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Drew Houston Trivia Questions

How much do you really know about Drew Houston? Below are 8 true or false statements. Click each one to reveal the answer and explanation.

1.

Drew Houston conceived the idea for Dropbox after forgetting his USB drive on a bus.

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Easy
✓ TRUE

While on a bus from Boston to New York, he realized he forgot his USB drive. This frustration sparked the idea for cloud file syncing.

2.

Drew Houston was a philosophy major at MIT before switching to computer science.

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Easy
✗ FALSE

He studied computer science from the start. He earned a B.S. in Computer Science and Engineering from MIT, with no philosophy major.

3.

Drew Houston was the only founder of Dropbox from its inception.

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Medium
✗ FALSE

Arash Ferdowsi co-founded Dropbox with Houston. They met at MIT, and Ferdowsi was the technical co-founder who built the early product.

4.

Drew Houston is an avid pilot and holds a commercial pilot's license.

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Medium
✗ FALSE

He has no known pilot's license. This myth likely stems from his love of aviation—he invested in a flying car startup—but doesn't fly commercially.

5.

Drew Houston's net worth once surpassed $2 billion during Dropbox's IPO.

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Medium
✓ TRUE

At Dropbox's 2018 IPO, his stake was worth over $2 billion. The stock opened at $21, valuing his shares at roughly $2.3 billion.

6.

Drew Houston once turned down a $10 billion acquisition offer from Apple.

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Hard
✓ TRUE

In 2011, Apple reportedly offered to buy Dropbox for $10 billion, but Houston declined. He believed the company could grow larger independently.

7.

Drew Houston personally coded the first version of Dropbox in a single weekend.

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Hard
✗ FALSE

The prototype took months, not a weekend. Houston built an early demo using Python and wxWidgets, but it wasn't a rapid weekend project.

8.

Drew Houston skipped his own college graduation to pitch Dropbox at Y Combinator.

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Hard
✓ TRUE

He missed MIT's graduation ceremony to attend Y Combinator's Demo Day. Dropbox was accepted into the startup accelerator's summer 2007 batch.

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