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.

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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