Top 26 Quotes by Drew Houston

You're not going to become a great manager overnight. You're not going to become a great public speaker or figure out how to raise money. These are the things you want to start the clock on as early as possible.

When I think about it, the happiest and most successful people I know don't just love what they do, they're obsessed with solving something that matters to them. They remind me of a dog chasing a tennis ball: Their eyes go a little crazy, the leash snaps and they go bounding off, plowing through whatever gets in the way.

People make basic assumptions based on what they have now. But you have to ask yourself, 'Is this really what people are going to be doing in five years?' Very few people ask themselves what they would actually want instead if they could wave a magic wand.

When you're in school, every little mistake is a permanent crack in your windshield. But in the real world, if you're not swerving around and hitting the guard rails every now and then, you're not going fast enough. Your biggest risk isn't failing; it's getting too comfortable.

With something like Dropbox, it was immediately like, 'Wow, this is literally something that anyone with an Internet connection could use.' Everyone needs something like this; they just don't realize it yet.