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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607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

Loren Castle turned a life-threatening cancer diagnosis at 22 into the spark that built Sweet Loren’s, a $120M-a-year clean food brand now sold in over 5,000 supermarkets nationwide. In this inter...

20 Nov 202551min

606: (Solo) The Week Before Black Friday: What Smart Ecommerce Founders Are Doing Differently

606: (Solo) The Week Before Black Friday: What Smart Ecommerce Founders Are Doing Differently

It’s not too late to win Black Friday. Even if you’re behind, there’s still time to drive serious results—if you focus on the right moves. In this episode, I share my final Black Friday checklist a...

18 Nov 202510min

605: He Bought an Airline for $0.30 (and made BILLIONS) | Tony Fernendes (Best of Foundr)

605: He Bought an Airline for $0.30 (and made BILLIONS) | Tony Fernendes (Best of Foundr)

Tony Fernandes turned a failing airline into a billion-dollar business and built AirAsia into one of the most recognized brands in Asia. In this interview, Tony explains how he bought AirAsia for ju...

13 Nov 202541min

604: (Solo) What Labubu and Apple Can Teach You About Scarcity Marketing

604: (Solo) What Labubu and Apple Can Teach You About Scarcity Marketing

Think scarcity is just a marketing gimmick? Used properly, it’s one of the fastest ways to increase perceived value, build community, and grow sales—without racing to the bottom on discounts. In th...

11 Nov 202512min

603: He Built a $1B Beauty Brand Selling $1 Makeup | Joey Shamah

603: He Built a $1B Beauty Brand Selling $1 Makeup | Joey Shamah

Joey Shamah built e.l.f. Cosmetics into a billion-dollar beauty brand by doing the exact opposite of every competitor in the industry. In this interview, the e.l.f. co-founder breaks down how he turn...

6 Nov 202551min

602: (Solo) What I Learned From Alex Hormozi’s $100M Book Launch

602: (Solo) What I Learned From Alex Hormozi’s $100M Book Launch

Everyone saw the headlines—but the real lessons from Alex Hormozi’s $100M book launch are in the planning, positioning, and pre-launch. In this episode, I break down the fundamentals you can lift s...

4 Nov 202513min

601: The Couple Who Built a 9-FIGURE Brand While Working Full-Time Jobs | Natalie Holloway

601: The Couple Who Built a 9-FIGURE Brand While Working Full-Time Jobs | Natalie Holloway

Natalie Holloway turned a $5,000 side hustle into Bala — a globally recognized fitness brand worn by millions and backed by Mark Cuban and Maria Sharapova. In this interview, the Bala co-founder bre...

30 Okt 202557min

600: (Solo) How Founders Should Actually Use AI (Without Getting Lost)

600: (Solo) How Founders Should Actually Use AI (Without Getting Lost)

AI is the biggest shift since the internet—and if you’re not using it daily as a founder, you’re falling behind. In this episode, I break down exactly how I use AI to think clearer, execute faster,...

28 Okt 202512min

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