Dropbox CEO to Penn State: Find Problems You Want to Solve

Everyone has problems. But if you want to be happy, you need to have problems you can get excited about solving.

At least, that’s what Dropbox founder and CEO Drew Houston thinks. You might not recognize his name, but if you’ve ever worked on a group project, or needed to send someone a file that was too big for email, then you’re probably familiar with his work.

Speaking at Penn State’s IST Startup Week on Friday, Houston said he got his start as an entrepreneur by starting an SAT prep company. But how many times can you write math problems about parallel lines before you get bored with it?

Houston needed a new challenge to tackle, one he could get excited about solving. In his own life, he’d dealt with the uniquely frustrating problem of transferring files between multiple computers and operating systems.

That wasn’t a problem for most people, but Houston was in luck. The world was about to change.

“This was late 2006, just before the iPhone was announced,” Houston said. “The smartphone was really the dawn of a new era where everyone has two computers: one in their pocket, and their laptop.”

Suddenly everyone was storing everything on the cloud, and everyone needed universal access to all their files on all their devices. For a tech head like Houston, it was practically a dream come true.

He describes the feeling of having a problem you can really enjoy solving like a dog chasing after a tennis ball: underneath the “totally ridiculous,” single-minded focus, there’s a real sense of happiness and joy.

Houston had been programming since he was a child, so the technical aspect of building Dropbox was like an enjoyable puzzle for him to solve. But as the company began to grow into its current multi-billion dollar incarnation, he faced a new challenge. How do you get a large group of people to do anything efficiently?

Thankfully, he had some training for that too – but it didn’t come from where Houston might have expected.

“If you watch Animal House, you don’t think of fraternities as a bastion of higher learning,” Houston said. “But in some ways, I learned as much through that experience as I did in class.”

He said fraternities, and other student groups, throw you into a random group of people, forcing you to learn to get along and work toward common goals. Houston had to learn interpersonal communication and problem solving – which have been invaluable to running the human side of his company.

“Even something silly like someone taking your clothes out of the washing machine and not putting them in the dryer can be a learning experience,” Houston said. “… My first way to deal with that was to write a long, bitchy email to everyone. And you quickly learn that’s not a good idea.”

He gave the gathered students some fairly standard advice, like making the most of their classes, taking internships and surrounding themselves with people who inspire them to grow. But Houston said there’s more to the college experience than just those pieces of advice. 

Houston encouraged every student to start or join some kind of group that they can care about, and to take on as much responsibility as they can. If you can learn to work hard with the weight of the responsibility on your shoulders at an early age, then Houston thinks you’ll have a fighting chance at anything you set your mind to.

“Whenever you get that feeling of ‘oh my God, I’m not ready for this,” instead of running away from it, run toward it,” Houston said. “Whether it’s true or not, if you’re convincing yourself that you can or can’t do something, then you’re going to be right.”

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