The Paradox of Success: Wil Schroter on Founders and Fulfillment

Success won’t fix what you think it will—and Wil Schroter, founder of Startups.com, explains why so many entrepreneurs hit major milestones only to feel more lost than ever.

Wil has built, sold, and acquired multiple companies, yet he’s seen countless entrepreneurs hit their biggest milestones only to feel more lost than ever. He sits down with Alex Raymond to talk about why financial wins don’t fix deeper struggles and how chasing an exit can leave founders grappling with purpose, identity, and unexpected disappointment.

Wil shares what he’s learned from working with thousands of entrepreneurs—why they conflate success with happiness, why scaling too fast can backfire, and how to build something sustainable without losing yourself in the process. He also gets personal, talking about the non-negotiables that keep his life in balance.

If you’re constantly pushing toward “someday,” this episode might change how you define real success.

Quotes

“Everything we thought was going to get cured, doesn’t change at all. In fact, it actually gets worse. Now, when people hear that, they’re like, ‘Oh, I’m so sorry that you made a million dollars. I’m so sorry your life is worse.’ It’s not that easy. Yes, it’s improved safety, but it hasn’t changed purpose.” (09:16 | Wil Schroter)
“The value of anything is the fact that you don’t have it. And once you get it, once you get that success, you realize that it didn’t change any of the things you were expecting it to. And it’s really depressing, which is ironic.” (11:55 | Wil Schroter)
“If you are unhappy on a canoe, you’re not gonna be happy on a yacht. You’re the same person just on a more expensive boat.” (14:13 | Wil Schroter)
“It feels very lonely, and that is kind of the worst part about the founder journey. It is incredibly alienating. That’s something that we’ve tried to kind of unpack for a very long time—to tell founders we’re in the business of showing you you’re not alone.” (26:32 | Wil Schroter)

Links

Connect with Wil Schroter:

LinkedIn: https://www.linkedin.com/in/wilschroter/