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

Episoder(587)

424: How Dragons' Den Star Michele Romanow is Removing Funding Barriers

424: How Dragons' Den Star Michele Romanow is Removing Funding Barriers

Michele Romanow joined the cast of CBC's Dragons' Den in 2014 after successfully selling her digital coupon business SnapSaves to Groupon. At 28 years old, she was the youngest "dragon" on the show, b...

1 Sep 202242min

423: Making Work Work for Humans with Oyster’s Tony Jamous

423: Making Work Work for Humans with Oyster’s Tony Jamous

After his first startup went public in 2016, Tony Jamous took time off to align what he does with what he believes in. In his previous company, Nexmo, he saw the power of distributed hiring worldwide ...

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422: How to Put Your Audience First with Lauryn Evarts Bosstick and Michael Bosstick of The Skinny Confidential

422: How to Put Your Audience First with Lauryn Evarts Bosstick and Michael Bosstick of The Skinny Confidential

In 2011, Lauryn Evarts Bosstick was in college and looking for a community. When a sorority came knocking, Lauryn turned to blogging instead, asking herself the questions every entrepreneur asks: How ...

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421: Why People Pay for Time Not Software with Rishi Mandal of Future

421: Why People Pay for Time Not Software with Rishi Mandal of Future

What's the secret to sustain healthy behaviors like exercise, diet, and stress management? Coaching.    Rishi Mandal discovered this while researching the challenges of America's health crisis. So, he...

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420: Starting a Multi-Million Dollar Swimwear Movement with Erin Deering of Triangl

420: Starting a Multi-Million Dollar Swimwear Movement with Erin Deering of Triangl

In 2014, Erin Deering gifted Triangl swimwear to relatively unknown legacy celebrities Hailey Bieber ( Baldwin) and Bella Hadid. Their friend, Kendall Jenner, loved the products and reached out to Eri...

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419: Why You Need TikTok Ads with Gerardo Perez of Marketing&

419: Why You Need TikTok Ads with Gerardo Perez of Marketing&

Are you ready to leverage the popularity of TikTok to grow your business? Gerardo Perez is the founder of Marketing&, one of the world's leading digital agencies focused on driving paid results on Tik...

4 Aug 202245min

418: Shopify President Harley Finkelstein on Building the World’s #1 Ecommerce Platform

418: Shopify President Harley Finkelstein on Building the World’s #1 Ecommerce Platform

Harley Finkelstein is an entrepreneur, lawyer, and president of Shopify. Harley was store #137 when he started on Shopify as a merchant in 2009. After law school, he joined the team at Shopify and hel...

29 Jul 202252min

417: Why Going Off-Script Led to a Billionaire Business with Jamie Kern Lima of IT Cosmetics

417: Why Going Off-Script Led to a Billionaire Business with Jamie Kern Lima of IT Cosmetics

Jamie Kern Lima spent 2 years pitching QVC for a segment to promote her business, IT Cosmetics. She was about to go bankrupt when she finally got her shot on the network. But moments before going on a...

21 Jul 20221h 1min

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