Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More | My First Million With Sam Parr and Shaan Puri (#370)

Key Takeaways

  • The decision to put your book in paperback is a multi-million dollar decision (most authors have never even thought about it)
  • As you start selling lots of copies internationally you start seeing a lot less money
  • Books are like operas— they punch above their weight culturally
    • “You could be very famous on YouTube and your average billionaire might not know who you are but if you write a business book or a political book that sells reasonably well you’re gonna have some name recognition in an elite group.” – Ryan Holiday
  • He feels lucky that his books haven’t sold as much as James Clear or Mark Manson’s books
    • When you hit the one million mark in several months, your whole world changes; expectations change, inbound inquiries change, and it becomes harder to do what you love
    • “There are just more people who haven’t heard of me than have heard of me and that is a nice place to operate it.”Ryan Holiday
  • Quality and quantity don’t necessarily have to be at odds with each other
    • Quality versus quantity is a false dichotomy; quality IS the quantity
  • 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)
  • The problem with the monthly book subscription club businesses is getting to a place where you can move a lot of books and the revenue is high
    • At the very very best you’re gonna be able to get those books at 50% off from the publisher
  • The more successful people Ryan meets, the less impressed he is by their money or accomplishments and more about:
    • Are they good parents?
    • How do they stay grounded in reality?
    • Are they able to wake up and enjoy their day?
  • Ryan wants to be world-class at what he does and be a somewhat normal person
    • “It’s almost easier to be great than it is to be good.” Ryan Holiday
    • People like “Manu” Ginóbili or Chris Bosh make it seem like their mentality is achievable; they are normal/relatable
  • Ryan is one of the owners of Cerro Gordo, an old ghost town in the Sierra Nevada mountains

Intro

  • In this episode, Sam Parr speaks with best-selling author, podcaster, and bookshop owner, Ryan Holiday (@RyanHoliday) about the ins and outs of the publishing industry, what he learned hanging out with Emanuel “Manu” Ginóbili, and a certain well-known musician, buying a ghost town with his friends, and more!
  • Host– Sam Parr (@TheSamParr)

Does the Bestseller List Still Matter?

  • The 3 national lists you have to hit to be called a national bestseller:
    • The New York Times
    • Wall Street Journal
    • USA Today
  • People generally don’t buy books because they see them on the list
    • Most people don’t even know where they would find such a list

Breaking Down the #S of the Publishing Industry

  • The book business is actually great; the publishing industry is a 40 billion-dollar industry
  • The decision to put your book in paperback is a multi-million dollar decision (most authors have never even thought about it)
    • On a hardcover book, the standard publishing contract is 15% of the hardcover price
    • In this case, an author makes 15% of 27 dollars whether you as the customer buy it for 17 dollars on Amazon or for 27 dollars at an indie bookstore
    • A paperback sells for about 10 to 15 dollars less than a hardcover, but your royalty is 12 and a half percent
    • Ryan’s agent said to him that he will never let his books go into paperback
    • You have to sell third more books for the same amount of money that you sold in hardcover
    • This is why Tim Ferriss’ books are not widely available in paperback
    • “Good to Great” by Jim Collins is still in hardcover even though it’s a 20-year-old book
  • What about audible and ebooks?
    • Audible and ebook are about 25% off the list price; it’s a higher royalty, but at a lower price point
    • You make about 2 or 3 dollars a book across formats
  • Publishers were skeptical about Ryan’s book “The Obstacle Is The Way”
    • An obscure book about stoicism is not going to sell that much, they thought
    • They didn’t believe it would sell millions of copies as it did
    • His advance on the book was 75,000 USD

The Quirks of Business

  • As you start selling lots of copies internationally you start seeing a lot less money
    • E.g. somebody sent Ryan a copy of one of his books from Iran
    • Iran doesn’t recognize copyright they just do whatever they want
    • He never saw a penny from these books
  • If you sell a million books in Russia right you’re not getting your standard royalty rate
    • You might get an initial advance, but you may never see a penny of that
  • As you sell, there is less transparency in the accounting
    • You can’t simply go and find out the total number of copies sold by a person
    • Using that as a metric to find out how much money the author makes is not really legitimate

Writing a Book vs. Investing

  • Sam Parr was thinking about how Tim Ferriss’ book earnings pale in comparison to his other revenue streams (Shopify, Uber, and many other seed investments)
    • Ryan doesn’t do that many investments but he was an advisor early on to ButcherBox
    • He took part in some of the private transactions; it was both humbling and surreal to get a check and realize that he would’ve had to sell a lot of books to get the same amount of money
    • A lot more money for a lot less work
  • Tim Ferriss told Sam Parr that writing a book sucks; it’s very uncomfortable and a lot of hard work
  • A lot of rich people read books
    • Books are like operas— they punch above their weight culturally
    • “You could be very famous on YouTube and your average billionaire might not know who you are but if you write a business book or a political book that sells reasonably well you’re gonna have some name recognition in an elite group.” – Ryan Holiday
    • Ryan got to meet many successful business people over the years and they all want to write a book

Do You Really Need Money to Do What You Want to Do?

  • Doing stuff that you like is what people do with their money once they get rich
  • Ryan tells a story about a friend who wrote a couple of books and then started a venture capital company
    • To raise the fund, he had to quit writing for a while
    • Ryan asked him about his plans if he is successful and walks away with a lot o money
    • He wanted to do something like Alain de Botton’s School of Life; an educational company that offers advice on life issues
    • Ryan couldn’t help to burst into laughter because that was something he can do right away
  • People think financial freedom is this abstract good that will solve all your problems
    • When people get rich, they still don’t know what to do when they get up in the morning

How Does Ryan Manage to Output So Much Great Stuff?

  • The vast majority of his content is based on his books
    • He also has people help him translate that content into different mediums (YouTube, podcasting, etc.)
  • Ryan wants to be like Bob Dylan in that way, creating lots of great stuff:
    • The Daily Stoic, The Daily Dad, the books, the podcast, the youtube channel
  • He actually likes doing it; some people do it to make money
    • The more you do, the chances are you’ll get something magical or important
    • Quality and quantity don’t necessarily have to be at odds with each other
  • He feels lucky that his books haven’t sold as much as James Clear or Mark Manson’s books
    • When you hit the one million mark in several months, your whole world changes
    • Everything shifts; expectations change, inbound inquiries change, and it becomes harder to do what you love
    • “There are just more people who haven’t heard of me than have heard of me and that is a nice place to operate it.”Ryan Holiday

Quality Versus Quantity

  • Quality versus quantity is a false dichotomy; quality IS the quantity
    • Quality + quantity = total reach and impact
    • You need quantity, you need the swings to get better
  • Imagine a stand-up comic that doesn’t do much stage time
    • The way you get good at it is by doing it a lot
    • It’s very hard to get to quality without years of quantity, especially online where you’re giving something away for free 
  • 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)
    • Ryan sent a free email every day for six years
  • When someone says it took them 5 years to write a book…
    • “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 in saying that they’re doing the thing that they’re really focused on quality.”Ryan Holiday
    • Most people take way too long to do things 

Monthly Book Subscription Club Businesses

  • The book of the month concept goes back quite a bit; it used to be a way that you would guarantee a book success if you were selected to one of those clubs
  • The problem with the business is that not many people read in the first place
    • Also, the logistics are tough
    • At the very very best you’re gonna be able to get those books at 50% off from the publisher
    • The really hard part is getting to a place where you can move a lot of books and the revenue is high
  • Ryan thinks there are ultimately better ways to monetize that attention than a list of subscribers you have to service each month for a specific kind of book

Who Does Ryan Admire?

  • Emanuel “Manu” Ginóbili
    • Manu has four championship rings and got inducted into the Hall of Fame
    • Manu is just a normal guy; usually when you think about someone who has four rings you think more of like a Michael Jordan character who is fundamentally out of balance
    • Jordan is one of the greats, no doubt about it, but “…we tend to think that to be that good requires some fundamental trade-offs about what kind of person you are and what your life looks like.” – Ryan Holiday
  • The more successful people Ryan meets, the less impressed he is by their money or accomplishments and more about:
    • Are they good parents?
    • How do they stay grounded in reality?
    • Are they able to wake up and enjoy their day?
  • Ryan wants to be world-class at what he does and be a somewhat normal person
    • “It’s almost easier to be great than it is to be good.” Ryan Holiday
    • People like “Manu” Ginóbili or Chris Bosh make it seem like their mentality is achievable; they are normal/relatable
  • There is also a certain musician whom Ryan doesn’t feel comfortable naming
    • The mysterious musician contacted him after he read Ryan’s books and invited him to a dinner in New York
    • Talking to this person, Ryan realized that at the end of life, when you reflect on your success, you are going to think about:
      • Do my kids want to spend time with me?
      • How good is my marriage?
    • Despite selling millions of albums and flying in a helicopter just to have dinner (which is fundamentally not normal), this person still worked very hard to remain rooted in some semblance of normalcy (good relationship with his kids, married to his high school sweetheart)

Peter Thiel’s Revenge on Gawker

  • Peter Thiel spent 10 years chasing Gawker because they outed him as being gay
    • Ryan has trouble understanding the anger and resentment that drives that kind of behavior
    • Sam Paar would do the same as Thiel in that situation; if someone wrongs you so casually and cruelly and you have that much power, why not crush them?
  • Ryan compares the situation with the Count of Monte Cristo; the oldest revenge story in history
    • However, the problem that Ryan sees is when people start to feel like they can bend the world to their will and that gets them sucked down other avenues (e.g. some of the political bets Thiel made)

The Pros and Cons of Reality Distortion Fields

  • Bending the world to your reality; it’s incredibly intoxicating according to Sam
  • Examples of bending the world to your reality:
    • Writing a book that millions of people read
    • Becoming powerful in politics
  • Basically, making money on your own is the easiest and most practical way for most people
  • “I’m 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.” – Sam Paar
  • Early on in his career, Ryan saw people who could do that also destroy themselves
    • He used to work for Dov Charney
    • The beauty and the danger of the entrepreneurial journey is that you have an idea for something that is insane, and then you do it and it works
    • Creating something out of nothing that violates everyone else’s conception of what’s possible
    • The danger of that is seeing yourself as a person who now does that, and you see people who criticize you as the enemy
    • That is exactly why Dov Charney crashed and burned; when you think that rules don’t apply to you and you think you can bend reality to your will

Ryan’s Ghost Town

  • Ryan is one of the owners of Cerro Gordo, an old ghost town in the Sierra Nevada mountains
    • Cerro Gordo was purchased by Brent Underwood and co. for $1.4 million
    • Ryan is one of the investors and owners of the ghost town
  • Ghost Town Living YouTube channel by Brent Underwood – the content kept Sam entertained during the pandemic
    • Ryan’s son was also obsessed with the videos during the pandemic; that’s why Ryan decided to invest more money in it
  • Ryan Holiday has known Brent since he first hired him as his intern over 10 years ago
    • He didn’t just randomly start a Youtube channel one day; he already had experience working with Ryan and Daily Stoic
    • Brent was the one who built out the systems and created the universes for Ryan
  • “People often underestimate how long you have to spend developing like a baseline of skills before you know the sort of the man meets the moments, so to speak.”Ryan Holiday
My First Million : , , , , ,
Notes By Dario

More Notes on these topics

Top Insights and Tactics From

31 Best Podcasts of All Time

FREE when you join over 35,000 subscribers to the
Podcast Notes newsletter

No Thanks