An Interview with Me

October 25, 2011 — 77 Comments

Andrew McMillen posted an email interview he did with me. You can read it here.

At 24, Ryan [pictured right] is a year older than me. I’ve viewed his blog as a kind of counsel since I first became aware of his work. His thinking and writing has, in turn, shaped my thinking and writing. It is fair to say that I wouldn’t be on the path I am now if I hadn’t been closely studying another young male on the other side of the world, fearlessly kicking down doors in search and pursuit of his goals. For a couple of years, Ryan’s ambition, persistence and confidence all directly influenced my day-to-day thoughts and actions. Which is another statement that will make Ryan blush, because it’s a pretty fucking weird thing to type, let alone think.

I am having to put a press kit together and prep for some media stuff anyway, so if anyone wants we can do an open Q&A in the comments. It’d be helpful to me and I know a lot of you have questions since you email them to me. We can talk about anything that is on your mind or anything you feel like I haven’t addressed before.

Ryan Holiday

I’m a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

77 responses to An Interview with Me

  1. Great read, it’s nice to be able to finally put a face with all the writing you’ve done. The quote about happiness ensuing is Victor Frankl. I could have sworn Bill Bennett said something similar though.

    One question I have, does your answer at the end about breathing at the end and letting things flow tie back to what you’ve said in comments here before about feeling compelled to turn everything into an opportunity? I wish I could remember exactly how you phrased it, but I feel like it’s been a common theme across multiple posts where you’ve struggled to balance ambition with serenity– the stuff you mentioned about needing to turn every connection into an opportunity. I’m curious if you ever made progress on finding a balance. It’s been an issue I’ve struggled with a lot.

    Thank you, and sorry if I’m way off-base with what you’ve said in my question.

    • I wouldn’t call it a constant battle, but it is something I struggle with and think on often. It’s a theme because it is there at the top of my mind. A lot of progress? Probably not. But I’m happier and less jerked around by it for sure.

      I don’t like the metaphor of “going with the blow.” I like Seneca’s Euthymia better–“the belief that you’re on the right path and not led astray by the many tracks which cross yours of people who are hopelessly lost.” It’s a firmness of mind and purpose, which actually begets a kind of freedom and fluidity.

  2. Ryan, what was in your hean when you decided to drop out of college?

    I remember hearing you say that the day you left college was the day your real education began (although I haven’t been able to find the original post for some reason) and I was wondering what was on your mind when you decided to do that. How did you handle things with your parents and with your friends?

    I’m asking because this has recently become a very personal issue to me so was wondering about how you had handled it.

    I was also going to ask if you had read any of Ayn Rand’s books but a simple search answered that question.

  3. Comments here or on his site?


    1. What day to day task planning / to do planning do you do and follow?
    (For example Pomodoro technique)

    2. Can you recommend any books, blog posts on longer term goal planning?

    (I saw what you accomplished in the Tempation post… so if I had to guess there is some organization going on there.)

    • 1) None. I think GTD planning is pointless and counter productive. If I have a lot to do in one day, I write the stuff down on a 4×6 index card. Otherwise, I remember and I go where I am drawn to go.
      2) Tim Ferriss is all I have read and liked.

      There is no organization there, just strength of will and purpose. If you know what you want to do, and who you are, it’s easy not to be distracted by your own bullshit. If you have illusions about who you are–that is an inflated sense of it–and are, deep down, averse to hard work, it’s impossible to not be distracted by it. Your fear of failure and your creeping awareness that you are a fraud makes it a certainty–a necessity even–that you detour just enough to prevent ever facing a legitimate opportunity to fail. If you fail, the entire edifice collapses.

  4. Interested in what you think.

  5. Ryan, here are my questions:

    (1) When you slip-up and fail at stoicism – what does that look like?
    I am speaking of those small failures that only you know about.
    How do you correct yourself and move on?
    And when a person fails at stoicism – what does that indicate? Is there a different philosophy that should be in balance with stoicism?

    (2) Have you run or do you plan to run in the Crecent City Classic? What about the Cajun Cup? I grew up running in those races. When you walk on the flat Louisiana land – don’t you just feel it call out to your legs asking you to run?

    (3) In the interview you say that you run, swim, or box. I think that is very appropriate – because it allows for cross training. When you said that you ran every day (some other post) I thought that seemed off. Bodies need rest days. It is hard to believe that you run 5 miles 365/365 days. So what does your workout schedule really look like? Do you feel irresponsible for not incorporating free weights?

    (4) Have you been to Cane’s?

    (5) Have you been to an LSU football game?

    (6) Have you been to any small-town Louisiana festivals?

    (7) How often do you wear American Apparel?

    (8) Do you have a girlfriend/boyfriend? How do you anticipate falling in love will change your core values? Has it already?

    (9) Have you been running in a hurricane?

    • 1) It’s impossible to slip up and fail at Stoicism.
      2) No, plans to do any races. re: flat land. I guess. I like to run on St. Charles. I work out at the NOAC.
      3) I used to do that 5 miles shit everyday, not so much anymore. My schedule usually ends up being something like 10 days on, accidentally forget or get too busy to run/work out one day, 10 days on. The body may need a rest but my MIND does not. I don’t do free weights but why would that make me feel irresponsible? I do sit ups, pushups and box too.
      4) Cane’s Chicken? I try not to eat factory farmed meat but I’ve had their delicious sauce.
      5) No. Been to a Saint’s game though
      6) No, don’t think so
      7) Seriously, almost everyday head to toe. It’s all I own or wear with two exceptions: Bonobos (for some pants) and Lulu Lemon ( workout stuff )
      8 ) I have a girlfriend. Same girl for the last 5 years. We live together. Why would love change a core value? I like this quote from Emerson on the matter. I have always felt this way.
      9) Only been in a tropical storm (Lee) and I did go running but it was during a lull.

      • (1) Why is it impossible to fail (even in a small way) at stoicism? Is enjoying pleasure in moderation OK under stoicism as long as you don’t LIVE for pleasure?

        (8) Love changing a core value – maybe I should say that love may relax a core value – because a relationship is about compromise. Have you not experienced this? If you are not compromising at all – it makes me think your girlfriend might be doing all of the compromising.

        New Question:

        (10) What are your favorite things about life?
        (11) How many hours do you sleep a night?


        We want to hear about your failures big and small because they make you more human to us. It seems this has been left out of your posts. Perhaps because you are set on being your own “stand up for yourself” guy- which is good- BUT isn’t being OK and open about your failures part of growing as a person?

        • Dude, I absolutely have not left failures out of my post. This is the thing I write about most of all. Here’s two most recently:

          10) Here’s one of my least favorite: ridiculous questions that don’t mean anything. Favorite thing about life? If I could answer that question, how would that help you? Anyway, I can’t, no one can. Why would you try to reduce something so complex down to a handful of favorite things on a blog comments section?
          11) A normal amount. I’m not fucking Tyler Durden. I am a normal person just like you guys. I don’t even work more than most of you. I just do it really well.

      • (3)

        This article made me think I need to lift weights.

        Also- Muscle Mass starts decreasing with age without weight training. I guess this does not matter to you?

        • Well first off, nothing in Men’s Journal is ever going to make me re-examine my life choices. Second, why would that matter to me?

      • Could you elaborate on what you mean by it is impossible tosliP uP and fail at stoicism?

        • Stoicism is not a religion. It is not the law. It doesn’t even have tenants. It is a series of observations and principles that smart people suggest you put into action–as they will reduce your suffering and increase your contentment. You can’t fail at them, you can only forget or not do them. And if that bothers you, wake up tomorrow and get back on track

      • Normally I’m against killnig but this article slaughtered my ignorance.

  6. What have you seen is the biggest difference between a successful CMO and an unsuccessful one?
    Who are the top 3 marketing people that I should be learning from?
    What is the biggest mistake you’ve made and what did it teach you?

  7. Thanks for the link, Ryan, and thanks again for taking the time to answer my questions.

    KG (above) made me think of one more. What does your girlfriend think of your online persona, and the following you’ve built here on this site?

    • I mean, the idea is that it is not a persona. I’ve met a lot of people whose work I was familiar with online first and most of them have been disappointments. It’s because they abuse the power of the web to create a fantasy version of themselves–they exaggerate their accomplishments, they omit important negative details, they’re too polished, etc. I try not to do that. I’ve written about this a lot, the importance of being honest, humble, of practicing contemptuous expressions, not buying your own shit. I’m saying those things TO MYSELF most of all. Of course I’ll slip up sometimes and she’ll say “you’re not like that at all, why are you pretending?” (this would mostly happen say, when she is mad, but you know…)

      As for the following, fortunately it’s pretty manageable at this point.

  8. Great interview and site, Ryan.

    I’m interested in your (voracious) reading habits. How often do you find yourself going back to re-read books (especially “books to based your life on” list, or marketing/business books that are on your Amazon list), or do you find your method for “devouring” books is sufficient enough for most books on your list to read thru once, get the message(s), and be able to apply them to your life/logic?

    Are you a scatter reader (ie. spreading out multiple books at once) or do you try to focus your day/week on as few books at a time?

    How do you find audiobooks vs reading in terms of effectiveness?

    Thanks and good luck.

    • I’ve never listened to an audiobook actually. Rarely do I reread an entire book, instead I like to consult or refer to them as often as I can. If I am thinking of a passage, I’ll pick it up and read it again, in context to jog my memory of it. I find this works best–and it’s why I prefer physical books to ebooks.

      I don’t like reading two or three books at the same time. When I find myself doing it it usually means that one lost my interest and I’m not being honest with myself about giving up on it.

  9. As time goes on, and I find myself reflecting on what I value, the more I find that at the core of what I do is a desire to be more compassionate with myself, and with others. Out of that comes a desire to help reduce the suffering I experience and others experience. What are your thoughts about compassion and reducing suffering? How do these fit into the work you engage in?

    What do you find to be at the core of what you value? How do those values fit into the work you do?

    What do you do with ambivalence about whether or not an opportunity is consistent with your values?

    Thanks for sharing your thoughts, Ryan. I enjoy reading your writing.

    • I think these questions are probably a bit above my level, but it sounds like you are struggling with a higher calling and I think you should follow that. Something is telling you that you have the ability (or the need) to help people in a real and tangible way and for some reason whatever you’re doing now does not answer that call or fulfill that burden. We all have different duties. Of course, I think we’re all obligated to reduce suffering when we see it, and more importantly to do as best we can to not inflict it. But maybe you are drawn to something more direct.

      I feel that I am a writer, or a communicator. At other times, my job is that of a strategist or adviser–I help people accomplish what they feel compelled to accomplish. That is my task. We’re all different.

      • Thanks for the response. I’ve come to the conclusion that these values are somewhat universal, and that recognizing the role that compassion plays in what we do, and why we do what we do, can help us be happier people. It may be presumptuous to say that everyone has these instincts, and that increasing our awareness of how they fit into our lives is usually revelatory, and liberating – but I’m still young and willing to make mistakes 🙂

        Appreciate your insight on the questions. It’s sometimes hard for me to remember and respect that everyone is coming from a different place and experience, that we’ve all got our own path.

      • I think I’m struggling with the same sorts of questions, except I think I’m more concerned with finding some sort of work that I was meant to do or close to it.

        Ryan, it seems like you’ve got that pretty well down in your life. I was wondering if you had any advice for people looking for purposeful work or how to find work they give a shit about.


        • I think you have to look really hard at what your drawn towards. Not what seems easy, not what makes people perk up when you tell them you do, not whatever you decided to do after college because you were afraid of the real world. But what are your passions? What are you drawn to do day in and say out? Are you good at? Does it fulfill you? Does it keep you awake at night thinking and excited? THAT is purpose.

  10. I’m sure many people would like to see you and Tim Ferriss together talk about stoicism and productivity. Are you going to do a “Random Show” together?

  11. Have you ever had any trouble or anxiety when it comes to socializing with an objective? I know you wrote in one of your earlier posts that it helped you to act like you deserve “the king’s share” to succeed at a networking event. That’s something I have a lot of trouble with and would love to hear what thoughts, strategies, or actions you use. Or if it’s something I’m just over-thinking.

    Thanks in advance, Ryan.

    • Of course. I hate that shit. So mostly I don’t do it. I think the awkwardness of the phrase “socializing with a purpose” tells us a lot about the concept. It’s not true for everyone of course but it is for me.

      Anyway, the short of it is this: have something interesting to say, enjoy saying it and stick with that.

  12. Ryan,

    I personally would like to see a list of your anti-library as well as the books you haven’t finished. I know you have your amazon wishlist, but was thinking more along the lines of the books you actually own. You have probably learned just as much from this process as you have from the books you have finished.

    Lastly, found this video series on Marcus Aurelius. It’s older, but I think you might enjoy it:

    Thanks champ and keep up the great work.

  13. Hey Ryan,

    Question: How do you view Stoicism and its relation to ‘the gods?’ Are the writings and doctrines of stoicism a set of psychological tools you use to reach your goals or are they a system of thought, the underlying premises of which you ascribe to?

  14. I find New Orleans to be what Robert Greene referenced when he tied Henri de Toulouse-Latrec to Montmartre to make his point of getting down and dirty with the people (customers/clients). Have you been mixing it up with the locals? Is there a ‘vibe’ you get there that has influenced you/your creativity?

    Are you doing anything else creative outside of writing?

    How long are you gonna be in Nola (I am making a move there in Dec/jan)?

    • I’m here for the foreseeable future. But things can change.

      It’s not the locals I find to be particularly inspiring, just the city itself. The down and dirty part you’re referring to is sad and discouraging.

  15. I love Tucker Max, he’s a hilarious guy with great pranks that stem from a great intellect. However, as a Stoic, I’m having a hard time explaining why I respect him. Clearly he lives a life searching for preferred indifferents; namely infamy and sexual exploits. Seneca talks in his letters about how men who dress lavishly and slovenly are making the same mistake of vainly seeking attention; Tucker Max’ obnoxious exploits, while hilarious, seem to fall under that category. There appears to be a redeeming quality to the stories, because he uses the excessive preferred indifferents as a means towards achieving humor, rather an end in themselves; but when you fill a cup with water to the point that it is overflowing, is the water or the cup more in control?

    Have you ever had trouble reconciling Tucker Max’ personality with your own Stoicism? And if you have, have you been able to solve that puzzle?

  16. How often do you make it over to Cafe Du Monde? Those beignets are criminally good. Speaking of, Camelia Grill’s got to be pretty close to where you’re at. How do you stay thin down there? You can’t shake a stick without hitting a good meal in New Orleans.

    • Never? It’s like asking people in LA how often they go to Pinks Hot Dogs or people in New York how often they hang out in Times Square. Of course it’s good and is worth seeing, but not if you live there.

  17. Ryan,
    Where are you “from”? And do you think place matters when it comes to shaping your outlook as a person?

  18. Nick from Vancouver, BC October 31, 2011 at 6:08 pm

    Hi Ryan,

    Further to Bo Sun’s post above re: your reading habits, I would like to share what works for me regarding ‘making the decision to read.’ For me, I find it most effective to block off one hour each morning (scheduled in my gCal) for ‘active reading’ where I have my flag highlighter out and pen ready to go. Your post on ‘How to Digest Books Above Your Level’ ( has been my guide.

    My questions are these:
    1. Do you follow something similar where you schedule in your daily reading time through a calendar?
    2. How much time do you commit to reading on a daily basis?

    • I think if you get in the business of scheduling your reading time, you miss the point. If you make it a priority–one of your highest priorities–you will find the time to get enough of it done. You’ll pick up a book because you want to, rather than because from 9-10am, you HAVE to. It doesn’t matter how much time I commit to reading on a daily basis. Sometimes it’s a lot, sometimes only a little. What if I was stuck somewhere and didn’t have a book on me? It doesn’t mean I can’t be thinking of something I read recently (still part of the reading process). As Marcus writes, “with no books to read, I subsist on the logos.” What matters is that at the end of the day, I read enough to keep me challenged and introspective. Make sense?

      • Nick from Vancouver, BC October 31, 2011 at 10:47 pm

        Makes sense. I find your perspective interesting. Perhaps I’ve been scheduling it in as a form of mental commitment but your comments made me re-think the fact that I am really not making reading one of my highest priorities. Just as what time to go to sleep and what time to eat are usually not strictly scheduled, so it should be for reading, if it truly is a high priority.

        • Exactly. Food and sleep are good analogies.

          • I think Tim Ferriss has got something down when he said it’s better to design your environment than your time. I remember an interview where he said at first he tried to write during the day like many great authors, but he kept tearing his hair out in frustration. Then he tried writing at night (where he was in the right environment with no immediate distractions) and it turned into a habit. I think that’s the best you can hope for.

            For me, reading has to be in a place where (a) it’s quiet and (b) it’s relatively warm and comfortable. Personally I’ve found university libraries to be a great place to read some great books, cause (most) open so late for students.

  19. If you ever have the desire holler at a brother and let’s kick it. Or if there’s anything I can help you with. As a meathead that used to have military aspirations we can nerd out about running, and as a nerd we can nerd out about anything. I’ve spent a lot of time in NOLA too. Consider it payment for my acting a fool when I was 18 and drank too much and slept way too little.

  20. Ryan what’s your favorite animal?

  21. Hey Ryan,

    1) What do you read online? (Meaning do you have any sites you regularly read/people you “follow”)

    2) What is the subject of your new book/when will it be published? : )

  22. Ryan,

    Thanks for answering these questions. I wanted to ask about some of your thoughts on the current state of marketing. It seems likely, based on the young age that you started your job at American Apparel, that you went in with little professional marketing experience – did you ever feel hindered by this or did it allow you to think about marketing strategy in novel ways that more experienced professionals would have missed?

    Second, how did you initially go about forming a marketing strategy for American Apparel? In the few marketing classes I’ve taken it is a very linear, analytical process composed of identifying a target market, segmenting it and developing an appropriate marketing mix (4P’s), but somehow I can’t imagine you going about it in such a linear fashion. I’m just curious as to your thought process as you decided how to communicate the value of American Apparel to a brand-saturated society? Where did you start?

    Finally, one of the main things the media has been keen to tee off on is the use of raw sexuality in your marketing. Can you talk about your thought process in using sexuality to communicate your brand? Again, the little I know of you I can’t imagine it was as simple as “sex sells,” but had to have more substantive thought behind it.

  23. Hi Ryan,

    What was researching for Robert Greene’s The 50th Law like? What did you get to do?

    • I talked about that in the interview man.

      • I knew I should have explained myself better. I was asking about what you got to research on, or even better, what was your research process like on any given topic?

        I’m asking because if someone came up to me and said “Research the technological advancements of the 1920s” I would have no idea about what to do besides typing it into Google and Wikipedia.

        • Actually, you’d be surprised. Those are not bad places to start.

          That being said, I don’t do that kind of research, at least for Robert. His books focus on stories and powerful images. My job is to help find some of those stories. The best place to find them are in memoirs, biographies, and the classics. Personally, I’ve found that the older the book the better its stories are, so I tend to look in libraries and for out of print old books on Amazon.

          In the 50th Law, Robert explained the basic outline of the book, the types of characters he was looking for, (more importantly who he was NOT looking for) and I had a basic timeline of when those areas needed to be filled in. What I actually ended up covering I can’t really discover but I researched everything from black boxers like Jack Johnson to people like Joan of Arc.


  24. Do you use any tool for making decision about your next step or strategy like MindMap?

  25. Hi Ryan. I’m just curious what you do with all of your books after you’ve read them. Obviously you keep the ones you wish to refer to later but what about the others? Ebay? Library donation? New coffee table props? Thanks.

    • I keep every book I buy. When I moved from LA to New Orleans I had to rent a uhaul just for my books. I guess I don’t make a distinction between books I want to refer to later and books I don’t. How can you know? In fact, a lot of times I buy ebooks or borrow one from a friend or library and need to buy my own copy after just in case I might need it again.

  26. I’ve been reading Max for years (I recall when that first email made the rounds on the internet but didn’t connect the dots until after the first book was published). I’ve read a few random people such as yourself off and on for a bit (Philalawyer, etc) based almost entirely upon their connection to him, but am interested to know why you support Ferriss so much, as it he seems to be essentially self-serving. Given his history in marketing and the internet as a whole, it all seems to just prey on peoples’ insecurities and essentially seems like snake oil for the 21st century.

    Bear in mind this is not an attack, I’m just curious to hear what it is that you see in someone who just doesn’t seem to be entirely on the up and up. Success doesn’t necessarily mean it’s something to be admired or emulated.

    • In what way is he self-serving? I’ve found his advice to be incredibly helpful in my own life (as well as meticulously researched, interesting and accurate). He’s also a good friend.

  27. Got a nerd question for you…
    How do you keep track of your books? I consistently come home with books that I purchased a year ago and got distracted from. thx

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