/Drew Houston — The Billionaire Founder of Dropbox (#334)

Drew Houston — The Billionaire Founder of Dropbox (#334)

“Write an interesting story, not a perfect story.” — Drew Houston

Drew Houston (@DrewHouston) is co-founder and CEO of Dropbox. Since founding the company in 2007 with Arash Ferdowsi, Drew has led the company’s growth from a simple idea to a service used by 500 million people around the world.

Drew received his bachelor’s degree in Electrical Engineering and Computer Science from MIT in 2006. After graduating, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what became Dropbox. Today Dropbox is one of the world’s leading business collaboration platforms, with 11 million paying subscribers and 1,800 employees across 12 global offices.


Want to hear an episode with the co-founder of another product that makes the modern workplace possible for many? — Listen to this interview with Jason Fried, co-founder of Basecamp, in which we discuss selective ignorance, negative visualization, the importance of written communication, and much more (stream below or right-click here to download):

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Drew Houston:

Dropbox | Twitter


  • What’s Drew’s Dr. Evil story? How did the boy become the man? [05:10]
  • And the mathlete voted most likely to start a company award goes to… [08:32]
  • World domination begins from a folding chair on the roof. [09:54]
  • How this engineer approached learning about the business world. [12:00]
  • Books instrumental in teaching Drew (and me) about the nuts and bolts of business. [17:23]
  • The books Drew would assign as required reading if he were teaching a class on starting a business from an engineering background. [20:39]
  • What does OPP mean for Drew, and what concept would Bill Gates and Warren Buffet agree is the best way to overcome this? [31:51]
  • Drew’s best practices for cutting through email and managing time like Peter Drucker and Dwight D. Eisenhower. [36:36]
  • How adopting No Meetings Wednesday proved transformative for Drew and his crew. [44:12]
  • Peter Drucker’s mason jar analogy for time management and Paul Graham’s separation of schedules for makers and managers. [47:06]
  • What steered Drew away from SAT prep and online poker as business models, and what fateful event sparked the idea that became Dropbox? [49:12]
  • Who is Paul Graham, and how did Drew first manage to catch his attention? [57:28]
  • How did Drew’s first meeting with Paul go? [1:04:47]
  • What was Drew’s self-talk on the humbling plane ride home? [1:07:41]
  • How did Drew manage to get his prerequisite co-founder in time to get a do-over interview with Paul? [1:08:33]
  • Now that Dropbox is one of Y Combinator’s most successful investment to date, does Drew ever remind Paul of their first meeting? [1:11:05]
  • What might have been Dropbox’s original name if it hadn’t already been taken, and the weird negotiations it took to secure dropbox.com as a domain. [1:12:24]
  • How Drew addressed legitimate concerns from early naysayers without letting the more negative feedback crush his soul. [1:26:02]
  • Why it’s important to constantly revise mental models of how the world works. [1:28:43]
  • Coping with self-doubt over meeting the expectations of investors who had more faith in how the business would scale up than he did. [1:31:35]
  • Why taking care of your body is ultimately more important than working 80-hour weeks. [1:35:53]
  • What Drew has learned from coaching — particularly the painful but rewarding 360 degree review process. [1:38:46]
  • Why Drew considers the Enneagram to be more useful than the Myers-Briggs personality typing system. [1:42:18]
  • Given the chance, why would Drew send his younger self a cheat sheet with a tennis ball, a circle, and the number 30,000? [1:44:28]
  • Parting thoughts. [1:49:46]


Posted on: August 27, 2018.

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Who was interviewed? Here’s a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.