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History of Dropbox

May 15, 2014 by · Leave a Comment 

Written by Phineas Upham

Drew Houston first showed up on the Silicon Valley radar for reverse-engineering Apple’s file management system and replacing their logo with his own, an unfolding box. Steve Jobs was naturally intrigued and asked the young Houston to a meeting at Apple’s headquarters.

Houston still recalls the moment before he unveiled his laptop to show Jobs what he had done. Jobs waved him off, “I know what you do,” he said.

What Jobs was interested in was the beginning of Houston’s company, Dropbox. Houston was gaining one new user every second. Jobs wanted this opportunity, but Houston cut him off. He wanted to develop a big company, and no matter who the buyer was, he wasn’t selling. Rumor has it Jobs offered him nine figures to settle the sale.

Houston’s rebuke of Jobs is well noted. Jobs retaliated with iCloud, even bashing Dropbox on stage. How could one get all files and storage into a single device, he sarcastically asked. Apple’s solution was iCloud.

In response, Houston immediately sent an email to his employees. It mentioned Yahoo, MySpace and Netscape among a list of fast rising companies that fell like a meteor. The company never had a problem acquiring users, but did struggle to monetize them for a period. That changed in 2011, when the company was on track to hit over $200 million in revenue.

Thousands each day blow through their free storage space and the upgrade is cheap and convenient. Dropbox has so many users that it doesn’t actually need to acquire new ones anymore; it simply needs its original clients to use up their space. Though that hasn’t stopped the Silicon Valley powerhouse from expanding and aggressively pursuing signups.


Phineas Upham is an investor from NYC and SF. You may contact Phineas on his Phineas Upham website

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