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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576: (Solo) This One Trademark Mistake Nearly Killed My Business - Here's What I Learnt

576: (Solo) This One Trademark Mistake Nearly Killed My Business - Here's What I Learnt

I got sued just a few months into starting Foundr—and it nearly crushed everything I was building. In this short episode, I’m sharing the full story behind how I was forced to change the name of my...

5 Elo 20259min

575: Ty Haney on Being Ousted From Her Own Company: The Lesson's Learnt & How to Bounce Back

575: Ty Haney on Being Ousted From Her Own Company: The Lesson's Learnt & How to Bounce Back

In this episode, Ty Haney, founder of Outdoor Voices, shares how she turned her public downfall into the blueprint for an even bigger comeback—building multiple new brands and redefining how community...

1 Elo 202551min

574: He's Building a $250M+ Business That Measures Success in Lives Saved | Andrew Lacy

574: He's Building a $250M+ Business That Measures Success in Lives Saved | Andrew Lacy

In this episode, Andrew Lacy, founder of Prenuvo, shares how he went from two startup exits to building one of the fastest-growing health tech companies in the world—revolutionizing preventative healt...

25 Heinä 202551min

573: Building a $74M a Year Beauty & Community Empire | Trinny Woodall

573: Building a $74M a Year Beauty & Community Empire | Trinny Woodall

In this episode, Trinny Woodall, founder of Trinny London, shares how she turned her mission to help women feel confident into a multi-million dollar global beauty brand. She reveals: • Why she fo...

18 Heinä 202551min

572: (Solo) How to Build a Brand That’s Uncopyable: Even If Your Idea Gets Stolen

572: (Solo) How to Build a Brand That’s Uncopyable: Even If Your Idea Gets Stolen

Worried someone’s going to steal your business idea? You’re not alone — and you’re not powerless. In this short episode, I’m sharing exactly what to do when copycats come for your product — because...

11 Heinä 202510min

571: No Funding, 104 Rejections & $411 Left in the Bank - How She made $65M+ on Flowers

571: No Funding, 104 Rejections & $411 Left in the Bank - How She made $65M+ on Flowers

In this episode, Christina Stembel, founder of Farmgirl Flowers, reveals how she built a $65M+ floral business from her dining room—with no funding, no degree, and no industry experience. She revea...

4 Heinä 202542min

570: Your Toothbrush is GROSS - They Fixed it and Made MILLIONS | SURI

570: Your Toothbrush is GROSS - They Fixed it and Made MILLIONS | SURI

In this episode, Mark Rushmore and Gyve Safavi, co-founders of SURI (Sustainable Rituals), share how they turned a simple personal care item into a sustainable, design-led movement—challenging legacy ...

27 Kesä 202559min

569: The Email Expert - How to Get Your Customers Attention

569: The Email Expert - How to Get Your Customers Attention

In this episode, Rytis Lauris, co-founder of Omnisend, shares how he bootstrapped a leading email and SMS marketing platform used by over 125,000 eCommerce brands worldwide. He shares: • Why most eco...

20 Kesä 202548min

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