“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…
SELECTED LINKS FROM THE EPISODE
- Connect with Drew Houston:
- Accolade Prep
- Emotional Intelligence: Why It Can Matter More Than IQ by Daniel Goleman
- Getting to Yes: Negotiating Agreement Without Giving In by Roger Fisher and William L. Ury
- The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton Christensen
- Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers by Geoffrey A. Moore
- Getting Past No: Negotiating in Difficult Situations by William Ury
- High Output Management by Andrew S. Grove
- The Effective Executive: The Definitive Guide to Getting the Right Things Done by Peter F. Drucker
- The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
- Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger by Charlie Munger
- Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values by Robert M. Pirsig
- Principles: Life and Work by Ray Dalio
- Andreessen Horowitz — Software Is Eating the World
- Warren Buffett and Bill Gates’s Top Secret to Success by Carol Roth, Entrepreneur
- Brain Pickings
- The Eisenhower Matrix
- Why Every Company Should Have A No Meeting Day by Kevin Kruse, HuffPost
- Maker’s Schedule, Manager’s Schedule by Paul Graham
- Y Combinator
- Stopping Spam by Paul Graham
- Summer Founders Program
- Hacker News
- Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business by Jay Conrad Levinson and Jeannie Levinson
- Dropbox Started with a Couple of Checks Written for $15,000 — Today It’s Worth $12 Billion by Chloe Aiello, CNBC
- MIT Entrepreneurs Club
- Dropbox’s Summer 2007 Y Combinator Application
- Leadership Coaching: The 360 Degree Review Process by Bea Fields, Fast Company
- The Nine Enneagram Type Descriptions, The Enneagram Institute
- Myers-Briggs Basics, The Myers & Briggs Foundation
- Meet the Man Who Sold a Month-Old App to Dropbox for $100M by Ryan Tate, Wires
- Tribe of Mentors: Short Life Advice from the Best in the World by Timothy Ferriss
- Drew Houston’s 2013 MIT Commencement Address, MIT News
- 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.
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.