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Drew Houston has not joined FLAPSS and has not endorsed it. This page is a reference record assembled from published interviews and public remarks. Every answer below is a direct quotation with the source and date shown next to it.

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Drew Houston

Co-founder and chief executive of Dropbox

United States · b. 1983

Co-founded the file-hosting company Dropbox in 2007 with Arash Ferdowsi and has led it as chief executive since. Graduated from MIT in 2005 in computer science.

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How has a failure, or apparent failure, set you up for later success? Do you have a favourite failure?
No one has a 5.0 in real life. In fact, when you finish school, the whole notion of a GPA just goes away. 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.

Recorded MIT 147th Commencement, MIT News (Massachusetts Institute of Technology), 7 June 2013 source

What are bad recommendations you hear in your profession or area of expertise?
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.

Recorded MIT 147th Commencement, MIT News (Massachusetts Institute of Technology), 7 June 2013 source

In the last five years, what new belief, behaviour, or habit has most improved your life?
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.

Recorded MIT 147th Commencement, MIT News (Massachusetts Institute of Technology), 7 June 2013 source

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