#108 Ryan Holiday

Ryan Holiday (@RyanHoliday) joins James to talk about hard work, meeting the right people, and creating win-win situations. Holiday has written three books; Trust Me, I’m Lying, Growth Hacker Marketing, and The Obstacle Is the Way. Holiday was a previous guest in episode #18. What I liked about Holiday’s interviews is that he tells James, “I’m a person who’s worked hard and had some success, I don’t feel like I’m some prodigy or something.” This matters to you and me because we can learn from the things he’s done in life. If you aren’t taking away life lessons from these interviews, you’re really missing out.

Holiday’s admission means that we can tease out natural talent as a reason he’s had success. Austin Kleon (episode #19) told James that “genius can’t teach you anything,” meaning that someone who didn’t need to work, hustle, and dig around to find nuances, has less to teach you than someone who did. Stephen Dubner (episode #20) told James that this is a tool he uses when writing the Freakonomics books. Dubner’s success is built on figuring out what might have been randomness and what was not. So what did Ryan Holiday do that we can learn from?

Their conversation turns to when Holiday just getting started. He was writing for a school paper and liked what Tucker Max (episode #80) was doing. So, he wrote an article about Max, “without needing anything” Holiday says.  He sent it to him, hoping it would lead to an interview but not dependent on it. Holiday wasn’t seeking money, or a job, but instead the chance to talk to Max. Tim Ferriss (episode #22) mentioned this idea in his interview with James when he said that we don’t need money for a lot of things. (And James modeled in when he interview Maria Popova (episode #89)) In fact, money probably couldn’t have bought a meeting between Holiday and Max, only his effort could.

And you can’t be fixed on the goals, because sometimes the goals don’t ever come. Jon Acuff (episode #106) tells James, “you can’t do it for the money, results, or affirmation because you’ll stop as soon as that stuff doesn’t show up.” And that stuff takes a long time to show up.

Astronaut Chris Hadfield might be the best example of this. Hadfield was a Canadian who needed to be accepted to test pilot school in America and then get launched into space on a Russian ship to the international space station. He had to stay healthy (and did barely) be better than many others and luckier than some. He had to actually survive, because each year he saw one of his peers die. About getting to space he writes:

“It’s probably not going to happen but I should do things that keep me moving in the right direction, just in case – and I should be sure these things interest me, so that whatever happens, I’m happy.”

Holiday’s internship with Max led to a connection with Robert Greene, who had hired Max to do some work for him. Creating nodes in a relationship network have proven to be fruitful to other guests as well. John Acuff told James that this was how he got featured in the Southwest Airlines inflight magazine. Ditto for Adam Carolla (episode #25) who never intended to become friends with Jimmy Kimmel, but did, and it launched both their careers.

Holiday went from his internship with Max to working for Robert Greene, about which he says: “I would not be here right now, I would not be a writer if I hadn’t been Robert’s research assistant.” That job meant sorting through Greene’s unread pile of books and finding things he might use for his work-in-progress. It was, “far and away my favorite job of all time.” Holiday says.

Now that Holiday has earned his own success, he tells James that he gets people coming to him in similar situations and saying they would be happy to work for him for free for the experience but “for me to train this person to do something for me is not free for me.” If you’re reading this thinking about having a mentor in your life you need to take a different direction. Do not email someone and offer to work for them. Tim Ferriss suggests helping other people and not expecting any return, a refrain that Adam Grant (episode #73) suggested too. Ramit Sethi (episode #36) told James that he wants people to come to him prepared, to read something he’s written, and bring value by asking a new question about it.

Greene’s mentorship to Holiday led to an introduction at American Apparel where Holiday organized the marketing division of the company. It sounds like this is where Holiday developed the idea of a story about the story. American Apparel did this with advertisements that featured naked porn stars. About this Holiday says, those ads only ran on two sites, but the story about them were picked up on hundreds. It was a campaign around the campaign and has been leveraged since; Tucker Max tried to sponsor a Planned Parenthood, Tim Ferriss talked about being excluded from Barnes and Noble, and even James Altucher got in on things when he accepted Bitcoin for his books. Click the image to watch him on CNBC.

Screen Shot 2015-04-24 at 6.16.35 AM

Holiday calls this “leaning into the problem” and it’s another thing to learn from.

At this point in the interview the pair dive into some rapid fire advice:

  • About Marketing Mistakes. “People don’t do the work beforehand because they get so caught up in their love of their own creativity and ideas.” Holiday says. They need to dive deep and figure out what people want, not only what they can provide.
  • Holiday’s Two Rules for Writing. “Who am I writing this for and how will it reach them?” Make sure you know what group of people is going to buy the first thousand copies Holiday tells James.
  • About Email Lists. Start small and slowly build it up. It’s the most valuable metric Holiday has because 1 email newsletter subscriber is more valuable than 100 page views for an article.
  • Write at Other Sites. Holiday says that “everyone needs content” and “no editor has ever said, ‘we have too much good content.’”

The interview concludes with the pair talking about the publishing industry and what it looks like. Holiday says that he hasn’t self published yet because the “constraints make me better and stronger.” Constraints helped David Levien (episode #85) write his most recent book series. Astro Teller (episode #81) told James that time constraints lead to better time spent with kids for divorced couples.

But Holiday is keeping his options open to self publishing. This is the sort of optionality made Nassim Taleb rich (but not smart) about that  billionaire business man Seymour Schulich writes “is a terrible thing to give but a wonderful thing to own.” Holiday owns his future writing options.

Thanks for reading, I’m @mikedariano.

One final note. A lot of what Holiday talks about sounds like it’s passion driven but what Holiday really has is control. He went from having no skills and no control (sleeping on Tucker Max’s floor) to have valuable skills and much more control (owning his own business, writing the books he wants. Holiday built up career capital that he traded in for control (and presumably a bed ;)) If you want to learn more about the ideas of control, capital, and why following your passion is bad advice check out http://gum.co/sogoodbookclub which teaches So Good They Can’t Ignore You.

19 thoughts on “#108 Ryan Holiday”

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.