Forget Snapchat. One of the most speculated about potential IPOs in Silicon Valley this year is file sharing and storage company Dropbox.
Dropbox was one of the earliest Valley unicorns to seem to defy any logic in valuations, and at its last round was valued at $10 billion making it one of a handful of so-called “deca-corns.” At one time, it and Airbnb made up some 95% of the value of Y-Combinator’s entire portfolio. And it was backed early on by top venture capital firms Sequoia Capital, on their way to raising some $600 million in capital. Its office was so lavish it reportedly spent up to $40 million a year just on employee perks. Its lobby sported a $100,000 statue of a Panda.
Yes, for a while, Dropbox and its co-founder and CEO Drew Houston seemed to have a charmed life. But then Google, Microsoft, and other Web giants started to compete hard. Dropbox’s valuation kept rising as its product strategy appeared rudderless. It bought buzzy companies like Mailbox and launched products like Carousel, only to reverse course and shut them down or sell them off. It’s gone back and forth on how serious it is about enterprise, unlike its smaller rival Box.com who was laser focused on enterprise and went public years ago. Box’s stock is nearing it’s 52-week high, for what it’s worth, but the company is still valued at just over $2 billion– one-fifth of Dropbox’s last valuation.
But recent days are hardly the first time that Houston has struggled against a world that didn’t seem to believe in him. It’s hard to remember that before Y-Combinator, before that funding from Sequoia, before Bono and the Edge invested, before Condoleezza Rice joined the board, and long before it raised anything like $600 million, Y-Combinator’s Paul Graham couldn’t even be bothered to watch a 30-second demo of the product, Houston struggled to find a co-founder, and the company utterly flamed out when it tried to launch at TechCrunch40 (the precursor to the HBO-lampooned TechCrunch Disrupt competition.)
In fact, Houston did so badly on stage at TechCrunch40 that the video editor for the conference cut out 30 seconds of the painful awkwardness, before posting the video. He did so badly that his mother called as soon as he got off stage. He did so badly, he made Pied Piper’s fictional Disrupt launch look good by comparison.
You think Drew Houston has only known the good times in Silicon Valley? Read the interview below...