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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431: Breaking Down Barriers Led to Billions with Alex Bouaziz of Deel

431: Breaking Down Barriers Led to Billions with Alex Bouaziz of Deel

Some might say Alex Bouaziz, cofounder and CEO of Deel, was simply in the right place at the right time. Deel, an international payroll, compliance, and HR solution, launched in 2019 and, by May 2020,...

28 Loka 202243min

432: How “Recovering Accountant” Guy Pearson Built the Shopify for Services

432: How “Recovering Accountant” Guy Pearson Built the Shopify for Services

At 24, Guy Pearson turned down a partnership to start an accounting firm. His early clients were digital companies, and Pearson was jealous that there wasn’t an online commerce system for his industry...

26 Loka 202252min

430: Not All Leads Are Created Equal with B2B Sales Maverick AJ Cassata

430: Not All Leads Are Created Equal with B2B Sales Maverick AJ Cassata

Does the word “sales” make you squeamish or intimidated? If so, then this episode is for you. AJ Cassata is a maverick B2B sales consultant who helps entrepreneurs grow their businesses fast with his ...

14 Loka 202240min

429: Why the Impossible Is Fun with Brian Scudamore of O2E Brands

429: Why the Impossible Is Fun with Brian Scudamore of O2E Brands

33 years ago, Brian Scudamore was sitting in a McDonald’s drive-thru when he saw his future–a beat-up pickup truck filled with junk. Scudamore started a junk-hauling business to pay for college, but w...

7 Loka 202245min

428: Why Your Business Assumptions Are Wrong with Tim Fung of Airtasker

428: Why Your Business Assumptions Are Wrong with Tim Fung of Airtasker

Airtasker is Australia's #1 marketplace for local services. Over the past decade, they've acquired more than 4.3M registered users, built a worth of $255M, created a $1.7B value of job opportunities, ...

28 Syys 202247min

427: How to Pick a Winning Product with The Oodie Founder Davie Fogarty

427: How to Pick a Winning Product with The Oodie Founder Davie Fogarty

Davie Fogarty created Australia's fastest-growing ecommerce brand, The Oodie, which sells wearable blankets and accessories. But success didn't happen overnight. After multiple failed businesses, at 2...

21 Syys 202257min

426: How to Open Talent Doors with Jen Proctor of Cultivated Entertainment

426: How to Open Talent Doors with Jen Proctor of Cultivated Entertainment

Jen Proctor loved being a performer. But when her dream to be a professional singer ended, she pledged to be a good person in the entertainment industry, something she knew wasn't a given. So in 2015,...

14 Syys 202238min

425: Why Kendra Scott Risked Everything on the Customer Experience

425: Why Kendra Scott Risked Everything on the Customer Experience

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...

7 Syys 202247min

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