Before David Risher was tasked with scripting a “comeback story” for ride-sharing company Lyft , he made a career move so audacious that it prompted a direct, and blunt, intervention from Microsoft co-founder Bill Gates. In a recent appearance on Fortune ‘s Leadership Next podcast , Risher shared the moment Gates told him he was making “the stupidest decision I’ve ever heard anyone made.”
The year was 1996, and Risher was enjoying a successful career at Microsoft during the heyday of Windows. In fact, Risher noted he and his wife just had their 30th wedding anniversary, having met “on the first day” at Microsoft. He said it was a very formative time for him and his career at a very competitive company.
But he had been in talks with a man named Jeff Bezos, who was running a brand-