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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631: He Built a $125M Brain Food Brand With Just 10 People | Will Nitze

631: He Built a $125M Brain Food Brand With Just 10 People | Will Nitze

Will Nitze went from selling Linsanity T-shirts in his college dorm to building IQ Bar into a $125 million brain food empire—with just a team of ten people. No bloated headcount. No burning through ...

12 Helmi 51min

630: (Solo) How to Find People Who Actually Care About Your Business

630: (Solo) How to Find People Who Actually Care About Your Business

Most founders are desperate to hire — but they're asking the wrong question. It's not "How do I find great people?" It's "How do I find people who care as much as I need them to?" Here's the truth:...

9 Helmi 10min

629: $50K to $300M+: How Two L'Oréal Employees Built Glow Recipe | Sarah Lee

629: $50K to $300M+: How Two L'Oréal Employees Built Glow Recipe | Sarah Lee

Sarah Lee went from cold-emailing 700 journalists by hand and sleeping two hours a night to building Glow Recipe into a nine-figure global skincare brand inside Sephora. And she did it without raising...

5 Helmi 59min

628: (Solo) The Content Playbook I Wish I Had When I Started

628: (Solo) The Content Playbook I Wish I Had When I Started

If you’re staring at an empty Instagram feed, TikTok account, or LinkedIn page thinking, “What the hell do I even post?”, this episode is for you. Every early-stage founder hits this wall — and most s...

3 Helmi 10min

627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

627: How Lia Georgantis Built an Iconic Aussie Fashion Brand in Just 5 Years

Lia Georgantis took over a multi-brand fashion boutique with no business experience, lost most of her suppliers overnight, then rebuilt it into one of Australia’s most recognisable fashion brands by...

29 Tammi 56min

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

626: (Solo) Work Life Balance Is an Illusion. Here’s What Works Instead

Most founders won’t say this out loud… work-life balance doesn’t really exist. At least not in the early years. I didn’t want balance — I was obsessed. I worked until 5 a.m., skipped sleep, skipped ho...

27 Tammi 10min

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

625: From $70M in Debt to $1B Amazon Deal in 45 Days | Jamie Siminoff

One billion dollars. That’s what today’s guest built — after being rejected on Shark Tank, nearly going bankrupt multiple times, and spending millions before making a single sale. In this video, Jam...

22 Tammi 53min

624: (Solo) How to Create More Than You Consume (Without Burning Out)

624: (Solo) How to Create More Than You Consume (Without Burning Out)

Most founders drown in content — YouTube, TikTok, newsletters, podcasts — but they rarely create anything themselves. And here’s the problem: consumption doesn’t build businesses; creation does. In...

20 Tammi 9min

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