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.