Drew Houston
MIT · Dropbox
He Kept Forgetting His USB Drive — So He Built Dropbox
3 April 2026
Drew Houston was an MIT student who kept forgetting his USB drive. On a bus ride from Boston to New York, he started coding a solution — a way to sync files seamlessly across devices.
Y Combinator and the Demo Video
Houston applied to Y Combinator with a working prototype. His viral demo video on Hacker News generated 75,000 sign-ups overnight for the waitlist, proving massive demand.
Steve Jobs Tried to Buy It
In 2009, Steve Jobs reportedly offered to acquire Dropbox for a nine-figure sum. Houston turned it down, believing cloud storage would be a fundamental platform.
700 Million Users
Dropbox went public in 2018 at an $8.2 billion valuation. It now has over 700 million registered users and 18 million paying customers. Houston's frustration with a USB drive created one of the defining cloud companies.
Get weekly tips straight to your inbox
Join 2,000+ students getting our best content on tools, side hustles, and student life.
No spam. Unsubscribe anytime.