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Dalton Caldwell: The One Trait Every Successful Founder Shares

By Dalton Caldwell · Leadership · 1 min read

Caldwell says there's no personality type to copy. Tony Xu, Patrick Collison, Ryan Petersen — completely different people. But they all share one thing.

Key Points

There's no personality type to copy — successful founders are wildly different
The shared trait: somewhere deep inside, they believe they're the one who will make it work
Nobody has this conviction at the start — it builds as customers validate the idea

Somewhere deep in their psyche there's something that says: I'm the one. I won't accept this not working.

No Personality Type to Copy

Caldwell: I don't think there's a personality type that people should copy. I don't really believe in that because there's just so much variation. Tony from DoorDash is so different. Patrick is a different kind of person. Ryan from Flexport — these are just very different personality types.

The One Thing They Share

Caldwell: The thing that folks who build really big companies have in common is they just really want it. They really believe in themselves. They really believe they can make it work.

Somewhere deep in their internal psyche there's something that says — I'm the one. I won't accept this not working. Even though objectively there's all this data coming in that it isn't working. My employees want to quit. My executives want to quit. Somewhere deep down they're like — I'm going to make this work. This company is going to be big.

It's almost like that internal gravitational force inside of them is so large it warps the world to bend to that will. People start to believe it because they believe it so much.

Somewhere deep inside, there's something that says: I'm the one. I won't accept this not working.

Nobody Starts With This Conviction

Caldwell: This is the big but — no one has this at the early stages. When they don't have a good idea and don't have customers and it's objectively not working. I know a lot of founders who say — I don't feel that way. Maybe I'm an imposter.

Of course you don't feel that way if you haven't talked to any customers and haven't built a product. What usually happens is you pivot to a good idea or start with one you care about, you launch it, and the better the product does, the more obsessed you get with your own company.

In the case of Stripe, I recall Patrick saying he wasn't as sure it was going to work until they were a year or two in. Then once it started working, they really believed in it. You build conviction as customers and data reflect back that you're on the right track.

You build conviction the more customers reflect back to you that you're on the right track.