Podcast Episodes
Back to SearchWhere were you when I was broke?
Episode 338
Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is hig…
9 hours ago
What if I'm the Best, but don't know it?
Episode 337
What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by…
1 week ago
Founders Don't Retire
Episode 336
What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: …
2 weeks, 1 day ago
The Right Time to Start is Right Now
Episode 335
Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite…
3 weeks, 1 day ago
The Most Expensive Equity Doesn't go to Investors
Episode 334
Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return?…
4 weeks, 1 day ago
How to be Great at Worrying
Episode 333
Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant v…
1 month ago
Can Startups Be a Team of One?
Episode 332
What happens if building a startup no longer requires a team? The conversation explores how AI is rapidly turning the classic “product + developer + …
1 month, 1 week ago
Why are we Really Building a Startup
Episode 331
What are you really trying to fix by building this company—and what happens when you finally admit it? The conversation unpacks how founders often de…
1 month, 2 weeks ago
We Rarely "Control" Our Startups
Episode 330
Worried about “losing control” because of dilution? This episode breaks down why equity is a poor proxy for control in startups: the cap table splits…
2 months, 2 weeks ago
Founders Need Finish Lines
Episode 329
Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers…
2 months, 3 weeks ago