Simone Stolzoff

And something like building your own business or building your own platform can be more stable and secure than even getting a job in, say, Big Tech or on Wall Street.

Well, I'm curious, what do you think about young Jordan allowed you to take that risk of starting putting your podcast on the internet or starting to publish things to iTunes when there weren't necessarily models of that all around?

There was nobody making money.

Totally.

But you were able to build your uncertainty tolerance by taking each of those steps sequentially.

Like by saying, I'm going to charge $100 for this, you're like, oh, I can just make it up and go as I... And then that gave you more confidence to charge $5,000.

It gave you more confidence to see yourself as a podcaster and pitch yourself to Sirius.

There's so many parts of that story.

One, like Alex was able to raise your ambition.

He was able to show you the peak that existed around the corner that you weren't seeing.

Two, you were able to lower the stakes.

And so taking this uncertain bet didn't feel as risky as if you had built it up in your mind and it was all life or death.

And that's what allowed you to build more uncertainty tolerance by actually getting proximate to these new experiences as opposed to just thought experiments in your mind.

Like an example, a lot of people send me DMs asking, I want to be a writer.

I want to write a book.

I want to be a journalist.

And I often ask them like, okay, so like, what have you written recently?

What do you like writing?

And they'll say, I haven't actually written anything, but I have all of these ideas of things that I want to write.

And what I tell them is the best way to learn about whether you want to be a writer is to write.