Ryan Holiday

Behind the Conspiracy

Episode #331

SUBSCRIBE ON APPLE PODCASTS SUBSCRIBE ON YOUTUBE SUBSCRIBE ON STITCHER
Download The Podcast MP3

Ryan Holiday has access to one of the most surreal conspiracies of modern day. Here’s what happened.

Nick Denton founded Gawker. Gawker wrote an article that outed the sexuality of billionaire Peter Thiel. Peter’s privacy was invaded.

100%. There’s no arguing that.

Then Gawker released Hulk Hogan’s sex tape. Hulk Hogan needed to sue. But he couldn’t afford it. So Peter (secretly) funded the lawsuit to get revenge himself.

Here’s what’s weird, though. No one knew Peter Thiel was funding Gawker’s death. Not even Hulk Hogan. He was told “a rich businessman” was helping.

At the time, Gawker thought they were just up against Hulk Hogan. “A single digit millionaire.”

THIS is where the conspiracy takes place.

5 years goes by…

Gawker is wondering “When will Hulk quit?” When will he run out of money?

They have no idea a billionaire is funding the bill.

Finally Hulk wins. $115 million.

Nick goes broke. Gawker shuts down.

And then one day… Ryan Holiday gets an email from Peter Thiel. And in the same period, he starts talking more to Nick Denton…

The seed of the book is watered. Ryan realizes he’s the only person with his skillset to have total access to the two biggest players involved (Nick Denton and Peter Thiel).

He made a move.

And left his lane (where he wrote “The Obstacle Is the Way” and “Ego is The Enemy.”) And before those, he left the marketing lane (where he wrote, “Trust Me, I’m Lying” (a cult classic) and “Growth Hacker Marketing”)

This time, Ryan went somewhere else. And I have to say, I’m a little jealous.

I am NOT jealous of the hard work though. I remember asking him about the project before it published.

“It’s the hardest book I’ve ever written,” he said.

“Why don’t you stop?” I asked.

And he didn’t think about it. It was just something he had to do. It’s the pursuit of a new challenge and a new skill.

He knew he could.

And he was right. The book’s called “Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue” It’s a narrative nonfiction.

This isn’t what we expect from Ryan Holiday. And that’s what makes it the best one he’s ever written.

Only 3 people at his publishing company knew what it was about. They had a code word. “UMB,” which stood for “Unnamed Media book”

Or unknown media book?

I forget.

“Why tell someone?,” Ryan said. “I don’t mean never, but think about [LISTEN]

I have a secret project. Sometimes I think about telling a few people. But I like to to keep it private because it makes me feel like if I fail, it’s okay, I haven’t started. And it’s all an illusion. The pressure and the fear stays away, like a sleeping giant. I keep my secret. And work in private.

I think that’s how Ryan started to find all these synchronicities in his work.

He was talking to Robert Greene, who mentored Ryan in the beginning. Robert told him to read some obscure chapter on Machiavelli in the book “Discourses on Livy.”

A week later, Ryan was at Peter Thiel’s house. And he saw the book. Opened it up, and found the outline for his book.

Peter walked over. And from his memory, he began discussing the book.

“What’d it say?” I asked.

“Machiavelli says that there are three parts of a conspiracy: the planning, the doing and the aftermath. Essentially, before, during and after. But the after is the most dangerous part.”

I don’t want to give the whole story away. I want you to read Ryan’s book and listen to this interview.

Because I think he did the impossible.

(And so did Peter [in shutting down Gawker] and so did Hulk Hogan [in winning the lawsuit]).

Ryan told me that was his goal all along… he was fascinated by the concept of someone solving an impossible problem.

Because it proves that “impossible” is up to the individual.

I’ll quote Ryan quoting Machiavelli. “States can wage war, but a conspiracy’s available to everyone.”

This one is available now.

Links and Resources

Also Mentioned

Thanks so much for listening! If you like this episode, please subscribe to “The James Altucher Show” and rate and review wherever you get your podcasts:

Follow me on Social Media: