When Drew Houston founded Dropbox, he knew he faced some fierce competition (hello, Google, Apple, and Microsoft). But he didn’t back down from the fight. Why? Because he believed in his product, and he knew he had an advantage those big, cumbersome competitors could never exploit: Dropbox was lean, focused, and fast. Hear how he outmaneuvered the big guys – and what’s next for Dropbox. Cameo appearances: Mark Pincus of Zynga, Shellye Archambeau of MetricStream.

Drew Houston knows if Dropbox is going to design for the future of work, then its own workforce needs to live in that future, right now. He discusses Dropbox’s move toward the virtual-first workplace — and how its benefits extend far beyond pandemic times.

Tinder. Top Gun. Roots. The Simpsons. What do they have in common? Media icon Barry Diller. Barry is what we call an “infinite learner.” He’s only interested in things he’s never done before. And if they’ve never been done by anyone? Better yet. He succeeds by embracing that he is, in fact, a master of nothing. Entrepreneurs, take note: You just might be an infinite learner yourself, and Barry shares a lesson or two you can use.