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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615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

David Royce went from a broke college kid in a door-to-door pest control job to building and selling four service businesses for nine-figure exits by applying Silicon Valley systems to an unsexy blu...

18 Joulu 202558min

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

If you’re dragging yourself toward the end of the year feeling exhausted, overwhelmed, and mentally drained, you’re not alone. This is one of the toughest stretches for founders — you’re still runni...

16 Joulu 20259min

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

DIBS Beauty went from zero to one of America’s fastest-growing makeup brands in just four years, with founder Jeff Lee scaling the business into the mid–8 figures and landing a top spot on the Inc. ...

11 Joulu 202552min

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

Should you raise money or bootstrap your business? It’s one of the biggest questions every founder faces — and the wrong decision can shape the entire future of your company. In this episode, I share...

9 Joulu 202512min

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

John Paul DeJoria went from being homeless twice to building two global billion-dollar brands, Paul Mitchell and Patrón Tequila, using nothing but resilience, sales mastery, and a refusal to quit. ...

4 Joulu 202559min

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

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...

2 Joulu 20259min

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

From professional rugby player to successful entrepreneur, Damien Fitzpatrick built a sports recovery brand trusted by elite athletes around the world. In this interview, Damien shares how he went...

27 Marras 20251h 4min

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

When I first started Foundr, I made a lot of short-term decisions — and most of them hurt us more than they helped. It took years (and a few hard lessons) to understand that sustainable growth only co...

25 Marras 202510min

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