Patrick O'Shaughnessy

In this conversation, Barry reveals his philosophy of creative conflict, pushing smart, opinionated people past their endurance point to generate breakthrough ideas.

He also shares stories of working alongside media titans like Rupert Murdoch and Bill Gates.

We discuss his current portfolio strategy, innovation in media, and how personal struggles can become professional superpowers.

Please enjoy my great conversation with Barry Diller.

When I ask around about you, as I've done the last couple of days, lots of mutual friends, the word that comes up in every single conversation is curiosity.

Insatiable curiosity, maybe, is the term that people use.

And I love the part in your book about the time in the William Morris file room reading everything you possibly could.

Where did the spark come from?

Is it just innate in you?

Has it always been this way?

What was it about entertainment that captivated you?

It seems like that was the AI of its day, all the top talent.

I was drawn to that.

In the earliest days when you knew you did not want to be an agent, but rather create things, there was this confrontation in your book.

I think you were 23 years old with Charles Bluedorn.

Can you talk about that fight that you had over something?

In that episode, did you discover a fearlessness in yourself?

Everything else.

We're going to talk about the decades more of that to come.

But when I read your book, I was captivated and amazed by how clearly you described things in your early life that so impacted you.