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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464: Silicon Valley Outsider Michelle Zatlyn on Building a Tech Disruptor

464: Silicon Valley Outsider Michelle Zatlyn on Building a Tech Disruptor

Michelle Zatlyn and her co-founders were outsiders when they moved to Silicon Valley to launch their web security startup. It was 2009, in the middle of a recession, but the team knew their visceral e...

17 Juni 202358min

463: Why Small Customers Matter with ​​Immad Akhund of Mercury

463: Why Small Customers Matter with ​​Immad Akhund of Mercury

Since 2006, Immad Akhund has been investing in and building startups. But he always struggled with working with traditional banks to run his startups, especially as a non-US resident. He figured someo...

9 Juni 202344min

462: Why Subscription Products Need Purpose with Jessica Rolph of Lovevery

462: Why Subscription Products Need Purpose with Jessica Rolph of Lovevery

Your first product won’t always be your best seller. Jessica Rolph’s organic baby food business Happy Family Organics failed twice before finding product market fit and scaling from $0 to $63M in sale...

2 Juni 202358min

461: Adrian Grenier’s Evolution from Movie Star to Social-Impact Entrepreneur

461: Adrian Grenier’s Evolution from Movie Star to Social-Impact Entrepreneur

Adrian Grenier was a rebellious artist before he was known for his acting roles in Entourage, Devil Wears Prada, and Clickbait. Now he’s a rebellious entrepreneur, investor, and activist. Learn how Gr...

26 Maj 202340min

460: 4 Stories. 4 Founders. 4 Lives Changed.

460: 4 Stories. 4 Founders. 4 Lives Changed.

For ten years, we've interviewed hundreds of elite entrepreneurs who’ve started and grown the world's most successful businesses. The reason we connect with these dynamic founders is to break down the...

19 Maj 202340min

459: Forging Meaningful Business Partnerships with Jean Oelwang of Virgin Unite

459: Forging Meaningful Business Partnerships with Jean Oelwang of Virgin Unite

Partnerships can be tricky, especially when you’re starting a business. For ​​Jean Oelwang, creating meaningful partnerships has been her focus for nearly 30 years. Oelwang is the founding CEO and Pre...

12 Maj 202358min

458: Break One Rule and Break It Hard: David Lester of OLIPOP PBC

458: Break One Rule and Break It Hard: David Lester of OLIPOP PBC

David Lester learned a lot from his first venture. After spending a decade in the beverage marketing industry, he teamed up with his co-founder Ben Goodwin to work on formulating a soda that’s good fo...

5 Maj 202352min

457: Why This Generation Will Be the Strongest Founders with David Shein of OHF Ventures

457: Why This Generation Will Be the Strongest Founders with David Shein of OHF Ventures

David Shein was an entrepreneur before it was in vogue. For over three decades, he’s founded, mentored, and invested in exceptional startups. He sold his first company, COMTECH, for over $1 billion–ar...

28 Apr 20231h 8min

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