Chris Larsen, co-founder and Executive Chairman of Ripple

"There's a feeling of fear, like I shouldn't do this. And then there's a feeling of being scared, but like you just know. All three companies, I felt scared, didn't sleep, especially when you didn't have money in the early days. But you know, it felt like, yeah, I'm gonna do that."

Chris Larsen, co-founder and Executive Chairman of Ripple, has spent over 30 years building at the frontier of fintech - E-Loan, Prosper, Ripple. Each time, he built where banks didn't want him to exist. Each time, he felt that fear.

When I worked in fintech, we were constantly looking at Ripple. They were the market. Last week, I got to sit down with Chris for dinner with Icons. What I wanted to understand: how do you keep building for three decades when the system is designed to stop you?

A few insights from our conversation:
1. That fear never goes away, and sometimes it's right to be scared.
All three companies terrified him. But he's also been fired, nearly went bankrupt, and spent eight years at Prosper when he should have walked away after two. That "yeah" feeling doesn't mean you won't fail. It just means you're willing to find out.

2. Don't hang on too long.
Chris spent eight years at Prosper. His biggest regret isn't that it didn't work, it's that he didn't walk away sooner.

"Try to fail sooner, don't hang on too long. This is a very short life. You don't have any time to waste."

VCs can always recapitalize a company. You can't recapitalize your time. This one hit harder as we continue to navigate the fast-changing world.

3. Self-awareness matters as much as capability.
After four years as Ripple's CEO, Chris brought in Brad Garlinghouse. That was 11 years ago. The boundaries are ruthlessly clear: any email Chris sends to Ripple employees copies Brad. Nobody can come to him and undo Brad's decisions.

"The CEO has to be seen as the person making decisions."

Knowing what he's good at gave Chris his life back. He's 65, still building, but now he has time for what matters. He swims. He works on climate. He spends time with his kids.

He's good at chaos. Brad's good at scaling. That partnership works because the boundaries are clear.

4. Culture requires relentless repetition.
"Talk about your core values all the time, until you are blue in the face. You think people can't possibly want to hear this again. Nope, they want to hear it all the time."

Chris and Brad talk about core values in every meeting. They do celebrations. People get jackets with the values on them. It sounds corny, but the discipline is rare.

All three of Chris's companies were built where banks didn't want him to exist. The pattern: find where the system is broken, build the alternative, fight the incumbents.

Success wasn't just about the technology or the strategy. It was about having the conviction to build where everyone said you couldn’t.

Thank you to Chris for the time and the honesty he shared with us. Thank you to everyone who joined us.