The Tim Ferriss Show #334 Drew Houston — The Billionaire Founder of Dropbox

Full podcast here.

  • Do you revisit books? I do. You read a lot of books and it helps to revisit them- coming back 5 or 10 years later and you can absorb more of the material. (18:58)

  • Book recommendation: High Output Management by Andy Grove (21:51)

  • Book recommendation: The Effective Executive by Peter Drucker “don’t confuse motion for progress” (22:50)

  • Book recommendation (about the experience of running a company): The Hard Thing About Hard Things. Also Poor Charlie’s Almanac (24:01)

  • Book recommendation on the philosophical front: Zen and The Art of Motorcycle Maintenance (26:31)

  • Book recommendation for concise and clear thoughts on how to approach life: Principles by Ray Dalio (28:37)

  • The idea for Dropbox came from emailing files to myself. Think of the physical equivalent of that: taking an envelope, putting something in it, putting your name in the to and from, putting it in the mailbox and then getting it back. That’s what we do to manage our files.(55:05)

  • We paid him $300,000 for the domain. If he would have accepted stock instead it would have been worth a few hundred million. (1:23:54)

  • I wasn’t trying to create a billion dollar company. I was just trying to solve a problem. I think setting your sights low can be helpful at the beginning because you are not putting so much pressure on yourself. (1:28:01)

  • Things going on in my mind at the time: I’ve never built a successful company before. I’ve never managed people before. The idea of Dropbox being a 100 person company is terrifying. This treadmill is just going to go faster and faster until I’m thrown off of it.......Your instinct will be to run away from that feeling but what you need to do is run towards it. Because things will keep happening. (1:32:47)

  • Lesson from Principles by Ray Dalio: Pain plus reflection equals progress. People don’t like the pain part and they don’t bother to do the reflection part. (1:34:53)