Podcast Episodes
Back to Search100 CEOs
Season 1 Episode 345
What if the reason so many former employees become CEOs isn’t genius hiring, but creating the conditions that let CEO-level potential show up? The co…
11 hours ago
We Need "Unfireable" Founders
Season 1 Episode 344
Why do founders have to be “unfireable” for a startup to work? The episode argues that founding is the only job where you create the role yourself, h…
1 month, 2 weeks ago
How to be a Horrible Startup Advisor
Season 1 Episode 343
Ever gotten startup advice that sounded like a fact—but was really just someone’s confident opinion? This episode breaks down why so much startup adv…
2 months, 1 week ago
Which Version of Me is Coming to Dinner Tonight
Season 1 Episode 342
Ever wonder which “version of you” should show up to dinner, a board meeting, or a team update? This episode breaks down why founders feel like they’…
2 months, 3 weeks ago
The Death of the Technical Cofounder
Season 1 Episode 341
What if you could build a working prototype without giving away half your company? The episode argues that tools like Claude have ended the old “tech…
3 months ago
We Do What Other's Won't
Season 1 Episode 340
What are you actually willing to do to get what you want as a founder? Using Will’s 6:00 a.m., 15-degree framing session and a dumpster-diving Bobcat…
3 months, 1 week ago
Everyone is a startup... Again
Season 1 Episode 339
What happens when AI turns your hard-won moat into a weekend project? This episode argues that AI has effectively forced established companies back i…
3 months, 2 weeks ago
Where were you when I was broke?
Season 1 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…
3 months, 3 weeks ago
What if I'm the Best, but don't know it?
Season 1 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…
4 months ago
Founders Don't Retire
Season 1 Episode 336
What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: …
4 months, 1 week ago