The Rich Roll Podcast - Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way
Episode Date: August 17, 2015I love talking to smart people. Today's guest is certainly that — and so much more. Contravening millennial stereotypes, Ryan Holiday is a prolific, rising literary talent. A maverick media strateg...ist. Not to mention a philosopher of sorts — a guy with big ideas often at odds with the status quo. An autodidact, Ryan dropped out of college at nineteen to apprentice under acclaimed author Robert Greene, author of (among many other great books) The 48 Laws of Power*, later graduating to advise many New York Times bestselling authors like Tim Ferriss and RRP #154 alum Tucker Max, multiplatinum musicians like Linkin Park and startups like Casey Neistat's ( RRP 73 & RRP 144 ) recently launched social media platform Beme. By the time he was legally allowed to drink (21!) Ryan had already ascended to director of marketing duties at American Apparel, where his iconoclastic campaigns and tactics have been used as case studies by Twitter, YouTube, and Google and written about in places like AdAge, the New York Times, and Fast Company. Ryan is also the bestselling author of 3 books, including Trust Me I’m Lying* – a highly entertaining and admittedly disturbing first hand look at the machinations behind digital media's dark underbelly — and The Obstacle Is The Way* – a modern and practical reframing of stoicism, the ancient Roman philosophy originated by guys like Marcus Aurelius, Seneca and Epictetus, with a focus on functional applicability of stoic principles for turning modern day obstacles into opportunities and adversity to advantage. If you think philosophy is purely academic — a useless waste of time reserved for the arrogant intellectual elite — Ryan has a message for you: think again. I really love this book. I found it to be eminently practical. An incredibly insightful and utilitarian tool box for navigating crises, strengthening character and maximizing excellence in any situation, irrespective of circumstance. On RyanHoliday.net and places like Thought Catalog and Observer (where he is editor at large), Ryan writes frequently on a wide variety of business and marketing related subject matters. But it's his fresh and unique take on real life stuff that keeps me coming back. Enjoy! Rich
Transcript
Discussion (0)
Yeah, it's interesting. I think at the root of a lot of these life hacks is the idea that
people really don't like uncertainty, and creative endeavors are inherently uncertain.
And so they're always looking for some sort of shortcut, or some person that says, if
you do X, Y, and Z, you will get this thing. And that's just not how it works.
That's Ryan Holiday, and this is The Rich Roll Podcast.
The Rich Roll Podcast.
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the news, what's going on. The podcast is going on. That's what's happening. My name is Rich Roll.
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the big forward thinkers, the out-of-the-box minds and personalities across all categories of excellence and positive culture change to mine the tools, the insights, and the principles that can help all of us
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Okay, so this week I got Ryan Holiday on the show, prolific literary talent, maverick guerrilla marketing iconoclast, and media strategist. And
generally, Ryan is just a really cool, young, incredibly well-read guy with some really
interesting and compelling ideas on a wide array of topics. And I've been a big fan of Ryan for a
long time. I've been reading his stuff forever. So it's super cool to have him on
the show today. A little bit more about Ryan and his background in a minute. But first.
All right, Ryan Holiday. So Ryan is an extremely bright young man. He's very savvy. I think it's fair to characterize him as an
out-of-the-box thinker. Again, he's a media strategist, and he's a prominent and rather
prolific writer on a wide variety of subjects, not the least of which are strategy and business.
He's also an autodidact, which means he's predominantly self-taught because he dropped
out of college at 19 when he had the opportunity to apprentice under the famous author Robert Greene,
who wrote an amazing book called The 48 Laws of Power, among many other books.
And then Ryan went on to advise a number of bestselling, at times controversial, authors on their book launches,
guys like Tim Ferriss and Tucker Max, who's a former guest on this show, as well
as multi-platinum musicians like Linkin Park. He also served as director of marketing at American
Apparel for many years. He tells a lot of amazing stories about that experience in his book,
Trust Me, I'm Lying, where his unique and maverick campaigns and tactics have been used as case
studies by Twitter, YouTube, and Google, and written about all over
the place in places like Ad Age, the New York Times, and Fast Company. He's also the best-selling
author of three books, including, again, Trust Me, I'm Lying, which is a very entertaining,
at times disturbing, firsthand look at how, how do I characterize this, the dark underbelly of the
modern media machine actually functions and how
it actually can be leveraged or to use his words, manipulated to work in your favor. And also his
newest book, The Obstacle is the Way, which is a modern, I guess you could call it utilitarian
reframing of the ancient Roman philosophy of Stoicism, which was a philosophy pioneered by guys like
Marcus Aurelius, Seneca, and Epictetus. And essentially, it's kind of a primer on
the functional applicability of Stoicism for navigating today's world, including formula
for turning obstacles into opportunities and adversity to advantage. And I really love this
book. I found it to be incredibly insightful and helpful. And really, it's a practical roadmap for
maximizing excellence in any situation, irrespective of circumstance. And the principles
behind this book really form the basis for much of our conversation today. Ryan also writes and blogs frequently on, again, a wide variety of subjects and like real life stuff.
He does this on his website, ryanholiday.net, and on places like Thought Catalog and The Observer, where he is editor at large.
Ryan is a voracious reader.
So I highly suggest that everyone subscribe to his monthly reading recommendation
newsletter of books that he's read, reviewed, and thinks you'll like. It's really great.
You can do that at ryanholiday.net. So I love talking to smart people, and Ryan is certainly
that and more. This is a really interesting conversation about many, many things, not the
least of which include how we misperceive struggle, how it's actually a defining characteristic of success. In other words, the gift of obstacles.
It's about how the principles of stoicism can help eradicate the barriers that hold us back.
We talk about reconciling the principles of stoicism with populist notions of life hacking.
And we get into a really interesting dialogue about how modern
marketing actually works in our clickbait schadenfreude internet shaming culture.
And also kind of how to discern the internet snake oil salesman from the valuable content
that's available to us online. So, all right, let's tap this brain, shall we? Ryan Holiday.
We got to go on a run, man.
That's all I was thinking about when I was driving out. Yeah, look behind you, look at the hill.
Actually, you should be sitting where I'm sitting so you could look at the mountain,
but maybe that'll be distracting for you.
But there's plenty of trails out here where you can get lost.
I might go for a run on the beach on the way back.
Yeah, that would be good.
So what are you doing here in LA?
Just some meetings, some client work, and then I'm just doing some podcasts.
That's right.
You came out just for the podcast.
Awesome, man. Well, I'm honored and I've been a big fan of your work for a long time.
I love your writing, your books, as well as all the articles that you write. And they're always so insightful. And I feel like you're on a different level than a lot of people out there.
So it's a pleasure to talk to somebody who I think grapples with
and really thinks deeply about things that are important to me
and I think are relevant to culture in general.
It's weird.
A couple years ago, there was all these people that you felt like you knew
because you read their stuff.
And then now with podcasts, and then with you specifically
because I've been following you on Beam, not to plug it right out of the gate, but like, I, you feel like you have this insight into,
like, you feel like you've known these people or you, even though you've never actually met
and you don't actually really know anything about them, but like you've, you like dive right into
their life from like the get-go. And it's, it's very strange. It is strange. It's cool. I mean,
I think beam, you know, to kind of take a tip from, you know, Casey's mission statement on that is to, you know, make it more authentic.
So you're stripping away all the filters and the editing and all of that.
So you are getting kind of a more authentic portrayal of someone's life and all its pimples and, you know.
Yeah.
Or like, cause people be like, oh, like I listened to your audio book.
And then it's like weird because like, so you heard me for like eight hours right directly like in inserted into your brain like that that like
makes me uncomfortable well it's it's very personal you know and i can tell you from doing the podcast
i've been doing it for like two and a half years now that when i not so much in la it doesn't
really happen in la but when i travel to other places and and and you know people will stop me
on the street or in the subway and and they really do feel like they know you. And in certain respects they do,
you know, like, like I have 400 hours of me talking out freely, you know, floating around
in the internet. So it was like, they probably know me more than most people. It was like you
were in the passenger seat in their car while they drove to work every day for a month, right?
With their earbuds in, it's very personal.
And I have that experience from, I've been a fan of podcasting for a while.
So I feel like I have that relationship with Mark Maron.
I've listened to him so much.
I feel like I know that guy.
And you project onto these people this relationship that is an illusion.
You feel like he's your friend.
Yeah.
With Maron, I think it's weird.
It's like you hear it, like he has these different laughs,
and you know when he really thinks something is funny.
It's like you're analyzing a person way deeper
than you would ever actually,
you would even get with your friends.
Right.
It's weird.
And I think with him in particular,
because he wears his emotions on his sleeve,
it's not a canned presentation.
Like, you're getting who that guy is.
Totally.
And there's something special about that.
Yeah, I think so.
So anyway, all right.
All right.
I feel like I know you from your writing,
and I have listened to two of your audio books.
Awesome.
Here we are in person, which is, it's almost like it's just a,
what's the word, a formality.
Yeah, yeah, yeah. Oh, hey, Ryan, Ryan's here. You know what I mean?
Right. So cool. Well, there's so many inflection points and so many things that we could talk
about. You know, I feel like I could do a two-day podcast with you and we could just talk forever.
And we actually did a half hour podcast that was not recorded before we sat down. So, you know,
in terms of trying to focus it a little bit,
I think a good place to start off with is really, you know, just talking about your latest book,
The Obstacle is the Way, which I absolutely loved, and the ideas behind stoicism, which I find to be
highly relevant in my own life. They really resonate with me deeply, and I'm interested in
kind of, you know, exploring these ideas,
you know, a little bit in depth. So to kick it off, maybe sort of explain a little bit what
Stoicism is for the uninitiated. Yeah. So Stoicism is a Roman philosophy,
a Greek and Roman philosophy, sort of three most prominent practitioners. Like I could go into the
ethics of it, but I think that sort of misses the point.
I like to focus on the people
that are sort of identified with it.
But sort of most prominent would be Marcus Aurelius,
the emperor of Rome.
He's the guy in Gladiator,
if you know nothing of Roman history.
So you have the most powerful man in the world
who wanted to be a philosopher,
who sort of, his father was not the emperor.
He was sort of selected for the throne.
And so you have this weird idea of a philosopher king,
maybe like the only time that ever happens in history.
The other prominent Stoic is Epictetus, who was a slave,
who was banished by a different emperor
and actually sort of like physically crippled as a punishment.
And so you have this philosophy that on the one hand is sort of embodied by like the most
powerful man in the world, and then one of the least powerful men in the world.
And they're both sort of struggling with these sort of eternal questions of like, you know,
what is the meaning of life?
How do you deal with a world that you don't control?
How do you, you know, sort of subtracting God out of it?
How do you find purpose? What's right and wrong? How do you, how do you, you know, sort of subtracting God out of it? How do you, how do
you find purpose? What's, what's right and wrong? How do you live your life? You know, what, what,
what is the, what is the path to the good life? And then practically, how does one actually do
this? These are the sort of questions of Stoicism. And it's, it's the most sort of practical,
readable, accessible philosophy. It's not, you know,
how many angels can dance on the head of a pin?
It's not,
you know,
um,
what's,
what's the,
you know,
is,
is all of life a dream?
You know,
it's not these sort of esoteric academic pursuit.
It's,
it's the a hundred percent opposite of whatever you think philosophy is and
whatever you may have experienced in school.
It's not that.
It's very practical. Like Marcus Aurelius is a guy with an immense burden
and immense temptations sitting down every night
and writing little notes to himself
about what he should do or what he shouldn't do
or what he's learned.
And then this work survives to us
and it's called Stoicism.
And I was introduced to that. I was like Stoicism. And that, I was introduced
to that. I was like 19 years old, a really smart person was like, Hey, you should read this. And I
did. And it just sort of, yeah, yeah. I was at this conference and I was like, Hey, like, you know,
what book would you recommend to like a young person who's like trying to figure out their life?
And he was like, I think you should read the Stoics. And so I did. And it just sort of, you know,
totally blew my mind. Tyler Cowen calls them quake books, like a book that shakes everything
you think you know about the world. And that happened to me. And it's been this sort of
journey ever since. I've probably read the book 500 times.
Have you gone back to Dr. Drew and given him a book of, given him the obstacles away?
Yeah, yeah. So I mailed it to him and he didn't say anything.
And then somebody I knew told him about it.
And I got this crazy email from him.
And he'd read the book and he loved it.
And so it was this full circle moment for me.
It was like, honestly, if no one had read the book,
but he'd read the book, it would have been like my dream come true.
So it was crazy. And I'm like such a huge fan of him so it's right right right right so well implicit in
it is also this in terms of like the applicability to life you know modern life in particular
there's also kind of an inherent optimism that that it's infused with right yeah it's weird like
the uh so if if you look So if you ask the person,
what does the word Stoic mean?
And then you ask them what the word Epicurean means,
their definitions would be the exact opposite
of what those schools of philosophy are actually about.
So people think Stoicism is about resignation.
Aestheticism.
Yeah, and just like bearing just the blunt
of the awfulness of life, which is in fact,
not what stoicism is at all. And I base the obstacle in the way as this line from Mark
Cerullo where he says, you know, the impediment to action advances action. What stands in the way
becomes the way. And basically what he's saying is like, look, you don't control what happens,
but you control how you respond to what happens. And so you might as well respond in a positive
way. So to me, that is a much more
resilient sort of definition of optimism than simply saying like, I'm going to believe that
the glass is half full, even though objectively it's not half full. Like, you know, like there's
this, it's not about sort of delusional positive thinking. It's about saying, this is what
objectively is the case. I'm going to choose to do something about it.
I think that's a better...
Well, really at its core, it's about mastering perception.
And it's about overcoming default perceptions of the world and events that occur to us.
Yeah.
I mean, the first thing that most people do when something happens is they decide whether
they like it or not, whether it's fair or not, whether it's reasonable or not.
All these things that the Stokes would say have no actual bearing on the event itself.
Well, we're hardwired to make immediate judgments on everything that occurs, right?
And I don't know whether we have this sort of dualistic mind that sort of just naturally gravitates towards that.
But we're
so quick to label something as bad or good or tragic or awesome. And the truth is, is that we
lack, you know, even the most, you know, de minimis amount of evidence to make those judgments when
they occur. Yes. And what I always say is like, look, this thing that you think is so bad,
there are what a billion, two billion people on this planet
who would trade everything to experience
whatever that bad thing that you're experiencing is.
You know what I mean?
But that refrain doesn't necessarily salve the wound.
Because you can hear, somebody will tell you that
when you're in the midst of feeling sorry for yourself or whatever,
and you're like, yeah, yeah, yeah, please go away.
Sure, but I think it's about, it's about seeing this thing with a bit of
objectivity and that it's not to say that like, it's not going to make, it's suddenly going to
make you not sad, but perhaps it'll make you not sad for six months. Right. It's about like,
like I say, like, okay, if you get in a car accident, your body's going to have an emotional response.
It's going to have a hormonal response. You're going to get that adrenaline dump.
You're going to be scared. You might go into shock. All of this is great.
You don't, you don't, you can't, or not great, but you don't choose, you can't change that.
But what you can choose is how you respond generally to that accident. Right.
You can decide whether, you know know you're going to be scared of
driving anymore whether you're never going to get back in a car whether you're going to you know
you decide this sort of the larger response not not necessarily the immediate reaction if a if
if that painting fell off the wall it's going to catch you by surprise but you choose what you're
going to do about it after that. Yeah, I think in analog,
and the way I kind of came into these principles
was not through meditations by Marcus Aurelius,
although I would have benefited from reading that.
I probably did read it in college.
I don't remember.
Probably not.
College professors hate it
because there's not a lot of room for interpretation.
Like, he just says what he means.
Right, yeah, yeah, yeah.
What kind of paper?
What kind of modern spin are you going to put on that? You were able to do
that a little bit, but I just took, I took what they said and then I just found stories from
history and I matched the two together. Um, I learned these ideas in a different form through
what, when I was, when I was in rehab, uh, and I came into the serenity prayer, which is very similar.
You know, God grant me the serenity to accept the things I cannot change,
the courage to change the things I can, and the wisdom to know the difference,
which is a very similar kind of idea at its core.
And I think ultimately what it's about is shifting perspective and embracing,
sort of distancing yourself from results and embracing process.
Yeah, yeah.
And look, there's a bunch of connections between stoicism
and the sort of 12-step communities.
There's a bunch of connections between stoicism and cognitive behavioral therapy.
It's this idea of like, look,
you have to first decide whether this thing is in your control or not in your control.
And the things that are in your control, they require a full amount of your effort and energy and passion and all these things.
And the things that are not in your control, like I think about it when I'm writing the book.
I have to sit there and go, I'm writing the absolute best book that I can.
This is 100% in my control. And then I'm going to do, I'm going to kill myself to market it, to get in
front of as many people as possible. But ultimately I don't control whether there's a hurricane the
day that it comes out. I don't control whether the New York times list screws me over and decides
not to include it. I don't control whether people like it or not. I don't control whether I'm ahead
of my time or behind my times. Like I don't control any of like it or not. I don't control whether I'm ahead of my time or behind my times.
Like, I don't control any of those things.
All I control is the product.
And if that's not enough for you, then what you're essentially saying is,
you just spent a year of your life working on something.
And the only way you're going to be happy about it is if something you don't control
breaks your way, which is a real crappy recipe for being
a happy person. But I feel like our society is structured on that premise. Totally. It totally
is. And it's why a lot of people are very, very unhappy. And it's, again, like, all of this is
way easier said than done, right? Like, understanding that intellectually does not
change the fact that every day you have to wake up and your instincts and your natural inclinations are to put your
happiness on things that are conditional to other people. Um, and so you, you work on it,
you try to get better every day. So one thing that's really interesting to me about all of this
is, you know, what you're talking about, like timing and timeliness. And one thing that's really interesting to me about all of this is, you know, you're talking
about like timing and timeliness. And I think there's something about this message that you're
putting out that is resonating with the culture that's allowed your book to kind of, you know,
permeate our consciousness. But I'm interested in how you reconcile that with this fascination
or obsession that we have with like the life hack, like how can I
shortcut my process to get to the result, you know, which I feel like I've written about this
before. And I do a lot of, I've been thinking, I do a lot of thinking about this and I'm,
I'm kind of, look, I'm, I'm all for a good idea that will kind of streamline your life and get
you closer to where you want to be.
But I'm also disturbed by the amount of attention and focus that is placed on, you know, sort of
this idea of sort of shortcutting the work that it takes to get where you want to go. Because my
whole life, basically the value of anything that I've achieved
is a result of engaging the process on the deepest level that I can.
Like allowing myself to give myself over completely to something is,
that is the value of it.
It's not the result of that endeavor.
It is the process itself.
And so I feel like in certain respects,
your book is really a
call to action to really embrace that ideal. But also you're a guy who writes on Lifehacker and
you're part of the cabal of Lifehacker writers. And so how do you reconcile those two notions?
Yeah, it's interesting. I think at the root of a lot of these life hacks is the idea that people really don't like uncertainty and creative endeavors are inherently uncertain.
And so they're always looking for some sort of shortcut or some person that says, if you do X,
Y, and Z, you will get this thing. And that's just not how it works. You even see this with
the 10,000 hours theory. People are like, oh, so it's just 10,000 hours? this like with, with 10,000, like the 10,000 hours theory,
like people like, oh, so it's just 10,000 hours. Like if I just put in 10,000 hours, like you're
telling me, like you're promising me that if I put in 10,000 hours, like I'm set and it doesn't
work that way. When I think about like life hacks or tricks, I'm thinking about, and I think Tim
Ferris is a friend of mine and a client of mine and someone who's been very good to me over the
years. I even think with Tim, like people are like, oh, Tim only works like four hours a week.
It's like, no, Tim does four hours of bullshit work every week because that's the minimum or that's the minimum that he felt he could get away with.
So then he could spend the rest of his time doing the actual work that he actually likes.
Right. And I think that that gets lost in the discussion.
You know what I mean? I think that that gets lost in the discussion. You know what I mean?
I think that that was Tim's intention from the beginning.
He's like, get rid of all the stuff
that's not moving you forward
so you can invest yourself completely
in what gets you out of bed in the morning
and gets you excited about your life.
But I feel like that aspect of the conversation
sort of gets shoved aside
and it's all focused on this 80-20 rule
or how can I how can i you know
complete a marathon with the least amount of training possible which is sort of like to me
like that defeats the purpose of the endeavor altogether yeah totally like i think look like
exercise is a good example uh where it's like i don't i don't i exercise my favorite part of the
day i'm not trying to like get it in as little amount of time. I'm like, I'm, I'm doing these other things I don't like. And then this is my hour and a half to do it.
My like, there's more than just physical benefits to exercise. And it's not about shortening them.
And, and it's like, like, I see this with, uh, cause I read a lot and I'm, I'm somewhat known
for like my book recommendations and stuff. And so people are like, oh, you must be like a speed reader.
Right.
And I'm like, no, like I love reading.
Why would I try to do it as quickly as possible?
Like, this is what, this is, this is the thing.
Like no one's like, no one's ever think about it this way.
No one's like, um, do you have any tips for like, uh, having sex faster?
Like, I don't want to like, I don't want it to take so long.
Like, in fact, they're like, how can it take as long as possible? Right. Like, and yet with like work, which I think is a
pleasure. And I think with relationships, which are a pleasure and with reading, which is a pleasure,
it's not about shortening them. It's, it's in fact about eliminating all the extraneous
unnecessary parts so you can fully enjoy it and you can actually engage in it and i think
i think a lot of people miss the point on that like i a hack for me is like oh hey if you uninstall
all these things from your phone you're going to be less distracted that's a life hack not
hey if you use evernote and scrivener and uh this other thing and this other thing um you can you
can have a magical way of organizing all your information that means you don't have
to think about it. That's not the point. Right, right, right. Yeah. So why do you think that
that gets lost? Well, because it's a lot easier to talk about working than it is to work, right?
So I would say that anytime I've written about creativity or productivity, I'm usually doing it probably because I'm struggling with the actual project I'm supposed to be working on.
And this is a way to get maybe a little bit of momentum going.
But yeah, I think people are looking...
The idea that you have to do your work and then at a certain point it kind of leaves your hands, is such a terrifying idea to someone.
Someone who's dropped out of college,
or someone who's quit their job,
or someone who has a kid on the way.
All they want is for someone to say,
like, look, if you do this...
If you do this thing, it'll be okay.
Yeah, and that's just not...
Well, behind that is fear, right?
So the real work should really be looking at how you're, how you're dealing with that fear. Yeah. Yeah, of course. And
the Stokes talk about this. They're like, look, like you could die tomorrow. Let that order how
you live your life. And, and so I think, I think one of the ideas is, is to think like, I I've,
I've had to do this. Like if, if the thing is not intrinsically valuable
or intrinsically sort of pleasurable,
it's probably not a good use of my time.
Like, so it's like, if I'm writing the book
only because I think I might make a lot of money from it,
then...
That's a flawed premise.
That's a flawed premise.
And it might work out my way,
but there's a huge... It's a huge contingency dependent on something I don't control that might
make me unhappy. And so I, I, I think one of the hardest things in the world for people to do is
to turn down money. Um, it's obviously a first world hard thing to do, but it's a hard thing to
do. And like a lot, I think a lot of the tests comes from like, at least for me, it's like this
person wants to pay
me to work on this project. I don't like that project. Am I going to be able to say no so I
can do what I actually care about? Right. That's the, that's the litmus test of like living your
authentic life. Totally. Totally. And that, that's perhaps the hardest thing to do. Yeah. Especially
the more like, cause at the end of the day, you're selling pieces of your life to other people for money, right?
And so if you don't know what you're getting money for, and more importantly, you don't know how much you sell your time for,
it sets a really bad, uncertain situation where you're just like, oh, that, especially if you get paid well, you're like, well, of course.
And this is how people end up being lawyers working 100 hour weeks doing stuff they hate. Or, you know, this is how people end up signing
on to projects that make them miserable. And it's because they don't want to think about those
things. Right. And I live that life. You know what I mean? Like, I've been on both sides of this coin.
So I feel like I can speak to it uniquely because I didn't get to a point
where the pain was sufficient enough
to make the appropriate changes
to live the life that I wanted to live
until I was like 40 years old.
I'm like old enough to be your dad.
And so I know what it's like to walk a mile
in the shoes of somebody
who is doing something that they don't like
but is being compensated for it
and is so miserable that you try to deal with that
by purchasing things that are out of your budget range
and then basically shackling yourself to this life
that you feel like you didn't even consciously sign up for
to begin with.
Well, I think for you, so you had that moment
from what I've heard and read,
is that you had that moment you're walking up the stairs and you have to stop to like catch your breath those stairs
right there oh really yeah and you're like and then uh most i would say most people would have
that realization it would make them feel crappy and that they would go back to doing exactly the
same thing that they were doing before and i think that I think that's the sort of inflection point.
Like, I see this all the time.
Like, people are like, oh, like, you know, I'm struggling with this.
They'll ask me for my advice.
I'll give them my advice.
And I'll talk to them, like, two months later, and they'll have the same problem.
And I'm like, oh, the advice didn't work?
It's like, no, they just didn't actually do it.
They didn't do it.
They didn't read the book that you recommended.
They didn't take the advice.
And, you know, this is the plight of being human, I think. And I spent a lot of time thinking about that gap that exists
between inspiration and action, right? That's really where the rubber meets the road. And being
somebody who lives on social media, and I'm always kind of looking at what other people are doing,
especially thought leaders out there. And what I've seen, particularly on Instagram lately, is a lot of people putting inspirational quotes on pretty
pictures and posting them. And I find that to be not helpful. I find that to be-
I totally agree. I think we're probably thinking of some of the same people.
They get a lot of likes, but I'm thinking, is this actually getting anybody to do anything?
Like, people will give you a thumbs up.
And I think what happens psychologically is somebody reads that, and it gives them some kind of adrenaline or hormonal boost, where they suddenly feel good for a moment.
But they don't actually do anything.
And then there's a sense of accomplishment that is, that is falsely placed.
I think it moves you away from actually making any changes in your life that
are holding you back.
I think I,
I think about that a lot.
I have a bunch of thoughts on it.
There's actually a chapter in the book that I'm writing now that it's all
about this,
but like it,
I think a couple of things.
So one,
I think those people are being late.
They're throwing up the quote because it's lazy,
right?
Because it's,
it's easier to find a quote of someone else saying something smart.
If you have something interesting to say, go for it.
Although I hate when people quote themselves.
I think it's like, you could just, like, I don't have to go like, you know, the obstacle
is the way, dash, Ryan Holiday.
Like, I just say it.
You don't have to quote yourself.
Like, it's implied.
But so I think they do that lazily because it's easier than creating some actual insight.
And then it's rewarded by these fake internet points, which are hearts or likes or retweets or whatever.
And then they feel like they are making progress, even though they aren't.
And so I think that's a big part of it.
But I think the other thing is, my rule for myself, I don't talk about projects until they're done. Because it's so easy to, as the tools for making a thing have gotten much easier. Like anyone can say they're writing a book, anyone can say they're creating an album, anyone can say they're starting a blog or course or whatever.
can say they're starting a blog or course or whatever. That's not the hard part. The hard part is making something so good that it breaks through the noise or the hard part is doing the
marketing so that it breaks through the noise. And like, I'm very much of the mind that like,
it's not till it's done until you've actually jumped over that thing that you tell, like,
it's easy to train for a marathon. It's hard to do a marathon, but people have realized that if I say I'm training for a marathon on Facebook, I could get 20, 30% of the validation from just saying that I'm going to do it.
So why would, like, they're arbitraging.
And then the next morning when it comes time to go out and run, you're like, I don't need to because I already got the validation.
Right.
If actually doing it is very hard, and if I just talk about doing it, I can get a significant proportion of those same rewards. It actually
creates a real disincentive. It's like illogical to actually do it for a lot of these people.
Well, that brings up an interesting, you know, uh, sort of discussion that we could have around
goals and goal setting. And I want to get back to the inflection point of being on the stairs,
because I think that's interesting as well. And there's, I had some thoughts on that,
but, but, you know, in terms of setting a goal and then setting about achieving that goal,
it brings up notions of, you know, accountability and sort of, you know, these ideas of creating
community around it that can propel you forward or dissuade you. Like we just pointed out, like how that can actually distract you from the ultimate goal.
I think it is important to, you know, set a goal that scares you, but then to bring it
back to stoicism, it's about the process.
It's not about that destination.
So when I set a big goal that scares me, whether it's, you know, doing Ultraman or, you know,
writing a book, as soon as I kind of put that on the
calendar, however far away it is, I forget about that. And then it's just about what is in front
of me to do today and embracing every aspect of that, because it's about action, right? And I
think at its core, that's really, you know, what Stoicism speaks to.
Yeah, it's ultimately a philosophy of action. It's not the
secret, right? It's not like, oh, you wished for it. Now it will become real. Certainly what you're
wishing for and what you're thinking about has a real impact on your action. Like you've said,
like sort of, uh, what mood follows action, I think is, I think that's very important. Um,
or action follows mood. Um, but like the other way around mood follows action, mood follows mood. It's the other way around. Mood follows action. Mood follows action.
Okay.
But I also think action follows mood, right?
But then, in any case, action is the critical sort of variable, right?
Like, what are you actually doing to get you towards what you're talking about?
Like, what are the actual tangible steps that you're getting towards your goal?
Like, one of the examples I talk about in the book, and I think is one of my favorite, and it was weirdly
controversial. I tell the story of like Amelia Earhart, who, you know, her first offer as a pilot,
she was like, you know, she was a woman pilot, women could just earn the right to vote, not a
great time to be a woman in America, especially like an ambitious woman. And her first offer for
a transatlantic flight was from this rich donor who decided to sponsor a female flight. But the offer
to the woman was a man is going to fly the plane. There's going to be a male co-pilot and you have
to sit in the back with the maps, but we're going to tell everyone that a woman like this is,
everyone's going to congratulate you and think you're the, you're famous, but you're really not.
And like, um, to me, like, so I
remember telling the story, and I gave it at a talk recently, and this one woman got very upset.
And you're like, dude, you're saying that she should have just, she should have just, you know,
endured this like indignity, she just should have taken it. And I was like, yeah, like what she,
what she did was she put her own ego aside. And she said, I'm willing to temporarily eat shit to advance my goals forward.
And then from the platform and the money that she got from there,
she funded her own solo transatlantic flight like two years later.
And it made her actually accomplish what she was doing.
But I see this like with my peers,
like my college class graduated into the financial recession.
And what most of them did was move back home with mom and dad or go to grad school because like the job market wasn't exactly
how they wanted it. And like, so people now are like, Oh, like you're so young. How have you
accomplished these things? It's like, I'm not young. I've just been doing it long. Like I've
been doing it since I was 19 years old. because I didn't spend an extra four years in
school waiting for the job market to magically get better. And I, so I think a big part of it is like,
can you put your ego aside? Can you start small and can you actually like do the work every day,
regardless of what other people think, what other people say about it, what, what you think you
deserve or are entitled to in life. It's that getting started
that's sort of the step one that I think people don't like, partly because they have this idealized
view of what the world is from these inspirational quotes that make them think it's like
passion and inspiration and excitement that are the critical variables. It's like, I could hire 100 passionate people tomorrow.
Could I hire someone I could actually rely on
to do the work that I would trust implicitly
and see real promise in?
Probably not.
Right, but I think in your particular case,
you had a very strong sense of direction early on.
Your compass was pretty well calibrated
about what
you wanted to do. Not everybody has that, right? So, so I think first you have to, you know, do
the, whatever internal work that you need to do in order to understand, you know, where your compass
should be pointed. Um, and that's, you know, uh, an ephemeral amorphous thing. That's, that's,
I think difficult for people. I mean, in my own personal life, like, I never thought about any of that. I was on this track, I was
going to be successful. You know, it's just, I was on the train to the mythical American dream where,
you know, you study hard, you get into the best school. And then, you know, I didn't know what
I wanted to do. So I went to law school, like, I just was propelling myself forward. And I was,
I was, you know, I could play that game, but never once
did I take that moment of solitude to go, what am I doing? You know, what am I doing? So that's why
I had to have this like midlife crisis over it. Like, you know, if I was 18 or 19 and maybe wasn't
drinking so much, maybe I could have taken the time to think about these things. But I don't
think that we, I think this is something that is very interesting about the millennial generation, because for all the flack that millennials get, I think that as young people, they really are thinking about these things in a way that my generation didn't or was not encouraged to.
Yeah, I suppose.
Although, like, I hear from lots of kids, they're like, oh, will you be my mentor?
Or like, oh, I want a mentor.
And they don't, like, it's the like it's the it's the entitlement aspect yeah it's this idea of like
oh sure i'll give you this huge gift because you asked that's how it works it's like no like uh
cheryl sandberg has this great quote she's like it's not about asking for a mentor it's doing
well and a mentor will seek you out and i think it's hard for people they're like oh i want to
be a filmmaker i want to be a writer i want to be a filmmaker. I want to be a writer.
I want to be an internet celebrity.
Whatever they want to be, they think it's the wanting to be it that is the important part.
So I think you're right.
Millennials have that figured out.
What's harder is the idea of, okay, so you have to get your ass kicked for five years.
Yeah, I don't like that part.
Right.
Or actually having something to contribute. at your ass kick for five years before like yeah i don't like that part right like look i want or
actually having something to contribute like i've always wanted to write books but like i started a
blog in 2006 and my first book in my first book came out in july of 2012 and i didn't get paid
for writing any time between there i had plenty of book Like, it wasn't the book idea that I was missing. It was
the anyone thinking that I, anyone actually wanting a book from me. And that took six years
of free work. Right, right, right. Well, I mean, to kind of pick up on this idea of mentorship,
I mean, I know, you know, your history is one of, you know, showing up to be of service and
provide value to people that you respected without asking for anything in return, right? Which is kind of the, that's the antithesis of
the entitlement generation, like this idea that, you know, you have to bring something to the table
and you have to trust and have faith that in some respect that that will pay dividends in the future,
you know, towards the goal that you're trying to achieve.
Yeah. Yeah. Like I got an email like yesterday and this guy was like, Hey, like, um, I want like
you to mentor me. I'll work for you for free. And then you can figure out if you want to pay me.
And it was like, it's like, I think you understand the logic, right? That's the logic, but that's not,
it's not a magical discussion. It's not a single life changing. Like I had this kid,
um, I probably shouldn't talk about it, but this kid flew from Australia and showed up at my door.
He just showed up.
Wow.
Because he'd heard that I was, like, looking for an assistant.
And I know in his head, he was thinking, I'm going to impress this person with this book.
He was thinking about his life as, like, this movie, right?
Like, this is the midway point in the movie
where the guy makes the decision that changes his life
and then everything is awesome because he took this risk.
And it's like, that's not how it works.
And he didn't think about how that thing
would be interpreted by me,
which is that like,
you think you're showing like passion and enthusiasm.
I think you're showing like a lack of boundaries
or like responsibility. And so I think,
I think again, to tie it into these quotes, not to like beat on it, but like, it's, it's,
there's inspiration is a commodity. What, what the other things are, how you differentiate yourself
and, you know, and, and how you, uh, or like with running, like speed is great, but endurance is
probably more important. Yeah. Well, it's that it's, uh, there, like speed is great, but endurance is probably more important.
Yeah, well, it's that, it's, there's a couple things, a couple thoughts that I had.
I mean, first of all, I think that for somebody who is grappling with, you know, beginning a project, right?
You hear Casey talk about this all the time.
Like filmmakers email him, how do I begin?
How do I have your life?
You know, they just have these grand ideas about, you know, the, they romanticize Casey's life and it's easy to do
because he lives in a very dynamic life. Right. And he makes it look really good on, in movies.
Right. That's part of, that's what he's got. Yeah. Um, but the first question is always like,
what's the camera, you know, that I need to get like, like as if that holds the key. And I think
in a, in a fitness context, it's about, you know, what kind of, what's the, what's the watch that I need to get
and what kind of heart rate and all of these things are actually barriers to you actually
doing it. And I think they are, they're indicators in my mind of someone's fear of just starting,
like they're overcomplicating something rather than just beginning it because they're,
they're afraid. Right. So, so rather than just make a terrible
movie or write a terrible book, um, you know, they want to have a discussion about all of the
artifice that surrounds those things, which actually is an impediment to them doing it in
the first place. And so to use the example of the guy who flew out from, from Australia, I mean,
he would have been better served to stay in Australia and figure out a way
how he could have benefited one of your goals from afar and then demonstrated that he actually
added value to your life in some respect without asking for anything in return. I think that would
have been more impactful for him and maybe put him in a better position for you to say,
sure, I'll employ you. Yeah, totally. Totally. Totally. So totally so um all right so so inspiration into action i
mean for me pain is really the only thing that's ever motivated me to change any kind of my errant
ways you know and so so in thinking about that you know and understanding that we all have the
facility to change at any given moment that you don't have to suffer some you know your elevator
doesn't have to crash all the way to the bottom in order for you to be reflective on your life and make
changes. I mean, what are some of the things that, that you found helpful in kind of turning a train
around? Like what pain in my life? No, not, not, I'm, I'm saying, you know, short of like having,
having to endure some kind of painful moment in order for you to do something different.
There's that great quote from Bismarck where he's saying, like, any fool can learn from experience.
I prefer to learn from, like, the experience of others, which is something I've always, like, tried to live my life by.
Like, I think I've learned from a lot of mistakes from my mentors.
I've learned, like, I obviously have read very widely.
my mentors. I've learned, like, I obviously have read very widely and I'm always trying to think like, okay, like what I definitely don't want to do is wake up one day and go like, this is not
the life that I want, right? Like, this is not where I want my life to be. I definitely don't
want that moment. And so I think I've made a lot of decisions to avoid, like, you know, I dropped
out of college. I quit really good jobs at various points.
And so I've definitely avoided that. And then of course you, you, you try so desperately to avoid something, but you end up just delaying, like this summer I woke up, I was, I was,
I worked a lot on the sort of transition craziness at American Apparel over the summer when, when the,
the founder was fired and who'd been a mentor to me, it was a whole period. And I remember waking
up, like they were paying me really good money. I It was a whole period. And I remember waking up,
like they were paying me really good money. I was, it was exciting. And then I woke up one morning
and I was like, I, I, I went out to breakfast and I was like, fuck, like I gotta get to the office.
And, and, and then I was like, wait, like my whole life, I made all these decisions,
like about where I wanted to live, what I wanted to do, like that I wanted to be a writer.
like about where I wanted to live, what I wanted to do, like that I wanted to be a writer.
And here I am feeling guilty for like not being in an office. Like what, what is this? Um, this is not what I wanted. And, um, and then I had, then I, and, and I had a similar, um, sort of,
uh, realization about, uh, one of the partners in my company and it, it, it become like a big deal.
And, and so I had to then,
I had to then detangle this like whole mess, like all these decisions that I'd made.
I had to sort of sit back and was like, what was actually motivating these decisions? It was,
it was greed. It was like pain avoidance. It was like, like instead of having a conversation,
a difficult conversation, I was like going along with things. And all that was really doing was
delaying the unpleasantness of what I ultimately needed to do. So I think it's
interesting. I think like I've always tried to avoid, avoid having to learn from pain. And then
I felt like what I really did was just delay it into an incredibly painful summer, which was last
summer that I'm only sort of now just kind of turned a corner on. So I don't know. I don't know. Does that really
answer the question? Yeah, I think so. I mean, but to then kind of apply the principles of Seneca
and Marcus Aurelius to this, I mean, that was an experience that you weathered that I'm sure,
you know, carries inherent value that you've learned from, right? So, you know, what is your
perspective on that now? You know, was that bad? Was that good? I mean, it was just...
It was what it was.
It was what it was, right?
Yeah, and it showed me very clearly the things that I do want by making it clear all the
things that I definitely don't want.
And it's like, I touched the stove, I got burned really bad.
I'm not going to touch that stove for at least a pretty long while.
You know what I mean?
So in that sense, it was very beneficial.
And the other thing is like,
what's really nice about being a creative person or an artist
is like, it doesn't matter how awful it was,
or even if I can never undo it,
like it just cost all this money.
It was all this pain.
It can never be undone.
At the very least, you can turn it into material,
which is so awesome about,
like that's something Robert Greene, which is so awesome about like,
that's something Robert Greene said to me. He was like, look, it's all material. So like,
it doesn't matter that he had abusive bosses or, or that he got screwed over by this or that. It's like, these are the lessons that I then wrote books about. And so my next book is very much,
it's not directly about the things I learned that summer, but I don't think the writing would be as
good if I hadn't
really truly experienced it firsthand. Can you talk about what that book is or will that defile
your, uh, your principle around not speaking publicly about your projects? It's done. So I
can talk about it a little, like it's in, in the realm of traditional publishing, it's turned in,
but it won't come out until a year from now. But, book is about ego and how sort of we are ruled by this force that we don't want to acknowledge. And we don't,
like nobody thinks they're an egomaniac and I wouldn't say that they are, but they don't
understand the way that ego sort of leads them further away from all the things that they want.
So give me an example of that.
So like, look, when you're young,
being sort of delusionally ambitious can be adaptive
in the sense that it helps you get over that uncertainty
or unpleasantness of the scariness of what you're doing.
But then as soon as you are successful,
that delusion is now your absolute worst enemy, right?
Your inability to, and I would say like, like, look, one of the,
one of the greatest assets that I've had is that I'm always willing to like learn from other people
and I'm always willing to take a sort of back, like, I don't need to be in charge because I'd
rather sit back and learn from, from the situation. But, um, if, if my disposition was a little bit
different, if I'd started to say like, well, I've done X, Y, and Z, I should be in charge. All of a sudden that learning stops. All of a sudden your ability
to take feedback from, I think the most critical thing that an artist or that an entrepreneur or,
or a business person has, um, is their relationship to the world around them,
their ability to understand and interact with and filter the reality that comes to them. And ego is a wall between them and that reality. And that wall can be defensive sometimes
and can have benefits, but it's almost universally negative. So then how do you reconcile that
against a survey of some of the most successful entrepreneurs out there who tend to, you know, uh, you know, fall on the, you know,
the spectrum of large ego and, you know, all the way to megalomania. Well, there's a certain thing
called the survivorship bias, right? Like, which I think is a big part of it. Um, and I think another
part of it is, is, is this idea of like, um, like you could say like Lance Armstrong, uh, was
successful because he was egotistical.
Right.
But Lance Armstrong also had cancer.
Was that why he was successful?
Or like correlation does not equal causation.
I think that's a huge part of it.
And then I think the other thing is like there,
I've met many,
many successful people in my life.
And I would say there's like two or three of them that I would ever trade
places with. So I think that there's like two or three of them that I would ever trade places with.
So I think that's the other big part of it. It's like, we think these people have these lives
because they've accomplished something that it must be meaningful, that it must be happy,
that it must be what you want. And you don't realize that to get this thing, you think that
you could be the same person that you are and have this thing. And that's not how that trade works.
Right.
We project idealized notions of what these people's lives are like in an aspirational kind of way.
But if you spend time with these people, and look, living in Los Angeles, I'm around a lot of really successful people, most of which, not all of which, but most of which are really not happy people, right? And so we're sold this lie that success carries the seeds of happiness, which no matter how many times we're told that's not true, we persistently continue to believe that to be the case.
And I also find with those people that the great work that they objectively have done came in moments of lucidity.
Because you were in the entertainment
business. You see lots of creative people and everyone's like, they're fucking nuts. This
person is insane, but it's in these moments when they're not nuts that they do great work. Right.
And, and everyone sits there and goes like, what could this person have actually accomplished if
they could have gotten out of their own way? You know what I mean? Like, like what, what great work
could they have done or what huge what, what great work could they have
done or what huge failings and missteps could they have avoided if they could have gotten a handle on
their, their, their drug addictions or their inability to trust people or their, their need
to one up everyone or their inability to hear feedback, you know, like all these things. Um,
I think not only, not only do they prevent some
people from being successful at all, but I think they also hold really talented, amazing people
back from being even more successful or great. Well, I think what happens is that, you know,
somebody who's in that situation holds on to that character defect and ascribes to that part and partial of why they're successful.
So the alcoholic or the heroin addict who's a painter who thinks, if I get sober, I'm never
going to be able to channel any more creativity, or if I don't throw temper tantrums, nobody's
going to do what I say, or if you're Steve Jobs and you're not holding that like super hard line, then you're not going to be getting the excellence out of your team that
you demand of them, right? So the character defect becomes the recipe for success. And that belies
this sense of, you know, this elusive sense of balance that perhaps, you know, if you look at
it in a longer term, might fuel a better outcome ultimately.
Yeah. I mean, you talked to plenty of addicts who came out the other side and they're like,
look, I'm just, that was my huge fear. I'm more creative now than I was before.
Yeah. I hear that all. I mean, I'm around a lot of those people. And so I've experienced
that firsthand, but the fear is so palpable.
Totally.
That it prevents embrace of that idea.
And it's not just fear. It's also, I think it's your dependence
or your, like, whether it's a character trait
or an addiction,
it's your comfort with the status quo
that is rationalizing the change,
rationalizing the resistance to change.
It's like, oh, like, well, it's like, look,
it's not that you're afraid of being creative.
It's that you really like doing drugs
and you don't want to stop doing drugs right well that's the lie right yeah that's
the lie that's that that you want to just buy into completely right
all right so that's interesting so so basically the the underlying premise behind that is if you can squelch the ego or rein it in, that ultimately you could be more productive.
And so what's behind that?
Yeah, I mean, like, so look, one of my favorite historical figures, period, is George Marshall.
So you look at George Marshall.
So he's the chief of staff during World War II.
He wins the Nobel Prize for the Marshall Plan.
He's a diplomat.
He does all these amazing things. Most people have no idea who he is. They have heard of
MacArthur or Patton, these sort of very, very egotistical generals, but who ultimately had a
much bigger impact on the world. It was this humble guy who, he didn't keep a diary because he felt like
keeping a diary would make him perform for history.
He wouldn't, he turned down a million dollars
for his memoir because he didn't want to embarrass anyone.
There's this story where like he's forced to sit
for this like official portrait
and he goes like two or three days in a row
and then he's, the guy's like, okay, you're done. And then he gets up and he leaves. And the guy's like, wait, don't you want to see your painting? And he goes like two or three days in a row and then he's the guy's like okay you're done and then he gets up and he leaves and the guy's like wait don't you want to see
your painting and he's like no like why i know what i look like you know it's this idea of like
if you can if you can become as self-contained as possible and is as unreliant on these sort of
external factors these sort of ego hits that we need it actually allows you to do much better work, not just much
better work, but much more selfless work and much less sort of encounter much less resistance
on that work.
And I think you ultimately have a greater impact on history, on the world, and on sort
of fulfilling your personal potential.
Humility.
Totally.
It's humility and being service-oriented.
Totally.
The problem is no one will read a book about humility because humility sounds Totally. It's humility and being service oriented. Totally. The problem is no one will read
a book about humility because humility sounds boring. Like I think, and so this is something
obviously I think about as a marketer, but it's interesting. Like, like we all know that humility
is like where we want to end up. Like we want to be a humble person, but nobody thinks that
humility will get you there. Like you're like, look, I want to have the weakness, right? You're
like, I want to have this nice house and I want to have a, an audience and I want
to have all this stuff and I want to be humble and well-adjusted when I'm there.
And then you tell yourself that you have to be a fucking dick who screws everyone over
or puts, you know, does things you don't agree with or like in order to get there.
And I think that's probably not true.
No, I think, I think you're absolutely correct about that.
I think that's probably not true.
No, I think you're absolutely correct about that.
I mean, I think that that requires a level of faith that I think most people don't have the facility for. Because you have to approach whatever it is you're doing from a perspective of service rather than, you know, instead of approaching whatever it is, your career or whatever scenario you're walking into and saying, what am I going to get out of this?
And saying, what am I contributing to this?
Sure.
And really divorcing yourself from the idea of how you will be rewarded, I think ultimately is like the secret to long-term success.
And that requires reigning in your ego.
And it requires really grappling with who you are inside of
yourself. Can you get to that place where you really are outside of what it is that you want
and you are truly in a place of just serving, right? And I think that when you do that, the,
the, the path unfolds naturally in front of you and creates the decision tree where the, the,
you know, the moves that you're going to make naturally unfold.
But it's an ephemeral idea, right?
And I think you can anchor it in the mystic of the moment
or whatever kind of spiritual principles or read the Bhagavad Gita.
And all of these kind of ancient texts will resonate with this notion,
but that's not really part of Western
culture and the sort of ethos around success. Well, let me ask you, because I remember reading,
so it was your first Ironman. It was, what did you place? I did Ultraman in 2008, and I was,
I got 11th in that, or I think I was the second fastest American that was in 2008
yeah so if I remember correctly you weren't even sure you were going to be able to compete you to
finish it right no I just didn't want to die right yeah like I didn't I wasn't there to race it I was
there to celebrate this kind of change in my life and so I remember reading that and thinking like
how do you think you would have done better or worse if you'd gone in with an idea of what you were going to, like, if your goal had been to get second, do you think you would have gotten second?
No, there's no way.
There's no way.
I mean, I think that when you're approaching something like that, like, I was coming from a place of I had never done an Ironman.
You know, I was not, like, I had no pedigree as an endurance athlete. And I approached that race with, I think, an appropriate level of
humility because it was so overwhelming. And I think there's something in particular in a
mystical sense about the big Island, you know, like there's, you know, if you want to talk about
the kahunas and all of that, and like the kind of, you know, all the sort of spirituality that surrounds Hawaii, like it will force you to your knees. And I think if you
approach that race with a sense of ego or entitlement, you will be reckoned with in a very
gnarly way. And you will hear that with any of the Ironman champions. Like if you talk to Chris
McCormick or Mark Allen or Dave Scott, you know, all of them were insanely
talented and, you know, sort of were winning races all the time. Like Macca talks about this all the
time. So, uh, you know, he was like king of triathlon, he'd won every distance. And so he
just thought like he was going to go to Hawaii and he was just going to walk away with the Ironman,
you know, world championship title. No problem. There was no reason why that wasn't going to
happen. And it just crushed him. And it took him years and years and years of going back and studying before he could finally master
it and win it. And he had to learn, you know, he's a very, he's, the guy's got a big ego. He's a very
dynamic personality, but he had to be, he had to get to a place of humility before he could
really come out on top of that. And I think that's a powerful lesson, you know, because he,
because he is such a big personality that he had to weather that makes it all the more beautiful.
Yeah. I quote Mike Tyson in the stoicism book where he's like, if you're not humble,
life will visit, will visit humility upon you. Right. And you can't escape that.
Yes. Although the more humble you are, the less likely that will be a catastrophic lesson in humility.
Versus like, oh man, that was embarrassing.
I shouldn't do that again.
Because Neil Strauss was telling me this idea of two cars in the garage addict.
Which is like the addict who can get sober before they end up homeless.
That's the trick.
Right.
You know, like when I'm talking about like pain being my motivator and having that inflection
point on the staircase, you know, I was in enough pain where I was ready to like do something
about it.
And it, and what happened on that in that moment was that it reminded me of the day
that I woke up and, and was ready to get sober.
And I think there's something precious about these very discreet moments in time where the door cracks open and there's a window of opportunity.
And you have the ability to act and act swiftly and decisively in that moment or it passes.
And you don't know whether that moment is going to revisit you.
So I understood on the staircase that I was getting another chance like that
because when I woke up that morning
and decided to get sober,
it changed my life so dramatically.
But had I just blown it off
or said I'll deal with it tomorrow,
who knows whether I would have ever made that change.
So there's something very special about that.
But can you make that change
short of having that kind of experience?
Can you do it when you have,
when the elevator,
perhaps you have a perception that your elevator is going down or the train is moving in the wrong direction, but before, you know, it crashes into the ground, can you redirect?
Yeah. I think it's the more sensitive you are to the feedback that the world and reality is
giving you the best, like you got to feel out of breath was enough for you to say like, Hey,
something is not right. Rather than heart palpitations or,
you know,
a diabetes diagnosis or,
you know,
like any,
any number of the much more severe signs that you could have gotten.
Like,
yeah.
Like for me,
like this summer,
it's like,
I had this wake up moment,
but like,
it could have been when my wife,
like it could have been because my wife left me.
Right.
Or it could have been,
you know,
that I turned in my book and the editor was like this is shit like where you were working
on this what happened you know like it could have been a the wake-up call could have been much worse
and like what i saw this summer with dove was like like i mean what what happens when you get
fired from the company that you founded and legally barred from ever reentering it because, you know, you blew past so many intersections and stop signs and red lights and warning signs and police blockades and every other thing that could have told you, like, do not do this.
You blew past and then you lost
everything. And I'm sure he would tell you that those character traits were part and parcel of
what made American apparel successful to begin with, right? So the seeds of destruction are
planted, you know, in the same fertilizer as the ones that allow it to flourish.
No, I mean, sadly, even worse, he would tell you that he was screwed over and he's going
to get it back. And it's not. So he's not learning the lesson. No, not even close. Right. So, you
know, similarly, if you look at Lance Armstrong, you know, it's a very similar case, right? You
could say, however you fall, you know, in that discussion, and there's a million opinions,
and I don't presume to have a strong opinion one way or the other.
I think it's far more gray and nuanced than people want to admit or embrace.
But the character traits that made Lance Armstrong a champion were also the ones that sowed the seeds of his destruction, right?
So if he hadn't decided to make a comeback, you know, this would
have never happened. And if he had decided not to screw all those people over along the way,
those chickens wouldn't have come home to roost. But it was because of that very behavior pattern
that propelled him into that rare air that allowed him to be so successful in that domain.
Yeah. One of my favorite, I've wrote about this a long, long time ago. One of my favorite books
is Fight Club. And the premise... It's incredible.
The premise of Fight Club is that he's living a horrible, miserable life and he cannot see it.
And so his alter ego or him while he's asleep has to blow up his apartment with everything he ever loved inside of
it. And even that is not enough, you know? Like, so I call them these like sort of fight club
moments where someone calls you out or someone blows up your stuff or you fail. And it's like,
you can, you can, it's in those moments that you see truth, right? And you can decide whether
you're going to look at it in the face or whether you're going to avert your gaze and go right back to doing what you're doing. And I think, you know,
the longer you put it off, the more dark and unpleasant that truth is going to be. And
paradoxically, the harder it's going to be for you to accept it. It's cognitive dissonance,
right? Like nobody wants to, you think you're a good person. It's very hard for you to accept it. It's cognitive dissonance, right? Like nobody wants to, you think you're a good person. It's very hard for you to accept that you've done a bad thing or that you've messed up
or that you're bad or any of these things. Right. Uh, absolutely. Unquestionably. Uh,
my wife calls it, uh, your divine moment. Sure. Right. And it's your reckoning, right? And are
you going to wake up and heed that call or are you going to blindly propel yourself forward until it gets worse and worse and worse? And there's something,
you know, to bring it back to stoicism and the obstacle is the way, this is an obstacle that
you face in your life that could be the most beautiful, you know, rebirth and flowering for
your life if you're willing to face it head on and accept it and deal with it objectively and
really kind of grapple with who you are to then set yourself forward in a new trajectory or you
can blow it off, right? And like, that's been my experience. And so, you know, those divine moments
bring you to your knees and we as, you know, people living in America will immediately label
that as tragic or disastrous,
or this is the worst thing that's ever happened to you. But I'm sure, you know, I know, and I'm
sure, you know, many people have experienced this yourself, where you look back on it five years
later, and you're like, that was the greatest thing ever. Like, look where I am now, because
of that thing that forced me to look in the mirror in a new and different way.
Yeah. And not that every moment is going to be so dark terrible or that every obstacle is gonna bring you to your knees.
Sometimes it's like, hey, I thought this would work.
It didn't work, but what are you gonna do about it?
You know what I mean?
Or like, hey, this person is being an asshole.
Am I gonna be an asshole back to them
or am I gonna use this as practice
for dealing with assholes?
Yeah, there's the macro and the micro, right?
And so you don't have to suffer
some cataclysmic, you know, result
in your life. These obstacles come in the form of, you know, the person who cut you off on the
highway or, you know, your boss being a douche or whatever. Like, how are you navigating that? Like,
are you being reactive? Are you being of service? What kind of humility are you bringing to that
equation that ultimately might, you know might provide you with a different result?
Like in recovery, they call it contrary action, right?
Like you have these behavior defects.
You're reactive.
People push your buttons.
You generally do this, and this gets you that negative result.
What is, you know, do the opposite of that.
Like can you retrain your brain to act differently?
act differently. And for me, that comes back to, you know, meditation and, and other ways of trying to rewire, you know, the brain and the personality to behave differently. Yeah. Right. Can you,
can you not, can you be more than the sort of like an, a reactionary robot, right? Like this
is what I normally do. So I'm just going to do that. Even if all evidence points to its ineffectiveness.
Right, right, right, right.
Have you read Sam Harris's Free Will?
No.
I love Sam Harris.
You've got to read it.
It will bend your mind about decision making and our capacity to make decisions.
Well, we can talk about it later. I can,
we can go down a rabbit hole on that, but read that. You should read that. Okay.
Well, uh, from here, like I want to talk about, um, maybe some, some, uh, you know, practices
that you found helpful, perhaps their morning routines or things that you do on a daily basis
that help keep you kind of in check.
Maybe there are things that help remind you of your humility and keep you in that service-minded set
or kind of help you focus on confronting and overcoming those micro-obstacles that you face on a daily basis.
Yeah, it's weird.
I think one of the things about the books that I've written is that like the
natural assumption is like,
Oh,
he's writing about this cause he like,
he's some sort of expert,
but really I'm writing the book because like it's for me.
And then I just happen to sell it to other people at the same time.
Do you know what I mean?
So like I,
I,
for me,
like the books were actually hugely therapeutic,
sort of huge,
hugely necessary,
like codification of these ideas.
And I actually like, it sounds weird, but I like read my own books and like when i'm it's like because i don't see myself
in them i see smarter people than me organized in a way that's more accessible for me but like
like i journal every morning about the the day before um i try to meditate like, you know, 10 or 15 minutes a day.
I'm not very good at it.
It keeps me very,
the idea of not doing anything is like very hard for me.
And so I've actually spent like the last year
like trying to like say no to things
and trying to actually,
like Louis C.K. talks about these like moments
where you're uncomfortable
and your first instinct is to like reach for your phone
or do something
instead of like sitting with that discomfort. It's, it's the hardest thing. It's the hardest
thing. It's so awful. It's like antithetical to, I mean, who deliberately feels uncomfort,
discomfort. And like, we have these magical sort of like solves in our pockets at all times.
Right. Like standing in lines is no longer a problem because we all have a phone and we can, you know, distract ourselves. Yeah. Yeah. And so I, like I've, I've spent a lot
of time trying, like, like I don't check my email until I've journaled and done at least one other
thing every morning so that there's like, um, there is time that I'm awake that the world is
mine and no one can impose on it. And, and I've tried to sort of like exercise is that moment for me too.
So it's also why I don't try to make it happen as fast as possible.
And I'm not looking for shortcuts,
uh,
or like hacks to make it more effective.
It's like,
I like what it is and I like that it's time that I'm not plugged in.
Um,
so that those are the sort of things I think about.
And stoicism is really,
it's, it's this set of exercises and meditations, right? It's the idea of like,
it's reminding yourself in some situation, like there is not a good or bad here. There is my
perception about that thing. And every cognitive behavioral therapy is, is that idea of like,
here's what happened. Here's my normal reaction.
Like you said, is that, and then putting that beat there so you can say, is that the reaction
I want to consciously allow in this situation?
It's like, like this happened.
Here's my emotion.
Is that a positive or a negative emotion?
Am I going to like sort of give into it?
And so for me, it's been a lot of work about creating that the ability to have that control over my thing so it's like maybe i got
mad but two seconds later i'm aware that i'm mad and i'm gonna stop being mad and i'm gonna
apologize for being mad and i'm gonna reset right right a friend of mine calls that uh if you're
gonna eat crow eat it hot yeah sure right so if you're going to eat crow, eat it hot. Yeah, sure. Right?
So if you had to inventory your character defects or the things that you struggle with
that you're still trying to overcome,
what would that look like?
I think intensity is my biggest one.
Even now, I'm all over the place.
I'm getting excited.
It's that intensity, which is a benefit to me.
It's made me good at what I do,
but it's also problematic
when most people are not that intense
and so like
if I'm quick to something and I'm intense about it
all of a sudden a very minor thing
can get
become a very major deal very quickly
because I've thrown
the other person has thrown two seconds of thought at it
and I've thrown
my entire intellect behind this thing and what it means and
whether i like it and whether i'm going to accept it and whether what i should do about it and what
it means and all this blah onto uh a pretty everyday you know human interaction right so
you're kind of you're kind of putting gasoline on the, on the flame. Yeah. And, and so I think about that too, with the discomfort where it's
like, if I don't feel like doing anything, maybe I don't have to do something. I don't have to
respond to a feeling of fatigue or, um, you know, frustration or, you know, lack of progress.
I don't have to like, like, uh, I go to therapy and my therapist, she's, frustration or, you know, lack of progress. I don't have to like,
like, uh, I go to therapy and my therapist, she's like, Ryan, like thoughts are not facts.
Like just because you thought about doing something or you wanted something to happen
does not mean that it must happen. And that's, that's something I've spent a lot of time on
recently is it's just this, like, relax. relax like every it's it's 85 percent how you want
it to to think that you that to make yourself miserable about that 15 percent is like a very
needless compulsion and how does running play into it i love that post that you wrote on on
on i don't know what it's called, Why I Run or something like that.
Yeah.
Running is really good for me, and then also I can see how it's bad for me in the sense of it's a time where I'm not connected to any device
other than music.
I'm doing something that's good for my health.
I'm doing a lot of thinking.
I get into a flow state when I run, and so that's like good for my health i'm i'm doing a lot of thinking i i get into a flow state when i run
and and so that's really great but on the other hand it's like like i'm i can see myself like
in it was once an activity that i loved and then i you can ritualize something like that and make
it an obligation which strips it of its purpose and meaning so it's like like, like, you know, I was thinking about like,
cause I'm, I'm out here and I had to get up early and then I'm doing some other things today. It's
like, I'm like, I have a bit of anxiety about whether I'm going to be able to run or not. Not
like I really want to run and I should be able to, but it's like, like, am I failing if I don't
like, am I letting myself down? That is not a healthy relationship with an activity.
Yeah. That's interesting. I mean, I definitely struggle with that as well. Right. I'm sure the
thing that, the thing that brings you joy can be, can be, can be undermined by the sense of,
of, you know, obligation to use your word, um, to do it. Yeah. That's interesting.
I turn everything into work. That's my sort of demon. Right. So like now we're do it. Yeah. That's interesting. I turn everything into work. That's my sort of
demon. Right. So like now we're getting it. Yeah. Like, so I work like, or sorry, I love reading,
but if I'm not reading, like it was only until recently that like I could go like five or six
days without reading. Cause I was busy or I wasn't into it. And I didn't feel like I was like
cheating myself or letting myself down. And, and so it's like the same with
running. Like, so for me, the discipline would be decide like today is Sunday. I'm spending time
around the house. I'm, I'm going to commit to not running, you know? Like, so that's, that's the,
the harder part for me. Yeah. Yeah. Yeah. I totally relate to that. It's interesting because
most people are looking for the motivation to run. Sure. And, and for me, it's being okay with the fact that perhaps it's not going to happen today,
you know, and like, you know, I'm in this transition right now where, you know, I'm sort
of known as this athlete who's done these things and, and now I'm kind of maturing into a different
kind of thing where it's more about advocacy and like doing the podcast and the next book and all
that sort of stuff. And, and, you know, I have four kids
and I have, you know, like I wanna be happy in my life.
And, you know, perhaps if I lived in a cabin in the woods,
I would train all day long and just write
and I would be content in doing so,
but that's not my life.
So how do I have all of those things in balance in my life
and be happy with that?
And I don't, you know, I don't think that going out
and training 25 hours a week right now is really the right thing for me to be doing. Maybe it will
be in a couple of years or get, you know, thinking of some crazy new challenge because I, I worry
about, am I still going to be relevant if I'm not, you know, out there doing one of those things?
Is there a new way to, you know, to redefine what I'm doing? What makes sense? What's the best way
to carry a healthy message? Um, message. And that can become burdensome.
The Stoics talk about this a lot, and I've been reading about it.
And he's like, there's this one line where Marcus Reyes, he's like, take the people who
felt the most intense anger or passion or drive to do something in history.
And he's like, and where are they now?
He's like, they're dead.
And that is dissipated.
And so it's like, you know, you have
this emperor who was the most famous man in the world. And even 50 years later, people barely
remember his name. And so it's crazy to have this Marxist who's also that person. It's very easy for
a nobody to say like being famous is meaningless. It's much more powerful when an actual famous
person is sort of talking about what these things mean.
And so, like, I think that one of the things I've had to start to remind myself of is like, look,
you're not building some fucking monument here for all time that like, and even if you were,
you would be dead and you wouldn't know that people appreciated said monument. So it's like,
if you're not enjoying it now, that's not good. And you've got to think about that. And so sometimes like getting a reminder of your own mortality helps
you relax a little bit, you know, because you, it's not, it doesn't make things meaningless,
but it helps you go like, relax. Like you're doing fine. Like you're doing better than most people.
You've accomplished this stuff. You should be proud of it. You don't need to feel shitty because
you haven't done enough. So that's a big thing for me. And then the other thing for me is if
you want to look at like, you know, look at your friends, look at your family. Like my,
my parents live in Hawaii. And when I go and visit them, they're just like, we got to do this. We
got to do that. My parents are just total activity addicts. Like I love them, but like my parents
live in paradise and all they want to do is activities all the time instead of enjoying
the fact that they live in this place.
And like, clearly I internalized that as a kid. And so now I live in like my version of paradise
in Texas. And like, like my, my wife will go out and was like, sit and be surrounded by animals
or just like, look at things. And I'll be like, like, we, we have a pool. I've never had a pool
before. And like, I get in the pool and I'm like, what are we doing? Like, should we a pool. I've never had a pool before. And, like, I get in the pool, and I'm like, what are we doing?
Like, should we do laps?
And she's like, no, we're in the pool.
And I'm like, I don't get this.
Like, I don't get what, what are we doing?
Like, this feels so weird to me.
Right.
But I'm trying to learn.
It's a fusion of Eckhart Tolle.
Yeah, right.
Like, you can actually be in the present moment and not do
something, and that is just as meaningful. Like, why is me spending 20 minutes swimming from one
end to the other somehow, in my mind, a good use of time, but standing in the middle of it feeling
nice is like heretical waste? Right. Well, that's the, that's the plight of modern man,
I think.
Right.
And I think that is,
that's what's propelling so many people to be miserable.
I don't think it's a plight of modern man.
Cause I think other people have no problem watching seven hours of
television on average a day.
So I think it's,
it's the plight of certain modern men.
But that's,
but that's not being present.
That's,
that's,
that's like,
you know,
that's like taking a drug, you know, that's escaping your reality rather than embracing just the moment that you're in and appreciating it.
And to your point about death, I don't think that we talk about or think about death enough.
I think we should objectively be quite aware of that in every moment, and I think that that would give our lives more context
and meaning. But, you know, again, it goes back to, you know, these cultural paradigms where
we're all walking around thinking that we're going to be the exception, that we're not going to die,
or, and even when somebody is on their deathbed trying to, you know, tell them that it's actually
not going to happen, as opposed to just appreciating it, I think would give, would
infuse our lives with a
lot more kind of appreciation and gratitude. Yeah. There's this great line from Marcus
Aurelius where he's saying like, um, uh, Alexander the Great and his mule driver were both buried in
the same ground. And it's like the same, the same thing happened to both of them, which is that they
died. Although one of them was murdered by his own soldiers. So you got to ask like, who was,
who, who had a better end? And then they're both buried in the ground and then uh you know it doesn't mean
anything to alexander the great that alexandria still exists and is named after him he's fucking
dead and he's been dead for a long time like he doesn't he's not just sitting there like you know
enjoying it like he's gone and so you know he probably was a super miserable, awful person. It just seems like, you know, centuries later, like, oh, I want that.
But you don't want that.
I promise you, you don't want it.
How to be present.
Yeah.
The most difficult thing, right?
Totally.
I mean, no.
Surviving is much more difficult, you know, obviously much more difficult things.
But in the first world, being present is the most difficult thing. First world problem. Yeah world problem. Yeah, for sure. All right. Well, let's shift gears a little
bit here. I can't let you, I can't let you out of here without talking a little bit about, um,
marketing, which is the other side of, you know, kind of what you do. Sure. Um, and you know,
it's kind of interesting what's going on right now. you wrote an interesting piece about the the recent you know gawker episode uh where they where they outed um the uh the cfo of condé nast for an
indiscretion and it kind of speaks to our our schadenfreude you know uh obsessed culture and
kind of where media is going right now and you, you know, is there like, how are we,
you know, how is this going to play out? Like, is it just getting worse and worse?
I think it's getting worse, but I do think in the last year you've had, I think the fact that
people are angry about this Gawker post is the result of like some great work from people. Like
Monica Lewinsky has that awesome ted talk about shame um john
ronson's book is amazing yeah and he's been doing the podcast rounds and like i love that guy oh
he's fabulous like i'm so glad that he wrote that book that he could write a book about people that
you hate and make you feel empathy for them is what like literature there's great studies that
show that literature increases empathy
and that's what his book does and so i think like look if you if you want to improve the quality of
your life right now you're looking for some life hack to like improve the quality of your life
um stop watching the news or like current current event oriented content because because 98% of it does not affect your life in any way.
It changes your perspective on things and it frees you up to do,
to focus on the fact that for 5,000 years,
really smart people have been writing things about timeless subjects and,
you know, timeless wisdom that you should be.
It's like once you've read all the classics, then fine,
read Gawker in the morning, but you haven't.
So what are you doing?
You know what I mean?
So I think media and marketing are very different,
but I am very bearish and disappointed in our current media system.
I think it's really bad.
Of course, there's also some marketing opportunities within that,
but generally I think Gawker is a force for evil in the world
that has been tolerated by society for far too long.
Right. Well, systemically, it's, you know, it's wired to be that way because the entire foundation upon it is premised upon page views. Right. And so when that's the case and it's, you know, driven by ad sales on page views, then you're going to get cats and you're going to get, you know.
Yeah. Inspirational quotes. views, then you're going to get cats and you're going to get, you know, inspirational quotes,
like all this stuff that is complete nonsense and is not really advancing our, you know.
Sure. But also like, you know, our response to drugs or other addictions is a biological
mechanism. That doesn't mean that you should be a drug dealer or you should do drugs. And I think
that's how I see a lot of these, like Gawker will say, oh, people want this.
Well, people want a lot of stuff.
That doesn't mean you should give it to them or that it's good that they have it.
You know, and I'm not being paternalistic.
I'm just saying, like, we only have so much time on this planet.
Are you going to waste it consuming crap?
And are you going to waste it producing more crap that we don't need?
Not great.
So how do we shut it off?
Read books.
Read books, I think is a big one. I got in this spat a couple of days ago with an info
marketer friend. He put out this quote where he was like, you should spend 20% of your
time producing, 80% of your time marketing.
I hate that.
I was like, I'm a marketer. This is what I do. And I'm telling you that it's the biggest crock of shit that I've ever heard.
All right. So let's camp out here for a second because I get insane about this kind of thing.
And, you know, as somebody who, you know, who, again, I'm some, you know, I'm, I'm kind of like
living my life on social media and I'm kind of in this health and wellness space.
And so I pay attention to a lot of the quote unquote thought leaders that are making waves in this world.
And so I subscribed all their newsletters and I just kind of try to analyze kind of what they're doing and how they're pursuing their business.
Because I'm trying to think about how I'm cultivating a responsible profession around what I'm doing.
Right. And I'm just dismayed, you know, I'm just made, I, you know, I, I get these,
these auto responders and these emails and I get stuck in these, you know, these
labyrinth thing, you know, kind of email chains that I can't escape from. And just the pure language of it
is so disappointing to me. It's all, it's all like clickbaity, you know, Buzzfeed,
gawker-y kind of language where like, here's the blog post no one wants you to know about. Like,
I just found out the secret and, you know, you could do it if you click here. And then there's
always an upsell and all of this kind of stuff. And I'm like, I was talking to James Altucher
about this and I was like, how do you,
as somebody who is a writer online
and somebody who understands implicitly marketing
and has an audience,
what is your perspective on this?
And he said something very interesting,
which is he finds it distasteful as well,
but he said when you test it,
it's not even close.
It's like nine to one in terms of how people, you know, kind of respond to it.
That's true.
And I love James's stuff.
And he was a client and a friend of mine too.
So I wouldn't say, I wouldn't disagree with him.
But what I would say is like, first off, look, saying you're too good for this, that's a
problem, right?
Where people are like, oh, you just got to make something amazing and it'll take care
of itself.
That's a delusional attitude Where people are like, oh, you just got to make something amazing and it'll take care of itself. That's a delusional attitude.
That is delusional also.
But I think this, what I see is all of these people who are spending all of their time
on marketing and almost no time on creating anything of any value or quality.
Well, that's what I was going to say.
I think the other people on the other side of it are responding to overwhelmingly short
term incentives and building nothing
that will last.
Right.
The most important thing is building an email list and not even secondary or tertiary, like
way down the line is the product that they actually are asking people to buy.
Right, right.
Because then they're selling their email list to other people's email lists.
It's like a total, it's a Ponzi scheme, basically.
And so I definitely
hate that. And I think, you know, my goal is to write books that will last and I want to,
I want to market them to the best of my ability now, but I'd like for a decade from now for them
to still be selling. And that's the sort of timeline that I'm thinking about. I'm not thinking,
I don't see the internet as this cash grab where I can make a lot of money with some crappy online course right now.
Scorched earth thing.
Yeah.
And one of the reasons that, like, I think it's really interesting, because you know a lot of these people, that they talk about how much money they make with these courses and all these things.
They're making crazy money.
Yeah.
Crazy money.
But then what are they doing?
All of them want to write New York Times bestselling books.
Right.
Well, and then they, but then they get then they write a huge check to Results Source.
They buy their own book back.
Then they get on the New York Times bestseller list.
And the unassuming consumer doesn't know the difference.
They don't realize that they've just
gamed this entire thing.
Like, as somebody who is an expert in gaming the system,
which you are, and reading, trust me, I'm lying.
I learned so much.
And it was fascinating.
But as somebody who's kind of standing by on the sidelines, I look at that and I go,
there's a, it's a, you know, on the one hand, I'm jealous.
Sure.
I'd like to have a book on the New York Times with Sotos, but I'm not going to write a check
to results.
I'm not going to do that.
Like I'm interested in longevity.
Totally.
And ultimately the most important thing to me, above anything else, is credibility and
authenticity.
And the minute you start to do that, you are undermining that.
That's sort of my point, though.
To me, it's very telling.
These people who are making all this money, all they really want is credibility and influence.
Like, that's all they actually want.
But every action they're taking is underm and influence. Like that's all they actually want. Every action they're taking is underwriting that.
Right, right.
No, that's why I'm, it's like,
like they think that they had to make millions of dollars
selling scammy products to then pay
to get on the New York Times bestseller list
when really they could have just sat down
and wrote an actually good book.
All that energy on doing something good.
Right, no, it's a crazy model and and i i and i think this
is another instance in where tim ferris is misunderstood because he's so masterful at at
being transparent with like all the tactics that he used to make his books successful yeah and that
gets all the attention what doesn't get the attention is how much time and work he put into
creating books that people actually enjoy and find useful. Well, like, because I'm thinking about this for a project now,
maybe the metaphor I've been kicking around is like,
look, it takes the same amount of time to get,
or energy to get a plane up in the air
as it does like a glider, right?
But like, if it doesn't have an engine,
what's the point, right?
Like, if you're going to do all this work
and all this energy to make something that doesn't last,
why? Like, why?
Why would you do that?
These people are like, oh, my book is a business card.
That's why I'm doing it.
Well, it's like your business card has an expiration date on it.
That doesn't make very much sense.
For our work week, people think it was this expertly marketed book, and it was.
But it's also still in hardcover like a million and a half copies later selling because right it's a good book right he didn't market his way to 1500 reviews on amazon
he marketed his way to 200 reviews on amazon in the first year that's market marketing is
marketing is the catalyst that kickstarts a process. And I've just seen too many people, especially in the fitness space, have huge lists, write crappy books, get immediate success, and then fall off the face of the planet.
And I just don't understand the point.
It's not, I don't, I mean, look, I'll take their money, but like, I don't understand the point of that process.
It doesn't, it's not worth it. Ultimately. Yeah. It's, it's, it's just a short term thing. You know, it's never gonna,
it's never going to be sustainable in the long run. And so I'm always watching and saying,
seeing how these things are playing out over time. And for me, like I've kind of, you know,
I got into this without any understanding of marketing whatsoever. Sure. And I kind of,
you know, engage the, like, I love podcasting,
right? I didn't do it because it's a lead generator for something else that I'm doing it. I love it
because it's the greatest scam in the world to get people like you to drive over to my house and sit
down and talk to me for two hours. So now I know you, you know, it's amazing. And the fact that
other people will enjoy that is great, but I just love the medium. I'm trying to create the best
product that I can, and I'm not looking for a payday.
But I trust that if I'm putting great content out, whether it's through a book or a podcast or whatever it is, a blog post, that that ultimately will translate later on into something that perhaps I can't predict right now.
But that has been proven to be the case for me time and time again.
So I'm playing the long-term view on the whole thing.
But I'm not worried about my list. Maybe I should worry, you know, like I don't think
about those kinds of things. Like when I was starting, I would hate that people go like,
all you got to do is write a great book. Like, I feel that's very disingenuous because it's more
complicated than that, but it is the most critical step. So like the best analogy that I've heard is
someone, they were like, it's a marathon and a
sprint. And you've got to, you've got to understand that. And I think the info marketer people are
really great at sprinting. And then if they stayed as sprinters, that's fine. But then they also try
to create these other products or they have, they tell you that what's really important is building
something to last. And I, I don't think in five years, half these podcasts are going to be here.
Half these blogs are going to be here.
They just won't because what do they,
it's like, it's like you're reading it
and you're like, is this a riddle?
Like, is this a poem?
Like where there's that saying,
there's no there there.
Like, when are you going to tell me something
that's real intangible instead of, it's like, I already signed up for your list.
What are you selling me here?
Like, I just want some facts.
And they can't do it.
Right.
You're always like almost there, but then there's one more thing that you have to do.
You're almost there, and then you got to do a webinar.
Or you're almost there, and then you got to come to their meet you're almost there. And then, then you gotta, then you
gotta come to their meetup or buy their course or do this stuff. And it's like, I, and, and I,
I'm sure, I'm sure you've talked to those same people that are like, you can make a million
dollars a year if you created a course. And when we talked about, you know, um, the hardest thing
in the world to do is to turn down money. It takes a lot of discipline to say, I know,
but I don't like that.
And so I'm not going to do it.
Yeah.
I've said no to a lot of that kind of stuff.
And I would say almost every single day I get an email from somebody about
how they're creating some online summit.
All they want to do is they want to,
they want to eat,
they want to interview me on Skype for 30 to 45 minutes and I'll be joined by
all these other luminaries.
They list a bunch of names and then they say, all you have to do is send four emails to your list and post
it on Facebook 50 times. I'm like, and then you'll get a commission from their thing. Right. Or even
if it's free, because there, I go, there's nothing to this. They're just trying to build their own
email list on the shoulders of other people. I'm like, I don't want to participate in that.
Right. Like, cause it's not about the wellness summit. It's about building their email list.
No. When I got here, I got a letter from my speaking agent because I had, I'd forwarded
him something and he was like, no, this is another online summit. And he was like, you don't want to
do, you probably don't want to do this. I was like, you're right. And, and it was like, it seems weird,
but it's like, I would rather take less money up front for you to say, like, we're paying you X amount of money to come to this place to give this talk to this audience.
And then you do your job and we'll do our job.
And then that's it. Um, if people stopped believing that they could do the same thing themselves, like if
people stopped believing that like, Oh, I could also create my own huge email list one
day, I think a whole, the whole thing would collapse.
Well, it's going to be interesting to watch how it plays out and more separate time.
So, yeah.
All right.
Well, if you were me, like what, what, what would you recommend that I do?
Like, what am I not doing?
Well, where could I improve? What am I, what, you know, like as a Like, what am I not doing well? Where could I improve?
What am I, you know, like, as a put on your marketing hat?
I mean, I would write another book.
I think you should write another book.
I might update your first book and do a second round on that.
Yeah, I mean, when I look at it now,
there's so many things I would change.
Yeah, and like, I would be looking at it as like, this many things i would change yeah and and like i i would be i would be looking
at it as like this is a classic timeless book so how now that i know now that you've made it over
the gap like how old is that book five years 2012 okay so yeah so now that you've made it over you
you're not you're now a backlist title how can you ensure its success as a backlist title i think
that would be a big thing um Um, I don't know. I
don't, I think it, I would, I would push back and say like, what are you, what do you not have that
you wish you had? And then I would talk about what you should do. Cause I think that's the hard part.
It's like, um, you know, people like, I think about this a lot with these info marketer people.
I'm like, Oh, I heard so-and-so is making like six figures a month doing X, Y, and Z. And then I'm like, but I don't want to do X, Y, and Z. And also I, it, this sounds
weird, but it's like, I'm not like, I don't wake up every day and go like, I need more money. Like
I need more money, you know? And money is not what is important to me and it's not what gets me
excited. And so I'm like, I have, you have to be able to go like
they're running their race and I'm running my race. And all that matters are individual times.
Um, we, if we're comparing each other, we're going to be, you're going to totally throw each
other off. So I think that's, I always clear on that. I'm clear on that. Like I don't get caught
up in other people's. No, I just mean mean like it would be impossible to ask answer your question without actually like like when i do a session
with an author i'm like what are your goal are your goals to sell a lot of copies is your goal
to be on the bestseller list or is your goal to make a lot of money because you think those goals
are the same but they're not right they're very fundamentally different and so i would like you
know what is you know it would be like what what do you feel like doing or what do you feel like it would be really nice to have or do?
And then I'm sure there's tons of creative things to, to do that. Like, yeah, I think that would be,
I think that would be the place to start. Right. Well, the new book is another book is definitely
happening. That's the best marketing thing in the world is to start. Right. Well, the new book is, another book is definitely happening.
That's the best marketing thing
in the world is to write another book.
I'm wrestling with what that's going to be, but...
Yeah, right.
And I just violated your principle.
No, no, no, no.
It's not a mystery that I'm going to write another book.
No, no.
Uh-uh.
No, no.
Well, then, and it's weird to think
that the best marketing you will do for that book will be in thinking about what it is and who it's for and how you're going to do it.
Like, you're going to make all the critical writing, all the critical marketing decisions before you write and then write about the time you finish writing.
And then everything else is tactical.
Everything else is how do you best utilize your list?
You know, do you do an event
at this store or that store? You know, um, what, what are the bonuses you want to, all that stuff
is tactical and it's all determined by what book you write and who it's for. Right. But in, in the,
in the, uh, principles of stoicism, it's just about writing the best book that I can
and engaging in the process of that on a daily basis.
Yeah, and stripping out the vanity or the selfishness
or the insecurities that are inherent.
Everyone wants to write it.
It's like, why do you have these artists
who have sold millions and millions of copies
and then
they're miserable because like some shitty critic at rolling stone thinks they suck it's like you
wouldn't care about that guy's opinion at a party but because he wrote about it in a magazine
you're like ready to invalidate like years of your work yeah well. Well, it takes, it takes a strong sense of self to be able to rise above all
of that. Yeah. Not too strong. Cause you gotta be, you have to actually be available to hear
from your wife when she's like, Rich, like this is, you're not there. You're not done yet. Like
you got to go back to the drawing or whatever. Right. Well, I mean, that brings up the importance
of mentors and, and, you know, to the extent that you need to kind of covet your idea and be, you know, somewhat private about it.
It also is important to have people in your life that give you objective feedback and tell you the way that it is.
Yeah.
It's not about going off into a cave and coming back with your masterpiece.
Yeah.
And that's the illusion of writing, writing i think for a lot of people
yeah like one of my least favorite creative sayings is that one from hemingway where he says
like writing isn't hard it's sitting down at a typewriter and bleeding it's like that's not
what writing is it fucking all and and considering the fact that we can look at your meticulously
edited drafts of your manuscripts we know that you didn't believe that
either. But if you're a 22 year old MFA student and you're struggling to come up with your idea
for a book, sitting down and letting it bleed, you know, sounds, sounds like what it should be.
Right. Right. All right. Well, I think this is a good place to wrap it up,
but I want to close it down with one last question,
which is somebody's listening to this
and they're stuck in a cubicle somewhere
and they're hating their job and they're hating their life
and perhaps they have a spark
or some inkling of a better way to live.
What are some tips or tools that could be
utilized to start to be more expressive of that passion? I don't know if this totally answers
your question, but I'm sure you, in some of the 12 step stuff I've done, I've seen this too, where
like the idea of like a conditional future is very dangerous, right. So it's like, if this happens, then I'll be happy.
And so I think when people are like, I hate my job,
and so I want to do something different,
they think about what it needs to be for them to quit their job or whatever,
and they don't go like, look, it's not going to magically happen.
You have to start right now now it's something really really small like it another train is not going to pull
up alongside you and you just jump off yours and get on that one you see you got to start and so i
think i think it's like people people like oh i want to be a writer and i was like well what do
you have to write about like what are you doing that's interesting that would make for good writing
and it's
actually a good thing that you have a job because now you can fund that. Right. And so I think the
big thing for like creative people or like people who want to do something, it's like, you don't
need to come up with a genius business idea that is immediately self-sufficient, um, blah, blah,
blah. Um, Ramit Sethi, who I actually think is, is, is in the space we were talking about earlier,
but actually really great. He's like, you, your goal should be like, I want to make a thousand bucks
a month on the side with my passion project. He's like, that's very attainable. And once you make
it to a thousand bucks, then you can decide whether it's, you can see very clearly whether
it's scalable to becoming a sort of full-time income replacement or whatever. But it doesn't, it's not about inventing Facebook
in your garage. It's about, I had this fun idea. It's you deciding I'm going to start a blog or
like, Hey, it would be cool if I did a podcast. It's not like, uh, let's pull the emergency break.
Let's stop everything. Let's burn all the bridges behind us and then uh have our flash of creative inspiration
and immediate success and all these things well that's not sexy of course you know what i mean
like that doesn't make that's the truth it's sort yeah it's like there's this idea that we hold on
to that it is going to be you know that that it has to be this big dramatic thing but the truth
is everybody has free time no matter what your is. I don't care what your circumstances are. If you sit down and you plot out how you spend your time in 15 minute increments
throughout the day, you will be amazed at how much time you waste, or you'll be able to identify
places where you could create efficiencies. And then what are you going to do with that free time?
Are you going to watch Dancing with the Stars and spend an hour on Facebook? Or are you going to put
some thought into how you perhaps could, you know, take a step in a different direction and you don't have to
explode your life to do that. It can work in tandem with that life. And I think then you start
to just incrementally on a persistent basis, put more and more energy into that. And it will lead
you into a different direction that will create a decision tree that you know will then inform like i really love the concept in the startup world of like a minimum
viable product right it's like you don't have to create like it's not like i had this idea so then
i got a lawyer to copyright it and then i did this and then i did that it's like no you start with a
landing page and you see if anyone cares like or or like um oh you want to write a book why don't you write a blog post
first and see if anyone reads it right you know like don't don't front load and even if no one
does who cares write another one like it goes back to embracing the process if that's what you love
doing trust in that and just make it better the next time like casey would say make a crappy movie
right don't front load hundreds of hours of work um because like uh there's that
great i love this quote from um ira glass he talks about the there's a sort of gap between taste and
talent when you first start and he's like what what happens is you have really great taste that's
what makes you good but your stuff sucks and it's the idea that that gap is like so hard for people
and so it's like don't go write your first crappy novel before you've interacted with a public
or readership at all,
because you're going to be crushed when,
when,
with,
by the indifference.
But if you write a blog post and 25 people read it,
you're like 25 people read my blog post.
I'm gonna write another one.
And then the next one does 30.
And then the next one does 50.
And it goes from there.
That's how you get started.
It's those little decisions that change your life um it was the idea that you know i wanted to
recommend books to people that built my email list that helped me sell my first book and this
this was an idea that i ran by my friend and he was like that's a terrible idea you shouldn't do
it and i was like well it doesn't cost anything so like I'm going to do it anyway. What does the opportunity cost of that? Right, it was nothing.
Right.
And so start small and be grateful for the success
rather than have these huge expectations that set you up to be discouraged
when you really can't afford to be discouraged.
Awesome, man. This was really great. I had a great time. Thanks for doing it. Yeah. I afford to be discouraged. Awesome, man.
This was really great.
I had a great time.
Thanks for doing it.
Yeah.
I think we did it.
I'm exhausted, but.
Are you?
Yeah.
Now I have to go talk the rest of the day.
Come on.
No, that was great, man.
Thank you so much.
Awesome.
It was great to have you.
It was so insightful.
I really appreciate it.
If you're digging on Ryan, the best way to connect with him is ryanholiday.net, which is his website, where he shares his thoughts.
Subscribe to his monthly list of books that he recommends and watch your life improve.
And you're pretty easy to find online at Ryan Holiday.
And you're still an editor at The Observer, yeah?
Yeah, yeah.
And you also write for Thought Catalog.
Where else do you write for?
I'll write anywhere that takes me.
Yeah, and when's the new book going to come out?
One will be July 2016, and one will be fall 2016.
Do you have a title yet?
Ego is the Enemy.
I've never told that anywhere.
I already have it.
Uh-oh.
Oh, you have it tattooed on you already?
I have both.
Yeah, I love that.
Now they can't force me to change the title now.
Not only that, you've set a precedent that every time you write a book,
you have to tattoo the title on your body.
Well, one of my books is called Growth Hacker Marketing,
so I probably won't be tattooing that anytime soon.
Do you have Trust Me Online on your tattoo?
No.
These are actual phrases that I care about.
All right, cool, man.
Well, thanks a lot, dude.
Yeah, thanks.
And hopefully you'll come back and do this again.
Anytime, we'll go running.
All right, cool.
Awesome, man.
Peace.
Plants.
Good guy, right?
Interesting guy.
Hope you guys enjoyed that.
Go ahead, check out his books. Start with
Obstacle is the Way. Read his articles.
Read his blog. You'll be
better for it. Very, very insightful.
Bright young man.
And it was a pleasure talking to him. Let me know
what you guys thought of the episode in the comments section
on the episode page at richroll.com.
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I'll see you guys in a few days.
Make it a great week.
Catch you on the flip side.
Peace.
Plants. Thank you.