(Founder Stories) Drew Houston: “Dropbox Users Save A Billion Files Every Three Days”

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We Came, We Saw, We Hacked #TCDisruptBJ

In episode II of Erick Schonfeld’s Founder Stories interview with Dropbox co-founder, Drew Houston, Houston describes how releasing a demo video to Hacker News during Dropbox’s early days catapulted his company into elite company.

“I hoped that the response would be good so that Paul [Graham] and Y Combinator would see it.” The response was better than good. Houston says the video held the top spot at “Hacker News for a couple of days” and it turns out the right people were watching. One viewer was Arash Ferdowsi, who was so impressed that he paired up with Houston as a partner. Houston also credits the video with helping him receive almost immediate and valuable feedback.

Asked if he was worried about copycats stealing the concept at the time – Houston responds, “It is easy for me to explain the idea, it is actually really hard to do it.”

Below, Houston takes us inside Y Combinator and describes how Paul Graham weighed in with key advice while Houston was under the Y Combinator wing. “Our first sort of marketing attempt was like throwing spaghetti at a wall …we really struggled in terms of how to articulate this with investors because we had never really done that before, and Paul was really helpful to us in terms of distilling down the idea into a much shorter and sort of more compact presentation.”

Advice in hand, the team went before a room full of investors at Demo Day, where you get “waived like a piece of steak” and hit it out of the park by walking them through an admittedly risky demo that could have wiped-out their entire PowerPoint presentation.

Having survived the high-wire act, Houston says today, “Dropbox users save a billion files every three days.”

Make sure to watch the entire video for additional insights and be sure to catch the first episode of Schonfeld’s interview with Houston here.

Past episodes of Founder stories featuring Eric Ries, Fred Wilson and Dustin Moskovitz are here.

Episode III of this interview is coming up.