Dropbox Founder Drew Houston On Meeting Steve Jobs And Learning From Pearl Jam

Drew Houston with Marc Benioff at Dreamforce 2013 / Business Insider Australia

Thirty-year-old Drew Houston has steered Dropbox from infancy to a company worth billions in the past six years, and while he’s had to give up full-time coding to become what he calls a “full-time recruiter”, he’s glad to put the early days behind him.

Houston spoke with Salesforce.com founder and CEO Marc Benioff at Dreamforce today about founding Dropbox, his inspirations, and Dropbox’s nine-digit acquisition offer from the late Steve Jobs.

He recalled seeing “both sides of the coin” when he and co-founder Arash Ferdowsi were invited to meet Jobs in 2009. Here’s what happened:

I couldn’t believe it when the meeting was being set up. We were clear that we weren’t going to sell the company but were told that Steve would really like to meet us anyway.

He was very gracious about the fact that we wanted to build this company … The meeting was really good but then six months later we find ourselves watching one of [Jobs’] keynotes and he’s calling us out by name saying how he wants to kill us with iCloud..

He said he was going to come after us at the end of the first meeting.

Houston famously began working on Dropbox on a bus ride from Boston to New York City, when he found himself at a loss and frustrated because he had forgotten to bring important files on a thumb drive.

In Dropbox’s early days, Houston was known to hire exclusively from his alma mater, MIT. He told the Dreamforce conference today that Dropbox had become “equal opportunity” from its 11th employee onwards. The company now has more than 400 staff in San Francisco, Austin and Dublin.

People ask me, ‘do you miss the early days where you had 10 people or 100 people’. I really don’t because I think there’s so much more that we can do [now].

We’re sort of at this stage of the company where we can think, ‘Okay, who are the best five people in the world for any position.’

Over the last year, we hired these really amazing people: the creator of the Python programming language is at Dropbox; the designer of Instagram; the creator of the [Facebook] like button. It’s a real privilege to work with them.

Now, it’s really exciting because where five years ago I would have been sitting in my IKEA chair fixing bugs, now we get to think about how should technology work; what’s broken in the world.

The canvas we’re painting on just gets bigger and bigger … nobody’s looking for a solution to a problem they didn’t even know they had.

Finding those types of problems – inside Dropbox, we call them ‘problems hidden in plain sight’ – is really exciting and there’s all kinds of them.

Benioff grilled Houston on the band Pearl Jam, noting that Houston had worn a Pearl Jam t-shirt every time the two had met – with the exception of the conference session today.

The Salesforce CEO also is known to have a taste for rock music, having invited Metallica, the Red Hot Chili Peppers and Greenday to perform at his Dreamforce conferences in the past three years.

Houston said he admired how Pearl Jam lead singer Eddie Vedder and the band had spent the past 20 years “building something, staying authentic and not selling out and just putting all that energy into every show, although they don’t need to work as hard as they do”.

Benioff suggested that Houston related to Pearl Jam because he, like Vedder, was an innovator:

I see a huge connection between the music industry and the technology industry because when I see innovators like [Neil Young and Eddie Vedder], it’s not that different to when I see innovators in our industry being able to pull a vision [together].

They hear music in their minds and write it down; I don’t think it’s that different when a great technologist like you can see this beautiful thread that could get created with file-sharing and replication.

I think that’s why you relate back to an Eddie Vedder – I think you very much are more like him than you realise. And also, you’re your own man – you’re going to be yourself and you’re very much dedicated to the spirit of technology and innovation.

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