Apple tried to buy Dropbox in 2009. Its founder said no.
In December 2009, Apple's chief executive invited the two founders of Dropbox, Drew Houston and Arash Ferdowsi, to his office in Cupertino. Dropbox was two years old. The idea had come on a bus from Boston to New York, when Houston forgot his USB stick and started writing software to sync files.
Houston opened his laptop for a demo and was waved away. Apple's boss pitched buying the company. Houston, who saw him as a hero, cut the pitch short: Dropbox was not for sale. "He said we were a feature, not a product," Houston told Forbes in 2011. In June 2011, Apple unveiled iCloud.
Dropbox listed on Nasdaq in March 2018 at $21 a share, with over 11 million paying users. For the second quarter of 2026 it reported 18.19 million paying users and $2.566 billion in annual recurring revenue.
Enterprise software buyers hear the same line from the makers of big software suites about smaller tools. One test is whether users still pay for a tool that works across all their platforms.
AI-generated illustration with narration by an AI voice.
What would a suite's built-in version have to prove before you dropped the standalone tool?
What the captions say
- This is the story of how Apple tried to buy Dropbox in 2009, and its co-founder Drew Houston said no.
- At the time, Dropbox was 2 years old, and it synced files across computers. Saying no to Apple meant competing with Apple.
- It started on a 4-hour bus from Boston to New York. Houston had forgotten his USB stick.
- With no code to work on, he started writing software to sync files.
- His co-founder, Arash Ferdowsi, dropped out of MIT with 6 months to go. A start-up investor, Y Combinator, gave them $15,000.
- In December 2009, Apple's chief executive invited both founders to his Cupertino office.
- Houston opened his laptop for a demo. Apple's chief waved it away: "I know what you do."
- He saw Dropbox as a strategic asset for Apple, and pitched buying it.
- Houston considered the man his hero. He cut the pitch short. Dropbox was not for sale. He wanted to build a big company.
- Apple's chief smiled and said Apple was going after their market. Houston later put it this way: "He said we were a feature, not a product."
- In June 2011, at his final keynote, Apple's chief unveiled iCloud, and knocked Dropbox.
- Dropbox stayed independent. In March 2018, it listed on Nasdaq at $21 a share, with over 11 million paying users.
- In August 2026, Dropbox reported more than 18 million paying users, and over $2.5 billion in annual recurring revenue.
- The idea started with a forgotten memory stick on a bus.
