Behind the founder: Drew Houston (Dropbox)

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about:
• The three eras of Dropbox’s growth and evolution
• The challenges he’s faced over the past 18 years
• What he learned about himself
• How he’s been able to manage his psychology as a founder
• The importance of maintaining your learning curve
• Finding purpose beyond metrics and growth
• The micro, macro, and meta aspects of building companies
• Much more

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Where to find Drew Houston:

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In this episode, we cover:
(00:00) Introduction to Drew and Dropbox
(04:44) The three eras of Dropbox
(07:53) The first era: Viral growth and early success
(14:19) The second era: Challenges and competition
(20:49) Strategic shifts and refocusing
(29:36) Personal reflections and leadership lessons
(40:19) Unlocking mindfulness and building support systems
(43:14) The Enneagram test
(50:35) The challenges of being a founder CEO
(58:11) The third era: Rebooting the team and core business
(01:22:41) Lessons and advice for aspiring founders
(01:27:46) Balancing personal and professional growth
(01:42:38) Final reflections and future outlook

Referenced:

Recommended books:

Lenny may be an investor in the companies discussed.

[TheJayMajethiya]

Never seen anyone so successful (& CEO), openly admitting "I don't know" and being vulnerable. Wow. Amazing. Great job Lenny

[iamaapj]

The humility in Drew's voice is fascinating. Such a blessed mind. Thank you for changing the world. This is so good, Lenny! Great job, thank you.

[blingblockchain]

Drew has to be the most humble and genuine founder that I've seen.

[TJMcCarty]

The most inspiring thing about this interview is learning that even multi billion dollar founders/CEOs don’t have any idea what they’re doing.

Even at that level, it seems like you just have to try things, experiment, and follow the customer whenever you happen to build something that they actually want.

[itsjensenkuo]

Unbelievable vulnerability and candidness coming from a legend that I've always looked up to. This is truly truly inspiring. Thank you Drew and Lenny for such a thoughtful conversation. 🙏

[psnomad]

Such a great conversation!

It was healing to hear Drew talk about the tool-overload that dominates work in tech today (and I guess all industries/roles where we just sit on our computers all day).

Excited about the future of Dash and other solutions that hopefully reduce the sheer number of products we have to manage to build even a basic, value-creating business.

[davidmoore]

The authenticity is appreciated and inspiring. Thank you!

[sowandscale]

incredible journey of dropbox - great lessons on leadership, learning ahead by reading, and the biggest growth being personal through entrepreneurship, thanks Lenny and Drew!

[jeswan]

This is super comprehensive and helpful. Especially love insight of the building support system.

[saad]

This was so good! Thank you for making this podcast happen!

[StoicProductManager]

The first half an hour is an amazing story, a rollercoaster of an adventure for Drew, but so many times his voice sounded like it was about to break and he was gonna shed some tears. At the same time it's the least I've seen Lenny not talk on the show.

[PitchDecks]

Truly a legendary journey! Dropbox's first pitch deck from 2007 is one of my favorite references (they raised with $1.2M from Sequoia with 200, 000 users at the time vs. 700M+ Dropbox users today)

[StoicProductManager]

One more thing this conversation made me realize, is that this behind the founder series is a great addition to the channel if you think about it from the perspective of writing a book like 'Tribe of Mentors' that Tim Ferriss wrote. I'd love it, and I'm sure plenty of people would buy it, if you wrote it some day Lenny. Where you do a few page write up about each interview, showcasing the highlights, answers to recurring questions/corners and that could really pull the reader to want to listen to the whole thing, read the books they recommend or follow the frameworks they describe. I know I would do it!

[Justin-zv]

Thank you. I got to visit the office in summer 2008. Didn't meet Drew but got to drop by from knowing the early team.

[SuchitraSinha-hc]

One of the best episode I have watched so far !!

[WyndoMitraBuwana]

He’s so calm, looks mature and grounded

[nuthinking]

I wonder, because they earned the trust of storing binary files, why they didn’t go into textual data storage. Like Airtable, instead of Paper 🤔

[James-mkjp]

Dropbox has an unbelievable logo (and brand, historically), but I do feel like the name (and likewise, concept) keep them in the past. They need a Meta-like rebrand.

[tracyhuber]

What Enneagram book was Drew referencing? There are a few Enneagram books out there.

[marc-antoineroy]

The only founder who can talk more than Brian Chesky