The Tim Ferriss Show - Episode 4: Ryan Holiday
Episode Date: May 6, 2014This episode features Ryan Holiday, who became Director of Marketing at American Apparel at age 21 (!).Since dropping out of college at 19 to apprentice under the strategist Robert Greene, Ry...an has advised many bestselling authors (including yours truly) and multi-platinum musicians. He is master of the media, and he knows how to both build massive buzz and respond to unexpected crises. I hired him to help with the launches of The 4-Hour Body and The 4-Hour Chef, and his unorthodox approaches always impress. He takes the paths less traveled.In this episode, we discuss dozens of topics, including the real-world strategies he uses to thrive (not just survive) when the world is exploding around him.Enjoy! ***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Good morning, afternoon, and evening, you sexy little people and even you large people out there.
This is the Tim Ferriss Show. In this episode, I will be having a long discussion and I hope it is an interesting
discussion with Ryan Holiday. I've known Ryan Holiday for quite a time now, since 2007,
South by Southwest. That is when we first met. And he has helped me with a number of my book
launches, including the four hour body and quite a lot of the four hour chef. He is very, very
clever, very unorthodox, and he got an early start.
He is known as a media strategist for controversial clients like Tucker Max,
best-selling author and founder of American Apparel, Dove Charney.
He dropped out of college at 19 to apprentice under Robert Greene,
known for the 48 Laws of Power and other best-selling books.
Went on to advise many other authors,
multi-platinum musicians.
He is director of marketing at American apparel,
where his work has been profiled all over the place.
And he's had to deal with everything from lawsuits,
scandals,
uh,
huge opportunities and everything in between,
uh,
his strategies and approaches in handling good and bad situations have been used as case studies by Twitter, YouTube, Google, on and on and on and on.
He is a good friend, very smart, very in control.
We'll delve into tactics, philosophy, his new book, and much, much more.
I hope you enjoy it, and thank you for listening.
Optimal Minimum.
At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? And thank you for listening.
So Ryan, to start off, I suppose we could talk about our mutual love of stoicism and how we both fell into the throes of philosophy. But for many people, I think they, number one, don't know perhaps the origins of how you encountered stoicism.
I remember one of your friends, one of our mutual friends, telling me about how you were one of the odd ducks out who was fascinated by stoicism in high school. I think
that is part of the story, but maybe you could give us a little bit of background on how you
ended up encountering all these various characters historically and getting into it.
Yeah, it was weird. It actually was in high school i was i was in college i was a i was writing for
a newspaper and i got sent to this conference that um that dr drew pinsky like he has a show
on hln he's the host of loveline he was like leading this private session with college journalists
about and i was so i sit through the whole thing and then after i walk up to him and i don't know
what possessed me to do this but i asked him if he had any books that he would recommend because he seemed like a very smart person who read a lot.
And he was like, you know, I'm reading this book about this philosopher named Epictetus.
It's a philosophy known as Stoicism.
I think it's really good, and you should check it out.
And so I went, and I bought it on Amazon.
I still have the Amazon receipt, So this would have been like 2006.
So I bought it and then I bought this other book called The Meditations of Marcus Aurelius,
which Amazon suggested when they link purchases.
And this was before Amazon Prime.
So Marcus Aurelius comes first.
And I sit down and I read it.
And it just totally blows my mind in the way that a book can blow the mind of a 19-year-old boy, I guess.
Tyler Cowen calls them quake books, books that sort of shake everything.
And it was that for me.
It was this book that totally turned my whole life upside down.
And at the time, I just got dumped by this girl that I dated for a super long time.
And I was deciding whether I wanted to do this college thing or not. And it was just this book
that was the perfect book at the perfect moment. And it's philosophy, yes. But as you know,
it's philosophy that you can actually read that helps you with actual problems that you're
dealing with. And so it was the perfect thing. And I got introduced to
it by the guy who does calls about STDs on the radio at like from midnight to 2am, which is not
what I would have expected. But you know, the rest is history. Yeah, it's funny. I actually had no
idea, which is hilarious, given how much we've talked about this type of thing before that that was how you're
introduced to all of this so dr drew also deals with uh is very involved with a number of
non-profits that deal with say heroin addiction and and uh i can imagine why he would pick that
book up as a side note what year of college was this, if you remember?
And secondly, not the year itself, but were you a freshman, sophomore, et cetera? Secondly,
how was Marcus when he was penning this notebook, I suppose, that became Meditations? And then
lastly, what type of decisions did you make as a result of reading the book?
Yeah, sure. So I was just starting my sophomore year of college, and I ended up dropping out at the
end of that year.
And I think we met, if I remember correctly, like a few months later.
And you quote Seneca in the four-hour work week, and I think that was one of the things
that we connected by.
Yeah.
So it sort of all was happening at the same time.
But Mark Ceruleus, he wrote
meditations, as far as I understand, while he was emperor. So he would have been in his 30s and 40s.
He died fairly young. We don't know how long he was writing the book. There's a few places that
allow historians to date it somewhat somewhat but we don't know like
what each specific meditation was referring to or why we just know that he was writing them usually
at night um during during what would only be a very stressful job that you would have to, you know, decompress about every day. And so for me,
like, you know, when you go through a breakup, you are usually you're angry, but then you're also
sort of not self-loathing, but you feel crappy and worthless and you don't know what to do. And so for me, it was this idea of like, look,
get off your ass. You can make the best of this situation. What are you going to do about it?
So one of the things that I did when I read this book was it sort of sent me down this path of
other things to read. Like he says in the book, he says, go directly to the seat of knowledge in terms of how
to learn. And so he actually says, throw away your books, go directly to the seat of knowledge.
So I did both. I went and I read every book that I could about philosophy, about life,
biographies. And that set me, I've read hundreds and hundreds of books since then, but I also snagged these mentors that showed me real life and they taught me things in person.
And I think that's when I learned that this idea of philosophy and a life of doing things and being successful and working were not at all mutually opposed.
I think a lot of people find philosophy and it just sends them down this rabbit hole of books
and they get further and further removed from reality as a result. And so
this did not have that effect for me. And how would you, I feel like philosophy, we talked about this when I originally proofed early, early, I guess, drafts of The Obstacle is the Way, your latest book, that, you know, philosophy, selling philosophy is problematic, right?
Sure. Because the, I think the term for most people brings, it conjures an
image of the, uh, schmuck in Goodwill hunting in the bar who's paraphrasing literature without
giving any credit or some like tortured graduate student at NYU who loves to sort of quibble over semantics of words that really,
at the end of the day, the argumentation is just a lot of fancy tail chasing. And that's,
I think, a very mainstream interpretation of this word philosophy. How do you view
philosophy? How do you present it to people so that it's palatable or attractive?
Yeah.
So when I sat down to write the book, I totally empathize with that.
No one wakes up and says, like, hey, I need philosophy.
They say, you know, I have this problem and I need a solution to this problem.
Well, it turns out that historically that's what philosophy actually was for, specifically
Stoicism.
Like, there's a great quote from Henry David Thoreau where he says, to be a philosopher is not about having subtle thoughts or founding a school. It's about solving the was considered to be a philosopher, but not because he wrote anything down, but because of how he lived his life.
You know, Socrates didn't write anything down.
Epictetus, we only have his lessons because a student of his wrote them down as notes.
And Marcus Aurelius is like, you know, he wanted to be a philosopher, but times are really, really bad.
So stoicism was very popular during the American Revolution.
George Washington read the Stoics as a teenager.
At Valley Forge, he actually put on a play about Cato, which is one of the most popular plays in the world at that time.
Thomas Jefferson died with a copy of Seneca on his nightstand.
And then during the Civil War and the Victorian era, you saw another resurgence of stoicism.
Stoicism was big during the American Revolution, the Industrial Revolution, the Enlightenment,
the Renaissance.
And then, you know, it was also like Marcus Aurelius was living in the decline
and the fall of the Roman Empire. Like, it doesn't get much worse than that. And so it's basically at
its core, it's this philosophy that says, like, you don't control the world around you. You only
control your response to that world. And so that's a very practical and beneficial philosophy when
a lot of things are happening around you that you wish weren't happening. at some point or been forced to read, I'm sure, some excerpt of, say, Epictetus or meditations,
probably in college. And as with most things you're forced to do, most likely did not find
a lot of joy in it. But Seneca really grabbed me. And I don't want to go into a long story of why
that's the case. But so you have this, let's just call it the,
the trifecta of, of stoicism or the, or the big three, right? You've got the Judas Marcus,
really a Seneca. It seems like Marcus is primarily your guy. I don't know, but I've been, I've been
very curious to see how different people resonate with differentoic thinkers. And I'm curious, number one,
who your primary influence is. And secondly, why you think that is and how you think different
people are attracted to different Stoic thinkers. Sure. Well, it's interesting too about philosophy.
Most people are never forced to read the Stoics because professors don't like them as much because there's not as much room for interpretation.
Like, it's pretty straightforward.
And I think that's why you like Seneca.
I like him as well.
It's like he says these sort of very timeless, eminently practical truths in a straightforward, clear way.
And they talk about,
they talk about it in the context of like our actual problems. Like they talk about,
Hey, like, you know, Seneca will be writing a letter. It's like, Hey, like, you know, I heard like your wife died. Like, here's some advice. Um, I hear you're getting slandered in the Senate or
there's a lawsuit pending. Yeah. Here are my thoughts. Yeah. Totally.
Totally.
So I, like you, I lean towards Seneca, but also Marcus Aurelius because they were two,
like Seneca was one of the most financially successful men in Rome.
He was an advisor to Nero.
He was a sort of famous tutor and playwright, but he was also skilled at investment. So he was very financially successful.
So when you read his stuff, he's dealing with sort of the same timeless problems that anyone who has success or works in business deals with.
Bad markets, luxury.
He's just sort of dealing with all the temptations of business he's talking about.
So I like him a lot as well.
Personally, I like Marcus Aure as well. Personally, I like
Marcus Aurelius. I like the notion. What's so fascinating to me about him is he was literally
the most powerful man on earth. He was worshipped as a god in his own lifetime. He could do whatever
he wanted. And you read this book that he wrote primarily for himself, and it's just notes about self-discipline, about being a good person, about forgiveness, about honor, about treating people well.
So that's where I like it.
I get the most practical benefit in terms of leadership and and, you know, self-awareness and stuff
like that. So that's why I like Marcus Aurelius. Although I will say, I think it's funny, like you
read this book and at the beginning, Marcus Aurelius is like sort of thanking all the people
who like gave him lessons. And like one of the lessons he learned was like not raping his slaves.
So it's like, it's sort of pretty it's it's very it's on the
one hand it's very relatable like he congratulates himself for never having laid a hand on his slaves
so you can sort of take a you know it gives you a pretty clear idea of what he's alluding to there
um but you you realize like it's very relatable but then also very foreign at the same time. But, you know, I, I mean, how,
what other foreign, like what other person in that position do we have a document about their
thoughts? Like when you could, you could literally do anything you wanted without repercussion.
Here's a guy like writing notes to himself about, you know, being a good person, not taking
advantage of everything that he could
take advantage of,
not forgiving people, and all
this stuff, which I take a lot of
personal value out of. And I think his writing
is so clear and straightforward,
and it's written in this sort of
it's written in these epigrams
that are easy to remember.
Epictetus is
great, too. he's a little more
lecturey um and because he was a teacher so like you're getting the lectures gets into the cosmos
a bit too and in some pretty esoteric ways that aren't immediate they're they're more abstracted
i think more yeah professor friendly for interpretation he he's the most religious of the philosophers of the stoics as
well um which personally not being a religious person doesn't have the same amount of of
relevance for me like when you read marcus aurelius he's not talking about like zeus and stuff
um which you know i think makes it feel a little bit more relatable. And it's definitely the same is true with Seneca.
Like if someone, if you'd never heard of Seneca
and someone took his works and translated them
and took out all the anachronisms,
you could very easily fool someone into thinking this was written
like in the last decade.
Oh, for sure.
Yeah.
No, that for me was critical.
And I mean, the way that I try to define philosophy for people who have never read philosophy or who have been put off by philosophy as they perceive it is, you know, this is an operating system for making better decisions in your life.
That's it.
And I found it so incredibly powerful.
You mentioned something just a moment ago
about Seneca being one of the wealthiest people in Rome,
if not the wealthiest at one point.
I mean, extremely shrewd investor, investment banker, financier.
And let's talk about stoicism for a second, because the word stoic or stoicism has developed
modern connotations that I think perhaps turn people off of the concept of studying something
or reading something called stoicism. And, uh,
I remember a quote, I don't remember the attribution, which was, you know, most feet,
most people face life with the same stoicism of, as a, as a cow standing in the rain. And, uh,
and I think that people, uh, a very common perception of stoicism, and perhaps this is
true for some people,
I mean, Cato seems the most kind of Spock-like in a lot of ways, is that you feel neither
pain nor joy.
You are just basically a cyborg.
And the goal is to not experience emotions whatsoever.
Right. whatsoever. And also, I think people perceive it as asceticism or foregoing all of your worldly
possessions. And of course, Seneca was very highly criticized and continues to be highly criticized
as the opulent stoic. How can he talk about foregoing riches or, and I'm kind of laying this one up because I've
obviously read a lot about this, but I'd love for you to talk about how you would reconcile
some of those things.
Like, does stoicism, is it compatible with material or financial success or being famous
or are they completely at odds with one another?
Sure.
Well, look, I think, weirdly,
I think since both of us are authors, we can very relate to the problem that's happened with the
Stoics over the last 2000 years, which is it's a bunch of people psychoanalyzing people they've
never met based on their work. And over the generations, it builds on itself. And the problem
is, they're forgetting is that the Stoics were, it's a philosophy that's designed to, you should laugh and have a good time.
Or like, you know, money is nice.
Like he's not, no one needs like a reminder of certain things, right?
And specifically, since he was not writing a book for other people,
he was writing a book for himself.
You could, I think you can safely,
you can safely assume that he's writing reminders to himself about the things
that he's particularly bad at. Right. Right. And so it's, it's a selected, deliberately selected
view of a person who's struggling with tough things in their life. He's not, again, trying
to explain a systemic worldview that you should keep in mind. He's working through problems in
his own personal way. And maybe if Seneca had had different friends that were really somber and sad
all the time, he would have written them different letters. Like Cicero was a Stoic or studied
Stoicism and there's more joy in his writings, maybe just because it was a totally different situation.
So what I want people to keep in mind is that stoicism is not about being sad or not having
emotions. It's about keeping an even keel and not getting upset or delusionally happy either.
And so I actually think there's a core tenet of optimism in stooicism. I call the book The Obstacle is the
Way, and it's based on this exercise from Marcus Aurelius where he's saying, look,
it doesn't matter if you're trying to do something and you get blocked. This is actually an
opportunity to practice virtue. Basically, what he's saying is, hey, I know this thing that
happened that you think is bad. It's actually good and it's actually a chance for you to do good things. To me, that's cheerful and that's happy and that's
the kind of attitude of someone who never gets depressed because they always feel like they have
a way out. And I think what the Stoics were saying is, if you go around thinking that the world is great and that it's always going to work out exactly how you plan and that people are always going to treat you well.
And one of the things Marcus reminds himself that tomorrow when he wakes up, people are going to be rude.
They're going to cheat.
They're going to steal.
They're going to argue with you.
They're going to do all these things. He's doing that so he can go out and interact with them in a positive way rather than feeling
let down and pissed off all the time.
Right, right.
Yeah, so I think that's super important.
And I think that's something that's totally been missed from stoicism.
And I think that's why you and I are attracted to it and find value from it in our lives.
It's not like confirmation of our pessimism or cynicism.
And on the contrary, I actually feel like it's intimately connected with being happy and
fulfilled as a person. And that's why I don't think it was a contradiction at all that Seneca
was successful and seemed to genuinely enjoy his life and had financial riches. I think Nassim Nicholas Taleb is another person.
The point is, making money is usually a result of being successful or good at something. It can also
be a result of luck or fortune. And having it doesn't say anything good about you, and it doesn't
say anything bad about you either.
And the only problem that really comes from wealth, well, there's a couple problems.
But being financially successful and, you know, I'm not a millionaire but I'm doing well.
There's temptation to, you know, spend money on, you know, negative things, let's say.
But the real problem is thinking that you need this money to survive.
And so it's funny, like, Seneca has this reputation for being opulent, but in Letters to
a Stoke, he talks about actually practicing poverty, like one day a month, pretending that
all his money was stolen or lost, and that he's walking the streets as a homeless person.
He's doing that so he can enjoy his wealth while he has it,
but never feel like it's integral to his survival or, you know, existence as a person either.
Right, right.
No, it's been, I think, you know, not to bring Fight Club into this,
but, you know, the things we own end up owning us.
And I think there's a big difference.
And this might actually be a Thoreau quote who had his own contradictions like we all do.
I heard he used to sneak off and have big meals at Emerson's house while he was at Walden.
And that is that, you know, the problem is not having riches.
It's when riches have you.
Totally.
And I think Seneca comments on that quite extensively.
And, you know, the problem is not having wealth.
It's when it becomes a source of sort of fear and greed and it dictates how you behave as opposed to being a tool.
Therein lies the problem. So besides, besides obviously these,
these fantastic works of literature, or I suppose that might not even be a fantastic
label. I mean, in some cases, they're war journals of sorts. Coming back to seeking out mentorship in real life, teachers in real life, was Robert Green really the first person to take you under his wing in that way?
Or was there someone else who was a pivotal teacher to you?
Sure.
And how did that come to be? Yeah. So actually, before I met Robert,
I was working with Tucker Max, who we both know. Right. And Robert, of course, just to give some
context, maybe you could explain, give some context on both of them. Yeah. So Robert Green
wrote The 48 Laws of Power, The Art of Seduction, and The 33 Strategies of War. And then I met him in 2006, 2007. I was in college. I met
him through Tucker Max, who's another number one New York Times bestselling author, known as a
really good internet marketer and thinker, and then also does crazy things. But I met,
Tucker showed me about marketing. He introduced me to Robert. Robert really showed me about writing and researching and learning.
And I worked with Robert on his last two books.
He wrote one called The 50th Law, which is about fearlessness with the rapper 50 Cent.
And then he wrote one called Mastery, which is about becoming a master at whatever it is that you do.
Yeah, I love it.
It was like an honor to be a part of it.
So those were my two mentors in sort of direct mentorships.
But I also think like, you know...
How did you, just not to interject,
but how did you, just in the sort of the details,
the nuts and bolts,
how did you initially connect with Tucker Max?
How did you initially...
It all goes back to this college newspaper. I was writing, I had a column there bolts. How did you initially connect with Tucker Max? How did you initially?
It all goes back to this college newspaper. I was writing, I had a column there and I decided I would use it to, as an excuse to write articles about people I wanted to meet. Um, and so I,
I wrote a review about Tucker's website and I emailed it to him and we just started this
relationship and then I would just email him and ask questions.
So it's funny.
I think you probably see this.
People think mentorships are these very official relationships. The way that an apprenticeship was like your parents basically sold you to someone in exchange for room and board for a certain gives you advice and teaches you things decide when you have difficult choices,
what would this person do in this situation? How would they act? What should I do here?
And so I would even say you are definitely one of those people. We don't have some official
mentor-mentee relationship, but you've taught me so much. And I've asked you questions,
and hopefully it's gone both ways.
But you're older than me, you're more successful than me, you've taught me things.
And that's what I think a mentorship is.
And you can have that with basically anyone.
I think a lot of people, they hold out for this sanctioned official relationship
rather than just learning from anyone who has wisdom or advice
or value that they could pass your way um and that you and if you put it into practice and
you do something with it they see value in that as well yeah no i i agree and i appreciate the
kind words obviously uh like you were the one you were were the one who, like, I was studying socialism is
interesting to me. And I think I mentioned it to you. And then you encouraged me to write an
article about it for your site, which sort of set me down this whole path to begin with. Um,
and so I, I think, you know, it's, it's weird how these little conversations can have such a big
impact on your life. Um, but it, it just depends on, I think, how people respond to and treat the opportunities that they get
that often don't look like opportunities
when they sort of first make their appearance.
Oh, definitely.
I mean, Jack Canfield, who co-created Chicken Soup for the Soul,
is largely responsible for the four-hour work week becoming a book.
And it was just one or two offhand comments that he made to me that were encouraging in the early days that produced the proposal because it coincided with a bit of downtime.
And he effectively helped force my hand by making introductions that led to conversations with agents. And, uh, it's, it's, it's incredible
how in the case of, uh, of Jack, you know, he became a mentor to me, uh, because very similar
to the newspaper, I used volunteering for tech nonprofits as a way to meet the people I wanted to meet. Uh, because these events would
put on these organizations like the Silicon Valley association of startup entrepreneurs.
It's a mouthful, but S base, uh, or tie the Indus entrepreneur put on large events, uh, every few
weeks or every quarter, they'll have an event where they bring in thought leaders and their
panels and so on. And so I volunteered for the-Phase when I first moved to Silicon Valley in 2000 and
really just kicked ass as a volunteer for a few months and continually took on more and more and
more responsibility until I was invited to sit in on the board meetings just as an observer, basically. And they were talking about
their next main event, I think is what they called it. And I just kind of raised my, they're like,
well, who are we going to get to do this and manage the event and wrangle the speakers?
And I just kind of shyly put up my hand and I was like, I'll do it. I'll take care of it.
And so they handed it over and I put together a panel. God, what was it called? It was called something like, you know, Titans of Consumer Products or something.
And I invited, you know, the creator of the clapper and the pet rock.
I invited the guy, Ed Bird, who is sort of the jointly responsible for popularizing creatine in the United States as an athletic supplement, which was a huge, huge deal. The founder of Clif Bar, Jack Canfield, and so on and so forth, and got to know Jack by
inviting him to this event and having a bunch of emails back and forth. And then over the years,
asked him every once in a while, pretty rarely, would ask him very specific, short life questions.
That's how the whole thing came to be. In the case of Tucker, for instance, how long
after you initially introduced him to the article you wrote, did you start asking questions? Over
what period of time? How frequently did you email him?
I think this is something people need to understand because asking someone to be a formal mentor is like the absolute best way to never have a good mentor.
Totally.
Because it's like, hey, you want to sign up for like a unpaid part-time job because you have so much free time?
It doesn't work so just be curious to hear sort of uh what you did
and what you would recommend people do if they're trying to find uh or looking for that type of of
teacher i think mentor is problematic because they think of it in such formal terms but
what maybe you could talk on that point yeah totally um i think it was like it was once it
was once every couple weeks or a couple months probably.
I would just ask questions that I thought would be helpful to me but very easy for him to answer.
It's like, hey, if you want me to read your manuscript, that's a lot of work for me to do.
This would be more for you.
If someone wants you to read their manuscript, you're like, okay, that's a week lot of work for me to do. Yeah. Or this would be more for you. If someone wants you to read their manuscript,
you're like, okay, that's like a week of my time.
If someone wants you to give a five-second instant opinion on a title,
you're like, sure, that's one email.
And so I think people don't think,
one, they don't think about what they're actually asking.
And then two, they ask a lot over and over again. It's actually interesting. There's
this thing called the Ben Franklin effect. I don't know if you know this story.
About the lending library?
Yeah.
Yeah. Why don't you tell the story? This is such a great story.
So Benjamin Franklin, there was this member in Congress or one of the things about the
American Revolution. I don't really remember where it is actually. But Benjamin Franklin
faced this sort of enemy in a legislative body who he desperately needed his
support. And they seemed to be intractably opposed to each other. And what Benjamin Franklin did was
he heard that this guy loved rare books and had a prized library of rare books,
one book that he valued above all the others. So Ben Franklin,
being a somewhat bold man, walks right up to this guy and just asks him if he can borrow
his most prized possession. And the guy sort of stunned is like, I guess. Benjamin Franklin
borrows it, just puts it on his shelf for two weeks, doesn't touch it, doesn't use it, and then returns the
book to the guy. And what he finds is that having borrowed this guy's most prized possession,
they now have not only the shared connection, but the guy has to justify in his head why he
would loan this thing that's so valuable to someone else. And so he starts to tell himself
this story that Benjamin Franklin must be good.
He must be someone worth loaning this thing to sort of using cognitive dissonance to your advantage.
Um, and basically it's been, it's been verified, um, you know, by psychological studies since then.
It turns out that when you do someone a favor, you actually feel indebted to them. You would think that doing
someone else a favor would make them indebted to you. In fact, asking something small of them
in some ways can build a better connection because now they're invested in you.
I would try to ask questions or think about things that they would like and that they would feel like they got value out of too.
And that's something that – it's like a subtle psychological shift that people miss for some reason.
Yeah.
Ben Franklin is such a fascinating character. I really enjoyed reading Walter Isaacson's biography of Ben Franklin, which leads me to ask you, I mean, which historical figures do you find most instructional, helpful?
I mean, who are the figures outside of the big three Stoics that you sort of repeatedly look to as your own benchmarks or to learn from?
Yeah, there's obviously a bunch. You know, in the book, I really, I talked a lot about Ulysses S.
Grant, who I thought was really interesting, and as sort of a totally underrated, underappreciated
historical figure. I talk about John D. Rockefeller, I thought you know and again all these people
have problems and so I don't want it
to descend into like hero worship of
any kind it's you look at the people
and you look at the good that they bring to the table
and you focus on that
not on you know the negative
stuff but
I talk about Ulysses S. Grant William
Tecumseh Sherman who is another Civil War general
I'm really interested in.
I think Richard Feynman is a fascinating character.
Yeah, definitely.
Who asks all sorts of interesting questions.
And he had this – what seemed to be this sort of joy and curiosity to him that I appreciate a lot.
Cyrus the Great is another really fascinating character.
Definitely. Cyrus the Great is another really fascinating character who was, again, one of the most powerful people in the world, but seemed to be universally regarded as a good person and not in a propagandist way.
So those are some of my favorites.
I don't think it's a stretch to use fiction either.
I find it weird that people don't look at fictional characters as either good examples or bad examples.
So who are some of your fictional favorites?
Well, one of my favorite books is this book,
What Makes Sammy Run by Bud Schulberg.
It's about this Hollywood screenwriter.
It's like a young Jewish kid who's like a total hustler
who's like endlessly ambitious.
And it's sort of um it's it's very
gatsby-esque um the book but the the point is this guy's like hustling and running all the time
but he never stops to question why and it actually he like the you know the the moral conclusion of
the book is that he gets everything he wanted and it's like the worst thing that you could ever wish
on someone right um and so that's something like I try to think about a lot too.
It's really,
I think it,
it's,
it's about finding the people that you relate to in fiction or nonfiction and
then seeing what you like about them.
Like you like about yourself and them and using that to bring out more of it
and also seeing what you don't like about yourself in them and using it as a cautionary
tale.
Right.
That's a really good point.
Yeah, I have a few books on my bookshelf facing out and I just moved into a new place.
I had the chance to organize my books however I wanted, which is a delightful and extremely
time-consuming, monkish process for me being as OCD as I am.
But the,
the one of them is Zorba the Greek.
So Zorba,
it's just such a great cautionary tale for me.
Cause you have like the,
the,
the intellectual slash want to be intellectual.
Who's very introverted and spends too much time tail chasing in his own head versus
Zorba who's so engaged in the moment, et cetera. Uh, you know,
very maybe Epicurean in some ways. And, uh, yeah, that's really interesting.
Also Dune, I thought, uh, you know,
a number of the characters in Dune were very, very interesting. Uh,
Stranger in a Strange Land as well. So let's look at where you are now because I've been continually impressed by how – at what a young age you have accomplished certain things, responding to huge responsibilities at American Apparel with marketing,
responding to those criticisms publicly,
dealing with all sorts of difficulties,
not difficulties, challenges that we all have,
but professionally on a pretty public scale.
You're 26 now, is that right?
Yep.
Yeah.
All right.
So this is your third book, which just to put it in a chronology, I mean, the four-hour
work week, I guess it was published or written when I was 29.
So you're still three years ahead of me with three books.
To what do you attribute your ability to get shit done. I'm just very curious as to if it's like, well, you blend my two
parents and here you are, like, that's how my parents are. This is how I am. Uh, how much is
nature versus nurture? I mean, what has contributed to your ability to, to multitask and also to get
this, this much stuff done, uh, at this age. I'm curious to hear your opinion.
Sure. Well, I mean, look, so obviously I had two smart parents. They inculcated in me a love of
reading and questions and sort of told me I could do whatever I wanted with my life, which was all
very helpful. And I wasn't like someone who came from, and I talk about those type of people in
the book, the people who came from sort of nothing or worse than nothing, and that's why they were successful.
That's not me.
And then I had these amazing mentors, which were very helpful.
And I also have a big head start on people.
I mean, I dropped out of college when I was 19 years old.
So I've been doing this for a long – like most people my age started at 21 or 22.
So they're sort of just getting started. But that being said,
I think I actually, and the reason I wrote this book is because Stoicism was like, I can trace
so much of the good stuff in my life to specific passages in Stoicism that helped me or made me
think about certain things. Like this idea of the obstacle being the way that there's no such thing as bad things happening to you,
that everything is an opportunity to prove yourself or to do something good,
is something that's been enormously beneficial to me.
There's also a quote in book five of meditations that I used to have printed up on my wall.
And it's this conversation where Mark is sort of actually having it with himself, like it's dialogue.
But he's like, so you're waking up in the morning and you're covered in the blankets and you know you should get up.
But you say to yourself, like, but it's so warm here.
Like, I want to stay here.
And he says, like, but look, you're a human being.
Your job is to get up and work.
And it's like, what do you mean you've worked enough? Would an animal
say that? Would an animal ever say that they'd done enough work? And then he says, people who
love what they do wear themselves down doing it. They forget to eat and sleep. They just work
because it's not work. It's who they are. And I think for me, getting stuff done has been a function of being
able to start having that conversation with myself when I was 19 years old rather than
partying late at night and then waking up hungover every day. I didn't do that.
But I really think it's the cumulative process of waking up every day and going to work and like really working and not caring about the
rewards or the success but working because i love what i'm working on that you know compounded
interest is one of the most powerful forces on earth right and you can apply that to your own
work and every day if you wake up and you work on something, you get a little bit closer and it grows.
And I think that's been – you write one book, it's easier to write another book.
And then you write two books, it makes it easier to write a third book.
And I've never been a fan of doing just – I think you're like this too.
I don't get how people do just one thing.
Like you're really good at investing, but could you just do that?
I don't think that would fulfill you as a person.
Yeah, I couldn't do that alone.
And I think it's weird, but I found that the more things that you're doing,
it's like, okay, if you do one thing, you can be really good at it.
If you do two things, you feel really busy.
But if you do three to five things, you're not that busy
and they all help each other and make you better at them. So for me, like writing and marketing
and like, you know, research and all the things that I was doing at the same time
made me better at all of them. And it sped the whole process of learning up really fast.
When you are most productive, how often are you running?
Because I know that that is another part of your life, or at least historically has been.
Yeah. So I run almost every day. I started, I run every day, but then I also, you know,
from some of your stuff and other people, I know it's not the best thing physically for you. So I usually do CrossFit like two days a week.
And then I try to swim one day a week.
And so I run the other days.
Right.
Yeah.
I found I think long walks are also very underrated.
Totally.
Which, yeah, I mean, we could go through the long list of people who've said that historically.
Yeah. Well, I actually, I try not to think about, I definitely don't think of walking that way. And
I actually try to not think of running that way, almost not as exercise. Like I think it's better
for your, it has a better impact on your brain than it does on your body. Definitely walking.
It's like, I've written huge chunks of my books
because I went for a walk
and then I had a breakthrough that I wasn't expecting.
Yeah, I think it might be N.N. Taleb
who also doesn't trust people who won't go for a walk
when they speak with him.
I could be just making that up,
but I'm pretty sure I'm not.
That sounds about right.
Yeah, it sounds about right.
And then he'll sprint to imagine, what did he say?
When he has to motivate himself to sprint, he will think of running after the head of the Federal Reserve and smashing them with a baton on the back of their head or something.
He's a hilarious guy.
Who do you turn to?
Actually, let me back up to a separate question.
You're a prolific reader.
You have a sort of recommended reading list that's quite popular, an email list that people subscribe to.
Yeah.
And I've really been impressed by your synopses of the books that you read.
But for someone who is not an avid semi-full-time
researcher like yourself, what are the top, say, two or three books that you either discovered or
delved into while researching The Obstacles Away? I mean, if you had to pick your top two to three,
you're like, all right, if you want to maximally gain in whatever way, I'll leave it open to you.
Read these two or three books. Like if these are the only two or three books you read
this year, you'll be better off for having that.
Okay. Well, I'm looking at the bibliography right now and some that jumped out at me that were
total favorites. Ron Churow's biography of John D. Rockefeller, which is Titan, The Life of John D. Rockefeller, was like a total game changer to me.
It was an amazing biography.
I like Sarah Bakewell's book, How to Live.
It's like a series of essays about Montaigne, who invented the essay.
What was your name again?
Sarah Bakewell.
Cool.
I like, let's see.
Oh, I read this book, The Fish That Ate the Whale,
The Life and Times of America's Banana King.
He was this totally fascinating but relatively unknown historical figure who started he started a fruit
company buying spoil like the the day old not day old but the about to expire bananas um that would
be imported in like late 1800s america and he would sell them um like he would sell them by
train car he ends up he ends up buying United Fruit.
He starts a small fruit company that he grows to be so big that it buys United Fruit Company, which is the biggest fruit company in the world.
So that's why he's known as the fish that ate the whale.
He's this sort of fascinating Jewish businessman.
I read a really good biography of Edison by Matthew Josephson called Edison,
a biography.
Got it.
And if there was any others,
I'm trying to think.
Yeah,
those were some,
Oh,
and I read a really good biography of Ulysses S.
Grant called Ulysses S.
Grant triumph over adversity that I loved a lot.
Cool.
Just writing these down myself because I need another 20 extra books on my Kindle that I
haven't read.
I'm just kidding.
Right.
I want to give you some more 700-page biographies because I know you need more of those.
Very cool.
The Fish That Ate the Whale.
That is a fantastic moniker.
Yeah. That one's really short
and you'll really like that guy he was crazy um and he he was like the i don't i can't even
describe you should just read the book it's amazing the writer that wrote it um uh rich
cohen wrote another uh amazing book called tough jews which was about J-E-W-S, about
Jewish gangsters. Basically
the people that you see on
Boardwalk Empire.
He's an amazing writer who you'd really like.
Cool.
I view books oftentimes
as tools.
Part of the toolkit
for making these better decisions.
Obviously, and enjoying life at the same time. I do love reading. right? Uh, part of the toolkit for making these better decisions, uh, obviously,
and enjoying life at the same time. I do love reading. Uh, what other, are there any other
tools that you use or rituals that you have had consistently and found useful? Uh, so I'm curious,
maybe we can start with the second part of that. What is the first 60 to 120 minutes of your day look
like? When do you wake up? What does your morning routine look like? And then maybe we can talk
about your daily routine if there is one. So I try to wake up somewhat early, like 7.30 to 8.
I'm not always successful at it. So I try to wake up early and I try not to check my email in the
morning if I can, but I'm not usually successful at that either. But I try to wake up early and I try not to check my email in the morning if I can,
but I'm not usually successful at that either. But, um, I try to sit down and I write for like
the first hour to two hours in the morning. Um, I find that there's less going on. There's less
people bothering you. Um, there's a great writer. Uh, he has a site called Farnham street. His name
Shane Parrish. What is the name of the site? Farnham Street, F-A-R-N-A-M. Okay. And he wrote an article recently where he's like,
look, the number one productivity secret is just wake up early because there's less going on.
You're more productive at the beginning of the day. So I try to get my writing done in the
morning, like whatever I'm working on. I try to like bust out an article from working on a book. I try to tackle a chapter. Um, I just try to, I try to write in the morning, um, for an hour
or two and then I sort of get to work from then when everyone else is kind of waking up and getting
going. Right. Okay. And then, uh, what does, what does your day look like from that point forward?
Yeah, I usually go out to breakfast. I try to eat at the same restaurant every day rather than deciding what I want to have for breakfast.
What do you eat?
Usually three eggs and two sides of bacon, so I get a ton of protein.
And then I'll have guacamole or something with it if I want to liven it up a little um get some non-animal matter yeah exactly um
although i got chickens at my house i don't always go out anymore i sometimes i have fresh
eggs at the house and you're in you're in austin yeah i live in austin um and then i then i go to
work like i have a one index card that I write usually the night before my list
of things to do that day. And I try to
keep that list pretty small, like
five to seven things usually.
And I
cross all those things off. They could be small
things like email so-and-so
or it could be like
write chapter three. It could be
big thing or little thing.
I cross those things off.
And then the rest of the day is just responding to stuff that's happening, whether that's emails
or phone calls that I've scheduled or meetings that I have to do. I try to avoid as many meetings
or phone calls as humanly possible. How do you go about doing that? Are you diplomatic? Or what's
your approach to deflecting meeting requests or coffee dates and so on and so forth? Yeah, Paul Graham actually has a great essay about this
called maker versus manager. Oh, it's such a good essay. Yeah, that's a that's a great piece.
But it's really hard. Like, you're someone who fits in this category when you're both a maker
and a manager. Yeah. Like most most makers are delivered are just not good at doing the other
things. So they don't
do it it's hard when you actually have stuff you have to manage um but i try to i just i just say
like hey like sometimes i'll just lie i'll say like hey i'm traveling i can't do the phone or
um like hey i really prefer email like if we can hammer this over out over email i'd be much better
and i know that sometimes email takes longer than doing a phone call because you have to go back and forth. But the point is,
it doesn't interrupt what you're doing and it does it on my schedule. So I just try to be up
front about it. I just say like, hey, look, I really hate email or I really hate jumping on
the phone. Can we just do this over email?
And most people are understanding.
And the people that aren't, I either don't care or I understand that they're more important than me and they get to dictate the terms.
I'm glad you brought up the point about, number one, I have the exact same habit with index card. That is the finite surface area I find, much like Parkinson's law helps to refine how you prioritize.
But the point you made that I think is really important to underscore, among others, is that just because email might take slightly longer does not mean phone is better. Uh, and similarly, you might choose
a slightly longer driving route because it's easier to remember and it's more scenic.
Oh, that's a great analogy.
As opposed to being like, yeah, I'm going to sit through like horrible traffic with people honking
where I have to really pay attention the whole time and can't daydream. But it's 15 minutes shorter route.
And there's a really important question that I've learned to ask myself.
And I'm sure I didn't create this, but I don't remember the attribution if I didn't.
And that is, it's not whether you can afford the time or not.
It's whether you can afford the distraction. And, uh, you know, that's why it's like, yeah,
it might only take you five minutes to call someone, but you and I both know if you're
writing something or if you're a coder, uh, that could mean you start over, you start the clock
from zero and it's going to take you 45 minutes to get back into the flow of what you were doing. Yeah. Uh, what, what speaking of flow and writing, I mean, what, uh, what do
you, I think that, you know, I admire your writing because it's a reflection of clear thinking and,
and I'm wondering what you see as the most common mistakes that writers make? What are some of the most common mistakes where you, you, you write for quite a few outlets online and, uh, you're really prolific. You, you write a lot more
than I do. And, you know, I'm envious in a way that you're of your output. What, what are the,
what are the biggest mistakes that you see writers making? Not professionally necessarily,
but just like stylistically,
editorially? What are some of the bigger mistakes, do you think?
Yeah, well, I think it's weird. I write a lot, but I think I write a lot out of humility. Like,
I'm trying to get better. And I think that the only way you do it is by making commitments to
write a lot, publishing and sort of getting feedback. And like, so I, you know, three books in three or
four years is a lot, but plenty of people do more. The articles are designed to make the books
better. That's the way that I think about it. But I think a couple of mistakes that writers make.
One, they don't have anything to say. They think that writing is good. Like they think that writing is the skill that is scarce and good.
Putting sentences and words together is good.
Look, I would read a biography written by someone with a seventh grade education if what they were talking about was fascinating.
Have you ever seen that thing where it's like, they,
they take a bunch of sentences and they take all the vowels out or they move the words around and
you can still read it. Yeah. It's not the technical skill that's rare. It's having something
interesting and compelling to say. So I think that's the big thing is people don't have that
much to say and they focus all their time on technical writing rather than like saying
something that's never been said before. Um, but the ties into that but i see a lot of writers who who start writing before
they've figured out exactly what they plan to say and who they're saying it for like they're trying
to find the point while they're going um and so i so I use note cards to organize my research.
And I very rarely write anything that isn't fully outlined and sketched out, especially
books.
So the writing is the easy part.
Figuring out what you have to say and doing the research and bringing something new to
the table, that's what's special and rare.
So I try to,
I focus my energy on finding the stories or the thing that I'm bringing to the table
that no one else but me could bring.
And I think far too many writers skip that.
And that's why we get these crappy bulleted lists
or, you know,
on the other hand,
like an 8,000 word article
that could have been 20% of the length.
I think those are mistakes that writers make a lot.
I think also just not being honest.
I think a lot of people are either pretending and puffing themselves up with their writing
or they're hiding something.
James Altucher, who you both know. I was just going to mention James.
He's so good at doing the opposite. Yeah. He has this rule where he writes the thing that he
doesn't want anyone to know about himself. Whatever he's afraid to say, that's what he
wants to write an article about. And look, sometimes that ends disastrously and he gets in trouble.
But most of the time, it creates this vulnerable, authentic voice that people relate to because no one else is saying these things.
And that's what your job as a writer is to touch something inside of the audience.
And you can't do that if you're lying to yourself.
Yeah.
No, definitely. Huh. side of the audience and you can't do that if you're if you're lying to yourself yeah no definitely huh uh i i find i find writing process just endlessly fascinating uh totally because no
one does it the same way yeah everyone's different um that's that's one thing i realized really early
on like there are there are best practices for marketing, bestselling books. There are
very, very few consenses about the best way to write a best reading book, if that makes sense.
I mean, that's part of the reason why I fell in love with daily rituals, which profiles,
you know, 170 or so, uh, world famous creatives, whether it's writers, composers,
scientists, et cetera, and how their daily schedules are laid out because they're so
different.
Um, it's, it's really fascinating to me.
Um, do you watch documentaries?
If so, what, what are, uh, what are your favorite documentaries that come to mind?
I love documentaries, uh, but I don't watch that much TV,
so I don't get to watch as many as I like because...
Yeah, but some favorites.
I like Fog of War, I think is amazing.
That Phil Spector documentary from a couple years ago was pretty crazy.
I think it's called The Wall of Sound,
but I forget what it's called exactly um there's the guy who did uh fog of war has a new one out about donald rumsfeld that i
want to see um called the the unknown known um but my i love ken burns i've watched like pretty
much every ken burns documentary you could ever see including all 10 hours about the civil war and all 10 hours about the national
park system so i think like what i love i love when you like all i love any art where the person
doing it is clearly like the master of their craft right and to me ken burns is like the best person
who ever lived at documentaries and i don't know how anyone could beat him. And so it's like, I'll watch, you know,
in 10 hours about national parks,
like, because it's that good, even if you don't care.
So I think I love his stuff.
Yeah, that's funny you mentioned that.
That's how I feel about John McPhee as a nonfiction writer.
Totally.
I mean, he's, for those people who don't know who he is,
he's at least a one-time, those people who don't know who he is, he's, uh,
at least a one time, maybe a two time Pulitzer prize winner. And I was fortunate enough to have him in seminar, uh, for nonfiction writing called the class was called the literature of fact when
I was an undergrad for one year, which was amazing. It was really hilarious too, to get back
a three page writing assignment and to have more red ink from him on the page than black ink,
you really feel like a dumbass when you realize how sloppy your thinking is when you get something
like that back. But he's written books on everything from an entire book on oranges,
an entire book on one tennis match, an entire book on hand-carved wooden canoes,
a book on Plymouth Rock. I mean, it's just the breadth
is so amazing. But if it's written by him, I just don't care. If it was a book on chopsticks,
I'd be like, absolutely, I'll read a 200-page, 300-page book on chopsticks written by John McPhee.
Right. I love he has that one control of nature that's really fascinating. It's just about like,
it's like about the Mississippi River, some volcano in Iceland, and the hills of Los Angeles.
And you're like, this should not be fascinating, but I'm hanging on every word because you're so good.
Oh, it's so good.
I mean, chances are he's been writing for so long.
He's been a staff writer at The New Yorker for decades and decades and decades.
I think he's got to be in his 70s or 80s even now.
But I remember researching The 4-Hour Chef,
and I was like, I bet there's something
that McPhee has written on cooking and food,
and I bet it's going to be one of the best pieces
in the English language.
And lo and behold, there is this piece
from sometime in the maybe 80s
called Brigade de Cuisine, written about this tiny
restaurant in New York and just this maniac executive chef. And it was like, all right,
there we go. Like, yeah, the best I've ever read about cooking or food. And of course,
it's John McPhee. Yeah. What are some of your goals for this year uh i'm just i'm very curious to know if if
do you believe in resolutions that are long-term resolutions is it tiny habits day by day i mean
what are some of your goals uh whether for this year or or or shorter term mean, how do you, or longer term for that matter? Sure, yeah.
I don't know.
It's not that I don't believe in goals.
It's actually been a weird, and this sounds, I'm sure, like a humble brag,
but it's a genuine problem, or a first world problem.
Like, I wanted to write books.
Like, that's what I wanted to do.
And, like, I wanted to be a writer.
That was my thing.
That's what you wanted to be even growing up. that what you thought you were right yeah and so to i accomplished it very early and and now
it's it's it's like okay now what and but there's i don't have like well now i want to be the biggest
author in the world like part of one of the benefits and then also consequences i guess of stoicism is that it's very humbling and it it sort of helps filter out like very selfish or materialistic goals i
would say so like i'm not like oh i want to i want to have millions of dollars i want to have
hundreds of millions of dollars like it's like i'm comfortable. I would like to continue to be comfortable, but that ambition is somewhat sated.
I have more book ideas, so I'm in the process of thinking about and potentially selling
another book.
But I'd like it to take longer, and I'd like to challenge myself in ways that way.
I think I may get married.
Well, I'm engaged.
I'll probably get married this year.
So that's like something – I think like in a lot of ways –
I would hope you would have some plans for getting married.
Or if there's just like, no, I figured out the engaged part, but I'm not sure on the marriage part.
Right.
Well, no.
It's like a hold option.
Yeah.
Right.
Right.
Now I've got some time.
I bought myself some time.
Option agreement with your girlfriend.
Right.
I locked it down and now I'm just going to wait.
No, I think I would like to focus on less sort of external goals and maybe more internal goals just like you know i i think we're i don't
think there's anyone out there that's like i'm exactly as like low stress as i want i'm exactly
as sort of like kind or forgiving as i want i'm exactly as you know like um happy like i i'd like to focus on sort of internal personal um stuff in in terms of adjust like
integrating and adjusting all the things that have come into my life over the last few years
into the kind of like everyday norm that i would like so it's it's not a specific thing and that
might hold me back in some ways but i i think it's it's less about like sort of external
publicly validated success and more about just like all right is this the person that i want to
be well kind of but here are three or four things i would fix well like let's focus on those right
so two two related questions that are follow-ups the first is if you if you want to be a writer
and you write a lot, you mentioned one
of the problems with a lot of writers is they just don't have anything to say. How does one
go about having something interesting or meaningful to say? And how do you do that?
Let's begin with that. And then I have a question about working on internal goals.
Sure. So the best writing advice I ever got, and I think it came from Tucker, but I don't remember.
But someone asked him, like, how do you become a writer?
And he said, writers live interesting lives.
And that's how you find something to say.
Like, you go and do interesting.
And yes, this is true for fiction or nonfiction. Go do interesting things, experience the world, and develop some sort of perspective or knowledge or wisdom that you can pass along through your writing.
So the four-hour work week came from your experiences running a company and then deciding to travel. And my first book, Trust Me, I'm Lying,
came out of my experiences in marketing
and doing a specific kind of marketing
and having a sort of existential crisis
that came along with that.
And this book came out of my studies and experiences,
like researching and reading and just living my life
in a high-pressure, high-stakes environment.
And I know that seems weird,
but just like the best marketing decision you can make for a product
is to have a really good product that people want,
the best way to have writing that people want is to live a life
and have experienced the world in a way that allows you to communicate something to people that
they've never heard before and and i think it's actually especially true in fiction because you're
like at least in non-fiction you can like someone could go out and study and objectively find like
academics can write good non-fiction books um based on their research. But nonfiction, you have to be able to communicate all these intangibles to the reader.
You mean fiction?
Yeah, sorry, in fiction, yeah.
You have to communicate all these intangibles about life and about relationships and about
how the world works.
And if you haven't gone out and lived it and experienced it, you're at a distinct disadvantage
when it comes to communicating
those things because it's like you're like the 40-year-old virgin who's trying to talk
about sex.
Right.
Like a bag of sand.
They felt like a bag of sand.
Right.
You can fake it.
You can fake it until you say something that's so obviously wrong that just everyone in that
instance knows that you have no idea what you're talking about.
Yeah, good point. And I mean, that's been really my maybe way of compensating for what I perceive
is a very imperfect writing style. I don't think that I am the best writer out there. I view myself
as a teacher, first and foremost. So my cheat has been to
follow in the footsteps of someone like George Plimpton, who is a really fascinating character,
who's the editor of the Parish Review and really popularized what he called participatory
journalism, where he would go become a professional football player for a season. He would go try to
join the circus for a season. He would go try to box three rounds with Archie Moore, for instance, and then write about the experience.
And you do not need, just to underscore what you said, you do not need to be a college-educated wordsmith to have compelling writing if you have a good story to tell.
It's just that simple. And I remember
talking with Tucker about this, and a lot of it really just comes down to,
I think, writing in a natural voice, basically writing as you are, which takes practice,
but having a good story to tell. Working on, actually, before I get to the internal goals, what does financial security mean to you?
How do you define that for yourself personally?
Are we talking like specific numbers or are we just talking about like what is financial security sort of generally?
You know, I, but you know, both to the extent that you're comfortable.
I mean, it's, you know, it's whatever you're comfortable talking about.
It's just that I think this is such a huge, uh, piece of so many decisions that people
make, um, bad and good.
So I'd be curious to know how you have resolved this for yourself to the extent that you have.
Sure.
Well, I guess there's a couple of ways to be rich, right? One is have a lot of money so you
can buy a lot of stuff. Or the second, if you sort of express being rich as being able to buy
whatever it is that you want, right? Whenever you want it, there's two ways to do that. One is to
have tons of money, or two is to not want as much stuff, right? And so I think if you meet somewhere in the middle where you keep your tastes under control, like for instance, I don't fly first class.
I could afford it, but I don't fly first class because – and I have before.
But the point is I just don't want to get in the habit of flying first class because now it means if I want to to travel somewhere it's going to cost me x amount
right and i'm going to have to do things that i maybe don't want to do to be able to get that
money right and i'm going to make decisions for the rest of my life around that assumption and
i don't want to have to do that so it's like like, how do you limit what you, like, there's that quote from Paul Graham about keeping your identity small.
If you can keep your tastes at a level at which a reasonable salary or financial situation covers it, then you don't need to go out and do certain things for money that other people do. To me, financial success is
I have a house that I live in that's nice,
that I can keep my stuff in,
that I have my books in,
but I don't have six spare bedrooms
that I needed to fill up with furniture
because I wanted to send a message to people
that I have a really nice house.
And I don't live in New York City
because I don't need to live in New York City, which means that I have a really nice house, you know? Um, and I don't live in New York city because I
don't need to live in New York city. And which means that I spend a lot less just to have the
same thing, you know? Um, and like, I, it's like, can I, can I go to a nice steakhouse and buy
whatever I want and not care what the check is to me, that's being financially secure and about sort of what I need to not care about money.
Got it.
And so like, and then I think the other, it's not just being financially smart on your spending,
but like, you know, do you actually understand like investing and managing your money in
a smart way?
So it's not, you know, like there's all these people i'm sure you deal with
investors uh or startup founders or whatever who have like credit card debt and it's like why are
you trying to like invest in startups when you could just make 13 more a year by not paying off
your by not like having carrying a credit card balance you You know what I mean? Right. So I think just sort of basic financial responsibility
and management helps you make what you're doing go further.
So that's been beneficial to me.
But there's the study about
if you make more than...
Any amount over $70,000 a year
does not correlate with any increased
amount of happiness. Um, I think that's definitely true having made a lot more than $70,000 a year
and a lot less. Um, so for me it's like, you know, somewhere, somewhere above that is happy
and comfortable. Um, and the rest should just be, should be and managed, like the Stoics say,
for a much worse time because you never know what's going to happen. Don't spend the money
you make because you might not have it and you might want it some other time.
Sage advice. Yeah, it's hard to predict, nay, impossible to predict when the next black swan will hit.
Totally.
And, you know, I've been thinking a lot about this, not to misdirect the conversation, but the fact that much like human action and climate change technology, in a sense, has led to super storms, let's say storms of the century, perhaps happening as often as every three to 20
years now, which was a recent piece that came out of MIT, the instantaneous sort of
dissemination of hysteria through social media, I think, greatly increases the probability of higher frequency black swans because everything is so interconnected.
And humans are, for better or for worse. But that's pure speculation on my part. the book, there's the line from Warren Buffett about being greedy when others are fearful and
being fearful when others are greedy. And we definitely live in a time where people are very
greedy. And I think it's really important too that you don't at all correlate being financially
successful with worth as a person. So the fact that I know someone who's worth X million and I know someone who's
worth less than nothing doesn't say anything about their value to me as people and how I should
respect or treat them. And if you can keep that in mind, you won't feel like the fact that so-and-so is making, you know, $80,000 a month on info products.
It doesn't, like, I know this, but it doesn't make me care about making info products. Like,
I want to write my books because they pay me enough to be happy. And that's what matters.
So speaking of sort of valuing people and different people.
Feel free to answer this however you like.
For your circle of friends,
number one, you know, these days,
how do you curate them, right?
If it's not on net worth, which I agree it shouldn't be,
how do you curate your friends that you end up being the average of as a group?
And over time, let's just say over the last five years, ten years, what has become more important or less important?
It's weird.
I think a big part of it is keeping toxic, unhealthy people out of your life, like people who have drama and problems and pathological issues. I think that's important. I think people who I don't have to try to impress.
Like it was weird.
One of my friends from high school was in town like over the weekend.
And it was like I don't think we talked about like work at all because he was doing his thing and I'm doing my thing.
And what matters is that we have like a shared history or a thing that we relate over. And so to me, like, I don't know about you where when your work is also tied
up in your personal relationships, I really value people who I can exist in the present moment with.
So it's like, I can do something with them. I can have a conversation with them.
And it doesn't, like, the fact that, you know, they do this and I do this is irrelevant.
And the fact that they live here and I live here is irrelevant.
I look for people that, like, I may have gotten this for you, is, like, the idea of someone you can sit and have a nice long dinner with. To me, that's a friend,
not someone I have to meet at a bar or any other context.
Makes perfect sense.
If you had to pick,
let's do just a couple of rapid fire questions.
Okay.
And one to think on just as we're doing this
is I'd like to hear a story of, uh, what, uh, uh,
I should, uh, Tyler calls self-inflicted wounds. So just like a ridiculous story, a debacle,
a fiasco of some type that was self-created. Uh, sometimes that's involving alcohol for,
for people that doesn't have to be true for you. Uh I don't think I, I'm not sure I've ever seen you drink alcohol.
But okay.
First one,
what is your,
what would be your theme song or your like ring entrance music?
If you had to choose one?
Ah,
um,
I,
let me pull up iTunes.
Let me see if I have anything.
Uh,
I don't know.
I like Iron Maiden.
If I had to pick like an awesome entrance song probably something from iron maiden okay uh if you could change one
thing about yourself what would it be uh this is ironic i don't love my voice that much
i feel the same way not about your voice but about mine do you think there's any like anyone who's not like a narcissist
that enjoys the sound of their own recorded voice i haven't yet met them but i'm sure they exist
i heard it's actually because you hear your voice differently like the apparently it's like when
you're just talking the voice that you hear is different than like how it's recorded. And that that's,
it's just the difference that makes you feel bad about yourself.
You know, that's an enabling belief. So I'll take it. Sure. Thanks for that.
When you think of the word successful, who is the first person who comes to mind and why?
No one comes to mind. Well, I talk about john d rockfeller in the book so there's an
example one of the world's richest men got it all right uh if you could study a new subject
with any expert in the world uh who would it be and what would you study like a new subject or
just a subject different than the one that i study? By new, I mean new to you. So yeah, different from what you've already immersed yourself in.
Yeah, I think I'd love to do like archaeology or something like that. I don't know a specific
person, but some sort of ancient site or dig would be fascinating to me.
And you spent time in Rome looking at like the burial site of Seneca and so on.
Is that right?
Yeah, yeah.
I spent some time in Rome when I was finishing up the book,
and I just went to the sites and stuff that are in the book for sure.
And I was in Dublin two weeks ago.
You'll love this.
They took us into this crypt, like a burial site that preserves the bodies.
And they had these mummies there from like the 12th century.
And they let us touch them.
Wow.
I was like, we are a long ways from America.
We touched the hand of this guy who died in the Crusades.
Wow.
Yeah.
That would definitely be cordoned off in the USades wow yeah that's uh that would definitely be corned on cordoned off
in the u.s i think so yeah not chew on the money uh if you could offer your younger self uh one
piece of advice what would be let's let's let's place that younger self freshman in college
relax relax yeah why every young person that i i think you probably get this too every
young person that i talk to i feel especially like an ambitious one that seems to want to talk to me
i feel like they're on the verge of like a nervous breakdown or an explosion of some kind
because everything is so serious to you when you're that age and i think it maybe it's our
parents that did
it to us or whatever but i i feel they're like you know if i i gotta do this or like i'm gonna die
like it's like everything feels like like an issue of life or death you know right and it's so the
opposite of that it's like you are you could in in all of history you are in the safest, most nerf, bumpered area that has ever existed.
You could do anything short of murder and you're probably going to be fine.
You know what I mean?
You have unlimited time.
Just relax.
Take it easy.
You're not going to care about this in a little bit of time.
That's probably what I would tell myself.
So just to take a quick sidebar from the rapid fire, you dropped out of college. I feel like there is a survivorship bias in media that leads to a romanticizing of dropping out of college. And I'd love to hear your thoughts on
who you would advise to drop out of college, who you would advise to stay in college,
because you ended up very uniquely, in my experience, extremely well-read and extremely
well-rounded. And when people drop out of college, oftentimes they say, well, it's because it's not going to prepare me for job X or Y or Z. In my opinion, at least in a liberal arts college still is that the goal is not to prepare you for a single career. The goal is to make you a well-rounded developed human being. So I'd just be curious to know what your caveats are, who you would recommend, consider dropping out versus not.
Yeah. So it's funny. I was looking at that. There's a Wikipedia page that's like a list
of college dropout billionaires. And it's funny. It's like, yeah, it's the definition of the
survivor bias because there's like, let's say there's 500 billionaires in the world and like
20 of them were college dropouts, that means even among billionaires,
most of them went to college, right?
But you only care about the ones who dropped out of college.
So I think, like for me, dropping out of college,
it was a pretty simple calculation.
It was, would I stay in college and graduate
and hope to have this same opportunity
that I'm being offered right now.
And the answer was, yeah.
And that was the Tucker opportunity.
It was Tucker, Robert Green, and then working for Aaron Ray, who we both know,
at The Collective in Hollywood. So it was three things that either one of them individually,
I would have killed for as a post-grad job. And so I said, you know, I'm going to do this
now and see how it goes. What I think people, the problem with dropping out of college that
everyone misses in the discussion is that dropping out of college is not a thing.
You take a leave of absence from college, meaning you can go back at essentially any time. So again, when I'm saying relax the 19-year-old
version of me or whatever, it's like, dude, it's not as black and white as you're making it out to
be. Take risks. You're in a cohort where you can absorb risk. And then understand that you're not
going to starve to death if this goes poorly.
For me, it was like, I'm going to take advantage of this and a year from now, if it's not working
out, I'm going to go back to college because college is the best default option if you
don't know what you want to do because it keeps you on the level with everyone else
and it gives you some sort of certification that sets you apart
from people who didn't go to college. So that's how I think about college. And usually, and I'll
say this, the people who should not drop out of college are the people who are doing poorly in
college. Because college is exactly like life. It's a system that you have to figure out how to
get the most out of and do your best at. And if you're failing out of college, you are probably
going to fail at life because you are, if you don't address the root reasons why you're doing
bad at college, you know? Yeah. So yeah, learn, learn to learn to game the system while you still have headgear on.
Exactly.
Cool.
All right.
I appreciate that because it's something that I get asked about a lot.
So it's nice to have your input.
All right.
And one other note on that.
I always hear from people, it's like, oh, I want to leave college so I can travel.
Or I want to go to college so I can start a company or get a mentorship.
And it's like, these are not things that you have to leave the womb to do.
You can do them in college.
And so you should leave college if you have an opportunity to do something that can only be done outside of college. And you will kick yourself if you let that
opportunity pass and it doesn't come back your way again when you're graduating.
Yeah, that's a great point, actually. I think that it would be very fascinating to look at
billionaire dropouts and see how many of them had started the company that was going to later make them a billionaire
and proven to themselves that it had very real legs and a time-sensitive window before they
dropped out. Because I think the percentage is probably very high. Right. That's what Zuckerberg
did. Yeah. Yeah. And many others. Awesome. So we'll take just a little bit more time. I'm going to do a couple of rapid
fires so people get to know you and not just your thoughts on stoicism. All right. So you walk into
a bar. What do you order from the bartender? If it's in Austin, I order Topo Chico, which is like
a Mexican sparkling water. If it's not Austin, I'll probably just get soda water with lemon and lime or cider.
Do you ever drink?
Just cider.
It's the only thing that I like.
Got it.
So it's not a moral decision.
It's a taste decision.
It's a little of both, but yeah.
Okay.
Okay.
What makes Mexican sparkling water different from normal sparkling water?
I have to ask.
I just like it better than pellegrino but i will say that i fully embrace the ridiculousness of eating or of drinking imported water from mexico especially mexico all right
right uh who is your favorite person to follow on twitter or uh and you can give two or three if you'd like.
I like Fake Jeff Jarvis, who I think
is hilarious.
I like Felix
Salman a lot. Who is Felix?
Felix Salman, he's a blogger
for Reuters.
And then, I don't
know who else. Oh, Media Redefined
by Jason Hirshhorn
is a pretty good Twitter feed to follow.
Oh, and Maria Popova of Brain Pickings.
Yeah, yeah, that's a great site.
Speaking of sites,
what sites do you visit on a regular basis?
I don't visit a ton of sites.
I use my RSS reader.
So I use Feedly,
where I subscribe to a bunch of sites. I use my RSS reader. I use Feedly where I subscribe to a bunch of
feeds.
Felix is one of my favorite. I like Ta-Nehisi Coates who blogs for the Atlantic.
I like Mark Cuban's blog a lot.
I think Reddit, if you
subscribe to the right
subreddits, is a really good way to get sort of highly curated news.
What subreddits do you subscribe to?
Stoicism is a good one.
Besides not suitable for work.
Yeah, sure.
Stoicism is a good one.
Philosophy is a decent one.
History porn is a pretty good one, which is just like old photos from history
yeah um ask historians is my favorite so smart people act like people ask unusual questions
about history that only like academics or historians answer um today i learned is a
great one where it's just like a fact uh that you know people was unexpected um i like first world problems i think that's a
funny one um and then is there is there any uh there's there's one about civil war there's one
about writing and then i like reddit books as well yeah reddit books is big yeah uh the what
is the first face that comes to mind when you think punchable?
Punchable.
Uh,
I don't know.
That's a good question though.
Um,
we can,
we can come back to that.
It could be, it could be fictional character too,
if you'd like.
Sure.
Uh,
dogs,
you cats,
uh,
dogs,
of course.
Why?
Uh,
cats are just an animal that lives in your house.
Got it.
Okay, so elaborate on dogs because you said something to me that I was hoping to have you elaborate on,
which was that you think dogs make you a better person.
I was curious how you think they make you a better person.
Dogs exist totally in the moment.
Dogs are the definition, I i think of sort of unconditional
affection i think it's really interesting to have an animal that evolves to live and depend on
humans the way that dogs did like dogs they think were domesticated because they like wolves would
come and eat scraps from the um like the campfire. And basically, we slowly selected the most sort
of docile, friendly, you know, mischievous of the animals. And that's where dogs come from.
So I think dogs are great because they're this thing that's dependable, or this thing that
depends on you and needs you. But at the same time, you can never
truly disappoint. So it's this great sort of metaphor for life. I think it's just great
practice. And plus, they're super cute, and they do hilarious things. I have two pet goats also.
I don't know if I told you this, but I have two goats, which are pretty funny they're like really dumb dogs do you do you milk the goats or do you just have them for uh comedic effect just mostly for comedic
effect like i don't like people have asked that but i just don't have that much need for goat's
milk so um it's not you have to breed them to get uh because they're nigerian dwarf goats so you
have to breed breed them to get milk which I'm not really interested in doing.
Sounds really low yield.
It's kind of like milking cats.
Right.
Like what do I need?
Then I'm just this guy who's always trying to pawn goat milk on people.
Like let me give you some.
Right, right.
Like the friend that has an orange tree.
As delicious as Nigerian dwarf goat milk sounds.
That could become a thing in San Francisco.
You could export it.
Probably.
What book are you most likely to give out as a gift?
Probably Meditations.
God knows how many copies I've gone through.
And then the second one would be The War of Art by Steven Pressfield.
Yeah, that's a great book.
Let's see.
What movie can you not resisting if it's on,
assuming that you had a TV in an imaginary world?
Well, I have a TV.
I'm not a weirdo.
I love TV.
Probably Gladiator.
That's appropriate. I like Spinal uh spinal taps one of my favorite movies
have you seen sean of the dead no i haven't oh my god you have to see sean of the dead s-h-a-u-n
okay it it might become one of your favorite movies it is is splendid. I wrote about half of the four-hour work week
with that on repeat on a TV.
Yeah, I don't know how you do that.
I have to have total silence.
Well, here's where I am a weirdo,
among many other ways,
is I would play the movie,
because I tend to write late at night,
and it's easy to feel isolated and crazy
and like Nicholson in The Shining, if you're always by yourself, at least for me.
So particularly without any dogs or anything around or people.
So I would put the movies on with characters that I liked and I would mute the TV and then listen to music while that is just human motion, human forms and motion in the background.
Oddly enough.
Yeah.
Just,
just a habit that I have.
Let's see.
Who was your first celebrity crush?
If you've had one.
Celebrity crush.
Or current celebrity crush.
Any celebrity crush.
I don't know.
I really don't know.
Nicolas Cage?
Yeah.
I'm a big Nicolas Cage fan.
Do you cook?
Like, I cook bacon.
Okay, I can't end on that question and answer.
If you could choose three people, let's just say living people okay
to be your sort of uh circle of advisors or elders to help you with major decisions who would they be
it's weird like so i've gotten an iteration of that question where it's like oh you've worked
with all these people who else would you want to work with that you haven't um and i it's weird. I've gotten an iteration of that question where it's like, oh, you've worked with all these people. Who else would you want to work with that you haven't?
It's weird. I feel very fortunate that I haven't. Robert Greene is one of the most respected strategists about power and life and history. He's someone that I call when I have questions about stuff. I think you're one of those people that I call
and you're a world-renowned writer and marketing expert and investor.
And then the third person is my girlfriend, now fiance,
who I think is really good at reading people.
And more importantly, she knows me and what my weaknesses or issues are, which I think is really important.
It's not just about objectively what the best thing to do in a situation is.
Absolutely.
It's like, what can you do given your constraints or tendencies?
Like, oh, you should totally take this job.
Well, if you're someone who's pretty flaky, that's not a great, you know,
that's not great advice. Like it's oftentimes it's, you know, what you can do with your taking you as a person for granted, who's going to behave how you've always behaved.
You can have someone who understands you well enough to give really good advice.
I think that's super important. So I think that is a great note to wrap up on.
How can people better or best get to know Ryan Holiday? Where should they find you online?
What should they read of yours? Sure. Give us some suggestions so that people can dig a little
deeper, which I hope they do. Yeah. So my website is ryanholiday.net i'm ryan holiday on twitter um i i suggest people
start with the books too because i put myself into the book so the obstacle is the way uh trust me
i'm lying it's my first book did a book called growth hacker marketing which started as a
kindle book and now it's going to be a paperback um and then i write you know almost weekly for
thought catalog um and then i'm on the editor atat-large of the New York Observer, where I have a series of
columns about media and life and other things there.
Fantastic.
Well, Ryan, thanks for the time.
Always nice to chat.
And this gives me an excuse to sort of ask you 20 questions in a way that isn't totally
socially weird over a meal.
So this was amazing.
Yeah, this was super fun.
I will, I'm sure, talk to you soon.
So thanks.
Thanks for taking the time.
Yeah, thanks for having me.
All right, Ryan.
I'll talk to you soon.
Bye.
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