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(586)

552: She Went From $0 to $15M Selling Eyeliner | Iris Smit [VIDEO]

552: She Went From $0 to $15M Selling Eyeliner | Iris Smit [VIDEO]

In this episode, Iris Smit, founder of The Quick Flick, shares her inspiring journey of creating a multi-million dollar beauty empire from her dorm room. Iris opens up about her struggles with self-do...

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551: From $0 to $30M in 3 Years Selling Fashion | Aimee Smale [VIDEO]

551: From $0 to $30M in 3 Years Selling Fashion | Aimee Smale [VIDEO]

✅ Want all-access to step-by-step training from 7, 8 & 9-figure founders? Start your Foundr+ $1 trial today → http://www.foundr.com/startdollartrial ✅ Prefer 1-on-1 mentorship to launch or scale your ...

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550: He Went From $0 to $50M Selling THIS Product | Mike Smith [VIDEO]

550: He Went From $0 to $50M Selling THIS Product | Mike Smith [VIDEO]

In this episode, Mike Smith, founder of Zero Co, shares how a backpacking trip around the world turned into a mission to solve the plastic waste crisis. Mike walks us through the early days of bootstr...

7 Feb 20251h 6min

549: How Popflex Became Taylor Swift's Favourite Clothing Brand | Cassey Ho [VIDEO]

549: How Popflex Became Taylor Swift's Favourite Clothing Brand | Cassey Ho [VIDEO]

In this episode, Cassey Ho, founder of POPFLEX and Blogilates, shares her journey from rock bottom to building two eight-figure brands. Discover how Cassey combined her passion for fitness and design ...

31 Jan 202557min

548: He Made $20M in a Year Selling Supplements | Caleb Marshall [VIDEO]

548: He Made $20M in a Year Selling Supplements | Caleb Marshall [VIDEO]

In this episode, Caleb Marshall, founder of Tropeaka, opens up about his journey from battling chronic fatigue to building a global health brand. After discovering the life-changing benefits of qualit...

24 Jan 202554min

547: In Retrospect - Building a $200M Selling Swimwear | Erin Deering

547: In Retrospect - Building a $200M Selling Swimwear | Erin Deering

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 Erin...

17 Jan 202548min

546: In Retrospect - Building BigCommerce: Mitch Harper’s Guide to Scaling a SaaS Empire

546: In Retrospect - Building BigCommerce: Mitch Harper’s Guide to Scaling a SaaS Empire

We're diving back into another episode from the Foundr Archives to revisit my interview with Mitch Harper, founder of BigCommerce - as well as a long-time mentor and coach of mine who has been driving...

10 Jan 202553min

545: In Retrospect - How Kendra Scott turned $500 Into a $1 BILLION Jewellery Empire

545: In Retrospect - How Kendra Scott turned $500 Into a $1 BILLION Jewellery Empire

Kendra Scott started her self-titled billion-dollar jewelry business out of failure. Her first business failed after 5 years, and she started selling handmade jewelry door-to-door as a side hustle. No...

3 Jan 202539min

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