I am Ryan Holiday -- "media manipulator," Director of Marketing at American Apparel, and bestselling author of “Trust Me, I’m Lying” and “The Obstacle Is The Way”

If Marcus Aurelius read your new book, what's one bit of feedback he'd give you?

Wow, that's a really good question and one I haven't thought of before.

Obviously I hope he'd like it and appreciate the homage I was intending to pay. Maybe he'd remind me of the other parts of stoicism that I didn't address (but are important). And I imagine he'd point out that success and ambition are not the most important things in life. That yes overcoming obstacles is important but it matters which ones you decide to tackle and what for.

How do you personally decide which obstacles to focus on?

Like let's say there are certain obstacles preventing me from having a pristine six pack. I could focus on that, but what is motivating that goal? Is it real need? Or vanity? Couldn't one be in healthy, good shape without pursuing the goal that far?

So I try to ask question like that--so the obstacles I tackle and the problems I focus on are aimed towards admirable, virtuous goals.

Your six pack is pretty pristine, imo.

Well that's neither here nor there John.

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Well, I was fortunate enough to be Robert Greene's research assistant on his book with 50 Cent, The 50th Law. I got connected to Baby and Slim through their agent to work on a business book about Cash Money. It probably didn't hurt that I lived in New Orleans at the time. Their story is really one of the biggest and most impressive music success stories of all time. They've sold something like 500M songs...and they actually own their label. It's not a vanity label, they have a distribution deal with Universal. In other words, Cash Money made 85% of the profits from those 500M songs.

Our schedules have been crazy and made working on the book difficult but I have an intro written and a bunch of research done already. We spent a week or so together in Miami last year and now we are trying to get together and finish the thing. I desperately want to write this book and show people what geniuses they are.

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I got to ride on their private jet, that was pretty cool. But generally they avoid flying, so we drove in their tour bus from Atlanta to New Orleans. And for the most part, they sleep during the day and work at night--rolling into the studio around midnight. It was just very inspiring to be around two geniuses who don't get even close to the credit they deserve. Part of the reason for that is they are so busy working and doing stuff that they don't talk about it.

I also attended their annual turkey giveaway in New Orleans where they gave away 2,000 turkeys in the projects where they grew up.

What would you attribute their success to? 500M is an amazing amount of songs/sales.

Reinvention. Look at how many different iterations of their acts they have done. Also, they put out WAY more music than anyone else--because it's actually their business. It's not a branding play to sell other stuff.

New Orleans, eh? Ok I have to ask a random question - is there a Jonah Hill look-alike frontman for a 90's hip hop band in New Orleans? Or was I singing Jump Around with the actual Jonah Hill last summer?

He does spend a lot of time there.

What are the three most important things you learned from Tim Ferris?

• Build a platform
• Expand into other businesses, don't just be a writer
• Break things down and look at them from angles or perspectives other people are afraid of
• Be exacting and demanding with your work product. Don't settle
• Invest in yourself.

Can you explain what is meant by the first point: build a platform?

And also, what do you mean by invest in yourself?

I'm pretty sure I have a good idea on what is meant by both of these, but I would like some further clarification if you're willing to provide it.

Authors think their job is to write books. No, an author has to write a book and then market it. You can't market it if you don't have a base of fans, relationships with media and influencers, and the ability to spread your message. Who will buy the first 1,000 copies of your book? How will you reach them?

By investing in yourself, I mean spending money and time to accomplish the points above. These things don't magically happen. Tim traveled to dozens of conferences around the world on his own dime before his first book was out to lay the groundwork for his marketing plan. That's what it takes.

What advice do you have for someone just starting to write?

• Spend less time writing, more time doing
• Say the things that only you can say
• Be patient. I started my blog in 2006. I got my first writing check in Dec 2011
• Be ok with sucking at first
• Publish a lot
• Meet and learn from other writers (or as Austin Kleon says, steal from them)
• Read a lot

Could you elaborate on the first point. By doing, do you mean researching? Like if I'm writing a music blog, would you recommend that I go to more shows and listen to more music, or make more music? Or just stop being such a homebody?

Also, point two, do you mean write from experience and be very opinionated, or are you talking more stylistically?

I mean all of that. Writing as a craft is not difficult, having something to say is the competitive advantage. (post on that from me here) Saying what you have to say uniquely, and compellingly is also important.

Edit: I'm not saying writing is easy. I'm just saying with time, anyone can get good at putting words together. Spending your time seeing and living and learning is the best way to improve as a writer.

Hypothetically, how would one access the goat food?

YOU ALREADY EAT TOO MUCH BUCKET. AND LAST WEEK YOU CHEWED UP MY HEADPHONE CORD.

Hey Ryan, it seems like you're incredibly well-read. What advice would you give to someone who wants to get into learning about history but feels overwhelmed and intimidated?

Start with biographies. In order to tell a person's history, the author has to be able to distill and explain the history of the time they lived in in a simple, straightforward way. If you can start by reading about an interesting figure in an era you'd like to learn about, it will help get you going.

Here are some bios I like to start: http://thoughtcatalog.com/ryan-holiday/2014/02/25-recommendations-for-life-changing-biographies-for-voracious-readers/

. saving, [i also use your antilibrary concept now too]

To be fair, that's not my concept. It's from a bunch of people smarter than me.

What books on marketing have influenced you the most?

The best marketing books aren't really about marketing.

What are they, then?

Blue Ocean Strategy is good. So is 48 Laws of Power.

Here's my proof https://twitter.com/RyanHoliday/status/462256800994037760

Also yesterday was my cakeday. That would have been the ultimate timing.

Have you read "Additional Dialogue: Letters of Dalton Trumbo"?

He was screenwriter in Hollywood and was blacklisted in 1947 due to communist associations. His life reminds me of Demosthenes.

I am going to check this out.

I heard Tim ask Josh this question on the podcast, and I thought it was a great question.

If you could have a personal advisory board of any three people, living or dead, to serve as your mentors and advisors, who would you choose and why?

Thanks, Ryan!

Marcus Aurelius. BH Lidell Hart. Warren Buffet (or maybe David Ogilvy)

What are some amateur mistakes to avoid when trying to get press?

Honestly, most people are just really fucking boring and self-absorbed. And then they wonder why the press isn't interesting in talk about them. Look, I deal with a lot of reporters--I even manage some at Betabeat.com--there is not a single one on the planet who has ever said "Wow, there are too many great stories and companies and people out there for me to cover." They're all desperate for good stuff.

Should I get a goat?

It depends on where you live. It's been pretty fun so far.

http://betabeat.com/2014/01/i-own-a-goat-some-animals-and-a-mini-farm-give-a-tech-guy-some-peace/

what are the biggest misconceptions people have regarding what stoicism means?

That it's about being emotion-less and joyless.

Is there a difference between your commonplace book and your notecard system?

No, I don't actually keep a book. I keep a box of notecards, but it's the same thing.

reference here: http://thoughtcatalog.com/ryan-holiday/2013/12/the-notecard-system-the-key-for-remembering-organizing-and-using-everything-you-read/

You make time for reading no matter what, but how do you get absorbed in the book without thinking of all the pressing business and fully engaging with a book? How do you not wander in all the hundred other things going on?

If that happens, I blame the book for not being good enough and stop reading it. The author's job to be captivating. I don't have time for people who didn't fulfill their obligation.

Hey Ryan,

I've been following yours and Tucker's work since 2008 and I can't really express how much I've learned from both of you, and from the writing the two of you have published. I'm undoubtedly a life-time fan. So thank-you!

As for my question... You've met a lot of people who you knew about, maybe through their work, but either way you knew a little bit about them. Tucker Max is a good example of this. When meeting people you revere, aside from recognizing they are human like you, what's your strategy for not being super nervous? How do you even approach them, knowing so many people probably do the same thing everyday and whatever you say is mostly just self-serving?

I often avoid these meetings because I think my uncertainty with how I would handle the situation makes me wonder if anything good could come of it. At the same time, there's no doubt I've missed some opportunities by avoiding talking to people who I really respect and would love to talk to.

I try to think of one thing I might ask that would be a) beneficial to me b) not creep them out c) signal that I understand and appreciate their work

What other philosophies have you considered and have you ever had a moment where you seriously questioned the tenants of Stoicism?

If so, what in particular made you challenge it, and how'd you come back to it?

Stoicism is not an exclusive philosophy so I've never considered this. If I see something I like, I just start using it.

Why are you more of an Edison fan than a Tesla fan?

Because Edison was a hustler and Tesla seems like a snooty jerk.

Hi Ryan, I've been following you a lot this past year and really enjoy your reading lists, and your two past books were great! I'm curious about your daily routine. What does it look like? What's helped you with your self-discipline?

• Wake up around 8
• Check email
• Write for about two hours
• Eat
• Work, do phone calls, meetings, business stuff
• Run/go to gym to swim or do crossfit
• Eat dinner with my gf, walk dog
• Work a little more
• Watch TV/read/sleep

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Conflict is not the opportunity. How you behave in the conflict is.

Hi Ryan. I read your 'Growth Hacker Marketing' book, which I found really interesting! Do you have any recent examples of growth hacking in the music industry (other than the ones using BitTorrent)?

One of my firms client's is Young & Sick. We've done some pretty cool stuff there and I am big fan of his model of doing music + art + design

What is the grand strategy for your life?

This is it man.

You said Penguin paid for your two books around the same time. Did you plan on using TMIL (the book you had to write) to leverage an audience for TOITW (the book you wanted to write)? Or did it just make more sense to release TMIL first?

I sold all three books separately. First TMIL, the TOITW, then GHM. I always intended to do a book on stoicism, I just didn't know when or how. I took the success of TMIL as a chance to jump on it and Penguin did too.

Hey Ryan, I'm loving your new book. I'm self-publishing a book of my own in a few weeks.

What are some tips you can give to a first time author?

I tried to put all my thoughts on that here: https://medium.com/on-publishing/6c5df618499b

I've been interested in stoicism for a while. What is it about stoicism that attracts you so much? What are the most important ways it has affected your life? If you had to sum up stoicism in one sentence, how would you do it? If someone was interested in it, what resources other than Meditations would you encourage them to try out?

Also, what are your thoughts on Robert Greene? What's he like? I loved his books but they gave off a somewhat amoral vibe.

Also, I'm emailing you now for that reading list. Thanks!

If I had to sum it up in one sentence I would say: "We don't control the world around us, only our response--and Stoicism helps you with the response."

Re: Robert: He's amazing. One of the smartest people I've ever met and has been a patient and generous teacher. It's important never to assume that you know a writer because of their books.

Your outlook on young people who want to be writers is excellent advice. How do you stop yourself from internalizing that self-awareness to such an extreme that it prevents work? This might sound stupid or lazy, but isn't it a real fear in someone whose insecurity and self-consciousness causes them to feel unworthy and hide?

Of course and that's a perfectly understandable fear. What you have to understand is that those traits produce great writing. Most writers are fucking nuts. Most of our favorite pieces entail somehow exposing a core part of themselves. So lean into that. Get comfortable with it.

• what are your 5 top strategies to market a book?
• what are your 5 top uncommon strategies to market a book?

https://medium.com/on-publishing/6c5df618499b

Say Marcus Aurelius was still alive and you didn't know him, and wanted to work with him after all that he's done for you. How would you reach out to him without fanboying out? I find this extremely difficult...

I'd show him the book I wrote about him.

Who are your 5 favorite bloggers?

• Felix Salmon
• Tyler Cowen
• John Robb
• Ta Nehesi Coates
• Dear Prudence

Would you rather fight 100 goat sized Tim Ferriss' or 1 Tim Ferriss sized goat?

I would not fight Tim Ferriss at any size. He's trained longer and in more forms of combat than I have.

Hi Ryan! What is one book that you feel everyone should read?

Meditations by Marcus Aurelius. But I wouldn't stop at one book. I have a monthly list if anyone wants recommendations.

Ryan, I really enjoy your writing style. It's just so fluid and readable. Can you give any advice on becoming a more "natural" writer like yourself?

Thanks for saying that. Honestly, style comes from a mixture of your own voice and the early influences that you steal from. I suggest Austin Kleon's book Steal Like An Artist.

And also don't give a fuck about convention.

I have not read your latest book yet, but I wonder about the premise. Sir Basil B.H. Liddell-Hart points out in many many of his books, that the slaughter that occurred in WWI was a direct result in the mis-interpretation of Clausewitz. That doubling-down on strong-points, is a failed strategy. His ultimate realization was that commanders that adopted an "indirect approach" like T.E. Lawrence, William Tecumseh Sherman, Hannibal, Erwin Rommel and George Patton created success by being where the obstacle was not.

"Trust Me, I'm Lying" has delivered great insight to me, but the premise of the new book is puzzling.

I have a chapter in the book based on Liddell-Hart and the indirect approach.

The saying that "the obstacle is the way" does not mean you attack it headon like an idea. It means that you face it, lean into it and allow it to instruct you.

if you were 21 again, what would you be doing?

Probably working at a startup that I thought had potential. Or creating my own company.

Hi Ryan, long term reader here, love what you've done [work with tim ferris, robert greene, american apparel etc], and enjoyed your book on growth hacking. My question was about your most recent post that you made after having a series of unfortunate events [the crash, house getting burgled etc]

my question is how does one maintain an air of calm when lots of sh*t so to speak hits the fan all at once?

i am trying to create my own business on the side while i am work part time but honestly i find myself creating mediocre and living very much day to day, rather than keeping long term focus. it also does not help that i've had a world of shit events happen to those i care for around me recently, so its hard to spend my little free time on intense focus, rather than numbing myself to the shit thats going on [either through distraction, entertainment or other things]

so my question more specifically, how do you keep focused, not settle for comfortable and mediocre, and more importantly how to stay strong and keep moving forward even when it feels like the world is conspiring against you?

I have to be honest. I was wrecked after that accident. It took a long time to get settled down after. But that's ok. I didn't do anything rash, I didn't make it worse. I just let the emotions sit and I worked with them until they dissipated.

Thanks for your writings Ryan, long time follower here. Honestly, I don't have anything to add, but I would love if you read this speech by Charlie Munger (Warren Buffet's partner), and maybe someday write something about him, im pretty sure you would be interested.

http://ycombinator.com/munger.html

Already read it!

Hey Ryan, I'm two thirds through your book, it's fantastic. You nailed it. It's great to see the progression from your previous writing. I like how you managed to incorporate the growth hacking principles into the iterate chapter. One thing I've always wondered, have you thought about entering politics later in your career?

I imagine my first book probably eliminated any possibility of a major political career but maybe something some day.

Suppose I had questions I may want to ask in the future, outside of this AMA. What is the best method of contacting you? Are you able to respond to every person? I imagine this is a difficult task.

I try. Email me. It's just my name at gmail.

Hi Ryan. just a quick question...you mention that we humans are not endangered anymore to the extend to which our emotions react...but you know that there are people in Middle east, Africa, Ukraine etc where the fears are relevant right? I am just saying that your book is from a perspective of an American living in a relatively developed country so mostly the ideas apply to the same territory you come from. Just a brief remark.

Of course. But you understand that it's probably better to live in Ukraine now that it was say 750 years ago, right? You also understand that I based the book around a philosophy that is 2000+ years old, right? And that its main pioneer was a former slave, right? So its not a stretch to say that the ideas pretty much apply to anyone, anywhere--perhaps even more so in more difficult places, right?

What are the most important thing you learned from Neil Strauss?

He introduced me to my favorite fiction author ever, John Fante, so that's a big thing. If that wasn't enough, I'd say:

• How to be an unassuming nice person despite success
• How a book should take the author and the reader on a journey
• How to ask interesting questions
• How to be confident in yourself--as a man--without being like a macho douche
• How to create businesses off the back of a book
• And a lot of other stuff

Any book of Strauss' in particular? Or do you know him in real life?

I do yes.

Why did you decide to release GHM as an ebook before releasing the full book as a paperback?

The publisher bought it as a "single" meaning it was supposed to be a 10k word ebook. It ended up doing so well that they decided to expand it into a full book. Ironically, this is pretty analogous to growth hacking. You start with your minimum viable product and then based on market feedback, decide how to proceed.

Hey, I'm looking forward to reading your books... In all honesty I have never heard of you until now. I think it may have to do with the rock I live under here in Canada... I intend to spend some hours reading your blog and book recommendations... Anyways, as a stay at home mom, I have a huge passion for advertising, copywriting and marketing. I have a little business doing graphic design/logo design/typography art but I would love to expand more into the advertising direction... Being almost 30, with 3 small kids underfoot, My big question is do you think it's worth it to get a degree at a university or just try to make it on my own? I'm very naturally creative but tend to doubt myself sometimes.. I hope this makes sense! Thanks in advance! I hope you get to read this!

Edit: a few words

I think you should just go for it. If you're already working and have some small success, I'm sure you can see how little credentials actually matter. What matters is your work and your relationships and how your clients feel. Investing in excelling at that is going to pay far better dividends then spending a bunch of money on a degree.

I'm not saying that learning/education isn't important. The more you do of that the better. I'm just saying that for your position a diploma does not sound like it would be beneficial.

Wow thanks for your response! I've given a lot of thought into credentials would be worth it or not, and I agree with you that they are important, just in a time and place, which I also agree doesn't seem to line up with my time and place.

I love what I currently do and feel the advertising (etc) would push me more creatively, as well as offer something more to my clients. Do you have any specific favorite books/ blog posts about advertising/marketing... Sorry if you answered that already.. I'm just getting my kids to bed then I can really dig in to your previous posts :)

I actually have a whole list of my favorites at the end of my last book Growth Hacker Marketing, and I have some on my site under "Reading List." Enjoy!

which stunts do you regret the most?

None really. I'm not a big believer in regret.

What's your favorite sandwich?

I've been paleo since around 2009/10 so I don't eat a lot of sandwiches but I like that monster from 2nd Avenue Deli where the bread is made from latkas.

Whoa. That actually sounds amazing....but... latkes are made with flour. Sorry for ruining it. https://www.youtube.com/watch?v=FmWd6NIloLc

Oh I didn't say this was paleo. It's definitely a cheat food.

Who is your favorite General? And why is it Belisarius?

Is this who I think it is? Obviously my favorite general is William T Sherman. Then Grant. Then Eisenhower. Then Rommel. Then Ridgway.

Hey Ryan, I am a huge fan and loved your interview on Ramit's DJ! Youre awesome dude. Im trying to keep up with my reading. I know I can't make excuses.

Do you think it is worth reading while you're at work? (9-5) There is this office perception that having a book at the desk makes you look like you're slacking. Better to hide it? Read digital? Any thoughts.

Work from home so you don't have to deal with that shit :)

You apprenticed under Robert Greene. What is your relationship like today? I know you both use a similar form of commonplace books, but is there anything in particular? In the acknowledgements of "The Obstacle is the Way", what did you mean when you said that Greene 'subsidized' your reading? Also, you refer to Tucker Max as someone who you learned from when you were young. How did you meet? (I know Max went to the University of Chicago, where I'm currently an undergrad, and have heard his 'persona' doesn't exist in real life.)

I mean that Robert paid me to read books and learn. It doesn't get much better than that. I met Tucker with I was 18 I think? He was the first person (other than like fast food) that I ever worked for. He taught me as much as Robert did, but in a different way. I was actually just at UoC to do a TED talk.

I saw a poster but tickets were sold out. I believe it'll be on YouTube soon.

Yeah, May 19th I think?

Which translation of meditations would you recommend purchasing

The Hay's translation.

Yes, definitely.

What are your 5 favorite books, in any order?

• Meditations by Marcus Aurelius
• Civil War Stories by Ambrose Bierce
• The Great Gatsby by F. Scott Fitzgerald
• 48 Laws of Power by Robert Greene
• What Makes Sammy Run? by Budd Schulberg

Personally, how do you feel about the exploitation of garment workers in 3rd world countries?

It's fucking terrible. And when you really study the business of fashion, mostly unnecessary. Not only are the margins on clothes super high, but the most expensive part of the business is all the wasteful advertising, failed product, expensive stores, NYC headquarters, etc etc. Those parts of the business could be "made efficient" with far less human cost than squeezing an extra couple pennies out of some child laborer in Haiti.

A question from my girlfriend (a philosopher): "How do you feel about theoretical philosophy and philosophy in general? You seem to criticize it, or at least conflate the field with Stoicism, a subset. Philosophy is not limited to its use-value, and there is plenty of useful, life-changing philosophy that isn't strictly practical. Academics are trying to promote philosophy and work through it themselves, that's why they read. They are critical of a work as to understand it rather than easily accept it, as a casual reader might. It's not fair to say that their work 'co-opted and deliberately obscured' philosophy."

What philosophy that is not practice is useful?

Also, I think it's bullshit to call anyone a philosopher unless they've led a remarkable life and truly taught (and lived) real wisdom. I would never call myself one, nor allow someone else to call me one. Philosophy is absolutely limited to use-value--everything else is sophistry.

"Most of the major ethical systems are either theoretical or deduced from their metaphysics--the Greek Stoics included! Even Aurelius' use of logos stems from his view of the universe. Kant, Hume, Nietzsche, etc. did little in their practical lives but their thought still changes the way we live and ought to. You might call that a practical result but it is the product of deep, theoretical thought. The act of reading theoretical philosophy is in and of itself valuable--the very use of reason is what makes us human and defines us as philosophers.

Your definition of a philosopher--as one who lives a truly remarkable life of practical virtue--is problematic. Your postscript ('You're now a philosopher') is pretty misleading if not inconsistent with that definition. Seneca struggled to follow his own beliefs. Nietzsche was timid and weak. Epicurus was rich and immoral. But still philosophers." -P

As you can see, academic debate is alive and well in my relationship...

Cheers.

It's inconsistent with the modern academic definition. It is not inconsistent with the definition of philosophy for its first, and most crucial, years of existence.

You worked for American Apparel and one of the most odious men in the business Dov Charney. His behavior to women and others reminds me of another person in the news. Why did you work for him and how was your relationship?

Odious? Give me a break. He started a company that employs 12,000 people in 20 countries that is basically the only major fashion brand that doesn't exploit slave labor to manufacture its garments. I sleep plenty well at night and he does too.