How I Built This with Guy Raz

Dropbox: Drew Houston

Nov 9, 2020
Drew Houston, Co-founder and CEO of Dropbox, shares his journey from struggling with a forgotten thumb drive to building a cloud storage service worth nearly $8 billion. He reveals the sparks of innovation driven by early tech experiences and how network effects fueled Dropbox’s rapid growth. Drawing on challenges in fundraising and investor skepticism, Drew highlights the technical hurdles in creating a seamless file-sharing platform. He reflects on the balance of skill and luck in entrepreneurship, illustrating his path with a surfer's mindset.
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ANECDOTE

Early Programming

  • Drew Houston's interest in programming began with playing computer games like King's Quest.
  • At 14, he found security vulnerabilities in an online game and was offered stock options to fix them.
ANECDOTE

Stepping Stone

  • The stock options job led to another programming job at Soft Servo Systems, where he moved systems from Windows to Linux.
  • These early experiences exposed him to interesting projects and fueled his interest in startups.
ANECDOTE

First Entrepreneurial Journey

  • During college, Houston started an SAT prep company called Accolade, taking a leave of absence to work on it.
  • While it provided a side income, it was seasonal and eventually fizzled out due to constraints and loss of momentum.
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