Ryan Holiday, the best-selling author of several books (including The Obstacle is the Way and Conspiracy) interviewed Ken Kurson at exhaustive length for the philosophy website The Daily Stoic.
This is another insanely long interview conducted mostly by email. Ryan Holiday is a personal friend, so we did go back-and-forth a little bit on the phone. But mostly he sent me questions and I took my time in answering them.
I have an interesting history with Ryan. We met early in both of our careers, when he first started writing for the Observer, before I was editor there. I wrote him a fan letter because I had just finished re-reading my very favorite book, Tom Wolfe’s A Man in Full. If you know the book, you know that there’s a very powerful digression about stoicism. And just as I was reading it, Ryan started obsessively writing about stoicism. He has become famous for that now, and is possibly the world’s best-known proponent of the philosophy, which is a startling thing to say about a tattooed college dropout who lives with a bunch of goats on a ranch in Texas. But he really is world famous for spreading the word of stoicisim. In a bit, I’ll tell you another story that confirms it.
But first, Ryan responded to that note favorably, and in one of the kinds of coincidences that would occur in a Tom Wolfe book itself, I was soon named editor in chief of the Observer and became Ryan’s editor.
It wasn’t a fully comfortable situation. At the time, we had several journalists working there who kind of wanted to be what I would call Gawker types. They were automatically disposed negatively toward capitalism and any outward signs of ambition. Naturally, these types hate me, and I’m OK with that. But they also hated Ryan, and that’s more mysterious, since he’s really a lefty and even kind of a do-gooder who posts photos of himself cleaning up the beach and actually backs up this stuff with true acts of goodness. But early in his career as a public relations and crisis advisor, he had some clients of dubious reputation. To me, hating someone because of the acts of his clients is a totalitarian impulse. It’s like the people who think that the worst people in the world shouldn’t have a lawyer.
Anyway, one Observer journalist in particular, Nitasha Tiku, did not appreciate Ryan’s take. Early in Ryan’s career, he did intentionally lied to journalists as a stunt to prove how vulnerable they are to being misled. Nitasha thought that disqualified him as a journalist. She thought we should fire him, I did not agree.
Anyway, Nitasha and I actually edited several of his columns together, and that worked fine. She moved on soon enough, to Gawker naturally, and has since enjoyed a stunning career in journalism and continues to do good work all over the place.
Ryan and I became very close friends. He came to my house for Shabbat dinner. I took my daughter to his ranch and she got to pet his goats. We built a very strong columnist-editor relationship and he was just killing it on those things, to the point where Jack Dorsey was often tweeting Ryan’s Observer columns. Later, I asked Ryan to take over the editorship of all of Beta Beat, which was ironic since that was the role Nitasha had had a few years earlier. He did a great job.
And then another stunning Ryan-adjacent coincidence happened.
I was flying home on the redeye from having visited Ripple headquarters in San Francisco. Whenever I fly, especially late-night flights, I bring the biggest, craziest looking headphones plus a mask as a way of signaling to everybody “do not talk to me unless this plane is on fire.” I dread small talk in general, especially on planes when you’re trapped for six hours. So I’m snuggling in to my lie-flat seat, as is the gentleman next to me, when I notice that the book he has taken out is The Obstacle Is the Way.
I took off my headphones and said excuse me, I never talk on planes, and if you try to talk to me I will ignore you. But I want you to know that I edit the guy who wrote that book. He’s a good friend and it’s just such a stunning coincidence that you would pull that out on this plane. The man asked me for my card, I handed it over, and fell into the deep sleep for which I am famous.
A couple days later I got a call from a woman who told me she was secretary to Declan Kelly, the CEO of Teneo. I had never heard of Teneo, and had no interest in business consulting. I was the editor in chief of a New York City newspaper, which was so far above my greatest expectations for myself, as a college dropout who had arrived in the city 20 years earlier not knowing a single soul in media.
However, with Trump’s win things had gotten almost unbearable in New York media. The level of heat and anger was just so intense that it was starting to affect my health. Plus, I suddenly had alimony payments, not to mention 1000 other expenses that accompany divorce. I talked it over with my ex-wife, who knows me better than anybody. Then they made me the proverbial offer I couldn’t refuse. It really was like that, it felt like Don Corleone was recruiting me, not a bunch of Irish guys in Brioni suits.
Teneo turned out not to be for me. I was by far the best writer in the entire operation, but I don’t know shit about business. And although I was constantly told that what I did bring to the table – writing speeches for executives and stuff like that — was very valuable, I just was so self-conscious that these 24-year-olds fresh out of business school knew 10 times more about cash flow regression and excel modeling analysis. It wasn’t for me.
I founded Sea of Reeds Media, and got back to doing the only skill I really have, reading and writing.
This long interview with Ryan captures a lot of what was on my mind at the time I was working for Teneo.
