Podcast Episodes
Back to SearchHow 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…
11 hours 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 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…
4 weeks 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…
1 month 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…
1 month, 1 week 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…
1 month, 2 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…
1 month, 3 weeks 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: …
2 months ago
The Right Time to Start is Right Now
Season 1 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…
2 months, 1 week ago
The Most Expensive Equity Doesn't go to Investors
Season 1 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?…
2 months, 2 weeks ago