Oct 29, 2026 · 1 hr 2 min · 11 segments
What if the thing standing between you and your next chapter isn't a lack of talent, but a lack of courage? Ryan Berman spent three years studying courageous leaders, elite athletes, entrepreneurs…
Ryan BermanGuest
Tim ShieldsHost
Why courage? Like, do you remember a moment where it's like light bulb or was it something subconsciously you needed to embody or it was just a marketable idea? I

And I'm pretty sure that it came from me being in a room with our leadership team at the agency talking about positioning.

So I think it still came from like courageous ideas are the only ones that matter, which was a conversation.

Like it took a long time to get people at 72 and sunny and Sidley and Saatchi and Saatchi to move to San Diego.

Cause really smart, you know, San Diego is not exactly the Mecca of creativity.

And so I, I'm certain where the idea started from was on a, us talking about positioning and the power of a courageous idea.

And then as you go on the journey, you're like, wow, this is so much bigger than courageous ideas about courageous leaders.

And I, A few mentors presented themselves to me on that journey, that writing journey.

One of them was Steve Wilhite, who was hired by Steve Jobs to run marketing at Apple and like talk about a courageous guy.


I remember visiting him in Aspen for our interview and it was like a three hour interview and it could have been eight hours.

You know, one of the big things Tim that I've learned is like telling the truth has become an act of courage.

And it's pretty wild that, Like, what happened to us that just being real and being honest is now an act of courage? And it's not that people are lying on purpose, but they're biting their lip and they're not sharing.

Why courage? Like, do you remember a moment where it's like light bulb or was it something subconsciously you needed to embody or it was just a marketable idea? I

And I'm pretty sure that it came from me being in a room with our leadership team at the agency talking about positioning.

So I think it still came from like courageous ideas are the only ones that matter, which was a conversation.

Like it took a long time to get people at 72 and sunny and Sidley and Saatchi and Saatchi to move to San Diego.

Cause really smart, you know, San Diego is not exactly the Mecca of creativity.

And so I, I'm certain where the idea started from was on a, us talking about positioning and the power of a courageous idea.

And then as you go on the journey, you're like, wow, this is so much bigger than courageous ideas about courageous leaders.

And I, A few mentors presented themselves to me on that journey, that writing journey.

One of them was Steve Wilhite, who was hired by Steve Jobs to run marketing at Apple and like talk about a courageous guy.


I remember visiting him in Aspen for our interview and it was like a three hour interview and it could have been eight hours.

You know, one of the big things Tim that I've learned is like telling the truth has become an act of courage.

And it's pretty wild that, Like, what happened to us that just being real and being honest is now an act of courage? And it's not that people are lying on purpose, but they're biting their lip and they're not sharing.
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