My First Million: Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More

Hubspot Podcast Network Hubspot Podcast Network 10/4/22 - 1h 9m - PDF Transcript

All right.

Quick break to tell you about another podcast that we're interested in right now.

HubSpot just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell.

And they break down why these pitches were winners or losers.

And each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find Another Bite on whatever podcast app you listen

to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

So I've gotten to meet like a number of very successful business people over the years.

And like as a rule, they all want to write books.

And it was a reminder to me that like doing stuff that's cool that you like that means

something to you is what people do with their money when they have it.

I feel like I can rule the world, I know I could be what I want to.

I put my all in it like no days off on a road, let's travel, never looking back.

My man, Ryan Holiday.

What's going on?

Nice to talk to you.

Good to talk to you too.

So you, you asked to come here and I'll just, because I just want to get it out of the way.

I want to give you the love.

You asked to come on here because A, we're homies and I love you.

And also because B, you have a book coming out.

Yes.

What's it called?

Discipline is Destiny.

This is the new one for the series and yeah, it came out yesterday.

Oh, and how's it going so far?

Really good.

Really good.

It's already significantly higher than the last one.

I know where the numbers are, but I'm waiting.

The one thing you don't know until the end of the second week is audiobook numbers and

where it may or may not land on the best seller list.

What do you think is the outcome of this one's going to be?

It'll probably come in a bit above 40,000 copies the first week.

I would venture to guess it could be higher if they keep trending this way.

So because I have my own bookstore and I did the sales through my own bookstore, I probably

won't hit the Wall Street Journalist.

They skunked me last time.

And then the New York Times list is let's say 50, 50, all of which my publisher is very

concerned about and I've decided that I don't care about it all anymore.

Because if you own your own bookstore, that means that and you sell 20,000 copies, do

they not count all 20,000s in the rankings?

Yeah.

So I mean, just generally, if you sold 20,000 copies of a book through one bookstore, they

would find that to be suspicious or unrepresentative and there's a chance it could get tossed.

If you ever look at the best seller list and you see like a little, they call it a dagger.

It's like a little cross next to certain books.

That means that there was a lot of bulk purchases or like suspicious activity.

So there could be that, but the Wall Street Journal or BookScan, which is owned by Nielsen,

just flat out told me they just don't include sales from stores owned by the author anymore,

which doesn't strike me as that being a big enough category to have a rule about.

But I guess there's the potential for fraud.

Like I guess theoretically, I could have just inflated the numbers or something.

So there's a chance it could get tossed, but once you get it once, I feel like you have

it and then you also realize like kind of how meaningless things are.

So I care a lot less about sort of the status or the recognition of sales.

And I care a lot more about, you know, did I sell as many copies as possible to as many

people as possible, right?

Because the whole point of writing a book is for people to read it.

Does being on that list, and when you say the best seller list, are you meaning just

the New York time?

Is that considered like the list?

And does being on that help sales?

There's sort of three lists.

Because New York times, which you'd probably rank as number one, Wall Street Journal, which

you'd probably rank as number two, and then USA Today.

You have to hit one of those three lists to be called the national best seller.

Those are the three national lists.

I think people tell themselves a story about how being on the list helps them sell more

copies.

But as someone who buys a lot of books and talks to a lot of people who buy a lot of

books, I have never once heard of someone buying a book because they saw it on a list.

People don't even know where they would find such a list.

Dude, I was reading, it's Robert Murdoch's company, but he has two of them.

I forget which one is that owns, I think Penguin.

I was reading their annual report, and they were doing this entire section on Mark Manson.

And basically saying like, this has been like a breakthrough hit, and like, this is a, you

know, the company is like a 20 or $40 billion company.

And they're referencing Mark Manson, and I'm like, oh, wow, that must be a huge book

in order for them to like discuss this in a six pages of a hundred page document.

And then I Googled like Mark Manson house, because that's always like the tell of like

is someone like crushing it because it's you can't really like, it's hard to get a mortgage

for a $15 million house, unless you're actually raking it in.

And it said like, you know, Mark Manson sells Tribeca condo for $14 million.

And I'm like, damn, like I thought book, the book business was a bad business.

He must have crushed it.

He must be making millions.

It's actually a great business. So the, the publishing industry, I think is about a $40

billion industry. News Corp owns Harper Collins, Harper Collins publishes Mark Penguin Random

House, which is my publisher is the biggest publisher in the world.

And they are themselves.

Let's look Penguin Random House.

I think they're owned by a parent company.

I forget the parent company, though.

They're owned by Bertelsman or something like that.

Yeah, yeah, yeah.

That's right.

But their revenues, I bet four billion euro for, for Penguin Random House.

So it's a, it's a very big business and, and always has been.

And there are multi, multiple, multi-billion dollar, you know, businesses inside that business,

even, even Ingram, which is the distributor that sells books to most independent retail

is like a seven or eight billion dollar business.

But Mark's probably sold, I think subtle art of not giving a fuck sold like 10 or 15 million

copies.

Now a lot of those.

And what do they cost?

20 bucks?

So if you think about like my books, I've sold five million copies.

If you said 20, that's, that's a hundred million dollars in gross revenues, right?

That's crazy, right?

Now, now obviously there's a lot of middlemen, even before it gets to the publisher, right?

The publisher is selling the book at wholesale.

So right there, that's, you know, cuts it in half and then, you know, blah, blah, blah,

it goes down.

But if you think about how much a book sells for and the quantities of which successful

authors sell a lot of books, that, that number gets very, very high.

This is why JK Rowling is, is a billionaire, right?

She's probably sold a hundred, 200 million Harry Potter books, not including licensing

and all the other things, you know, different, the, the, the different formats, whether it's

audio or ebook or physical or hardcover, even hardcover and paperback is a big thing.

Like one of the, I bet Mark, for instance, and I know Mark and he's amazing, the distinction,

the decision to put your book in paperback is actually a multimillion dollar decision

for authors and, and most authors have never even thought about this.

So for instance, on a hardcover book, the, the standard publishing contract and pretty

much everyone, including the authors that are household names are on this same contract.

It's just, this is what it is, is 15% on hardcover price.

So an author makes, you know, 15% of $27, whether you as the customer get that book

for $17 on Amazon or for $27 at an independent bookstore, you're making the same amount,

right?

Your, your royalty is on MSRP, but 15% of hardcover, right?

A paperback sells for about 10 to $15 less than a hardcover, right?

But, and your royalty is 12.5%.

So my, my agent very early, who was in publishing, he was like, he was like, I will never let

your books go into paperback.

He's like, you have to sell about as third, you have to sell a third more books to make

the same amount of money that you've sold in hardcover.

And this is why Tim Ferriss's books are not widely available in paperback, good to great

by Jim Collins, which has sold tens of, you know, by 10 million copies still in hardcover,

even though it's a 20 year old book.

So there's lots of little decisions that you don't often think about.

What about audible and e-book?

So audible, you may, I think it's the same as, I think audible and e-book are 25% of

list price.

So you make, it's a higher royalty, but on a lower price point, audio books are like

15 bucks or nine bucks for, for e-books a lot of times.

So, so somewhere between two and three bucks a book, you make a cross formats.

So how much, if you're in hardcover e-book.

And so you think Mark's book has sold 200, is I think, did you say 200 million in sales?

So no, no, 20, he's probably sold 20 million books.

Sorry, in gross revenue.

Oh, was 20 million books times hardcover price, or, you know, it, it, it, it's going to be

a, a blend there of the price.

The only, the only thing that's worth pointing out, and this isn't a criticism, it's a, it's

just a quirk of the business.

Mark has sold a, Mark's books are very big internationally, right?

His books are big in Brazil, his books are big in India.

I, I've experienced the same thing.

As soon as you start selling lots of copies internationally, let's just say you start

seeing a lot less money for those titles, right?

Like, for instance, somebody sent me a copy of one of my books in, from Iran recently,

and I emailed my agent and I said, oh, I didn't know we did like a Persian translation.

And he said, we didn't, he said, Iran doesn't recognize copyright, they just do whatever

they want.

He's like, you'll never see a penny from these books.

So the point is, like, if, if you sell a million books in Russia, right, you're not getting

your standard royalty rate, you may never see a penny of that.

You might get an initial advance, but you'll, you know, it's, you start to get into, let's

say less transparency in the accounting as you sell.

So you can't, you can't simply go, well, what's the total number of copies sold by a person

and then times that by a number, you're probably going to be overstating the cash they have

on hand.

So you've sold a hundred million in books.

So then like the estimate based off of the numbers you said, it would be like around

13, 14, 15% take home.

I mean, how many authors are doing that?

Selling five million books, very, very few.

I mean, definitely there are a lot, there are lots of people who have done it and there

are people who have done much, much higher than that.

But like as far as people who write about philosophy, I mean, I'm not sure it's been

done ever, certainly not in, in, in like the modern world.

So, you know, when I went to my publisher and I offered them a, an obscure book about

ancient philosophy in 2011, 2012 for, for the Stoke book, for my first Stoke book, my,

my advance on the obstacle is the way it was $75,000.

They were not, they were not thinking, you know, that series would sell three or four

million copies.

Do you think that your life has or will become, so we were talking about Tim Ferriss and we're

like, you know, however much he's made on books, it probably pales in comparison.

He's arguably like just guessing maybe he's worth 150 to $250 million based off of his

Shopify and Uber and seed investments.

And he probably has done so many more things that I don't even know about.

Do you think that your business is going to be a similar thing where it's almost like

the books are awesome, but they're going to be tiny compared to the other revenue streams?

I don't know.

I don't, I don't do that many investments, but it is weird.

Like I was an advisor early on to like butcher box and they've done a few sort of private

transactions that I took part in.

And it is both humbling and surreal to get a check and be like, shit, I would have had

to sell a lot of books to get the same amount of money.

And this amount of money was, you know, a lot less work.

So I think for someone like Tim, you know, when, when you can invest in something that

scales at that level, I do think it makes you a little disinterested in the economics

of publishing, even though they are quite, they are quite good.

Yeah.

I mean, I was like, and everyone talks about in writing a book and they say, I think he's

the one who told me this.

He's like, it sucks.

He's like, it just, it stinks.

He says, he goes, I love it kind of, but I also really hate it.

It's very uncomfortable and it's a lot of hard work.

And I was like, yeah, I don't know why you'd write a book then when you, if you don't have,

if you don't, if you don't truly, truly love it, I have no idea if he does or just not,

but it's very hard.

It seems, it seems almost impossible.

It is super weird though, because like a lot, wealthy people read books, right?

The, the, the interesting thing about books is that they sort of punch above their weight

culturally.

It's like the opera or something, right?

And so like, you could be very famous on YouTube and your average billionaire might not know

who you are.

But if you write like a business book or a political book that sells reasonably well,

you're going to, you're going to have some name recognition in an elite group.

And so I've gotten to meet like a number of very successful business people over the

years.

And like, as a rule, they all want to write books or all want to talk about whether they

should write a book or not.

And it was actually very helpful for me to learn that early on, because like every author

I knew was trying to start a business or follow in Tim Ferriss's footsteps and invest in these

companies to get really, really rich.

And then I would meet really, really rich people and they wanted to write books.

And it was a reminder to me that like doing stuff that's cool, that you like, that means

something to you is what people do with their money when they have it.

And so they're like, like I met this guy, you actually probably know him, but I won't

put him on the spot.

But anyways, he'd written a couple of books and then he started a VC company.

He raised a fund.

He raised like a hundred million dollars.

And he had to put writing on the side to raise this fund.

And I asked him, like, why are you doing this?

Like, what are you going to, I was like, let's say you really succeed.

Like let's say your fund crushes and you walk away with like $20 million.

What would you do with it?

And he was like, he's like, do you know who Alonde Baton is?

He's an author who started this company called School of Life.

And he was like, I think I would do something like that.

And I was just, I just burst into laughter because like he was it.

Yeah.

He was, it's like that, that story about the, you know, the fisherman who meets that Western

businessman who tells him, like, you know, if you really scale up your company, blah,

blah, blah, blah, you know, one day you can sit on a beach somewhere and it's like, that's

what I do now.

And so there is kind of this weirdness where people think financial freedom is this kind

of abstract good.

And then you meet people who have it and they still have to wake up and figure out what

they're going to do all day.

Dude, I listened to your, I want to talk about the YouTube thing in a second, but I listened

to your YouTube videos every single morning when I take a walk.

And like it makes me feel so good about myself, not maybe not good about myself, but I feel

like I'm getting so much from it, whether it's education, whether it's just like you're

helping me think differently.

I don't know what it is, but I get so much from it.

All right.

A quick message from our sponsor.

You know, I was thinking about the shortest day of the year earlier.

And while we technically have the same amount of time as every other day of the year, the

lack of daylight makes it feel so much shorter, which is exactly the same kind of feeling as

working with disconnected tools.

Our work days, the same length as always.

But before you know it, we spent three hours just fixing something that was supposed to

be automated.

Thankfully, HubSpot's all-in-one CRM platform can serve as a single source of truth for

managing your customer relationships across marketing, sales, service operations with

multiple hubs and over a thousand integrations and an easy to use interface HubSpot lets

you spend less time managing your software and more time connecting with your customers.

Learn how HubSpot can help you grow your business at HubSpot.com.

When you, you're the one creating all this stuff, or at least you're paraphrasing like

interesting people, do you think that you are absorbing these lessons better than most

others?

Like, you know, like, are you, you just told this very simple story of like, well, why

would you go and do this, this and this when you're already doing that now?

Are you motivated by, like, are you motivated by money?

Are you motivated by all these things that you talk about, like, look, this and this

and this may not make you happy?

I think I certainly struggle with it, like every, you know, single person does because

it's not like just knowing it doesn't magically make it easy.

But I would say like, like a big lesson like that, like, why are you trying to make all

this money to get somewhere you're already, you already could be.

I feel like I do a better job learning those, those big philosophical lessons, like sort

of where do you reign ambition in, you know, sort of how do you define meaning or happiness

or contentment in your life?

I probably am better at that than I am at some of the more basic stuff.

Like, you don't have to be anxious about this or like, why are you letting this person get

under your skin or why are you losing your temper about X, Y or Z.

So like, I feel like the bigger stuff, the stoicism or the philosophy sort of connects

with me.

And by the way, that story about the fisherman actually traces back to like the 14th century

about this story about a prince advising a king or an advisor advising a prince.

So the story goes way back.

I feel like I get that better than I do stuff that might be, seem really easy for most people,

which is just like, you know, sort of day to day emotional management.

How you set something really cool.

I was listening to this the other day, there's two things that stuck out.

But the first one is with Matthew McConaughey, you're talking about content and you're asking

him about what he chooses, like which projects he chooses.

And apparently he, there was the whole part of the episode was talking about how he had

like 10 or 20 million dollar offer and he was like, no, I don't want to do this.

This doesn't, this doesn't speak to me.

This is not how I want to spend my time.

And he was like, he felt guilt over that.

And you guys were talking about Bob Dylan.

And I think it was you who said, I want to make content like Bob Dylan, which is quality

and quantity.

Don't necessarily have to be at odds with each other.

Like I can output lots of really cool, great stuff.

And you do do that.

And the Daily Stoic is an email.

Then you have the Daily Dad, another email.

And then you have the books, which is, you have dozens of them or a dozen of them plus.

And then you have the podcast and then you have the YouTube channel.

And I'm like, how are you outputting all of this stuff?

It's always awesome.

I love all your shit.

Well, thank you.

I mean, I, I think I actually, like, I actually like doing it, right?

So there's, there's some people who they don't like doing it.

And so to do it because you think it'll make money or it's what you have to do, that would

be not a reason to do it.

But like this morning I got up and I wrote and yesterday when the book came out, I was

excited not to come into the office to see how, you know, the discipline did, but like

I had saved like a really good chapter for what is the sequel because I'm doing this

four book series.

Like I was just fucking pumped to do that.

Like that, that's really what gets me excited is doing the stuff.

So I tend to have more energy to make stuff than there actually is like pipes to put stuff

out.

That's just like how it shook out.

And I agree.

Like I, I agree with the sentiment rebob Dylan in that, that like quantity and quality don't

have to be opposed to each other.

And in fact, the more you do, chances are you'll, you'll sort of get something magical

or important.

I mean, like I really admire people who are wired differently and they sort of painstakingly,

you know, put lots of years into something.

Although like if you, you know, I bet if you asked Mark, he would, and I actually I have

asked him, but like following up a massive, massive hit is really hard.

And I've been lucky in that my books have done well, but they haven't done so well that

like my whole world changed when the obstacle is the way it came out.

So obstacles the way it came out, they did not for me very much money.

It sold well at first, but it, it took like a slow burn.

Yeah.

And not even slow, but just steady.

Like it probably didn't cross the one million copies sold mark.

I know it crossed the hundred thousand copies mark within the first year because there was

a bonus attached to it.

So it took, you know, 12 months to sell a hundred thousand copies, but it probably took

an additional four to five years before it crossed the one million copy mark.

So like for someone like Mark or James Clear or other, other people, they hit the one million

mark in like a number of months.

And when you start to do that, everything changes, expectations change, you know, inbound

inquiries change.

And I think, I think it becomes hard to just like do the thing.

So I, I feel like kind of lucky to have a big niche, but for it still to very much be

a niche, right?

Like there's just more people haven't heard of me than have heard of me.

And that is a nice place to operate in.

Dude, so many people.

So the hustle, we were a daily email, then me and Sean do this thing three days a week.

And people are like, Hey, how are you doing quantity?

I want to get started.

But like, you know, I'm like banking 21 episodes before I start, or I'm like perfecting like

this blog post and you know, I'm going more for quality versus quantity.

And in my head, or sometimes I'll tell them, I'm like, no, that's a false dichotomy.

That's not true.

Like the quality is the quantity, the output here or like the, if this were like quality

plus quantity equals, it would be like the total reach and how impactful they are and

the types of people you're impacting.

And to do that, you have to have like something in there for quantity.

And it's really just kind of an excuse to procrastinate further that you're making up

for yourself.

It gets easier as you get into it.

So you need quantity.

You need the swings to get better and B, if you treat it like a job, you could have way

more output than you think.

Yeah.

I have a couple of thoughts there.

So one, it's like, try to apply that logic to like any other thing like imagine if you

met a comedian and they were like, I'm really focused on quality instead of quantity.

So I don't do a lot of stage time.

Like I just don't go up very often.

You'd be like, you're a shitty standup comic.

Like the way you get good at it is by doing it a lot, right?

And it's very hard to get to quality without years of back and forth with an audience,

right?

Like it's just really hard.

And so especially online where you're giving the thing away for free, like you should be

focused on quantity because quantity is how you get to a place where what you do is worth

paying for at a premium level, like with a book or something.

So like I've done a free email every day for six years, right?

That's built a business.

Are you writing that?

I write it every day.

I mean, every once in a while, like let's say 10% of them are, you know, hey, I'll work

with someone on my team, be like, hey, I already wrote about this.

Can you work this into a draft for me to approve or rewrite?

But like the vast majority of those daily emails were 100% original ideas that I put

out 100% of.

Is that for the dad or for the both?

Both.

Oh, I didn't know.

You're writing both of those every day?

Yeah.

Well, I don't write it.

I mean, I write every day, but I don't write the email every day, right?

So like I'm currently, let's say like I could pull this up.

Let me, I have a document where I have someone track them.

Like I am, I'm scheduled out on daily Stoic through and Daily Dad through October 14th.

And then I have 10 written that are ready to record 16 that are recorded, but not unscheduled.

And then nine on Daily Dad that are ready to record and eight that are recorded, but

not scheduled.

So that's your system?

Yeah.

So I'm just do it.

Like I might sit down today.

Like I have, I don't know where my to-do list is, but on my to-do list, I have three sort

of one sentence ideas for daily dad emails, and I might bust that out in 30 minutes.

And then that's, you know, almost a week worth of content right there.

Are you writing the scripts to your YouTube videos?

I think you're only doing one or two a week, right?

Yes.

Actually, wait, let me, I'll come back to that in a second.

The other thing I would say about the people who are like, oh, I really want to get to

quality.

That's why I take so long.

When I look at what those people make, I very rarely see the quality, right?

Like they're like, oh, you know what?

This book, it took me five years and I'm like, where show, show me five years of work in

this thing.

I'm not arguing with you that it transpired over five years, but I don't think you showed

up and worked on this, as you said, like a job every day for five years.

I think it either, because if that were true, I think it would either be a lot better or

I think it would have come out a lot faster, right?

So I think a lot of people are baking in a lot of inefficiencies and a lot of procrastination

inside that and then patting themselves on the back and saying that they're doing a thing,

that they're really focused on quality.

So that's just like a dispute I have.

I think a lot of people take way too long to do things.

When I see like a Robert Greene or a Robert Caro or, you know, one of these greats, I'm

like, I see the, I see the five years, like it's obvious.

Like Robert Greene was telling me the other day, he's like seven months into a chapter

on this book that he's writing right now.

And when I read that chapter, I'll see every fucking day, right?

Because like, he's not lying.

Dude, when I read Robert Greene and what's Carol's book, Moses, yeah, the Robert Moses

book, Robert Moses.

And then I just got done reading the rise of the third Reich, which is like, which is

like a 1500 or 1300 word like epic.

And then pretty much like Titan is like this too.

Anything Ron Chernow does every sentence to me, it's like a life's work.

And if they're lucky, they can maybe get three of them.

Then I read those things and they make me depressed because I just think like I, I can

never do anything this detailed oriented, this beautiful, it's, I think it's mostly

history books.

Every single sentence is amazing.

And I don't understand how you could do that for so long.

Yeah.

This is the William Manchester series on Churchill, which I would highly recommend.

This is the Taylor Branch series on Martin Luther King, also incredible.

In the acknowledgments of the last book in the King series, Taylor Branch talks about

how his youngest son was born, like the day he started the series, and then took a break

from college to help him finish the last book.

That's crazy, man.

It is so nuts.

Those are really like life's work.

They are.

And it's not just that every sentence is perfect, but like we don't see that if you think about

the iceberg, we don't see the research, the interviews, right, the on like location observing

that went into forming one of those state, those sentences.

So yeah, like there's definitely people who there's a reason they only do two or three

things in their lifetime.

And then there's everybody else and chances are like you're everybody else.

And so there's that.

And then as far as the YouTube videos go, I do a couple of different ones.

Like the easiest YouTube videos we do are like compilations of reels or Instagram clips

that I do.

So there's not a lot of script there.

It's just the intro.

It's like piecing together sort of meditations on a larger idea.

But if it is a like, you know, how to read Marcus Aurelius, how to read Seneca or, you

know, let me tell you the biography of this stoic or I have one coming out next week that's

about the relationship between Marcus Aurelius and Antoninus Pius his stepfather.

That's a combination between like having somebody give me an outline and then me usually drawing

on something that I wrote somewhere else.

So for me, the writing, particularly of the books is what generates the vast majority

of the content.

And then I have people who help me just just in the way that I don't do the Spanish edition

of my books.

I have people who help translate what I've done into different mediums are using Google

docs.

Yeah.

For them, for the most part.

Yeah.

And how big is the team?

Like 10 people now, probably, and that includes the bookstore.

And also, does it include daily stoic and a daily dad?

Yeah.

Yeah.

I'm saying I probably have 10 employees, maybe maybe 11 or 12, but but less than 15.

Dude, that is crazy, man.

The output is just awesome.

I think that's amazing.

Have you I was messaging you the other day because someone was like, hey, you should

start a book club to me and I'm like, well, I read a lot, but like you Ryan should really

start it like someone like that.

And I looked a while ago, I looked in the book of the month is the book.

It's called Book of the Month.

And it's like a company that's been around for like 50, 60, maybe even 100 years.

It's been around for a long time and it's traded hands a ton.

I think right now, last I heard they're in the 70 million range of revenue, which is

a big business, but I don't know if it's growing and I don't know if that makes a profit.

I don't know what this situation is.

But have you looked in these book of the month businesses?

I think Reese Witherspoon had one too that I think was profitable.

Yeah.

There's a there's a couple of different ones.

There's another company called Literati book of the month.

The book of the month concept definitely goes back quite a bit.

And that used to be like a way that you would guarantee a book's success would be if you

were selected to one of those clubs because they might buy a hundred thousand copies

or something.

There's and then there's what is it called the next big idea book club, which I think

Malcolm Gladwell is an investor and there's there's a there's a handful of them.

The problem with the business is, first off, not that many people read, right?

Unfortunately, second, the logistics of it are what is tough, right?

So like at the very best, you're going to be able to get those books from like, let's

say you're doing physical, right?

At the very, very best, you're going to be able to get those books at 50% off from the

publisher.

So if you start to get into, you know, like it drives the subscription, like already your

subscription is more than Netflix, which gets you unlimited of the best, most entertaining

content in the world, right?

So the really tough part is getting to a place where you can move a lot of books and

the revenue is high.

So I started this newsletter, like 15 years ago, where I just recommend books.

What do you have like 250,000 people now on it?

Something like that.

Yeah.

And and I just prefer to like, look, if you want to buy the book from my bookstore, I make

a little bit of money doing that.

If you buy it from Amazon, I get the commission, but I'd much rather just have that list in

that audience than try to monetize a book club itself because the bundle of including

the book plus fulfilling the book plus customer service and all that other stuff, it, I think

I think it's just hard to make the business itself work.

How much revenue can you make at one send from from the reading list newsletter?

I don't know.

I don't know.

I actually 10 or 20 grand maybe.

Yeah.

That would be that would be a lot because the other thing that I found is that the people

who read the most or at least the kind of readers that I attract are like, I don't want

to say they're lone wolves, but they're more like, like, I don't know about you, but like

the way I read is I just have at all times a long list of like books I'm going to get

around to reading.

I'm not like, oh, you're reading this book right now.

I have space for you in my life.

So like, if I think about the impact that the list has had as far as moving copies for

books, it's not like, oh, we sold this many copies of this book this month.

It's more over a time.

So I did invest in this company.

Do you know the company vinyl me?

I think I introduced you to them.

Matt Fiedler, the founder is my high school, he was my high or my my very, very, very close

college friend.

And for those listening vinyl me please is awesome.

I don't know how many I don't remember how many people they have 20, 30,000 subscribers

and they send out a record of vinyl of a piece of vinyl.

And I remember he was like complaining to me.

He was like, man, the like we whenever someone gets selected for our vinyl, like when we

pick an album, it becomes a bestselling vinyl in the country because we're the biggest.

But now they're not counting it anymore.

Right.

It's the same thing we were talking about with the bestseller list.

They would be the number one vinyl album in the country each month, but they just get

skunked from the billboard chart.

Yeah.

And I haven't asked Matt about the business lately, but it's been around for 10 years

now and it seems to be doing good.

But I think that's a different experience, right?

So I was, I guess I'm an advisor.

So I got some early shares in vinyl me when it came out.

So and that's been a surprisingly big business.

Like when I see the numbers, I'm always like, whoa, that's bigger than I would have guessed.

Right.

You wouldn't, you'd think like, oh, maybe a thousand people a month, not 20,000 people

a month.

Yeah.

It's a lot of people.

But, but I think in music is people consume more music than they do books.

Right.

Over and over again with a bunch of people.

It's a passive experience and the, the art of discovery is different, right?

Like you want to be suggested random things on a regular basis.

And I think with a book, like people have so little room to read in their lives that

I don't know.

I just, I like the idea of the business and it would be amazing to make it work.

I have struggled to actually see it work.

And I think there's probably just ultimately better ways to monetize that attention than

a list of subscribers you have to service each month for a specific kind of book.

You said something earlier about like you get access to all these amazing people and

I follow you on Instagram and I've talked to you a bit and I follow your content and

you are hanging out with like all these athletes, you're hanging out with billionaires and business

people and celebrities and all these interesting people.

Who are some of the people who you've met where you said, I want to emulate this particular

attribute or the way that they've done this, this and this, I admire so much or this person

is just wildly impressive.

Who do you admire of all the people you've met?

Ooh, that's a good question.

You know, I actually talk about this in the, in the end of discipline as I was sort of

struggling with the book kind of early in the process.

Like when I was just fucking tired because I've done a lot of books in a very short

amount of time and like the idea, it just, I don't know, it just wasn't gelling.

I had lunch with Manu Jnobli, we just got inducted into the Hall of Fame this month

and we were, we were having lunch at the, at the bookstore.

He, he'd come out and we were hanging out and it just sort of struck me.

This dude has four rings, like his four championship rings and he has two gold medals and is a

Hall of Famer and he was like, I don't want to say he's a regular person because that

sounds like that almost minimizes it.

But the point is when you think about someone who has four rings, I think you think more

of like a Jordan character who is fundamentally out of balance, right?

Like so there's no disputing Jordan is one of the greats, if not the greatest basketball

player, maybe athlete as a, as a whole, right?

But we tend to think that, that to be that good requires some fundamental tradeoffs about

what kind of person you are and what your day to day life looks like.

Tom Brady, right?

Comes back to football, you can't walk away and it may well cost him his marriage, right?

And people see that and they go, that's what it takes, right?

I'm not sure that that is what it takes.

That might be, you know, what it took in that specific scenario.

But like the more I meet really successful people, I become less impressed by like how

much money they made or like whether they have the most rings or the second most rings

or whatever it is.

And I go like, is this person like a good parent?

Do they seem like they live in reality?

You know, are they actually able to wake up and enjoy like what they have today?

Or is it like they're traveling here and there and they're just always doing stuff, right?

I think like to me, what the, the, the journey that I've tried to go on inspired by people

like that is I want to be world-class at what I do and be a somewhat of a normal person.

It's almost easier to be great than it is to be good.

If that makes sense.

Yeah, that's awesome.

So, you know, him and Chris Bosch are interesting.

I've read, I listened to a bunch of content that you made with those guys.

I felt the same way about Chris Bosch when I was listening to him.

I'm like, oh man, this dude's like kind of, yeah, maybe normal insulting, but like that's

what it, I was like, you're.

I'm never going to be seven feet tall, but like, you know, like your mentality is achievable.

You know what I mean?

Well, it's, it's kind of funny as I do feel the same way about Chris and his wife and

my wife and friends, but like every once in a while, I'll mention one of them to the other.

And then I forget that they, Chris said something to me actually when I had him on the Daily

Stoke podcast.

He's like, you know, he's elbowed me in the face like a lot, like, like it was like realizing

like, like their best and worst moments came like the, the moment in both of their careers

came at each other's expense, right?

Like Manu goes up for a rebound that Chris tips back to Ray Allen, who makes a three

pointer to win, to basically win the series, right?

Like it is also weird to think like, yeah, here are these like kind of two people that

I admire.

And then they're all like, uh, their careers were like on a collision course with these

other buddies now.

I don't think so.

No.

I don't think so.

Even though they, they live not far from each other, right?

One's in San Antonio, one's in Austin.

And I do not think that they see each other socially that it might take some time.

Like maybe, maybe in 20 years, the, that rivalry fades away.

Is there anyone else who you've met and you're like, man, the way that you're pulling this

off or the way that you're playing life, I just admire so much.

Well, you know, it was, I had a weird one a couple of weeks ago.

I, I don't want to say who it is, but anyways, let's just say I met this musician and he'd

read the books and he reached out to me through someone we know, and he was like, Hey, you

know, next time you're in New York, you should come see me or let me know.

I'd love to have dinner with you.

So I was like, Hey, I'm actually going to be in New York like next week.

And he was like, Oh, all right, my assistant will like send you the details.

And the details were like, go to this helipad.

And then the helicopter took me and his son and our mutual friend to their house in the

Hamptons where we had dinner and then it flew us back to Manhattan after dinner.

What?

Yeah, it was fucking nuts.

It was super nuts.

Like talking to this person, I was like, so what's going on with you?

And he's like, well, you know, my youngest just went away to college.

So we're empty nesters.

Like we're going to spend an extra couple of weeks here in the Hamptons.

And it was like, again, I think at the end of your life and when you reflect on whether

you were successful or not, you're going to think like, do my kids want to spend time

with me or not?

Am I on my fourth marriage or am I my first marriage?

And he's he's been he's still with his high school sweetheart, right, despite selling

a hundred million albums in between meeting and like the day that I was there, he's he

has a business that he founded with his son.

Like to me, when I see stuff like that, I'm like, OK, this is fundamentally not normal

in that like we just flew on a helicopter to have dinner.

And that was like, you know, like a wave of the hand for you.

But that fundamentally, you still worked very hard to remain rooted in some semblance

of normalcy where your kids are not monsters and you like spending time together.

One of my favorite books is Conspiracy, which is Nick Denton, I believe.

Is that his name?

Nick Denton?

Yeah.

Yeah.

Nick Denton, the founder of Gawker and Peter Thiel.

And there's just so many moments in that book where I've been like, oh, my God, I cannot

believe that that's true.

And basically like the fact that like Peter Thiel plotted and had people and staff for

like some amount of years, five or 10 years, like a long time in order to like, hey, when

you see Gawker screw up, you tell me and we're going to pounce and we're going to sue them

because they outed me out as being gay.

Or you also told another story about how Peter Thiel had a Mercedes, a black Mercedes everywhere

he went that was just ready to roll in case anything bad happened.

And I don't know if this was in the book or if I'm making this up, but I'm almost positive.

There was like a plane to New Zealand that like he knew about or something like that.

Is that true?

Am I making that up?

The Mercedes thing is in the book, the New Zealand plane thing that sounds true.

But that I think his New Zealand citizenship came after I finished the book.

Yeah.

Just like all this crazy stuff.

What?

Sure.

What was it like getting to know that guy?

I mean, he's one of those guys where like, I actually don't think there is.

I don't know him, but where there actually is no balance and he is just really quirky.

Well, I think it's both very understandable and then very inexplicable, right?

Like if you had made billions of dollars and you were very powerful, I don't think you

would like to be picked on, right?

Like I think people were like, why would he do this?

And it's like, wouldn't you these this bully came along and humiliated him in his eyes.

Like I don't like not being a gay man.

I can't really fully understand what the reaction would be to being outed and a number of people

that I interviewed for the book who were gay, like they didn't even understand.

So let's just stipulate that his explanation of his experience was that this was humiliating

and he found it to be very frustrating.

I think when you're at that level, one of the feelings that doesn't sit well with you

is impotence, right?

So when people are like, Peter, there's just nothing you can do about it.

He was like, then what the fuck is the point of everything I've done, right?

And so so in that sense, I think it's very understandable.

I think the problem is if you're the kind of person who it's like, I'm going to spend

10 years chasing down this media outlet when everyone is telling me not to do that.

You're also the kind of person who can get sucked into other things that I think are

going to pay off less well, whether it's backing JD Vance or Blake Masters or some of the other

political bets that he's made.

I find the sort of anger and the resentment of what it seems to be driving that of trouble

understanding it.

Dude, I don't have trouble understanding that.

I don't.

It just comes from, at least for me, I would have done the same thing if you have that

money and power and someone wrongs you.

I have that same mentality where I'm like, I want to crush them.

Typically, I've got my wife saying, dude, chill.

This isn't worth it.

And so I listen to her.

But if I didn't have her, I'd be like, no, no, no, let's destroy them.

And I don't know.

I get that.

I get that.

That, I understand.

That's the count of Monte Cristo.

That's the oldest revenge story of history.

I'm saying more, the problem is, when you sort of start to feel like you can bend the

world to your will, that you can do anything and everything, I think you get sucked down

other avenues.

And I think some of the political bets he's made, even Trump himself, the fact that it

worked doesn't mean that it made rational sense.

But how do you not feel like that?

With my very, very small amount of internet fame and my mediocre to small financial success,

I'm like, oh, like I just, I bent the, you know, in a, I'm a big fish sometimes in a

small pond and I'm a small fish in a big pond, but I'll be like, oh, sick.

I say it all the time.

I bent the world to my reality.

Like I just made my, my true, the thing I wanted to be true, I made it true.

And that is incredibly intoxicating.

I think that there's lots of ways to do that.

There's a lot of, if you wrote a book and millions of people read it, there's a way

to do that.

If you become powerful in politics, there's a way to do that.

The easiest and most practical way for most people is if you learn how to make money on

your own, then you're like, oh, like whatever I want, I turn into reality.

I have a joke.

I call myself a manifest cowboy.

Like I just make, I make the things that I want to, the things I think of, I am not

a business person.

I am an expert at making things that I think of be real.

And even at a small scale, I get intoxicated like that, but I get intoxicated by it.

Do you not?

I have seen up close, I feel like very lucky that up close and personal multiple times,

particularly early on in my career, I saw people who, who had the ability to do that

also destroy themselves, right?

So Dove Charney was my direct boss, right?

Like he would call me five times a day.

And I watched a guy who built a multi-billion dollar company that made 50 million t-shirts

a year, you know, start something.

I mean, I didn't seem to start it, but let's put it this way.

The arc of the entrepreneurial journey, the beauty and the danger of it is that you have

an idea for something that is insane, right?

Like people are like, that will never work.

Here's all the reasons you will fail.

Do not do that, you will regret it, right?

And then you do it and it works, right?

That's the definition of what entrepreneurship does.

If everyone knew how to do it or if it was easy, it would have already been done.

You were able to create something from nothing, you know, that violates everyone else's conception

of what's possible.

The dangerous thing you take from that is you now, as you said, see yourself as a person

who does that.

And you see people who tell you that you can't do it or shouldn't do it or criticize you

for doing it.

You see them as the enemy, right?

So when Dove Charney is like, I'm going to start a made in USA, sweatshop free fashion

company that doesn't print its brand on things, doesn't use professional models, and owns

all of its own stores, and I'm going to sell all those products for an enormous premium.

Like that's, that's fucking nuts, right?

Like no part of that should work.

So then he does it and then people are like, okay, you did it, but you should really have

seasoned operators around you.

You know, you really shouldn't over expand too quickly.

You know, by the way, it's not proper to have sexual relations with your employees, right?

All these things that they told him, he was like, fuck you, who are you to tell me?

Look at what I've done, right?

And so he crashes and burns as a result of this exactly what you said, like I'm a manifest

cowboy.

The rules don't apply to me.

I can bend reality to my will.

Like, do you ever, you ever heard that expression, the political expression about the reality

based community?

You know that?

No, what's that?

So as George Bush was contemplating the invasion of Iraq, I think it was Karl Rove, but one

of the officials in the Bush administration, you know, is responding to all the people

who are like, it's going to be an enormous quagmire.

You're not going to get the, like right now you have no international support, Bob, it's

going to cost this, you know, and they go, look, he's like, there's two kinds of people.

He's like, there's the people who live in the reality based community, and then the

people who believe in America, it basically says who believe in American exceptionalism,

who believes that America creates his own, creates its own reality, bends the rules,

the order of the world to its will.

And so they believed as they went into Iraq that, yeah, it was a bad idea for all these

reasons, but that could be changed through force of will and confidence and firepower,

etc.

But they're not always wrong.

That's not true.

It's not true, maybe in that case, but like that, that feeling is cousins to the other,

to it working.

Do you know what I mean?

To where?

Totally.

Where's Genobli from?

Argentina.

Like this Argentinian dude is going to come and like be the boss and like kill it and like,

you know what I mean?

Like that they're, they're cousins.

Yes, but, but here's the thing, like when you look at Manu's story, he did not wake

up one day in Argentina and go, I will be a Hall of Fame NBA player, right?

He makes his way, like almost all those journeys are much smaller and humbler than that, right?

He makes the Argentinian team, now he's pretty good.

He gets an opportunity to play in Europe where he plays.

He gets drafted like very late.

A total surprise.

He had not actually even entered the draft.

He was just drafted by the Spurs who let him play in Europe for like three years before

he comes over.

Almost nobody believed in him.

I mean, he knew what he, he knew he was good and he was confident in his abilities, but

there was not these delusions of great.

He was not Kanye West going around saying, I'm Steve Jobs, right?

Like this was in the Churchill book.

They talk about this Churchill did not at the, at when, when Britain is standing alone,

he does not know for certain that he will be able to bring America into the war.

What Churchill does is he buys some time, right?

Like all of these things start small and they build when the person has this vision that

they can clearly articulate that they know to be like that to me, that leads to disaster

more often than the prophecy comes true.

Dude, that's crazy.

Fascinating to me.

I got to keep thinking about that.

But another thing that you're associated with that I find like equally impressive, even

though it's much smaller now to all the other things that you've done is the ghost town,

which I'm a very, very, very small investor in, but the reason why it's awesome is, no,

you're not a small investor.

You're the guy.

The reason why it's awesome is the guy, well, you're, you're, you're, I, I view you, Brent

and Nathan and Nathan Berry as like, you know, the, the guys, but so basically like in 2015

or 14, you guys like, you know, got some money together and you bought this town that went

viral because it was like, you can buy a whole town for $1.3 million, a ghost town and you

guys bought it and it was like doing okay, whatever.

And then the pandemic hit and Brent spinups this YouTube channel and it felt like in a

matter of six months, it got a million subscribers and I remember being in my apartment in San

Francisco, miserable that I'm trapped in this place and I see these videos of him and it

felt like it got me through the first like 12 months of the pandemic watching those videos.

I felt so much better watching these like 20 or 30 minute videos of this charming, cute

dude named Brent like saying like, Hey, so here's this old mine that I just found in

my town.

Let's just like, you know, walk a hundred feet into this mine and let's just see what

we find.

And it's when you think of a mine, you think of like a cave and this was like a, like a

crawl space and you just like, it's going deep in these places and that was amazing.

What's your feeling on how everything's going with that and like, what's the plan?

Well, I mean, a hundred feet in a mine, one of the mines is 900 feet straight down that

he regularly goes in.

It's fucking insane.

It's crazy.

His videos are so good.

Did you advise him or you guys were partners on something to see, did he get the content

bug from you?

Are you advising him?

How is this shit so good?

It's an amazing story.

It actually goes to what we're just talking about like as an outsider or in retrospect,

it feels like Guy makes brilliant investment, buys town, turns it into a YouTube channel

and makes these amazing videos and it seems obvious now blows up.

Yeah.

But that's not how it went at all.

Right.

Like first off, by the way, what's the channel?

Ghost Town Living.

Okay.

When he first told me about it, I was like, dude, that's a horrible idea, not interested

at all.

Right.

Like I came in at a very small level at first because I didn't think it was a good idea.

But Brent's idea was buy this place, find, build a hotel on the site and make it some

sort of like luxury resort thing that they failed to do for like two years, maybe even

three years.

He had no intention of living up there.

It was losing money hand over fist.

Right.

Like he...

How many acres is it?

I wouldn't say it's 300 acres, but it backs up to like thousands of acres of government

land.

And it's like in the mountains.

It's basically unlimited land.

Like four hours outside of LA?

Yeah.

It's about three and a half hours from LA.

It looks down on Death Valley at about 8,500 feet.

It was once the largest silver mine in the United States.

But there's like no water and electricity, right?

Like...

I was just up there, like I took a nice warm shower.

There's water now.

Oh, but there wasn't, I guess is what I mean.

There was not.

I mean, historically there were some springs and then those dried up and I mean, it has

always been a battle of the elements, but it's funny that you bring up how you liked

the videos during the pandemic.

My four year old fell in love with the videos during the pandemic.

And that's part of the reason I ended up investing more money in it was that my son is obsessed.

Like he knows, he had trouble.

So Brent started as my intern 12 or 13 years ago, I think.

And my son is met, I mean, is known Brent his whole life.

And he's got so enthralled with the videos that he had trouble because it was the pandemic.

We couldn't see him.

He had trouble like conceiving of the fact that this was a real person that he knew,

that this was different than the YouTube channels of other people that he watches that he doesn't

know.

Well, Brent's like, he's so charming in these videos and he's so endearing.

And like, I don't know, I've not really hung out with him.

I've only chatted with him a couple of times.

It seems like he just kind of turned on this charm and charisma and it was like intoxicating.

He's always been like a behind the scenes person.

And I think that's what's so interesting is like, yeah, he didn't just randomly start

a YouTube channel one day.

Like he started the Daily Stoke YouTube channel and he started the Daily Stoke podcast.

Like he was the one who built out the systems or created the universes for me and then that

I am obviously the face of, but he was the one who was like, here, I think we should

do this.

And he's the one that figured like, you know, we probably had a hundred thousand YouTube

subscribers when he went to Saragordo.

So he had experience that he'd learned on the job, so to speak, working with me.

And then the funny thing is we had shot some videos for Daily Stoic, like the first week

of March, 2020 or maybe the last week of February.

And he had taken the camera home to like upload some stuff.

And so when he went to Saragordo, he just took my camera or our camera, like that Saragordo

was started with equipment that he had got for Daily Stoic and then use skills that he

had developed with Daily Stoic that ultimately blew up into this thing that I don't think

he definitely not I would have predicted, but like people often underestimate how long

you have to spend developing like a baseline of skills before, you know, sort of the man

meets the moment, so to speak.

Dude, I read that in mastery.

Mastery changed my life.

I remember like exactly where I was when I read it and I was like, oh, this, this is

called apprenticeship.

Like, but I remember reading mastery and that was like a life changing book because it talked

about that.

But Saragordo.

Do you ever think about that?

Like, do you ever think about the fact that the hustle and this podcast could actually

be the apprenticeship for like a company you start in your fifties that's oh, it's going

to be larger.

It's going to be.

And people like, you know, all right.

So the hustle we sold for, let's say, tens of millions of dollars, which is like, I think

by most people, if you do, I think I was 31, 31 we sold it, which so like that's six that

I would say it's objectively successful.

But compared to others, like it's nothing, right?

Like compared to the company that bought us, it's nothing.

You know, they bought us.

And so a lot of people were like, well, you know, like you guys only did that in four

years.

I'm like, yeah, we did it in four years.

I also spent four years before that, though, studying writing and like blogging and reading

and like being a student.

And I learned a skill, which my skill was copywriting and that skill led me to this

other thing, which led me to this other thing, which led me to this other thing.

And I often tell people, I'm like, everyone says overnight successes aren't true.

And I'm like, well, in a sense, actually they can be like, you could be a Mark Manson or

something and like write a book and like it get really big, really fast.

But learning the skill for five or 10 years in advance is often necessary.

Yeah.

To give Mark credit, though, Mark doesn't hit the lottery.

I mean, Mark was an online copywriter and marketer and had a platform for a decade before

he writes a book.

Right.

But what I mean is like the set functions and growth are real, you know, like it could

be like it's going okay, it's going okay, it's going okay.

And then a matter of like a month or three months is like, boom, something just changed.

Like that is real.

And I think people actually don't like acknowledging that because the story of like slow and steady

is preferred because that like there's more character to that.

But like a step functions exist, but you have to work a certain amount of time typically

in order to get that step function.

That's what I mean.

No, I think about Michael Lewis in that regard.

Like Michael Lewis is is a fantastic writer.

He's been a great writer for 40 years.

He wrote Liars Poker, which is about finance.

He wrote the blind side.

You know, he wrote a number of these books that were that were big.

And he was he was a leading nonfiction author.

And then 2008 happens.

And it's the most inexplicable, but widespread financial event of, you know, since the Great

Depression, and he is uniquely suited to write the Big Short, which was his big transformative,

you know, huge book, like Moneyball the Blind Side, the other movies that come out.

I believe they come out after the Big Short.

Like Michael Lewis today looks like he's always been huge, but you don't realize his

career was sort of like this and then like this, right?

Like I think about that.

I'm very proud of all of the books that I've written and I continue to write them and work

on it every day.

But I don't want to say I hold that hope, but I I feel like there's some part of me

that thinks all of this is training for like the book at the moment.

Maybe it happens.

Maybe it doesn't.

I mean, it's the moment, but the book only sells 10 copies.

But like I do feel like it's building towards whatever I'm meant to do.

Are you not satisfied with your career?

No, I'm very satisfied.

Like I was just writing about this in my journal this morning, like when I'm look at the sales

number of this book, this isn't just like what I dreamed of.

This is like 10 X what I even conceived of as being possible.

I'm just saying I want what I'm working on to set me up for something truly challenging,

so challenging that I or perfect for my skills and what I my worldview that I can't even

think of it yet.

Dude, consistently, I've said once I hit this wealth number, I likely won't want any

more.

And then I always do once I lift this much weight or do this type of athletic feet that

I've been really working hard towards, like I'll be happy.

And then I get there.

Like, but we could go a little, we could do a little more.

So like, I think that's just unilaterally true with at least people who are driven

up to achieve anything.

Interesting.

Like it's just like, I've just settled with it's just never enough.

And that's okay.

I've never heard of someone getting to the number, like actually getting the number because

the goalpost always moves.

So when I hear people say there's a number, like when I when I talk to an author and they're

like, my goal is to sell a million copies to whatever I go, like, I don't have goals.

Like, why would why would you even put a ceiling on it?

Right?

Like what you should just try to sell as many copies as it's capable of selling.

Do you have other than like, be a good dad and be a good person and all this stuff?

Do you have any professional goals for the next five, 10 or 20 years where you say, like,

this is what I want?

Or any people who you say, I want to be, I want my career to be similar to this type

of person.

Yeah.

So like, I sold this four book series.

So to do it for like four interlocking interrelated books in ostensibly four years, that's what

it could change.

But like, that is like the mountain that I'm climbing right now because it was unlike the

mountains that I'd done, I'd done before.

I don't have like a certain number of books that I'm trying to write or a certain number

of copies that I'm trying to write.

And there's like, I've never written one of those biographies that we were talking about.

And there's some part of me that thinks about maybe doing that at some point and doing it

from a place.

Anyone in particular?

I do have a person, but I don't want to say because someone might steal it.

But I have thought about doing a big, a big book like that.

And there's a part of me that thinks being able to do it and not care financially, like

if it takes five years or takes 10 years, like there's a part of me that thinks about

that.

And so I have a couple ideas like that where I'm like, that would be a cool thing to do.

But like, I have the weird sensation, I'm sure you have this too, of like very much

feeling like I'm playing with house money.

And that's both really fun.

And then it's also a little, it's like a little unmooring because you're like, shit, I thought

I was running with everyone else.

And then now I'm just like, by myself, am I going fast enough?

Am I going too fast?

You know?

You don't want to lose it.

It's like, that's a weird feeling where you're like, well, I have what I wanted.

I thought that I'd be willing to like spend this much to invest on my idea.

And then it's like, but I don't want to lose this.

And that, that also exists.

Well, you, you think that being successful will make you more courageous because you

are more secure, but it actually, the rational response to having a lot is to become more

risk averse because you know how hard it was to get it.

And so there's a tension there.

You know, how do you, how do you continue to push yourself without being reckless?

And how do you protect what you've built without being complacent?

Wait, but you, you just said something that reminded me of the Fisherman story you started

off with, which was, you said like, I want to write this biography and I hope I'll be

at a place where like financially it doesn't matter.

Do you, you don't feel that you're there already?

No, no, no.

I mean, I feel like I'm there.

I just have to get through these two books.

I've are like, I'm already creatively committed to an idea, like a director.

It's like, Hey, I've already attached to these two movies, three movies.

Then like once, once my plate is cleared and I'm not trying to, I'm not trying to put it

off into the future.

I don't feel rushed to do it.

I'm just saying like when I have a clear plate or open road in front of me, I think

that's probably something I might fuck around with.

Any topics that we didn't cover that you think need to be covered?

You know what?

Yeah.

I mentioned to you in text, you were like, well, can we talk about like how much money

your books have made?

That's what I said was, I go, how much money have you made?

How big's your dick?

And what's your social security number?

Yeah.

No, it's, it's funny, like on my first books, obviously books as a market are less interesting

to people than like the movie business, but like whenever I would sell a book, like your

agent or publisher, they're like, should we announce this deal?

Like there's trades, right?

And sometimes like a, my first book got a ton of publicity because I was like a kid

who came out of nowhere and sold a book for a bunch of money.

I was always, I was like, I want to press release.

Like I want to put this out.

And then probably starting, I think it was with stillness, it might've been after, definitely

with this series, I realized that there was no advantage to doing that.

That when you start talking about what something is sold for or how, like I've two things.

I thought, okay, so I saw this four book deal and it was a, it was a very large deal, at

least for me.

And I had two thoughts.

I said, one, telling people how much money I made from it, it makes you a target, makes

you weird, you know, it could, it could somehow be seen as selling out or something.

But then the other part, I thought, I don't want people, this is an idea that's going

to take me four plus years to get to the end of.

Why would I want to give people who might be writing in the same niche, like a heads

up about what I'm doing.

And so I don't think I've announced, you know, when I did a podcast deal, when I've sold

other projects, like I see no benefit to putting out specific figures.

I only see downsides to that.

Who'd you do a podcast deal with?

No, I do agree with that.

At first, you know, it's like that song, if dammit feels good to be a gangster, they

said, real gang, real gangsters don't flex nuts because they know they got them.

Yeah.

And that's how you you make the police come after you.

Right.

But I used to feel that way where I'm like, yeah, like when I I mean, I'm still insecure,

but when I was even more insecure, I would be like, yeah, I need to I'm going to rub

this into my high school friends face.

Yeah.

And now I'm like, I don't want to get sued.

I don't want to be a target.

I don't want people to pretend because I get all these fake people on Twitter or Instagram

pretending to be me or like people like threaten to sue you when you're not wrong at all.

Like now I'm like, oh, I don't want any of that nonsense.

Yeah.

I did a I did a podcast deal with Amazon Wondery like maybe three months ago.

How big is the pod now?

Or do you measure it in podcast downloads or YouTube views?

YouTube isn't wasn't included in the deal.

So it's separate.

But podcast is fantastic.

Okay.

I think we crossed 100 million downloads.

That's crazy.

We're getting close to being able to do that annually, like not quite, but like that to

me, that's that's where the numbers are heading.

Our monthly downloads on the podcast are range between 1.5 and 2 or 1.3 and 2 million.

And then the pod that and then the YouTube episode views are another one or 2 million.

So we're in the range of two to five on any given month.

And our next target, I'm like, how do we get to that five to 10?

Sounds like you're there.

Dude, I think I think YouTube is the it's weird to say like YouTube is the big thing

because it's been around for 15 years and it's already huge.

But like the growth I'm seeing on YouTube stuff, especially now even with shorts.

It's crazy.

And that's dude.

People are age and older.

They're like, what?

YouTube?

I'm like, no dog.

YouTube is TV.

Like, you know, YouTube is where it's at and it still has so much room because I only

watch YouTube as my TV.

It's the best.

Well, dude, you're awesome, man.

I asked you like who you admire and who you want to steal from.

And I have like a short list of maybe three or five people and you are on that list where

I just think like we're like, you know, I'm a family guy like you, I don't have kids yet,

but like I see you raise your family.

I see you with your wife.

I see like, you know, I also bought a kind of like a farm inspired by you.

I live in Austin most of the year.

Like there's so many things that you've done where I think this guy's nailing it and I

want to steal a little bits and pieces of how he's doing and how he's living life and

I admire your confidence, your drive.

I mean, I'm on I'm on the Ryan Holiday train and I've been on it since the first book.

So we got to hang out when you're back, I'll hold you when I get back and I appreciate

you coming on, man.

This is awesome.

And say the book name again.

Oh, discipline is destiny.

The power of self control as part of the Stoic Virtue series.

The first one is Courage is Calling.

Where do you make the most money where people buy it?

If you buy it from from dailystoic.com or my bookstore, the painted porch.

Awesome.

Well, I appreciate you, man.

This is awesome.

Thank you.

Thanks.

I know I could be what I want to put my all in it like days on a road less travel never

looking back.

Machine-generated transcript that may contain inaccuracies.

Episode 370: Sam Parr (@TheSamParr) talks to best-selling author, podcaster, bookstore owner, and former marketing director for American Apparel, Ryan Holiday (@RyanHoliday), about how to make money in publishing, creating a masterpiece, and investing in a ghost town.
-----
Links:
* Ryan Holiday
* Trust Me I'm Lying: Confessions of a Media Manipulator
* Brass Check
* The Painted Porch Bookshop
* Vinyl Me, Please
* Ghost Town Living
* Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel.
* Want more insights like MFM? Check out Shaan's newsletter.
------
Show Notes:
(03:55) - Does the bestseller list still matter?
(05:30) - Breaking down the #s of the publishing industry
(29:20) - How big is your team?
(35:10) - Who do you admire?
(44:40) - The pros and cons of reality distortion fields
(50:40) - Ryan's ghost town
-----
Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more.
-----
Additional episodes you might enjoy:
• #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits
• #209 Gary Vaynerchuk - Why NFTS Are the Future
• #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto
* #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett
• ​​​​#218 - Why You Should Take a Think Week Like Bill Gates
• Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More
• How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More