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/
Website: https://www.startups.com/
Connect with Alex Raymond:
LinkedIn: https://www.linkedin.com/in/afraymond/
Website: https://amplifyam.com/
HiveCast.fm is a proud sponsor of The Conscious Entrepreneur Podcast.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!