Jimmy Douglas didn’t learn how to fundraise in business school. He learned it at 14, selling vacuum cleaners on commission to help pay the bills after his father - an entrepreneur who once ran a semiconductor company - passed away.

In this episode, Jimmy tells the story of growing up on a Christmas tree farm in Oregon, feeling out of place, working sales jobs to make rent, and eventually leading used car sales at Tesla before deciding, on paternity leave, to finally start his own company: Plug. A marketplace for used electric vehicles that has raised two wildly successful rounds of funding.

We also talked to his first investor, Ann Miura-Ko of Floodgate, about what stood out about Jimmy that made her want to chase him down to start a company. Jimmy’s story shows how our most difficult circumstances shape our sharpest skills, and how good founders avoid getting attached to their first idea.

Peter Reinhardt co-founded the analytics firm Segment, and built it into a company that sold for $3.2 billion. But before it worked, everything else they tried didn’t.

In this episode, Peter and his co-founder, Calvin French-Owen, share their humbling story of finding product-market fit: hospital panic attacks, a crisis of faith, and how, with just a few weeks of runway left, they published a Hail Mary concept on Hacker News -- that blew up. It’s a story about how giving up control finally led them to build something people wanted. And forced them to mourn their attachment to vision.

Since then, Peter has only increased his ambitions: he launched another successful company, Charm Industrial, that permanently sequesters carbon underground, and is also the CEO of Revoy, that converts semi-trucks into electric vehicles.

Nathan Blecharczyk turned a social experiment into Airbnb: a company that would remake travel. But first, it had to survive.

Before it reshaped an industry, Airbnb looked like an idea that shouldn’t work. In this episode, Nathan retraces the moments that almost killed the company: convincing people to trust a stranger in their home, handling their first major crisis, and watching 80% of their business evaporate in a global pandemic. But with each emergency, he developed the philosophies that would engineer real trust in the company.

Alongside Sam Angus, the first advisor who believed in their idea, Nathan shares how they overcame one of humanity’s most instinctual fears and built something that refused to die.