The Social Radars

Drew Houston, Founder & CEO, Dropbox

51 snips
Mar 26, 2025
Drew Houston, the founder and CEO of Dropbox, shares his journey from Y Combinator funding to creating a vital tech infrastructure tool. He delves into early entrepreneurial struggles, including a memorable demo mishap that launched Dropbox into the spotlight. Drew discusses the importance of startup culture, the challenges of personal development in leadership, and the innovative creation of Dropbox Dash to streamline workplace searches. His candid reflections on resilience and strategic growth reveal valuable insights for aspiring entrepreneurs.
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ANECDOTE

First YC application

  • Drew Houston was first introduced to YC through a fraternity brother, Adam Smith, in 2006.
  • He applied to YC in 2005 with an online SAT prep idea, but didn't get in.
ANECDOTE

Dropbox Origin Story

  • Drew Houston's idea for Dropbox came from his own frustration of forgetting his thumb drive on a Chinatown bus.
  • Existing solutions were unreliable or incomplete, motivating him to solve the problem.
ANECDOTE

Co-founder Hunt

  • Paul Graham encouraged Drew to find a co-founder, leading to a challenging search.
  • Drew's attempts to impress Paul, including showing up unannounced at a YC dinner, didn't go well.
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