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Jessica Livingston on investing in Stripe when the Collison Brothers were teenagers

December 24, 2024

Jessica reflects on a 19-year old Patrick Collison telling her and the other co-founders of Y Combinator that he wanted to take on the financial industry with his younger brother John.

“We were like, ‘Do you realize how hard this is? And you don’t have connections.’ But they were intrepid. They were like, ‘Well, we don’t have connections, but we’ll find connections.’”

She recalls their determination and focus:

“You think the head of a bank is going to take a 19-year old startup founder seriously? It seems pretty implausible, right? But they were good enough that they were able to convince these banks to work with them.”

Determination, Jessica argues, is “by far the most important quality. More than intelligence. More than previous success in school.” When she co-founded Y Combinator, the hypothesis was that they’d just fund all the best hackers from MIT and Harvard and they’d turn out to be great startup founders. But that turned out to not be true.

“Determination is the most important thing. Understanding your users and building a product with a great user experience is second most important.”

Jessica also believes being flexible minded is very important:

“You have this idea, you test it out, and it doesn’t always work the first time. You have to be able to say, ‘Okay, I thought I was going to do this, but let’s try this, even though I have a lot of energy vested in this, let’s try this direction. You really have to be open minded.”

And then you have to be convincing and a good leader:

“You are going to be convincing employees to join you. You’re going to be convincing investors to invest in you. When you get to the point where you’re doing deals with bigger companies, you have to convince them. Your whole world is convincing people, and so you have to be able to communicate your idea and convince people why they should care about you more than any of the other hundreds of startups out there.”