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I want this article to be good because Ryan’s my friend. And I like to think he’s reading this right now…

He’s come on my podcast more than anyone (thank you)

And I feel he’s become a true member of this community. He helped us shape what “choosing yourself” looks like. Because my first time meeting him, he was a marketer for American Apparel. Correction THE marketer. He was 26. And we emailed. He wanted a way out of the filtered life (where you just keep checking the boxes on someone else’s check list).

Years later we became friends. And I hope you all feel like he’s your friend somehow, too. I think that’s why he comes on here for this show.

He told me one time that he doesn’t want to create his own philosophy. Or get you to buy into HIS ideas. He wants to deliver something that really “works.”

So he taps into his own pain points. And offers you strategies from thousands of years ago. Stoicism has worked for Roman emperors, it’s worked for prisoners of war. And it’s worked for me.

But Ryan is dedicated. And that dedication is contagious.

He told me about his next book (it’s not out yet). It’s coming in March. And I’m going to preorder it. Because he’s dividing the gap between a story I can’t get close to without his help.

It’s the scandal between Peter Thiel and Nick Denton. And how Gawker got shut down. It’s Ryan’s first narrative non-fiction. And most of it is underwraps.

“Are you in it?” I said.

“Yeah, but I’m not a major character,” he said. “I had some conversations with Peter Thiel and I had some conversations with Nick Denton. I realized I’m the only person on the planet that’s talking to these two people. Maybe, I thought, that’s a book.”

“Did you just call up Peter Thiel? And say, ‘Hey I want to ask you about this?’”

“He sent me an email,” Ryan said. “He liked an article that I wrote. Putting yourself out there, doing things, opens up opportunities.”

But there’s only one kind of opportunity that matters…

The one that’s open to you. The unique blend of skill X and love of Y.  It’s the one prime for your talent stack (as Scott Adams says).

It comes down to this:

“Competition is for losers” Ryan said. (He was quoting Peter Thiel.) And then speaking as himself… “Invent your own category.”

“Look, it’s hard to say, ‘Here’s the 30 things that no one is doing.’ Just do interesting things. It doesn’t have to be a book. It could be a video. It could be a statue that you make, ya know, it could be f—ing anything.”

I think everybody deep down has some artistic impulse they can pursue. People want to have a different way of expressing themselves other than the cubicle.

“Call it creative,” Ryan said. “Artist sounds too…”


“Yeah. Identify your pain points and make something that actually delivers value in that pain point. That’s what I try to do.”

And it works. (Ryan).

… I should’ve called this post “how to deliver value from your own pain and make it good (advice for the creative seeker).”

That’s the real root of this podcast episode.  

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