305: Dropbox’s Drew Houston on Continuous Learning, Decision Making, and Fixing the Way We Work

305: Dropbox’s Drew Houston on Continuous Learning, Decision Making, and Fixing the Way We Work

By now, the story is legend. When Drew Houston boarded a bus from Boston to New York and discovered that he had—yet again—forgotten to bring his thumb drive, he was frustrated. So frustrated that he sat down and began writing the first lines of code of what would eventually become Dropbox. After over a decade of changing the way files are stored, synced, and shared, Houston is changing the way people work, once again. This time, to solve a problem that likely plagues every single knowledge worker today: our fragmented, overcomplicated workspaces. In this episode, you’ll learn more about Houston’s journey—from ideation to launch—with Dropbox Spaces, as well as the most important lessons he’s collected while building a multibillion-dollar company with over 500 million users. Key Takeaways The relatable experience that inspired Houston to come up with the idea for Dropbox Why Houston doesn’t believe there’s any “magic” involved in building a multibillion-dollar company The importance of decision making and learning continuously on the job How a conversation with a SpaceX engineer sparked the vision behind Dropbox Spaces Houston’s advice on “harvesting” versus “planting” when it comes to your business Why Houston is such a huge believer in intentionally designing your environment—at work and with your personal relationships

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592: (Solo) The Truth About Originality: What Great Founders Really Do

592: (Solo) The Truth About Originality: What Great Founders Really Do

Most founders think they need a completely original idea to succeed. The truth? Great businesses are often built by borrowing brilliance — and putting your own spin on what already works. In this e...

30 Sep 20258min

591: From $0 to $3.4 BILLION Selling Socks | Bombas (Best of Foundr)

591: From $0 to $3.4 BILLION Selling Socks | Bombas (Best of Foundr)

David Heath and Randy Goldberg turned Bombas from a scrappy Indiegogo campaign into the most successful Shark Tank investment of all time—now valued at $3.4 billion. In this interview, the Bombas co...

26 Sep 202543min

590: (Solo) Why You Need to Do Things That Don’t Scale

590: (Solo) Why You Need to Do Things That Don’t Scale

When you’re just starting out, the fastest way to grow isn’t automation, ads, or scaling systems — it’s doing things that don’t scale. In this episode, I share why the most successful founders — fr...

23 Sep 20257min

589 : The Mad Scientist Behind One of America’s Fastest Growing Supplement Brands | Brian Littlefield (Best of Foundr)

589 : The Mad Scientist Behind One of America’s Fastest Growing Supplement Brands | Brian Littlefield (Best of Foundr)

Brian Littlefield is the co-founder and Chief Product Officer of Jocko Fuel—one of the fastest-growing supplement brands in America. But his story didn’t start in a boardroom. It started with a life-c...

19 Sep 202546min

588: (Solo) The #1 ROI Move You’re Probably Not Using

588: (Solo) The #1 ROI Move You’re Probably Not Using

Most ecommerce founders think the only way to grow is to get more traffic — but often, the fastest way to increase sales is by making more from the traffic you already have. In this episode, I shar...

16 Sep 20257min

587: She Built a $1 Billion Brand Selling Other Peoples Clothes | Julie Wainwright

587: She Built a $1 Billion Brand Selling Other Peoples Clothes | Julie Wainwright

Julie Wainwright, founder of The RealReal, reveals how she built a billion-dollar resale marketplace that transformed luxury fashion. In this exclusive Foundr Podcast interview, Julie shares how she s...

12 Sep 20251h

586 : (Solo) How I Solve The Biggest Problems in My Business (and How You Can Too)

586 : (Solo) How I Solve The Biggest Problems in My Business (and How You Can Too)

Every business has one major constraint holding it back from the next stage of growth — and solving it is the fastest way to scale. In this episode, I share the exact formula I use to identify the ...

9 Sep 20258min

585: The $100K Mistake Most Founders Make with Manufacturers (and How to Avoid It) (Best of Foundr)

585: The $100K Mistake Most Founders Make with Manufacturers (and How to Avoid It) (Best of Foundr)

Kian Golzari is one of the world’s leading experts in sourcing and product manufacturing—developing over 2,500 products and visiting 500+ factories. In this episode, he shares how to go from idea t...

5 Sep 202538min

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