Drew Houston

“Not enough consumers are going to pay for it. Enterprises could see the value they would pay. But if you want an enterprise, you need permissions. You need control... They had to rebuild the whole thing and realize the only way we're going to make money is by selling to companies.”

“And they're like, oh, we want to build a company. And Steve's, you know, you're a feature, not a company.”

“Houston closed his screencast with one form to join the waitlist and nothing else competing for the click.”

“Dropbox was a category-defining product...the company then spent too long trying to actually build a business in the consumer space, before finally realizing that the only way to make money with what was ultimately a productivity product was by selling to enterprise.”

“Referenced alongside news of Houston stepping down, May 2026.”

“When the Boston VC firm found out that Sequoia was interested, their opinion of Dropbox changed so fast that they probably gave themselves whiplash. They sent Drew, the founder, a term sheet. They faxed it to him... with a blank valuation. Let us invest.”