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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568: No Experience, No Investors, 5 x Million Dollar Businesses - How Brittney Saunders Did it

568: No Experience, No Investors, 5 x Million Dollar Businesses - How Brittney Saunders Did it

In this episode, Brittney Saunders, founder of FAYT, Staple Swim, Form Active, and OUTDŌ, shares how she went from YouTuber to multi-brand empire builder—running multiple 7-figure businesses with a ha...

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567: The Tiny Challenge Model - The Easiest Way to Get Your First 5 Clients | Richmond Dinh

567: The Tiny Challenge Model - The Easiest Way to Get Your First 5 Clients | Richmond Dinh

What You’ll Learn in This Episode In this episode, Richmond Dinh, founder of the Tiny Challenge model, reveals how he went from nearly going bankrupt to building a 7-figure coaching empire—without a b...

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566: From Celebrity Deals to Creator Empire - Maggie Sellers on Building 'Hot Smart Rich'

566: From Celebrity Deals to Creator Empire - Maggie Sellers on Building 'Hot Smart Rich'

In this episode, Maggie Sellers—founder, investor, creator, and force behind Hot Smart Rich—shares how she turned vulnerability, storytelling, and a scrappy content strategy into a multimillion-dollar...

30 Mai 202555min

565: From 3rd Grade Teacher to Beauty CEO: How Supergoop! Built a $700M Brand From ZERO! | Holly Thaggard (Best of Foundr) [VIDEO]

565: From 3rd Grade Teacher to Beauty CEO: How Supergoop! Built a $700M Brand From ZERO! | Holly Thaggard (Best of Foundr) [VIDEO]

In this episode, Holly Thaggard, founder of Supergoop!, shares how she redefined the sunscreen category and built a globally recognized $700M brand from the ground up. She shares: • The heartbreaking...

23 Mai 202546min

564: From $0 to $100,000 a Day Selling Neckties | Fameez Haroon

564: From $0 to $100,000 a Day Selling Neckties | Fameez Haroon

In this episode, Fameez Haroon, co-founder of OTAA, shares how he and his brother bootstrapped a fashion accessories brand from a Melbourne bedroom to $40M+ in sales—without outside funding. He share...

16 Mai 20251h 8min

563: From $500 to 120 Stores - How She Lost It All | Kristina Karlsson

563: From $500 to 120 Stores - How She Lost It All | Kristina Karlsson

In this episode, Kristina Karlsson, founder of Kikki.K and Dream Life, opens up about building a $100M global brand, losing it all, and why she's starting again—this time, on her own terms. She share...

9 Mai 20251h 20min

562: The Billion Dollar Woman Behind The Rock & Henry Cavill | Dany Garcia (Best of Foundr) [VIDEO]

562: The Billion Dollar Woman Behind The Rock & Henry Cavill | Dany Garcia (Best of Foundr) [VIDEO]

In this episode, Dany Garcia - founder, producer, chairwoman, and the powerhouse behind brands like ZOA Energy, Teremana Tequila, GSTQ, Seven Bucks Productions, and the XFL—shares how she built a bill...

2 Mai 202546min

561: $300M Worth of Facebook Ads Advice in 45 Minutes | Jordan Menard

561: $300M Worth of Facebook Ads Advice in 45 Minutes | Jordan Menard

In this episode, Jordan Menard breaks down what it really takes to scale Facebook ads in 2025. He shares why creative is now the targeting, why brands need to focus more on offers than tactics, and ho...

25 Apr 202545min

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