Top 48 Quotes & Sayings by Drew Houston

You think about who needs Dropbox, and it's just about anybody with a pulse.

A lot of really great, innovative things have happened when people just didn't know it wasn't supposed to be possible.

Reading a book about management isn't going to make you a good manager any more than a book about guitar will make you a good guitarist, but it can get you thinking about the most important concepts.

To the casual observer, the Dropbox demo video looked like a normal product demonstration, but we put in about a dozen Easter eggs that were tailored for the Digg audience. References to Tay Zonday and 'Chocolate Rain' and allusions to 'Office Space' and 'XKCD.' It was a tongue-in-cheek nod to that crowd, and it kicked off a chain reaction.

You only have to be right once.

Dropbox is my life.

What scares me the most is that both the poker bot and Dropbox started out as distractions. That little voice in my head was telling me where to go, and the whole time I was telling it to shut up so I could get back to work. Sometimes that little voice knows best.

Our users are trapeze artists, high school football coaches - I got cornered by a couple of theoretical physicists who said Dropbox lets them collaborate across the world and share their experiments' results. They were raving about how it's driving their research.

Devices are getting smarter - your television, your car - and that means more data spread around. There needs to be a fabric that connects all these devices. That's what we do.

No one is born a CEO, but no one tells you that.

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.

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.

If you're going to go to the moon, you don't shoot the rocket right at the moon. You have to go at it obliquely.

People do not choose Dropbox because it has this much space or gigabytes. They choose it for the experience.

Dropbox is useful to anyone with a phone. That's, like, two billion people.

One of the great things about moving to Silicon Valley is that you're surrounded by all these people who've done it before. This place is an assembly line that takes a couple of twenty-somethings and walks you through everything you need to learn.

If you start your own thing, you can learn a lot really fast from doing things wrong.

There are 30,000 days in your life. When I was 24, I realized I'm almost 9,000 days down. There are no warm-ups, no practice rounds, no reset buttons. Your biggest risk isn't failing, it's getting too comfortable. Every day, we're writing a few more words of a story. I wanted my story to be an adventure and that's made all the difference.

One misconception is that entrepreneurs love risk. Actually, we all want things to go as we expect. What you need is a blind optimism and a tolerance for uncertainty.

If you have a dream, you can spend a lifetime studying, planning, and getting ready for it. What you should be doing is getting started.

Where you live matters. Whatever you're doing, there's usually only one place where the top people go. You should go there. Don't settle for anywhere else. Meeting my heroes and learning from them gave me a huge advantage. Your heroes are part of your circle, too - follow them. If the real action is happening somewhere else, move.

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.

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.

Instead of trying to make your life perfect, give yourself the freedom to make it an adventure, and go ever upward.

There's this joy that comes from sitting down to solve a problem and standing up when it's done and good. Building a company or managing people is never just done.

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.

The only way to learn on a zero dollar budget is to talk to people

Reading a book about management isnt going to make you a good manager any more than a book about guitar will make you a good guitarist, but it can get you thinking about the most important concepts.

You need that hunger no matter what, because eventually the honeymoon period wears off. Somewhere between printing your business cards that say 'founder' on them and everything else you have to do, you realize, 'Oh, actually this is a ton of work.'

Where you live matters: there’s only one MIT. And there's only one Hollywood and only one Silicon Valley. This isn't a coincidence: for whatever you're doing, there's usually only one place where the top people go. You should go there. Don’t settle for anywhere else. Meeting my heroes and learning from them gave me a huge advantage. Your heroes are part of your circle too - follow them.

The happiest and most successful people I know don't just love what they do, they're obsessed with solving an important problem, something that matters to them.

You become the average of the five people you hang out with.

You can’t focus on what everyone else is doing — it has to be about what’s really broken and what you can do to fix it.

You have to adopt a mindset that says, 'Okay, in three months, I'll need to know all this stuff, and then in six months there's going to be a whole other set of things to know - again in a year, in five years.' The tools will change, the knowledge will change, the worries will change.

There are 30,000 days in your life. When I was 24, I realized I’m almost 9,000 days down. There are no warm-ups, no practice rounds, no reset buttons. Your biggest risk isn’t failing, it’s getting too comfortable. Every day we’re writing a few more words of a story. I wanted my story to be an adventure and that’s made all the difference. Instead of trying to make your life perfect, give yourself the freedom to make it an adventure, and go ever upward.

No one is born a CEO, but no one tells you that. The magazine stories make it sound like Mark Zuckerberg woke up one day and wanted to redefine how the world communicates [by creating] a billion-dollar company. He didn't.

Surrounding yourself with inspiring people is now just as important as being talented or working hard.

A lot of times it's an asset to not know everything about everything... A lot of really great, innovative things have happened when people just didn't know it wasn't supposed to be possible.

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.

You must maximize the probability that someone shows up at front door of your store or website and ends up with a solved problem.

I actually don't think it matters how early or late you are as long as you hit critical mass.

Don't worry about failure; you only have to be right once.

Learn early, learn often.

The hardest-working people don't work hard because they're disciplined. They work hard because working on an exciting problem is fun.

I'd be like, alright, I don't know anything about sales. So I would search for sales on Amazon, get the three top-rated books and just go at it. I did that for marketing, finance, product, engineering. If there was one thing that was really important for me, that was it.

We've had customers from the beginning. The reason people use Dropbox is because they really love it. We think more about who is going to be competing with what we are going to be doing, not with where we started.

Even if it doesn't work out, the experience is so valuable to so many employers that your worst case scenario is, 'Ok, so that was a bust, I'll get a six-figure job at whatever company.' Risk is this outmoded idea - your parents might not understand that, but taking these types of risks doesn't have a downside.

Software touches all of these different things you use, and tech companies are revolutionizing all different areas of the world...from how we shop to how farming works, all these things that aren't technical are being turned upside down by software. So being able to play in that universe really makes a difference.