Rory O'Driscoll

The guy really partially regretted leaving Stripe as the CTO on the fourth employee.

Sam recruits him from Stripe when it's worth $3 billion and says, don't worry, we'll make it up for you at our nonprofit.

Come do this thing.

We're going to change the world to Greg.

And it's very exciting.

And Greg really doesn't want to work on the Stripe API anymore.

He's already gotten payments to work.

It's kind of boring.

And he leaves in 2015, Rory, when the world seemed very flat and simple, right?

And he left and he turns around and he's like, my God, I left billions behind.

How would you feel as a human being that didn't make the money Sam had already made?

Sam's already become, he wasn't a billionaire then, but he's on the path, right?

He's raised hundreds of millions at his own venture fund to invest in YC startups.

He personally owns 2% of Stripe.

How would 99% of humans feel when you're like,

If I just stayed at Stripe and just played Minesweeper, I could be worth $10 billion.

And I think that haunted him.

And I think that's where these journal entries come from.

It's not him being douchey and saying, man, I want to.

It's him haunted by Sam getting him to leave Stripe at $3 billion.