetheless, if you focus on acquiring skills and relationships – acquiring – developing skills and relationships, if that’s your focus, over time, you will win.

Feloni: Do you see yourself as a role model at this point?

Ferriss: I … no. “Role model” is … I wouldn’t call myself a role model. I would call myself a teacher, certainly. I think there are certain tool kits that I’ve acquired, or approaches that I’ve tested that people can emulate, certainly, and use to replicate results. I mean, that’s what I do. But I wouldn’t anticipate, nor really want anyone to look at me and say, “I want to be Tim Ferriss.” No, that shouldn’t be the goal, and trust me, I mean, I talk about a lot of my demons. Like, I don’t think you want to sign up for that necessarily.

I want to be the teacher who makes his students better than he was. I want to give people the tools and say, “OK, look, I made this shitty little birdhouse that people seem to be impressed by, but you can go build a Gothic cathedral if you want with the same set of tools, right?” That’s a bit of an exaggeration, but you get the idea, and then send people on their way to have their own adventures.

Feloni: Well, thank you so much, Tim. I really enjoyed talking to you.

Ferriss: Yeah, likewise.