Deep Questions with Cal Newport - IN-DEPTH: Systematic Depth (w/ Ryan Holiday)
Episode Date: September 26, 2024In this episode of IN-DEPTH, a new semi-regular interview series with people at the frontiers of deep living, Cal interviews bestselling author Ryan Holiday about the systematic construction of an int...entional life. They begin by talking about lessons from Ryan’s new book. RIGHT THING, RIGHT NOW, then go deep on Ryan’s own journey from a college drop-out working in a Hollywood talent agency to becoming a fully independent and massively successful writer and media personality.Video from today’s episode: youtube.com/calnewportmediaINTERVIEW: Mega-bestselling writer Ryan Holiday [3:33]Links:https://www.calnewport.com/slowThanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the theme music, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
Transcript
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I'm Cal Newport, and this is in-depth, a semi-regular series in which I talk to interesting people about the quest to cultivate a deep life.
Now, because this series is new, I want to start by telling you a little more about it.
My idea is to just release these episodes as I have interesting people to talk to.
They'll come out on Thursdays. At first, it'll be sporadic, and maybe after a while it might be coming.
a little bit more regular.
I want to present these episodes with limited interruption.
So either no advertisements at all,
or they'll just be a single presenting sponsor
for the whole episode so that when we get into the conversation,
we can really get lost in the conversation.
I want to tell you more about today's guest.
My idea for the show was that there was two different categories
of people that might be interesting to talk to.
Those who have written about ideas that are relevant to the deep life and those who are living a deep life themselves, today's guest embodies both of those categories at the same time.
It's my longtime friend and number one New York Times bestselling author, Ryan Holiday.
So in this interview, I'm starting by talking about Ryan's new book, Right Thing, Right Now, which is about the stoic virtue of justice.
And we get into the idea that justice, the idea of doing the right thing even when it's hard,
having a code by which you live your life is critical to cultivating a deep life, but it's
something that we often neglect when we talk about this topic. So we get into why that's important,
why we neglected, and how to integrate this into your own life. The rest of the interview,
which is really the bulk of the interview, however, turns to Ryan and his story. I go all the
back to Ryan dropping out of college, taking a job at a talent agency in Hollywood and another
part-time job doing research for the writer, Robert Green, kind of stumbling from there into the
world of marketing. How did Ryan get from there to being one of the best known promulgators of
stoicism in the world who has this sort of empire, these multiple number one New York Times bestsellers,
and this really cool deep life he's crafted in Bostrop, Texas, where he's got.
this bookstore downtown and a historic building and lives on 50 acres outside of town and all these
famous people come to him and it's this really interesting deep life how did that happen we take
it apart piece by piece the approach i take in this interview um is one of a psychological
narrative so step by step what i keep pushing Ryan on you'll hear this in the interview I keep pushing
them on what was going on in your head right then like what was at this time in your
life, your vision for what you wanted in your life? What was it that had you make this particular
decision? So I use that psychological method so we can get into the mindset and the thought
processes behind living the deep life and not just the TikTok of what actually happened.
Anyways, I think Ryan is a great way to kick off this series because he captures so much
we care about in this topic. So without further ado, I hope you enjoy our conversation with Ryan
holiday. All right, Ryan, thanks for coming back on the podcast. I think if I've done my math
right, you are now my most frequent interview guest on the show, which is an honor for me,
but maybe means something more worrisome for you. Yeah, I might mean that I'm doing too many
books. I don't know. That might be, yeah, I think I have the same problem a lot of, hey,
weren't you just here? I was like, I know it's another book. By the way, congratulations. Your new
book right thing right now came out in early summer number one on the new york times bestseller list do i have
that right yeah that was a that was a surprise uh i don't know exactly what i was expecting but i assumed
it would get off to the slowest start of all the books in the series and then it got off to the
fastest start so yeah it was a total surprise yeah i mean as i learned i was number two on the list with my
most recent book there is a very small gap between number 10 and number two because it's
New York Times bestseller, but a large gap between number two and number one,
because you get to actually say number one.
But as we've learned, this is like insider author stuff.
No one cares.
No one understands what it is.
No one really cares.
My own family probably doesn't even know which of my books are bestsellers,
and yet we care so much about it.
Yeah, nobody really cares.
Certainly there's a huge amount of diminishing returns from doing it a second time.
Like, you know, you accomplish something,
and then there's some part of you that's like, well, if I don't do it,
again, it's a fluke.
And so this is the second time I've hit number one,
but it changes your life even less than hitting it the first time does.
Because nobody cares, nobody cares at all.
It's a weird thing.
You want it and it matters.
And then you also realize it doesn't matter at all.
And that oftentimes when you sort of find yourself chasing these very specific sort of bench
marks or goals, that there's actually a large opportunity cost to it. So like the strategy that one
might have when you are aiming to hit number one can mean not focusing on a bunch of other things
that really matter. So I've had this weird, this weird experience where I have cared less about
those things and spent less time getting them and had the paradoxical sort of benefit of somehow
getting them but I try to
I try really just to
spend all the energy like on
the thing itself and building
a platform and then
letting the sort of sales be
what they may. Yeah it is something
most non-authors don't necessarily
understand that it's sort of two
orthogonal pursuits
bestseller list placement and
ultimate success of the book.
The first being a lot to do with
your audience, mobilization
of audience. It's not that the book
doesn't matter. I mean, the book, they have to love the idea of the book, but it's sort of
unrelated to whether or not that book sells long term. I mean, your bestselling book and my
bestselling book were not New York Times bestsellers, at least not when they first came out.
So it's interesting. It's like you're playing it. It's a different game, but no other stands.
But I'm cleverly going to use this. Okay. It's a sort of metaphor for our longer
discussion today.
The pursuing the New York, thinking of the New York Times bestseller list is going to be sort of a
metaphor for how we think about cultivating a deep life.
And so I'm going to want to get, I want to get into your story more so than I've done before.
But before we do, let me just hit real quick on the new book because I really like the new book.
This is the, this is the third book in your four book series that's going to be on the cardinal virtues of stoicism.
Yeah.
This book is on the virtue of justice.
which I think is critical in thinking about the deep life,
which is the theme of this show.
But let me just ask you about that before we move into your life.
Justice is a hard word to define.
You took it out of your title because it's a word with so many definitions.
How do we think about justice in the way you're talking about it?
Yeah, I did take it out of the title.
Courage is a word that when people hear they like it and they want more of it.
When they hear discipline, they think, okay, yeah, I'm on board with that.
same thing. But when people hear justice, I don't know, there's something, there's something that feels
judgmental about it. There's something that feels moralistic about it. There's something that feels
I don't know, political about it, right? And it is all these things. So part of the reason I thought it
would sort of be off to the slow start is I felt like it had a sort of a strong tailwind against it,
which is why I was interested in writing about it and why I think it's important.
But I wanted to take justice sort of down a few pegs and make it something much more practical and accessible,
the sort of standards by which one lives and holds themselves to as much more a way of life than like these,
as you know in academia, like justice as a field of study is often about these really,
esoteric or abstract questions. And the more you study justice, almost like the less actual
understanding you get of it. Like you start to doubt whether it exists at all and whether it matters
at all or whether it's possible at all. And that just strikes me as so opposed to the idea
of like, are you a person who keeps your word? Are you a person who's honest? Are you a person
who treats other people well?
Are you a principled person?
Are you a person who makes the world better for you being in it?
That to me being just a much more practical and yet also aspirational idea of justice.
I think people often leave this out of their conception of what they're trying to do with their life.
I often use the terminology code in the sense of what's your code, right?
And somewhere that should be written down.
And it's going to change.
It's going to evolve, of course.
but without that foundation, it's like not having to keel in the boat.
And so then the winds are going to be blowing you all over the place.
Why do you think?
Why do you think this is something that in today's moment?
Because I think 100 years ago, like this is the starting point.
It's like what is your code?
You could specify those principles like in your sleep.
Why is this something that is a surprise to people or something we have to push people to consider in our current moment?
Well, looking at much more hobogenous.
in top-down society, we all agree or are forced to agree with certain definitions, right? So if we all
share the same religion, Christianity at one point, has the same cardinal virtues as Stoicism. So if we all
believe in the same God, or if we all accept or are forced to accept even the same definition of, say,
like masculinity or femininity, right, then the virtues of what a man or a woman is.
is very clear. How one should behave is very clear. The sort of religious tenets are very clear.
So it's easier to go like, hey, this is what is right and wrong without feeling, without, like,
what happens when you live in a much more pluralistic society, which I think is a wonderful thing,
is that suddenly your definition of right and wrong is not shared by everyone. So then we kind of have this
sensitivity and not wanting to say, hey, don't do that. Hey, that's bad. Leave those people alone.
Again, all positive things, but it has partly the effect, I think, of making it harder and harder
to give people strong advice or a strong sort of culture that enforces or celebrates a kind of a code.
You know, like the relativism of society is generally, I would say, a positive thing because it's more tolerant, which is a virtue of justice.
But it makes it hard to just go, hey, that's a bad thing to do. That's the wrong thing to do.
So I think what you end up with is a system, a culture that doesn't teach these values early on or even more confusingly holds up some of the old stories of the past.
that we used to use to sort of reinforce and inspire,
and it just pokes the holes in them, right?
So if you only look at the founding fathers
or you only look at the ancients
and you look at all the things,
all the ways that they were hypocrites,
all the terrible things they did,
again, it has this effect of sort of just confusing
one's definition of justice
without giving anyone really a code to replace it with.
Right.
So let's say I'm 25, right?
All right, I'm coming out hot out of college.
I sort of have some professional ambitions.
I've been listening to some Huberman, so I've got some physical protocols nailed down,
but I don't come from a religious background.
I have a generic yearning that I need some sort of code.
I need some sort of stability to live by.
Where do they start?
Yeah, you know, I think that space is a really interesting one because you're right.
There's a whole bunch of sort of thought leaders and,
information and books and stuff out there that's like, here's how to get stronger,
here's how to get faster, here's how to get smarter.
And by the way, those are kind of the other virtues, right?
This is courage and discipline and wisdom.
And then if you don't have this other component, this code, this sense of right and wrong,
what you do and don't do, how you treat people, what you allow, really what you see and
you see with some of those people is like the algorithm kind of takes over, right?
your ambition becomes the thing that guides you.
So what's ever best for your career is what you do,
as opposed to what you feel like is okay or not.
And I think you and I have probably both experienced this
where there are all sorts of decisions that you get faced with
that, hey, what's going to grow my YouTube following the most?
What's going to sell the most books?
I'm being offered to speak at some event.
if all I care about is whether the fee is large or not,
you know,
I'm going to find myself in some places that I'm not going to feel so good about
that are probably not going to age well,
that I'm going to have some explaining to do later, you know?
And I certainly struggled with this in my 20s.
I was just like, hey, what's best for me?
What's most interesting?
What's most fun?
What's most challenging?
What I was thinking less about was like,
hey, is this something I want to be a part of?
Like, is this something that's good for the world?
What would it look like if everyone acted this way, right?
My first book was sort of this expose of a media system
that I kind of woke up one day and realized,
hey, if this is what I am doing
to what we would call the information commons,
you know, and everyone is behaving this way,
how is anyone going to know what's true and not true?
You know, the system depends on, you know, some sort of self-enforcement mechanism.
And so I think that's really what we're talking about and what we don't hear enough about.
You know, there's lots of people who can give you advice, again, how to get bigger, stronger, and faster.
But then it kind of stops very suddenly when it says, you know, hey, doing that sucks.
Doing that is bad.
doing, behaving that, like, there are certain things that should be off limits, certain lines that we don't cross, you know, having Alex Jones on your podcast would probably get a lot of listens and views. Is it something that you should be a part of? Absolutely not for a whole bunch of reasons we could go into, right? But that sort of drawing on the line and say, hey, this is, I don't do things like that is kind of what we're talking about when we talk about justice. Well, and one of the
the aspects of that, which I think is captured well in your book because of the format you use.
The format which is based on stories, I think, is effective because it gets at some of the psychological
realities of the advice as opposed to just the systemic, systematic structure of the advice.
And one of the psychological...
Yeah, there's not like 10 commandments.
It's not...
You get a richer...
I mean, speaking of 10 commandments, you see the same thing in the Old Testament of the Bible,
is through stories, there's a more psychological...
complex analysis of an issue. And one of the principles at play that I don't think is emphasized
enough that people when it comes to things like justice, especially young people, is that actually
the value derived from applying a principle in a way that in the short term is negative in the sense
of that you miss out on reward or opportunity, that value is incredibly, feels really good and is
incredibly important. Like in other words, you're trading. I mean, I'm thinking about Clayton
Christensen, how did you measure your life? You kind of
gives this famous example.
I can't play basketball on Saturday.
I guess it was a Mormon thing.
And we're in the playoffs, I can't do it, right?
Really kind of stunk in the moment, right?
He was good on the team, was good for the team.
But there was like a larger value that came out of it, right?
Mining that value is important.
I don't want to give specifics, but, you know, I turned down a speaking gig not long ago.
Overseas, a payout that would have been like my annual salary as a full professor.
where it was, the country it was, who was sponsoring it.
I just can't do that, right?
I wonder if we were invited to the same thing, because I went back and forth,
not just myself with a very similar thing,
but I heard from several other people that maybe were also invited to the same thing.
I bet we're talking about the same thing.
I bet we are.
And yeah, it's, I love that expression.
You know, it's not a principle unless it costs you money.
You know, it's very easy to watch, I don't know,
like the Live Golf League and go, hey, it kind of sucks to blow up your sport to get paid a bunch
of money from a foreign government that's obviously just trying to sort of win a public relations
battle that's ultimately creating an inferior product for the sport and, you know, isn't sustainable.
And then by the way, a bunch of the people involved are just also gross, right?
Like it's very easy to watch that on the outside and go, you know, so and so should have done X or, you know,
I can't believe so-and-so did why.
And then I think it's much more interesting to think about what decisions you have made in your life that have cost you money.
We see this all the time and go, oh, these politicians in Washington, you know, they'll just do anything to be reelected.
They'd never take a vote that would threaten their job.
And then I try to catch myself.
Sometimes I bring it up to other people.
but I always try to catch myself when I feel that rising up in me.
And I go, okay, but what decisions do I have in my life that have threatened my career or my livelihood?
And if you don't have any, it either means you're sort of morally perfect and you've never found yourself in a tempting situation.
Or it means you're actually playing it much safer than you should and are, you know, haven't been on the right side of things.
as often as you think you have.
And so, yeah, those things are, I would love,
I would love to believe that at some point they become easy.
And it makes it more impressive to think that,
it makes it more impressive to think that it was easy for the person.
But what you actually find is that they were pretty vexing, difficult decisions.
And they thought about it up and down, up and down.
And then at the last minute, you know,
they made that call and it was tough.
But there's an expression about like we keep rituals, but then the rituals keep us, you know?
And I think there is something about those principles and those standards.
Yeah, sometimes they keep us from doing things, but they also kind of protect and serve us
and provide us a lot of meaning too.
Yeah.
I mean, I love this idea.
Seek sacrifice in some sense as eagerly as you're seeking professional success because it's
going to be just as nourishing, not just nourishing, I think resilience creating. It's going to give
you a better sense of yourself. You're going to have more ability to apply character in the future.
It's going to define yourself against the sort of near infinite space of possibilities of who you are.
But it's not on the list. We have, get your body in shape is on the list. Get your bank account in shape is on the list.
Get your love life in shape. Like these are obvious things on the list. That one's not there. So that's why I'm
glad this book is out there. I think this is a deep life guidebook. Well, thank you. Yeah.
You know, I was talking to someone the other day and I was kind of joking around. I said something
and I was like, you know, it's not that hard to not be a piece of shit, right? Like that,
but, but it, it actually apparently is hard, you know, these decisions that we make, you know, to not
screw people over, to pay the people that work for you fairly, to choose to, you know, if face between
an environmentally destructive choice and a non-environmentally destructive choice.
The decision to, I don't know, be faithful to your spouse, to uphold your contractual obligations,
to speak honestly, to tell people what's true as opposed to what people want to hear.
That's probably the most vexing and tempting of the sort of content creation space,
which is like you're always, in the short run,
you're going to do better telling people what they want to hear.
In the long run, you cannot build a career doing so, right?
Like you have to develop a reputation,
not just of telling the truth,
but like if you're just reflecting back to people what they want,
they're not seeing any of you.
They're only seeing themselves.
You're not actually building much in the way of a connection.
So there's this sort of constant struggle and tension between these kind of seemingly obvious short-term decisions and then this long-term sustainability and reputation and integrity.
And yeah, it's like we just don't even talk about it.
Well, let's shift here to a related gear.
You know, on the show, there's usually two topics we talk about.
either people who have written something that's relevant for cultivating a deep life or people
who have lived the deep life and we can learn from it.
You're both in one person, right?
So we were just talking about something you wrote that's relevant to people living the deep life.
Your life, I think, is also an interesting template or there's interesting lessons to extract
about how one cultivates a deep life over time.
So with your indulgence, I kind of want to jump back early to your story and then we're going to
move it forward.
I want to jump all the way back, you dropping out of college.
Bring us inside the, what I want to keep going back to is the vision at that moment about what you were thinking, what you were going for, what you had in mind for what you were trying to do with your life.
So what was the psychology of a young Ryan Holiday leaving college and those sort of, was that mid-2000s?
Yeah, I think I had a vague sense that I wanted to be a writer and I had a much stronger sense that I did not want to work in an office.
Like I just didn't want a regular life.
And I was studying writing and political science, and I had this chance to work in Hollywood,
and I had a chance to be a research assistant for a writer named Robert Green.
And it just struck me that, hey, to be a writer, what was a better way to learn how to do that?
Was it to go to college, to finish college where some of my professors were.
published writers, not particularly successful ones, but published writers? Or would it be better to go
directly learn from someone who had done the thing at a very high level and was doing the thing
at a high level? So I ended up sort of making that leap. And, you know, it was sort of scary and
terrifying in a lot of ways. But I just had this sense that someone had given me this piece of
advice. They said, writers live interesting lives, which I've thought about a lot since. And I was just
thinking, like, yeah, like, okay, let's say I just get my, get my normal degree and graduate.
Who's going to publish my writing? Do you know what I mean? I'll just be like literally every other
student who is graduating. I had about a year, a year and a half left in college. I would just be like
everyone else. I would be at the exact same point I was then, except for I would. I would. I would
have foregone this experience to actually study under someone who was doing the thing.
And so I just went and did that. And it was, you know, it was, it was a surreal experience in a
bunch of ways I learned a bunch of stuff. But, but mostly I was just trying to like go toward,
like go as directly as I could towards like real world experience and then also do some, do the
unusual or unexpected thing. Did you see the position with Grosven?
green specifically aiming towards your interest in writing.
And the Hollywood position as a mix of, I want to do something interesting and also what's the
thing that is going to be an income source that, how did you see?
Those are two, because Hollywood, in that position kind of is the epitome of office politics
and being in an office and like arbitrariness or whatever.
So, I mean, I love the complexities when we dig into like the reality of these stories.
So like what role did the Hollywood piece play in that?
You're working for an agency, right?
Yeah, I worked at a talent management agency.
I mean, like, when I was growing up as a kid and just had this sense that I didn't want to work in an office, I don't think, I was thinking office space, not like a talent agency in Beverly Hills. You know, like it was, an office is still an office ultimately, and you realize that pretty quickly. But, and a job is always a job. But it felt different and exciting and unusual and certainly far outside my ordinary experiences.
But I think it's funny.
I remember two things about it.
So I'd wanted to work for Robert.
I don't think I would have dropped out of college just to work for Robert.
I don't know if I would have had the courage to do that.
So then when I got offered to be the assistant to this sort of big movie producer,
who again, who was also someone who was doing the thing.
He wasn't coming up with the scripts or whatever himself, but he was making stuff.
So again, it was another doer.
But I remember he offered me $30,000.
And I remember thinking, wow, what am I going to do with all of that money?
You know, like it just seemed like an insane amount of money to me at the time.
Because my, you know, my expenses were nothing.
I wasn't married.
I didn't have kids.
Like my apartment was probably $800 a month.
And so I just kind of went towards doing this crazy unusual thing that would kind of introduce me to a world I knew nothing about.
But there was this safety net of like, yeah, I had a paycheck.
I think when people tell me, oh, I'm thinking about dropping out of college, I always go, like,
to do what?
Not like, what are you aspiring to do?
But what are you dropping out for?
Like, I think it's very, failing out of college is, or quitting your job is very different than
leaving college to go do a different thing.
Like, if you have lined something else up and you,
You are jumping from one ship to another.
To me, that's very different than what often happens,
which is your heart's not in a thing,
and you're not very good at a thing,
and so you fail at it or you bounce out of it.
That's a riskier proposition in my view.
So then I see you now, okay, during this stage,
you're working with Roberts, you're learning about writing,
you have the Hollywood job.
It's paying the bills.
It's interesting in its own right.
I imagine a young Ryan Holiday basically surveying the horizon.
Okay, I'm looking for where can I make my move.
Marketing became that first move.
So not just how did that happen,
but how were you thinking about those initial opportunities
to fall into marketing when it did occur?
You know, it's funny.
So when I was at this talent agency, I signed this kid.
He was like 16 and he was like uploading these YouTube videos.
And it was like the first sort of YouTube person that,
really any of the agencies had signed. It was like pretty new. And it's funny, he didn't end up
going anywhere. And then just like he's blown up like in the last like six months, like this person.
He's like middle age now? He's like 30 years old. He's like, I think he's like, I mean,
he must be like early 30s. Yeah, he must be like 30. Was this Mr. Beast, Ryan? Was this a young
Mr. Beast? I wish. But anyways, it was funny to watch like the actual development cycle of
something like I thought this guy was like the next big thing and actually you know it was more like
15 years later he would be a big thing and I think I probably realized pretty early on that I just
didn't have the patience to operate in that world and I didn't like I didn't like not actually
doing anything which is ultimately what most sort of reps do is they kind of just sit back and
help you with things you're already doing yourself so what what ended up happening
as Robert Green, who I was working for, happened to be on the board of directors at American
Apparel. And so I was sort of learning all this stuff. And he got me, you know, in the door there.
And I went and I did marketing there. And then I worked for a bunch of different authors.
And I sort of built this marketing business. What I think I was going towards is I understood
that creating stuff and selling stuff was two very different skills. But the best artists and
athletes and entrepreneurs and creatives are able to do both of those things.
Did you know that?
Did you know that when you took that marketing job, were you thinking, I've seen enough
in my agency position to know that this is really important.
And me mastering this is, I'm going to apply this to myself.
Like this is the next.
Yeah, I think I was always going towards applying this to my own stuff.
how explicit that was developed over time.
But I think I understood that like, look, anyone can have ideas,
but it's only the people who know how to sell the ideas that they have
that are able to sort of break through.
And so I spent, yeah, a good chunk of my 20s really just learning the ins and outs of that.
And what happened is that helping people do that gave me a lot of,
first off, I built a lot of relationships,
but second, I built a lot of experience and got a lot of reps.
So, like, when my first book came out,
it was not the first book that I had put out.
I think you had a similar version of this and that you put out those sort of guidebooks
first.
So by the time you were doing your first book, you actually, like your first,
let's call it real book, it wasn't your first real book.
And that is a really invaluable thing because,
you know, if you're a director of, like, how many movies is even a great director do in their life?
And it might be three movies.
And so if you don't have any experience working on other people's projects, you're going to be learning all your painful lessons on your own projects.
Right.
And what if what you learn is, oh, if you title the thing wrong or if you time the thing wrong, it fails.
Like, do you want to learn that on your project or would you rather learn it on somebody else's
project?
And so I got a lot of experience.
And that experience continued up until relatively recently, like, on other projects.
I was just learned, I got, I have so many more reps.
I've done a lot of books myself under my own name.
But I have more reps on putting out books than like basically any author you can think of
because I've just been through it with other people.
so many times.
The analogy that comes to mind from the movie world is James Cameron,
working in Roger Corman's sort of shop,
special effects, second unit directing,
took over the special effects shot.
They began to put him on more and more of the directing.
By the time he did Terminator,
he really had a lot of experience with, for example,
how to do really good on-screen effects.
He had a lot of experience with work with the cameras.
So in your own story, getting to your first book,
I know you went on to work with Tim Ferriss.
I know you went on to work for Tucker Max on the marketing side.
These are, along with Robert, really three of the bigger nonfiction, non-mimilar, non-fiction sellers of the 2000s.
All three of that was before your 2012 first book?
So these are all overlapped.
Overlapping the same time and a lot of it before.
And then by the time obstacle came out, you know, I'd done a lot of books.
What made you, how'd you pull the trigger?
So you knew you wanted to write.
You're looking for the opportunity, right?
And by the way, I'm an answer to the question of who would, who would want to publish someone just coming out of college?
What I found out was the only answer to that question.
And I actually talked to agents and was like, how could I possibly thread this needle as a 21-year-old and get a book deal?
And they basically said the only way you could possibly do this is if you're writing about students for students, right?
So basically, you were right in the sense that the only way at that age, like write out of a book,
college to get published. The only way to do that in nonfiction was to basically do what I did,
which was, I can write how to become a straight A student or how to win at college. Like, that was to
weigh in. So you were probably right there. But these years go by, what was it that made you pull the
trigger on, trust me, I'm lying, your first book? What confluence of factors came together that
made you say, okay, good, let me roll. I think part of it was discussed. Part of it was frustration.
part of it was
I felt like I understood this thing
and a great thing for a book
is something that you know a lot about
that nobody else knows anything about.
Like anytime there's a delta
between your sort of personal experience
and how the rest of the world
perceives something, that can be very powerful.
Like here, let me show you how this really works.
Let me show you what's going on behind the curtain.
And I had a chance
to do that with that book. I knew that that's not what I wanted to do for all my books. I just knew I had a
chance to do it with that book. And so I took a risk. And it was less risky than dropping out of college.
Like I basically took, I went from, you know, being full time to being part time at American repair.
I was like sort of an early remote employee before that was a thing or location independent or whatever
you want to call it. I was ready to leave and they were like, actually, what if you just like
kept working in a, you know, a reduced capacity? We'll pay you a little bit less. But, you know,
we just want to keep you on. And I thought, okay, I was ready to go and didn't end up having to.
But it put me in a position where I could go and write the book and just see if there was anything
there, which is not how the vast majority of nonfiction is done. The vast majority of fiction is
sold as a project first. And then, you know, it goes through a bidding process.
and then, you know, you have a while.
I just went and I wrote this book.
I wrote the first draft of this book.
And because I had worked on a bunch of other books, I knew agents, I knew, I knew publicists,
I knew other authors who had vouch for me.
So I had someone I could show it to.
I'd earned, hey, this is my first book.
Will you check it out?
Yeah.
And so I just went and did it.
And also I didn't, I had a job still, right?
Like I had a job and flexibility so I could go work on this project.
So I just went and I did it.
And what I'd put together was, I guess, provocative enough and different enough that a publisher was willing to take a shot on it.
It was going to go out to auction in Penguin Random House portfolio, which is our publisher, just bought it outright before it went to an auction.
And that's where I've been ever since.
So it was kind of this surreal, very lucky thing where I made a bet early.
on and that's just where I am still.
This is a time to resolve something I've always wondered.
So I remember as part of your marketing campaign, or at least my vague memory, correct
me if I'm wrong.
You planted a story, maybe with Galley Cat, that you had gotten a $400,000 advance.
That's the number I remember.
And the idea was this would catch attention.
And it did, I guess, for the blogging world, they're like, that's so much money.
What's going on?
What is this kid?
and it was reported as like that was you had wildly inflated or something.
Did you, is that right?
Did you plant that story?
And was that inflated or was that not?
It's funny now we look back.
It's like, that's not a crazy advance.
But in the world of blogging in like 2012, it was like no one has ever made that much money in books before.
What is the story at the Galley Cat League?
So what actually happened was one of the things I talked about in the book that you sort of realize in marketing is that nobody fact checks.
press releases. You can basically claim anything you want in a press release and people will pick it up.
And then once it's picked up, then other people will pick up that somebody else has picked it up and it
becomes real, right? You don't realize that what you're seeing on social media is traced back to
a press release, which costs $49 to go out over the wire, which isn't even a thing anymore.
The wires, you know, previously having been actual telegraph wire. So I, I would,
was making this point that that so much of our news comes from these very flimsy or if outright false
sources or susceptible sources. So what what it actually happened is I I gotten like 200 or 250 for the book.
And so, which is a lot of money then and is even a lot of money now. But what I decided I would do is I would
announce that it was like 500. I think I announced it was 500 or I maybe even just like
hinted that it was 500. There's like these weird for people who don't know. There's these weird terms
when you announce a deal in the trades in publishing. Very good. Yeah, it's a very good deal. It's a super deal.
And these mean like a band of advances. So I forget exactly what happened. But the point was,
I put out a press release implying that it was a $500,000 advance, which then got picked up by
what was then sort of an industry blog called Galley Cat. I don't think it exists.
anymore. So they reported that, you know, hey, this kid you've never heard of who's 24 years old
and has never written anything before, just got a $500,000 advance. That was sort of the,
whoa. And then so what I did was, then I emailed that to a bunch of gossip websites.
And I said, did you see that this kid got $500,000 advance?
I said something like
the only way someone would pay this much money
is if it's some kind of celebrity tell-all
so this kid must be spilling
a bunch of gossip about all these famous people
that he's worked for.
And then so that got picked up in other places
that it was this celebrity gossip.
So just to be clear,
so people, the purpose of this was to make the meta point
is there some self-promotional benefit to doing so?
Yes, but I wasn't just doing it because I wanted to be famous.
There wasn't even like social media to benefit from at this point.
I was making this point to show that one, I actually,
I was writing a book about media manipulation.
I wanted to show how media manipulation actually works with the book itself.
And I was trying to make the point that this is how information
that you consume on a daily basis, this is how it happens.
Like, this is how these rumors get started.
And so it worked in the sense that people picked it up.
And then in the book, I described how I had done this with the book that the people were then reading.
So I was trying to expose certain loopholes in how the media system worked.
So I'm interested in the upcoming transition in your career story.
I see this is phase one before the stoic phase, right?
So you have this book come out.
At this point, you've sort of incorporated your own company.
At this point, Braschak was an entity or your marketing company.
Around this time, too, you did, I think it was just a digital original growth hack, growth hacker marketing.
So I'm assuming at this point, if we interviewed you, you had a vision.
What was that vision for like your next five to ten years?
Was it at this point a successful marketing company writing books to help the company?
Is it I'm going to be writing about marketing and I'm going to be a known writer?
What is the vision like right in that pre-obstacle era?
I think I was a little conflicted because I was very good at marketing and yet I was writing
a book that was essentially making me radioactive in certain marketing circles.
So I had some element that wanted to get out of it entirely.
and yet it had this effect of also building this sort of company and consultancy that I ended up setting up.
And yeah, I was just, I'm just looking at this because I'm doing the 10-year anniversary of the Obstacles the Way right now.
I sold the proposal for what was the obstacle as the way.
Like in the early fall of 2012.
So just a few months after
Trust Me, I'm lying, came out.
And I think my publisher told me later, Nikki Papadopoulos,
who I know has worked with both of us,
she told me that later they were sort of just humoring me.
Like they were hoping that, you know,
I would do this one book and then I would go back to the marketing book.
So they were kind of happening around the same time.
But clearly the aim had been to get towards.
words writing about philosophy. That's what I really wanted to write about. That's who I wanted to
be as an author. So that early, even that early, you knew. It was like, trust me, I'm lying,
gets me in the publishing door. Right. But even that early, as that book was coming out,
so you were working on as proposal before that book came out. The vision you were beginning
the form is, and maybe this was more influenced by Robert, more influenced by Tim, you were thinking,
I want to be not hardcore marketer.
I want to be writing about,
I want to be in the philosophy space.
Yeah.
What were the contours of that vision at this point?
I mean, I know you had experienced with Tim.
He had a community.
He had these other ancillary things around it.
I mean, he had early, not really social,
but, you know, he was doing the Ning thing
and his blog was really big.
So what is the shape of that vision then in 2012, fall of 2000?
I really don't know how well-shaped it was.
I think I looked mostly at Robert Green, who was anomalous as a guy who wrote about big ideas in essentially at like at the level of an academic, but not supported by the academy.
Like he was, he's outside the system, but he is as deeply researched and, you know, sort of as, as, as, as, as, as.
established and and, you know, influential as any academic, but without that sort of structure
around him. So I knew that was like a viable path. So I think I was mostly just thinking about that.
I knew I just, I had this idea for a book about stoicism and I thought it could work.
I mean, clearly I didn't think it would work at the level that it ended up doing or I would have
demanded a lot more money than I accepted for that first book. Like I think,
the expectations of both myself and portfolio were,
were, maybe mine were a little bit higher than theirs,
but they were both pretty muted.
I mean, the Obstacles Away sold 3,000 copies at its first week
and didn't hit a bestseller list for several years.
I just thought it was interesting.
I was excited about it.
It was a thing I wanted to write about.
and I kind of just took it, you know, day by day from there.
I didn't plan really any of this out.
So I think the first time I talked to, you were conceiving ego, the second book, the second stowa book.
At that point, you had just moved to Austin.
I think you were in East Austin or something like this at the time.
Okay, so at that point, so you had moved to Austin, I mean, at this point, you were working on the second book.
were you now committed yet to the vision of I am going to keep writing books in this general space
and I'm going to build out a brand about it? So you knew that's what I'm doing by then.
I don't know if I thought I was building a brand, but I just knew I was writing books. And they were
commercially viable enough that my wife and I had bought a small house. And I also still had my job.
You know, I didn't leave American Apparel until the fall of 2015.
I think it lasted much longer than I had thought.
I was writing ego as the enemy when American Apparel fell apart.
And I came back and did some consulting during the turnaround and then left.
It was a long story.
I talk about it a little bit in the book.
But I just was a writer and a marketer.
and that was kind of my life.
I didn't, I was just kind of going from project to project.
And, you know, basically what happened is I wrote, you know,
I wrote The Obstacles Away and it came out and it didn't do like amazing,
but I'd sold ego as the enemy.
And so I was working on that.
And by the time, by the time obstacle really started to sell,
I was working on ego as the enemy, you know,
like I was just going from project to project kind of heads down.
And it didn't, it wasn't until, it wasn't until 2016, really, that there was anything close to what you might call kind of escape velocity as an author.
Most of the, like, all the authors that I was advising and working for were all selling much better than I was, you know.
And it was always this strange thing to be like, oh, you know, so-and-so just sold a book for double what you sold your last book for and now they want marketing advice.
So I was much more just kind of in the trenches doing the thing. And it took a while for the audience to kind of coalesce in the books to find, you know, their space in the world.
Where to get a little nuts and bolts, I mean, during this period was the way like you and Samantha were thinking about,
this is like from a financial perspective. This is sort of what we need, right? Like this is our number
and we want to, we have a, you know, I'm doing my marketing company. We have books. And as long as this
adds up to this, this allows us to move on and we're safe. Was that a lot of people think that
way. Is that where you were? Or were you thinking more, we got to, we're going to blow this up.
No, no, I wasn't thinking that at all. And I was very lucky. I remember it being like, I remember when I bought
when I bought my first house in Austin,
like that I was able to use my W-2 income
and not have to apply for a loan as an author
or as an entrepreneur,
just how lucky that was,
because, you know, it's a,
it's not a life that banks or sort of traditional financing favors.
And so I kind of snuck in under the wire.
And then like my transition to being self-employed
and eat what you kill,
sort of living on royalties was a slow, steady transition as opposed to some scary leap.
And so I think that was lucky in one respect. I'll tell you this is a first world problem,
but where I've had trouble adjusting and it's taken a while is that, like, you and I both know
authors or entrepreneurs, people who in one swoop, you know, they sell a company or a book
comes out and it just rockets to the top of the sales things or, you know, they sign a big
deal for a pot.
Like, when you get a chunk in one chunk, you're, you are forced to update your self-perception
and your tax bracket and your, you know, you just go, this is who I am, this is what I have.
I would say it was much more of a slow boil for my wife and I.
And so being able to adjust and being able to count on things, that was, that was a period,
that took, it's like our self-perception lagged behind the objective reality.
But because it's so, it can be so fickle and it's hard to anticipate what's going to happen.
It just took a while.
Like there was never both, my deal.
for
it wasn't until
So if I got 200 for
Trust Amendment line
I got less than half that for obstacle
I got roughly half that for ego
and I got
less than that for
the Daily Stoic
which I split with Steve Hanselman
my agent and co-author
So it was not until
20
18, I think, that I surpassed what I had gotten with my first book deal.
So I was, and again, look, I understand for people who are just trying to break through,
all these numbers sound very, very large.
And they were, but they were not like financial independence large.
They were just like getting two-year salary in, you know, spread out.
over two years. You know what I mean? So, so it was this, it wasn't, I used the word escape velocity,
but, but like, it wasn't until yet 2017, 2018, maybe that I, that I felt any kind of serious
financial security as an author. So it was like a slow adjustment period. Because, look,
at the end of the day, I'm writing about an obscure school of ancient philosophy. Like,
I'm not writing about productivity necessarily or writing about habits or writing about sales.
There are a number of other topics you could tackle that would be more financially lucrative
and establish oneself quicker.
So it was an adjustment period.
It was a slow, steady adjustment.
When you move to the 40 acres out in Bostrop, and I'm being careful now at the used to
ranch because I have a relative who lives out in West Texas who has like a real ranch no he has like
500 acres or a thousand acres and he gets very upset if I call it a ranch so I guess in west Texas
if you call it a ranch and you're not running 20,000 head of cattle or more you're going to get shot
if you don't have sections if you're not running a section yeah which is a you know a whole chunk of acres
but uh it's a hobby farm is what I have okay so when you move there was this from a deep life perspective
was just like one of the first points where you really began to think,
but wait a second, we do have all this autonomy, right?
Even if we're not at the massive escape philosophy yet on book income,
we might as well shape other parts of our life as well.
Like we're not going to an off.
Like what was the, because to me that always seemed like a romantic move when you made that
was like you have a, at least one cow, right?
Am I using the right word?
It has big horns.
Yes.
You have a pond, right?
I mean, to me, this is all like kind of romantic, right?
So talk about that, the role of that when you were trying to,
conceive of your life. Yeah, I do think coming out of ego is the enemy and the collapse of American
Apparel, I was like, I don't want any of this. I want to live a very different life. And what is the
point of being a writer or having some kind of career success if you can't set up the life that you want?
I lived in New York when I was right after the publication of,
of, trust me, I'm lying.
And while I was writing an obstacle,
and then I moved maybe right as I was finishing obstacle,
I think I moved to Austin.
But like, I remember looking at the first mortgage statement
when we bought a ranch, we bought about,
we ended up with about 50 acres now.
But the first sort of mortgage statement,
on our place was what I was renting a studio apartment in New York City for and just going, oh, okay,
this is like a transformatively different life choice.
And I think as a creative runway is really important.
So, you know, people think, oh, you got to move to New York.
You got to move to Los Angeles.
That's where you make it.
That might be where all the contacts are.
That might be where the energy of your industry is.
but you're going to have a lot less time to develop
and a lot less freedom to develop.
So when I went to my publisher and said,
hey, I want to write a book about ancient philosophy,
you know, because I had a day job, you know,
and because I, at that point,
I think I lived in New Orleans,
because I didn't live in a major city,
you know, when they said, okay, we'll pay you half
what we paid you for your last book,
I had the freedom to accept that.
You know, I didn't,
I didn't have, sometimes I read about these like, you know, aspiring novelists or whatever,
and I just, I just wonder how they could possibly, how, if it takes eight years to write the novel and,
you know, another year to put it out or, you know, whatever, you know, insert creative thing you're doing,
how you could do that in a city where a two-bedroom apartment is $4,000 a month.
That's just insane.
So you have roommates, you live in a bad part of town.
You're just creating an environment that I don't think is going to be conducive to being and doing your best.
And then also making the best long-term decisions.
Yeah.
So then, okay, this is fascinating.
So then your final phase I see is the phase where you're spending less time outside of writing, less time on marketing clients and instead build out this platform.
Right.
So like you're very associated now with a multimedia platform.
surrounding stoicism.
Was there a vision to that?
Or did it unfold and you just found yourself one day?
Because it's a pretty big operation.
I mean, I've been not seen it, right?
I mean, it's a pretty big operation.
You've got a good amount of staff.
It's multiple newsletters, video, like podcast, etc.
Walk us through, like, how that fit into what you were trying to accomplish.
Yeah.
So my agent suggested that we do this book called The Daily Stoic.
He had published a number of daily books when he was at Harper College.
This is my agent, Steve Hanselman.
And I wasn't even for, honestly, it was like not even familiar with that as a type of book.
I think I'd maybe seen one in my whole life.
And when I started going through, I got really excited.
It was just such a cool way to read, this idea of doing one page a day.
But I thought, like, so what are people supposed to do?
They read the one page and then they just close the book and start over, like when they get all the way through.
And it just struck me that you could build, by the time someone got to the end,
you had just spent a year together
and that that was right for a continuation.
And so I agreed to write the book,
but decided I would build this thing on the back of it,
this sort of page, this email a day.
And I remember I paid $6,000 for DailyStoic.com
and we started this newsletter.
And yeah, I've been doing that literally every day
for the last eight years.
And it's spun off this whole thing.
there's a bookstore and a podcast and multiple newsletters and social media and YouTube and all that
stuff. I would say I planned it in two ways. One, in the sense that I thought, hey, this is the first
book you're doing for which there is a continuation, like what's a community that comes on the back of it.
And then I, at that point, my marketing company had done quite well.
And I'd advised a bunch of different companies and individuals and public figures and authors.
And one of the things that I really hated about it was that you would spend all this time coming up with these ideas.
And then people just wouldn't do them.
Like, one of the exhausting things about consulting is that you realize at the end of the day,
people are paying you to give them advice
that they have no intention of actually using.
It's like this cathartic experience for them.
Yeah.
But if they use 1% of what you come up with,
that's like a success.
And that just drove me nuts.
It just felt like a bad use of one's creative energies.
And so I just, I was like,
what if I just spent my energy making my own stuff and I just put the marketing energy towards that.
So eventually, basically what happened is those two paths we were talking about that, you know,
sort of finally and fully converged, you know, sometime in the last four or five years.
So when you, you know, it's really grown, right?
So it grew from the email newsletter to a big YouTube investment, Instagram, multiple newsletters.
the podcast, et cetera, right?
What was the thinking behind growing it that way?
It's just realizing that most people don't read books.
Yeah.
And if you have ideas and things that you care about,
to leave your ideas siloed in books is sort of stopping short.
So just the decision to say, hey, I've already done the hard work of coming up with the ideas.
Translating this stuff into working in other mediums is not that hard.
And weirdly, the economics of the other things might be much better.
So, you know, you can make, you know, a podcast might have a fraction of the audience.
but be more lucrative than a book.
And so I guess what I was thinking is I love writing books.
That's what I care about.
That's what I want to focus the majority of my energy on.
But how can I get good at explore and build out these other things as a way of supporting that thing?
Right.
And as it happens, a lot of the mechanisms by which people discover stuff these days,
especially books is in mediums very different than books.
So, like, people who listen to podcasts are the kind of people who download audiobooks, you know?
And so the decision to have a podcast might seem like it's different than books,
but it's actually how you are building your book audience.
Right.
And the decision to say, oh, I only write books is actually a decision to say,
I want to have a very small audience for my books.
What number do you care more about?
Total eyeballs, let's say per day, seeing your stuff, or first six-month book sale number on your books?
You know what's weird?
I don't know either of those numbers.
Like I know what right thing right now did in its first week because my publisher sent me those numbers.
And now we're three months out.
I couldn't tell you even within 30 or 40% what that number is.
And I don't know if I know what our,
I definitely don't know what our daily or total audience is for daily stoic.
I just know that I make the stuff and that the reach is pretty big.
I try, I try not to think too much about those.
Like you're talking about sort of a deep life.
to me, it's a really shallow life if you're waking up every day and stressing whether the number is here or here or here.
You know what I mean?
I'm not saying I live in a bubble because that's not good either.
But I try to insulate myself from statistics and metrics to a degree that it allows me to just focus on making what I think is good.
Do you privilege books in your thinking at all?
Or do you really have a unified thinking of ideas to people?
I mean, to me, ultimately books are the most important and powerful medium to interact with someone.
So like, you know, you could have an Instagram reel that does 10 million views.
And that would probably have a fraction of the impact that selling a thousand, that a thousand people reading a book would have.
So ultimately all I care about is is writing books that I'm proud of and that those books are finding, you know, their audience.
And yeah, what I'm not, I'm not saying, I'm not chasing social media engagement at the expense of, you know, book sales, that's for sure.
I mean, what I think is innovative about your model, and I've seen this up close.
and I don't think people, most people are there yet.
Tell me if I have this wrong.
But the way you think about things is you are a producer of ideas that are valuable, right?
You've developed this skill and this is what you've done.
There's so many hours in the day that you can productively do that.
And sort of the insight you had is, okay, how do we take those ideas and get them to as many people as possible?
Well, there's lots of different channels.
And I think the channel overlap piece is one of the more innovative.
That, you know, if I'm there doing your podcast, you'll tell your team, hey, clip, minute this, minute that, minute that, turn those into, get that into a content for this daily email newsletter.
Your podcast is using what's going out in the email newsletter, except for when you do the interviews, which goes back and feeds into the newsletter.
Your books get sort of, it's ideas you've talked about those ideas, go back.
And it reminds me almost of like the innovations and licensing deals that, you know, people figured out in the 70s or 80s.
We have this IP that's valuable.
Well, it could be on lunchboxes and on stickers and in toys.
I don't think most creatives are there yet.
I think they think about channels as independent endeavors, you know.
Yes.
I write books.
You're effectively licensing stuff to yourself.
So it's like I write a book that has a bunch of ideas in it.
and then instead of waiting for somebody on YouTube to read that book and rip it off into a bunch of
different videos, I make videos about all those ideas in the books.
Instead of waiting for someone to take one idea from, you know, something I said and turn that into an Instagram real.
I want to make that.
And then, yeah, I think a lot about how do I get efficiencies.
So, like, I had to talk in Brazil on Friday.
Now, it's a big, you know, it's like a disruptive thing, right?
Like I had to get on a plane, I had to take two red eyes, I flew to another country, I gave a large talk.
But, you know, that talk was filmed.
And then I had to do a Q&A after.
And that Q&A was recorded.
And so, you know, that talk will become 15 clips that that Q&A will become a Q&A podcast episode.
So I try to think about, I try to think about.
how do I use this stuff in all the different mediums?
And I think Gary Vaynerchuk is kind of the guy that's pioneered a lot of this.
The idea of like, hey, each one of these platforms has its own kind of unique audience and its own
kind of unique language.
And your job is to figure out how to participate.
You don't have to, but do you want to cede that audience to someone else?
Do you want to, you know, miss out on that chance?
Now, I also happen to subscribe to a lot of the things you talk about, which is like,
how do you personally set up your life?
So like I don't spend a lot of time on social media.
I see social media primarily as a push medium.
And I, the reason I have a team, could I do a lot of it myself?
Probably would it be more profitable, you know, if I was more involved, probably.
But it would also quality of life, there'd be a quality of life reduction because I think a lot of these mediums are not super healthy for the individual.
but it would also just take me away from the things that only really I can do,
which is write the books that I write.
Yeah.
I love this way of thinking.
Yeah, I mean, I've been thinking about it.
There's also this theory out there that you need a certain level of ubiquity
before you can get big growth, right?
Yes.
It's when people kind of know who you are,
that then when you have the right idea that's right timed, you get explosions.
If they don't know where you are, it's hard for,
it's that like, yeah, I know Ryan Hall.
some of his stuff that then allows when you do something that time's right for that growth to happen.
This is what I think about like your pandemic years, right? I mean, I see 2016 through 2019
this, you kind of start launching a strategy daily stoic. You build up these audiences into the hundreds
of thousands, kind of somewhat painstakingly, right? Yeah. And then there's like a three year period
and everything jumps to millions, right? You can't go from 50,000 to millions. But like you can go
from 600. In other words, like, you were out there, right? Like, once there's a bit of a ubiquity
for your ideas, you've defined yourself in the mind of a lot of people. Now it's much more
easy when they see a Ryan Holiday book. Like, I know exactly who that is. And now the fact that
the topic is what I'm interested in, I'm super excited to buy, right? Like, if Steven Spielberg
does a movie on a topic I'm interested in, like, I'm 100% going to go see that, where that same
topic, if I don't know. So, I mean, there's an interesting curve. And I think there's a lesson there
as well, is that, you know, your audience grew and then it exploded. But you can't skip the
growth. Unless you're pure algorithmic, like, sure, on YouTube, you could do this. Like, if you're in a
purely algorithmic medium, it's possible, but that's a really low-touch audience anyways. But, like,
your email, newsletters, etc. There are definitely things that just take off like a rocket ship.
I think you see this in music, right? There's the kind of musician that writes a handful of
huge singles that just sort of break out. This is like lightning in a bottle. This is a magical thing.
And maybe you're that artist and maybe you're not. I happen to be more a fan. Like I'm a heavy metal
fan. I'm wearing an Iron Maiden shirt. Iron Maiden's a band that's basically never been on the radio,
but 50 years in, 40 plus years in, they're like bigger than they've ever been. It was this sort of very
slow and steady multi-generational thing. And they kind of just do like Iron Maiden makes
Iron Maiden Music.
Like I heard their manager once said,
someone said, you know,
you're one of my heroes in the music business.
And he said, I'm not in the music business.
He said, I'm in the Iron Fucking Maiden business.
And this idea of like, Iron Maiden makes Iron Maiden
music. And they make it for Iron Maiden fans.
And you kind of know what you're going to get.
But they've done it so long that you start to get into
that idea of like compounding returns.
So it's not exactly exponential.
but it is like linear in a very powerful way, right?
And you just kind of do what you do and you do it for your people.
And there are going to be moments that sort of punctuate it.
Like, yeah, the pandemic was a big growth thing.
But it's not like we quadrupled in size overnight.
It was like, oh, you know, the list grew by 25% this year instead of 10%.
Right.
But we've kind of just, Daly Stoke has just been this very,
steady, consistent thing that gets bigger and bigger.
I, like, look, you and I both know people who have put up videos that have done tens,
hundreds of millions of views.
Probably the most that any of my things have ever done is a couple million views,
which is a lot if your stuff is currently doing nothing.
But if you're Mr. Beast, that's...
Disaster.
Comparatively nothing.
So I kind of just make a lot of stuff.
I make it in a lot of different mediums.
And I do what I am excited and interested in it about.
And it's built this kind of, you know, this idea of a flywheel.
And it, yeah, it can become quite large.
But again, where your stuff has been helpful for me is like, could it be bigger?
Probably.
Will it be bigger in the future?
I would say yes.
But I would like it to be bigger sustainably and not at the expense of,
my deep kind of thinking and the pleasure of doing the thing.
Like if you told me Daily Stoic could quadruple in size,
but I wouldn't be able to write any more books or write them at the level.
And with the time that I currently do it, I would not take that trade.
Well, I love that model.
I know we're out of time here.
We both have school pickup.
We have school pickup speaking of the deep life.
We're honestly, we're mainly show first.
Let's be honest about this.
Yeah.
But to me, I was saying that like a rich life is being able to pick your kids up from school.
There's a version of that that's not rich, I guess.
But there's a version of like having the ability to do it and wanting to do it is a wonderful thing.
Yeah.
Well, Ryan, thank you.
I mean, I'm going to do a big summary of this for the listeners.
I think there's some great thoughts in here.
I think there's lessons from your story.
I think there's lessons from your new book, which I want you to check out the full series.
I think it really helps build that code.
And I love your specific just because it matters to me.
Because we're in the same world.
I love your specific story about how you think about growing audience,
doing something Iron Maiden style as opposed.
I don't know if the alternative would be Carly Jepson style.
I'm trying to think of recent one at Wonders.
Anyways, Ryan, always a pleasure.
Thanks, man.
We'll talk soon.
All right, have a good drive.
