Dropbox after Drew
Drew Houston and his new co-CEO make the case for Dropbox in the AI era. Also: An atheist Anthropic co-founder at the Vatican, Ive's Ferrari flop, Reflection's DC push, and more.
For the past two decades, Drew Houston has occupied a unique place in the firmament of Silicon Valley. He was the first founder to take a Y Combinator company public, and he famously turned down an early acquisition offer from Steve Jobs. His announced plan this morning to eventually step back as Dropbox’s CEO and become executive chairman comes as AI is rewriting the era of tech he came up in.
In a 2009 meeting at Apple, Jobs told Houston that Dropbox was "a feature, not a product." Houston proved Jobs wrong by turning down a nine-figure acquisition offer and building something that hundreds of millions of people use.
He also half-proved Jobs right. Dropbox never reached the scale of YC contemporaries like Reddit, Airbnb, or Stripe, and file storage has become a tentpole feature within the bigger work suites — Google Workspace, Microsoft 365 — that Dropbox competes with for dollars.
Houston insisted to me that he’s not stepping back now because of any structural changes in Dropbox’s business. "I think five years ago I would have been talking about needing to grow paying users and increase our cash flow," he told me in a joint interview with Dropbox’s new co-CEO, Ashraf Alkarmi. "I'm sure five years from now, Ashraf will be saying the same kind of things."
