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Drew Houston Quotes

Andrew W Houston

Drew Houston quotes: Dropbox don describes his journey to billionaire.

“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.”

“Don’t worry about failure; you only have to be right once.”

“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.”

“Even if it doesn’t work out, the experience is so valuable to so many employers that your worst case scenario is, ‘Okay, 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.”

“If you start your own thing, you can learn a lot really fast from doing things wrong.  Ask yourself, ‘Where can I find an environment where I can work really hard and learn the most?'”

“Learn early, learn often.”

“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.”

“But every weekend, I would take this folding chair up to the roof with all these books I got on Amazon.  I would just sit there and read all of them.  I would spend the whole weekend just reading, reading, reading.  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.”

“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.”

“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.”

“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.”

“The fastest way to learn is by doing.”

“Dropbox has been mine.  As you might expect, building this company has been the most exciting, interesting and fulfilling experience of my life.  What I haven’t really shared is that it’s also been the most humiliating, frustrating and painful experience too, and I can’t even count the number of things that have gone wrong.”

“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.”

Bill Gates‘ first company made software for traffic lights.  Steve Jobs‘ first company made plastic whistles that let you make free phone calls.  Both failed, but it’s hard to imagine they were too upset about it.  That’s my favorite thing that changes today.  You no longer carry around a number indicating the sum of all your mistakes.  From now on, failure doesn’t matter: you only have to be right once.”

“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.”

“The hard thing about planning your life is you have no idea where you’re going, but you want to get there as soon as possible.  Maybe you’ll start a company, or cure cancer, or write the great American novel.  Or who knows?  Maybe things will go horribly wrong.  I had no idea.”

“I’ve never really had a grand plan – and what I realize now is that it’s probably impossible to have one after graduation, if ever.”

“I was going to say work on what you love, but that’s not really it.  It’s so easy to convince yourself that you love what you’re doing – who wants to admit that they don’t?  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 an important problem, 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 problem is a lot of people don’t find their tennis ball right away.  Don’t get me wrong – I love a good standardized test as much as the next guy, but being king of SAT prep wasn’t going to be mine.  What scares me 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.”

“It took me a while to get it, but the hardest-working people don’t work hard because they’re disciplined.  They work hard because working on an exciting problem is fun.  It’s not about pushing yourself; it’s about finding your tennis ball, the thing that pulls you.  It might take a while, but until you find it, keep listening for that little voice.”

“They say that you’re the average of the five people you spend the most time with.  Think about that for a minute: who would be in your circle of five?  I have some good news: MIT is one of the best places in the world to start building that circle.  If I hadn’t come here, I wouldn’t have met Adam, I wouldn’t have met my amazing co-founder, Arash, and there would be no Dropbox.”

“One thing I’ve learned is surrounding yourself with inspiring people is now just as important as being talented or working hard.  Can you imagine if Michael Jordan hadn’t been in the NBA, if his circle of five had been a bunch of guys in Italy?  Your circle pushes you to be better.”

“[On meeting Steve Jobs] I didn’t want to get into much of a debate or make him angry.  I was just like: don’t make him mad, leave a reasonable impression.  That was the only goal.”

“And now your circle will grow to include your coworkers and everyone around you.  Where you live matters.  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.  If the real action is happening somewhere else, move.”

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

“There are 30,000 days in your life.  At first I didn’t think much of it, but on a whim I tabbed over to the calculator.  I type in 24 times 365 and – oh my God – I’m almost 9,000 days down.  What the hell have I been doing?”

“That night, I realized there are no warmups, no practice rounds, no reset buttons.  Every day we’re writing a few more words of a story.  And when you die, it’s not like, ‘Here lies Drew, he came in 174th place.’  So from then on, I stopped trying to make my life perfect, and instead tried to make it interesting.  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.”

“I feel really fortunate.  To be back on the flip side seven or eight years after graduation was surreal.  The premise for my speech: if I was to give myself a cheat sheet at age 22 knowing what I know now, what would I say?”

Cory Johnson: CEO of a business he has yet to launch. As seen on your mom’s phone. Scaled to 7-figures in seven seconds selling a course on selling courses. Kidding. Watch this.