IAmA former American Apparel executive who has written 4 books (before turning 29), never finished college, and live on a farm with mini-donkeys and a goat named Bucket. AMA

Do you have a personal schedule for time for each book (one per year for example)? Or is it more when it is done, it is done? How do you know when a book is done? What is that process like from start to end? Is there a point when any more time thrown at the book won't make a noticeable difference?

This is my favorite question. Actually, I just tried to put a whole imgur gallery together for r/DIY but the mods blocked it because "I didn't make the book myself." I don't know what that means but here's the whole breakdown of how a book is made.

https://www.reddit.com/r/somethingimade/comments/4o2dgn/two_years_and_dozens_of_drafts_later_i_made_this/

This one took a little over two years. I don't have a schedule, but I like to stay busy and I always try to have the next project ready to start as soon as the last one ends. This way one is not swayed by the success or failure or reception of the last thing. When Obstacle started to do well, I was already heads down on Ego. I think that saved me a lot of trouble.

How do you cultivate the discipline to get up early and do what needs to get done, especially when you don't feel like it?

When I was in college, I printed out this passage from Marcus Aurelius (It's the opener of Book 5) and I taped it next to my desk/bed.

At dawn, when you have trouble getting out of bed, tell yourself: 'I have to go to work — as a human being. What do I have to complain of, if I'm going to do what I was born for — the things I was brought into the world to do? Or is this what I was created for? To huddle under the blankets and stay warm?'

— But it's nicer in here ...

So you were born to feel 'nice'? Instead of doing things and experiencing them? Don't you see the plants, the birds, the ants and spiders and bees going about their individual tasks, putting the world in order, as best they can? And you're not willing to do your job as a human being? Why aren't you running to do what your nature demands?

— But we have to sleep sometime ...

Agreed. But nature set a limit on that — as it did on eating and drinking. And you're over the limit. You've had more than enough of that. But not of working. There you're still below your quota.

You don't love yourself enough. Or you'd love your nature too, and what it demands of you. People who love what they do wear themselves down doing it, they even forget to wash or eat. Do you have less respect for your own nature than the engraver does for engraving, the dancer for the dance, the miser for money or the social climber for status? When they're really possessed by what they do, they'd rather stop eating and sleeping than give up practicing their arts.

Is helping others less valuable to you? Not worth your effort?

In a weird way, I almost have the opposite problem now. I have to remind myself to take breaks. To take it easier. To make sure that what I am getting up to do is actually important and not some random, unnecessary obligation I have forced myself into.

Hey Ryan, as a fan of the stoics what are your thoughts on Marcus Aurelius' ego? Did he write about his own ego? Did he practice and/or at least acknowledge a philosophy similar to "ego is the enemy"? Thanks.

It's fascinating to me to read Meditations because there you have the most powerful man in the world writing private notes to himself. What did he write about? How to be a better person. How to control his temper. How to be patient. How to be accepting. How to avoid the stain of "imperialization" (that is, becoming all "emperor-like").

He didn't have to do this. He could have been like all the other terrible emperors. He could have been Nero. He could have been a tyrant or seen himself as a god. But he didn't. I think that's because he wrote Meditations and studied philosophy to fight against his ego and the temptations of his position.

There's that saying that absolute power corrupts absolutely. Marcus is the exception that proves the rule.

Ryan, you mentioned that you fed several stories to Gawker that were most certainly fake. Are you able to disclose which ones?

Of course. Here are two really obvious ones that still haven't been retracted

http://gawker.com/5860826/tucker-max-and-dov-charney-together-in-a-single-book http://jezebel.com/5860675/did-dov-charney-just-land-a-500k-book-deal

Even though I explained exactly how they happened in my book http://observer.com/2013/07/exposing-the-racket-a-simple-stunt-reveals-how-blogs-will-print-anything-for-pageviews/

Thoughts on the hype around entrepreneurship in the last couple of years?

A lot of ego there. "Oh those people are making tons of money and getting attention for it? Ok that's what I am going to do." The idea that one would actually need to have a good idea for a business, have the constitution to run it, or that it all might be harder than it looks? It's like it doesn't even occur to these people.

Congratulations on your new book! A little off topic and maybe even a little rude, but if you are still in touch with Robert Greene, do you happen to know any details surrounding the launch of his new book? Is it still happening? And have you played a role in its creation? Cheers Ryan!

Not rude at all. I just talked with Robert a few days ago. He's doing great. I asked him this same question because I wanted to be able to tell people. As far as I know, the book is about social intelligence--essentially, the kind of mindset and acumen that one must master in order to wield the strategies in his other books. I get the sense that it will be his magnum opus--the book that ties all the others together. It could not be more timely, in my opinion.

I also know that we both did extensive research on Howard Hughes for our books. It overlapped with our experiences at American Apparel toward the end. I wish I could give more details his book, but Robert slaves away on them and then comes out with something magnificent each time.

Completely unrelated question, but you're married and have been with the same girl from a very young age, how did you make it work?

She is a very patient, special lady. It has a lot more to do with her than me. But generally, I would say: Commitment. Being open to accepting change (we are very different people than we were 10 years ago). Do fun, ridiculous stuff together.

How do you manage to crank through 2+ books/week? Do you use any speed reading techniques or something along the lines of a Tai Lopez where he just reads the back and flips thru a few pages for "one book a day"?

Also, where does one draw the line on confidence vs ego? Along the lines of Henry Ford, "whether you think you can or you can't, you're right." It almost seems counterintuitive.

I HATE speedreading. I don't think it exists. And if it did, to me it'd be like learning how to have sex faster. Isn't that kind of missing the point?

My secret to reading a lot is making a lot of time for reading.

Have you ever thought about collaborating with SEAL Commander/author/podcaster Jocko Willink?

They say authors live interesting lives, have you ever thought about joining the military yourself?

I'm a big fan. Would love to meet him some day.

Can I come visit your farm and chill with the donkeys?

They are very chill donkeys. I'm sure you're very nice and we'd have a lovely time, though this sign on my gate sort of expresses why I have a farm in the first place. https://www.instagram.com/p/6Ab3x8ledQ/

Have you ever studied other philosophies, other than Stoicism?

Feels like a lot of what's in there could overlap with philosophies from the Far East or India.

Absolutely. I'll read anything from anyone. Stoicism is the framework that I think is best suited for our modern world, but there is great stuff in Buddhism, in Epicureanism and so on. This recent book is heavily influenced by Aristotle for instance. There is no overt connection between say Buddhism and Stoicism (that we know about) but I like to think that the similarities exist because these wise men (and women) were homing in on the same central truths.

You wrote about turning everything into routine/turning love into ambition. I find myself doing this too. You wrote "I sort of become enslaved to it instead of employing it to my benefit." Would you share how you've learned to best deal with this? Or perhaps direct me to any of your writing on this I've missed?

Thanks. Big fan. Last year I left college around the time my first boyfriend dumped me, and when we met to exchange items, he brought one book, The Obstacle Is The Way. I'd gotten him a copy of it as a gift the year before in the hopes he'd read it. He never did. Luckily I had already read it many times and I knew I was just presented with a huge opportunity. Obstacle has changed and continues to change my life. Thanks so much for your writing.

Actually the whole intro to Ego is about this very thing. It's still something I am struggling with. There is no real easy answer, besides catching yourself and trying to make better decisions. But my belief is that ego--trying to be better than, trying to prove something to other people, trying be able to 'show them--is a big driver of all of that. If you can learn to be happy with yourself and the present moment, it can reduce that urge.

Ryan, I've heard you mention a few times that, the perfect spouse is the best life hack no one told you about. And it seems that you and And Samantha have a really great relationship. Do you have any advice for someone who has trouble with dating in general and aspires to have a great spouse and relationship?

No relationship is perfect, but we both work really hard at it. And most of all, you have to work on yourself. I try to go into it thinking: It doesn't matter if she addresses any of her flaws. All I can control are my own and if I get a little bit better, the relationship will too. It's also about seeing yourself as a team. We've been a team for a long time.

Do you have any suggested strategies for growth hacking the clothing industry in a developing country's economy where there is both a strong consumer pull towards physical retail shopping, as well as growing online retail sector? Do you have any suggested readings/books for guidance on this too?

Growthhacker.tv is great. You might like my book on growth hacking too

Do you watch Breaking Bad? If yes, what's your favorite thing about it?

Who hasn't? It's amazing. I loved the first 2 seasons of Saul too. I like the idea that we all have evil inside us, we just have to decide whether we are going to feed it or not.

Hello Ryan.

How did you discover Stoicism and how long did it take you to embrace the philosophy?

If you put Stoicism aside originally, why did you and what prompted you to take a second look?

Thanks.

I was 19 years old and I went to this conference that Dr. Drew spoke at. There were only about 12 people invited, it was very small. Afterwards, I went up to him and I asked "Any book recommendations?" He said he was reading Epictetus. I had no idea who that was. I bought it on Amazon from my hotel room, along with Marcus Aurelius--who I had heard of from the movie Gladiator. Marcus came first and hit me like a pile of bricks. I was in a shitty place in my life then. I'd just gotten dumped. I hated my roommates. It was exactly what I needed.

In line with the lessons within Trust Me, I'm Lying, what marketing strategies would you suggest for a new business starting in an entrenched industry (think legal, accounting etc.) - assuming they are willing to deviate from the status quo, but do not have a lot of capital? What is the best way to set yourself apart and get eyes on your business?

PS. I'm a big fan of all your books and already grabbed my copy of Ego. Please never stop writing.

The key would be, I think, to focus on a key niche or service that those entrenched players are not serving and own it. Under Armor didn't go after Nike's shoe biz from the start. They sold compression shirts--a category they invented--and then slowly expanded from there.

Was there any unlikely source of inspiration while you were writing this book?

Sam Sheridan's book A Fighter's Mind was what first turned me onto the interesting paradox that some of the most successful, intimidating and strong people are actually incredibly humble.

Oh man! If you like that, and have time after this AMA, I think you'll love this piece from The Ringer about Julio Jones. For example, "Humility connotes a virtue. He sees no reason he should be commended. 'It wasn’t about being humble,' Jones says. 'It’s just how I am.'" https://theringer.com/julio-jones-atlanta-falcons-3fa47fb03461

Mike Lombardi who is a coach for the Patriots was telling me that ego is the cancer of his profession. It ruins players, coaches and teams. Going to check out this article now.

Which makes sense since the Patriots require everyone to check their ego out at the door. The people that make their teams/organizations better are the ones that lead by example.

Nothing is bigger than the team--even Tom Brady. As Belichick has said, they're all shareholders. Some own more shares than others, but ...

I think that's why the team has been so successful for so long.

Can you describe yourself in 4 words?

A guy who writes.

Hey Ryan

You have stated that you balance many projects a day. How do you go about breaking down the time needed for each?

Thanks

I'm not great at this. I would strongly urge anyone struggling with it to look up Eisenhower's Decision Matrix. The key is to make the distinction between what is urgent and what is important. They are rarely the same thing and we usually work on the two in the wrong order

I know that you're a heavy reader, has that always been the case? How did you build reading into your habits? I struggle with staying focused long enough to finish books, so I'm curious how you've built enough discipline to be a voracious reader.

I read a lot as a kid. I would get in trouble in 4th grade because I wouldn't pay attention and would be reading Louis L'amour books under my desk. I actually made that my resolution that year: "I won't sneak read in class anymore."

The problem was I wasn't reading anything good. That didn't really start until late high school. I went through a breakup in college and really got serious then. I went to Border's (miss you!) and bought like 10 books I'd heard you "had" to read. I read them in a couple weeks, came back and did the same thing. It's been like that pretty much non stop.

Do you see a lot of crossover between Stoicism and the teachings of Jesus?

Some yes. At the advent of Christianity, Stoicism was the most popular philosophy in Rome. There is an argument to be made that the rise of Christianity was made possible by the brilliant decision to absorb the ethics oh philosophy into the religion. This slowly supplanted the primacy of practical philosophy as a way of life. We're only just not returning to a secular lifestyle in which we have to asked ourselves: Why should I be a good person? What is the meaning of life? Why should I avoid hurting other people? Etc etc--all the questions that religion used to answer with: "Because God says so and you'll go to hell."

I'm going to ask another question, if that's all right.

What's a good way to reach out to people? I listened to the Canvas Strategy you narrated on the Tim Ferriss podcast and was intrigued by it. It seems in today's world, it's hard to reach out to people with even a small amount of public persona.

Can you give some advice on that? If you're looking to help someone and you're a nobody, any straightforward way of going about it?

I would push back on that. It has literally never been easier to reach out to people. "Public" people are 100x more accessible than they ever have been. I mean look at this medium we are connecting in right now. People a hundred years ago would have KILLED to be able to interact with a Winston Churchill or an Upton Sinclair. The idea that they'd be on something called social media where anyone could ask them anything? Or that they'd have an "email" address that they managed themselves instead of with a phalanx of secretaries and assistants? Unbelievable.

You gotta just do it man. Most people are going to say no. Many will not even respond, but some will. That's your shot.

Worked my way through your list of "Books to Base Your Life On" over the course of a year and wow, what a difference it made in my life.

So here's a question I have for you. If I want to reach the absolute largest possible audience to promote a cause, is growth hacking the best answer in today's world?

It's built some of the biggest companies in history (Facebook!). So yes, of course.

Do you think Trump will win the election?

I hope on the life of my unborn child, no.

[deleted]

That usually the wrong way to look at it. Casey and I are friends--and he happens to be an influential person and has been generous towards my work a couple times. If you go around trying to line up influencers, you're not only going to lead a fairly empty life but they're going to smell you coming a mile away.

What do you think of Trump's marketing strategy? (Regardless of his political beliefs)

I think he is both brilliant and insane and it's hard to know where one begins and the other ends when it comes to his marketing. Clearly its gotten him far--but at what cost and to what purpose?

What's one simple way a 23-year-old can start using the canvas strategy? Thanks!

Find someone whose work you respect. Think of a way that you can help them (don't ask: How can I help? That's not helpful). Make the offer. Rinse. Repeat.

Hey Ryan. Congrats on the book! Looking forward to diving into it.

Stealing a question from Peter Thiel (because I think it's such a great question): What important truth do very few people agree with you on?

Fewer people (in media) seem to agree with me and Peter that Gawker was a force for evil in the world and that killing it was a philanthropic thing to do.

My other one, said elsewhere in this AMA, is that I think there is a lot of hype around driverless cars and I'd be willing to bet that they're further off than most tech folks seem to think.

Interesting. I've certainly been on Peter's (and Hulk's) side throughout the whole ordeal, but I still laughed out loud when I read Peter call it "one of my greater philanthropic things that I’ve done." Probably just my own mental image of the word "philanthropy" and seeing it used in this context, but I do agree that the world is probably a better place without Gawker.

It was a cancer on our culture and I, would argue, has made our politics and discourse worse as a country. In the same way that Jon Stewart did us a great service when he destroyed CNN's Crossfire, Peter Thiel has done us one.

What's one personal opinion you have that, once revealed, would have the most disastrous impact on your career?

What kind of person would answer this question? "Well, now that you ask, let me really tell you what I think about Jews." I'd like to think I don't have any opinions like that.

Here's a controversial one, I guess: I think Virtual Reality is mostly hype and I don't think we'll be in driverless cars for a really long time.

What are some important things happening in the world today, that people aren't talking enough about?

I think we are seeing a rise of intolerance and fascism. Fascism on the right, intolerance to ideas and controversial thoughts on the left. Those are similar trends that we've seen at some of the worst periods in modern world history. I think that's very scary.

Hi Ryan. Been a big fan of yours after stumbling upon your advice about writing an essay using the Spartan strategy.

How exactly did you go about getting the gig of doing research for guys like Robert Greene? You've said in the past that Robert was (and still is) one of the great mentors you had in your life and I was wondering how you were able to find him in the first place?

Man, that was forever ago.

I was working for another author (who I'd met because I wrote an article about him) and I did a good job. Part of my reward was that I got to come to a lunch meeting he had with Robert. Robert complained about trouble he was having with his research assistant. I volunteered. He gave me a trial project and we went from there.

Funny story: It almost didn't work out because I accidentally gave Robert my phone number wrong (I'd just gotten it a few days before). He called and left a message for me. Nothing. Called again, a person picked up...and they pretended to be my friend. They said I was in the hospital and couldn't talk and strung him along for like a week. Finally, either they fessed up or slipped up. Robert got my real number and then called me. Close call--I almost blew it.

What are rich people like? What do you think most people don't realize about rich people?

There's a line from Fitzgerald where he said that "the rich are different from you and I." Hemingway replied "Yes, they have more money."

It's a little more complicated than that, but it's essentially true. Rich people have all the flaws and virtues we have--they tend just to be amplified.

Hey Ryan, what's your favourite tv show of all time?

Seinfeld. Current? Billions.

Hi Ryan. Big fan. What feedback would you give to people struggling to find meaning and purpose in the work they do?

Also, what is your single biggest productivity tip?

Shane Parrish at Farnam Street said it best: Forget hacks, just wake up early.

What's the last great book you read?

Easy. Lincoln's Virtues: An Ethical Biography by William Lee Miller.

One of the best books I've ever read.

Sorry to ask another question Ryan, but I was also really curious as to how your running is going?

It's been a consistent part of your blogs over the last 8 plus years but I haven't seen you mention it recently. Also, any good books about running that you would recommend?

I'll be going for a long run after I finished this AMA. 55min or so is what I try to do everyday. I had a piece on running I submitted to Runner's World that I am waiting to hear back on. If it doesn't run soon, I'll publish elsewhere.

Can you name all of the donkeys?

Just two: Buddy & Sugar. Sugar might be pregnant, if so, the baby will be named Bugar.

Very Clever.

Verne!!!!!!!!

Does it concern you at all that Peter Thiel went after Gawker in secret? So as to be clear, my very tentative position so you know where the question originates: Stepping back from however distasteful you may find Gawker, multimillionaires secretly funding lawsuits designed to financially end a free press organization seems a bit troublesome.

No one iota. If you found out that he had been backing their defense in secret, would that have bothered you? Or would most of the same people be saying very different things about Peter?

If he had attempted to bankrupt Gawker, by say, hacking into their computers or paying someone to steal money from them--then yes, that would be a bad thing to do. In this case, he paid the legal bills from someone who was already suing them and a verdict was ultimately rendered by a judge and jury. The other lawsuits? They haven't gone anywhere and Gawker (and their insurance) successfully weathered them.

You're obviously a prolific writer and reader. Do you have any tricks for dealing with distractions (such as Reddit)?

• Read physical books and leave your phone in the other room when you do.
• Cherish airplane rides. Don't buy wifi, don't watch movies
• Use quiet time before bed productively.

How do you feel about American Apparel filing for bankruptcy?

As director of marketing, could you see anything on the corporate side that could have saved the company?

Sad. Just sad.

I wish the new folks the best of luck. They were not given a fair chance to succeed and I hope this reset allows them to.

1. How does one become a 'director' at 22?

2. Can we see Bucket?

Here's Bucket as a baby: http://imgur.com/a/WYbi4

As for the job? The owner of the company says: "Here you go!"

If you had to write a book on dating, what would it look like?

I'm married and have been with the same girl since I was 19. I'm not the guy to write a dating book.

Do you ever make delicious cheese with Bucket's milk? Does Bucket even have milk?

You have to breed the goats to get them to start producing milk. We made the decision not to do that because 1) Not huge fans of goat milk 2) Don't need gallons of it every year 3) We travel a lot and don't want to have to milk them everyday 4) Seems gross to have to do.

Have you gotten any push back because of your recent articles on Gawker?

From who? From media folks? Yeah a few. That one Vox writer that was suspended recently said some dumb stuff on Twitter. You'd be more surprised by the well-known people who won't say things about Gawker publicly who emailed me afterwards. I was like "Holy shit, how did they get my email?" I was very excited to see that. Gawker exists in its own bubble--which is how they ended up in trouble in the first place. I don't think they understand how most people feel.

I love your books Ryan. What's the biggest challenge you're facing right now and how are you planning on overcoming it?

Well thank you. One of the things I struggle with is balance. I could so easily get lost in my work and disappear for days. I can get so wrapped up in my thoughts that I act selfishly or forget about how my choices affect other people (and ultimately, affect myself). I have all these obligations I make for myself about work, about staying in shape, about accomplishing things and they can become rather constraining. They can suck the joy out of your life. So getting a handle on that is something I am spending more and more time reading and thinking about.

What is the worst book someone has ever recommended to you in earnest?

If you get recommended a lot of books, a lot of them are going to be bad. It's part of the gamble, I think. You just have to be willing to toss it aside very quickly.

I won't say the book is terrible because I haven't read it, but I was recently recommend "Eat That Frog" only to see that the title and the premise are based a Mark Twain quote THAT MARK TWAIN NEVER SAID. The actual origin is Nicholas Chamfort. I'm not going to spend time reading a book where the author took so little effort.

At the risk of spoiling one of your pre-order bonuses, what books and sources were most influential in the creation of Ego Is The Enemy?

Easy.

Nichomanchean Ethics by Aristotle Howard Hughes: His Life and Madness The Score Takes Care of Itself by Bill Walsh

Hello from Finland! You recently visited our country and I would like to know what did you enjoy the most? How did you like Finnish people? Big fan of Obstacle is the Way and waiting for my Amazon package of your new book!

It was my second time in Finland. An amazing place. Unfortunately, it was too cold to run outside (which is usually my favorite thing to do in cities). But I did go swimming in that famous pool where guys aren't supposed to wear swimsuits? That was an...experience. You guys are nuts about saunas too. I had a bear steak at a restaurant which was also cool.

What one valuable advice that you have received? and What is one valuable advice that you can give?

Thanks Ryan!

"Be a good person. Do what you love." If I could pass that along to anyone, I would. It served me well.

If I haven' read your book 'Obstacle is the way', can I still start with Ego is the Enemy? Or would you recommend reading the former first?

Honestly, I don't know if Ego is a prequel or a sequel. I think it's pretty self-contained. Whatever you're interested in most--go with that.

How's bucket doing?

We chatted this morning. She's good. It's going to be like 100 in Texas today, so she's a bit grouchy about that.

Do you think the majority of jobs are meaningless? If so - is writing books about it also meaningless?

Meaning comes from what you put in, not what you pull out.

I apologize if this comes off rudely!

You are obviously a very public personality, and self-promotion is a core part of your business model. Do you have to buffer your ego from this type of work? Is it difficult to stave off narcissistic thoughts?

I wouldn't say very public, but yes anyone who deals with an audience every day has to fight against ego constantly. Here's the thing though: In the social media age, we all feel that pressure now. We're all performing. At least I know that it's part of my job. There's warnings for people like me. I'm more concerned with the 14 year old who has to grow up in the YouTube/Instagram/Snapchat world. It's very hard to develop the quiet, inner life that one needs.

The title of your book kinda reminds me of that Gordon Gecko quote about greed. Ego, for lack of a better word (or in this case, phrase), is the enemy. But I imagine you'd admit that ego has its merits. In your opinion, what, if anything, is good about ego?

I think confidence is good. Ego is bad.

Hey Ryan, I got Ego is The Enemy yesterday and I'm loving it so far. What's your advice for an ambitious high school student that's looking to be an entrepreneur? Thanks, and I'm excited to see what you you're going to do next.

Don't rush into starting a company. Work for a company first. Meet lots of people. Really study your market. You gotta know the terrain before you go into battle.

Have you ever seen an extra-terrestrial/UFO or had a related experience?

Nope.

Hey I've been a fan for quite a while now. I just finished relistening to The Obstacle is the Way in anticipation for Ego is the Enemy. Thanks for curating the wisdom of the greats into meaningful books.

I mostly listen to audiobooks for nonfiction and am wondering if you ever listen to books. If so do you have any favorites because of the book and also because of the performance? I like your performance in Trust Me I'm Lying the most out of all your material.

I listen to lots of podcasts (Marc Maron, Brian Koppelman, Tim Ferriss, Dr. Drew). I like the conversation. When it comes to comes, I like to be alone with them and read rather than listen. It's too hard for me to take notes on audiobooks.

How similar is your concept of ego to Steven Pressfield's in War of Art?

I don't remember his definition exactly. I think ego and resistance go hand in hand. They fuel each other.

Hello Ryan, a long time fan of yours. Also a practicing stoic (or wannabe) and love ancient stuff. I've got two questions:

1. You can suppress your own ego. But how to deal with someone else's? Specially when it's becoming a barrier in your way to achieve something?

2. A short advice to aspiring marketers and admen?

PS. Don't ever leave country. It's thousand times better than cities imo.

Thanks.

The first thing is to realize where you end and the other person begins. We waste so much time and energy trying to change other people. Dealing with their ego? That's their job. The best we can do is try to work around it. Accept it. Learn to work with it (for instance, one of the best ways to get egoistical people to do something is to convince them it was their idea all along). Also have a certain amount of sympathy. It terrible to be in the sway of ego. It might look nice from the outside but it's actually quite terrible.

Hi Ryan, huge fan. Many of your books use case studies and biographies to back up your point. How do you go about researching these potted histories? You've said before that you only use your commonplace book for quotes, wisdom, etc, but not facts. Do you use a similar technique to gather facts and raw historical information?

No, I definitely write down stories in my commonplace, especially when I am working a specific book project. If you see in this photo, I have all the different sections of Ego broken down. It's comprised of 3 "parts" with about 10 chapters per part. Let's say I know I want to have a section on detaching yourself from the outcome. I might write on a notecard "See Belisarius story in INSERT BOOK" or whatever and then as I accumulate more facts/quotes/examples, I'm adding to that stack.

If you could design a virtual reality experience based on one historical event, what would it be?

Can you imagine what it would be like to watch one of the naval battles in the Colosseum? Or Lincoln's second inaugural?

Can you post a video of you feeding carrots to your donkeys?

Have you tried Beme? I uploaded one there this morning! I am beme.com/ryanholiday

how do you acquire mini-donkeys!?!?!!?

Not a joke: Craigslist.

Do you still "Call New Orleans Home"?

I live right outside Austin, Tx

How did the goat get the name Bucket?

My wife thought it would be a funny name. I think she had the name before we had the goat. In fact, we might have the goat because of the name.

Do you have any tips on how to start reading books again instead of spending time on netflix/youtube/reddit?

I tell myself: In 50 years, what are the chances anyone is going to be watching that YT clip you are watching? But they've been reading and reciting the Iliad [or insert any classic work one hasn't made the time for yet] for 2,500 years. So what is a better choice?

If you decided to move back to New Orleans from NYC, what industry or businesses would you want to join?

I live in Austin now, but I loved New Orleans. I would want to be a writer there. It's a writer's city for sure. Growing tech scene too.

Love the new book. I waited for midnight to download the audiobook and have the hardcover coming in the mail.

In some of your recent interviews and posts you mention that you had a falling out with one of your mentors. Are you comfortable mentioning who this mentor was, how it transpired, and how it affected you?

Obviously American Apparel is the big one. I'm in a good place with the other stuff and I'd prefer not to kick off a whole thing by naming names. Hope that's alright. But basically, one day you wake up and you realize this person you've been modeling yourself after doesn't have things figured out the way they think they do. And that you will end up just like them if you don't make some changes.

Do you have any books other than the obvious (meditations) that you re-read on a regular(yearly) basis?

What Makes Sammy Run? is a book I have read many times.

Hey Ryan

How do you start the process of breaking down the questions, who do I want to be and what path to take? They both feel like they could lead to tail chasing if not approached properly.

One should come at it from two angles. 1) What they are (marketably) good at. 2) What they find satisfaction and meaning in. Finding where those things overlap--that's the key to a good career and life, I think.

When the market is so oversaturated and being a writer is seemingly a naive and unwise idea, how does a writer maintain a stoic approach to the craft?

Does one just have to see the chances of being published and gaining a readership as folly and if it occurs it occurs, bonus, if not then take the loss and find a pursuit that could be more fruitful?

I totally disagree with that. Now is literally the best time to be a writer in history. Is it harder to break through the noise than before? Sure--but in the past, 99% of people who wanted to write something had no means of making noise. It was too expensive and publishers were the gate keepers.

To me, the Stoic approach is to see the situation like that: to focus on the opportunity and not the obstacle and to put all your effort and energy into the parts you do control. You control how good your writing is. You control how hard you work. You control the marketing you do. You control how you manage your career. Focus on that--there's plenty there to keep you busy.

I really enjoyed Obstacle Is The Way. However, I was wondering whether all life situations actually have a "silver lining" that can be turned to an advantage?

For example, I have a dear and close friend with an eating disorder. Whilst she has picked up countless skills and tips in the "nutrition" space simply by being unhealthily attached and engrossed in it, it would seem unwise for her to exploit that knowledge in eg. some sort of fitness business post-recovery. It would seem more sensible for her to close the door on that part of her life and move on as much as possible.

Would love to know your thoughts on this situation specifically and, not withstanding the generally applicability of the method, whether you think the book's message has any limits.

I would say teaching people dieting hacks from an eating disorder is probably not great. But I am certain the experience has taught her things--about life, about herself--that are of value to her and possibly to other people.

I find we're always so focused on the result, that we often lose interest during the process. It's happened to me dozens of times. I've seen it happen dozens of times. Yet a guy like James Dyson creates over 5000 prototypes for his vacuum and doesn't lose interest or give up.

How do you think ego factors into those big goals that take a boatload of perseverance?

To go through 5,000 prototypes, you can't be focused on the result. You have to love the process. It's like in sports, if you hate practice--you're only going to be so good. I think in his AMA Jerry Seinfeld talked about finding the torture you're ok with. It's the same thing.

Using ego as a substitute for perseverance is a risky gamble. Craftsmanship and dedication are better, in my opinion.