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

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“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.

Enjoy!

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

#329: Jason Fried — How to Live Life on Your Own Terms
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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…

SELECTED LINKS FROM THE EPISODE

  • Connect with Drew Houston:

Dropbox | Twitter

SHOW NOTES

  • 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]

PEOPLE MENTIONED

Posted on: August 27, 2018.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

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.

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16 comments on “Drew Houston — The Billionaire Founder of Dropbox (#334)

  1. hey, I’m enjoying listening to your podcasts. I find them challenging and inspiring. There are some people and demographics I would like to hear from, partly because I’m interested in whats going on in their minds, partly because they are intensely disciplined & principled people that would have tips that could help me to grow in every area of life. Lauren Sutherland being one. I have seen some of her online material and it seems that general media reporters get defensive and hostile towards her because of her extreme views. I reckon you would be able to draw her out and convey the way she thinks. Also famous sports people and comedians, I’m from down under (New Zealand) so not 100% up with your national heros but to name a few – Lebron James, Tom Brady, Stephen Curry, Rhys Darby, Jimmy Carr, Richard Ayoade. Look forward to hearing more from you. Cheers.

    Like

  2. Dear Tim,
    Your eyes may not get to this comment because you have so much coming in, but nevertheless I hope it does.
    I love listening to your show and learning from it. Most of the time I am not taking notes on the episode I am listening to. Sadly, the name of the guest of a particular episode always eludes me.

    Do you have any way other than searching by guest name to search through your content? If not, would you consider providing access to it?

    I can only imagine this would be beneficial to your fans. And it would surely be beneficial to me. That is, as long as it’s not a pain in the ass for you.

    I do want to let you know I appreciate the content you put out very much. Please keep doing what you’re doing.

    Best,
    Julian Figaretti

    Like

  3. Hi Tim,
    Just a random suggestion.
    Can you please ask your guests about their favourite video games, when they mention that they got interested in computers through video games or which was the first game and do they still play video games.
    Thanks.

    Like

  4. Hi Tim,
    I absolutely love your podcast and the work you do in your literature. I’m so happy to read in your five bullet Friday email that you have watched wild wild country.
    I really found the role of Sheila incredibly fascinating despite what you think of her, her actions were absolutely incredible in the feat that she achieved.
    I would love to hear on the show.

    I would love to be part of that show in any form I can assist

    Like

  5. Great Show Tim! Drew had some of the best and most actionable lessons I’ve heard on the show in a long time. One follow up question I had (in case there’s a follow up show…) is about Drew’s studying habits. He mentions the difference between reading as entertainment and when he really wants to “study” a book. What are the methods he uses when he’s studying a business book?

    Like

  6. Hey Tim,

    I tried out the Enneagram assessment tool Drew mentioned in the interview. For anyone curious, I find that the Gallup StrengthsFinder tool is much more comprehensive and would recommend it over Enneagram.

    Thanks for the amazing content and all the effort that goes into creating it!

    Like

  7. I will start acknowledging that email, most often, is working other people’s to do lists, so I will be more selective. Knowing that is also going to make me more aware of the emails that I send to others. Don’t send it unless the content adds value to their day or has short, specific, actionable steps they can take and move on.
    You guys helped me find a new Golden Rule for managing email. Thanks!

    Like

  8. Hey Tim,
    I love this interview. The books recommendations and his insight on to focus on your priorities and others who did their homework. Really enjoyed it!

    Mamadou Diallo

    Like

  9. Hi Tim, I just want you to discover my brave friend, founder and CEO of Sakharoff.com, Misha Sakharoff. Why? Because you are an early spotter, and because I think now is the time to discover Misha and the new health paradigm he advocates. [Moderator: link removed.]

    Like

  10. Tim et al,
    I am searching for a quote from a 5-bullet Friday email from the last few months…it was from a female author, and the basic premise was that our main markers in life, the things we remember/the thing that motivates us is our next fuck. Who was that? What was the actual quote??
    Thanks,
    K

    Like

  11. Hi Tim – quote I that thought you’d like to ponder – “What you do when you don’t have to, determines what you will be when you can no longer help it”, Rudyard Kipling. When I am feeling unmotivated or procrastinating I read it for a jolt.

    Like

  12. Hi Tim and All,

    Excellent podcast! I was particularly fascinated by Drew’s mentioning of ENNEAGRAM types, which is something a friend told me about just last week (coincidence?). I would like to know which books do you recommend on this topic.

    Thanks!
    Rene

    Like