Drew Houston is the Co-Founder and CEO @ Dropbox, for over 700 million users and +600,000 teams, Dropbox is the choice for storing and sharing their most important files. Prior to their IPO in 2018, Drew raised funding from some of the best including Sequoia, Index, Greylock, and IVP to name a few. Drew also currently sits on the board of Meta and is a seasoned angel with a portfolio including Gusto, Scale AI, Pilot and Superhuman to name a few. Prior to Dropbox, Drew founded Accolade, a bootstrapped online SAT prep company he started while in college.


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Timestamps:

0:00 Drew’s Origin Story
1:32 The Y Combinator Story
6:24 How to Pick a Co-Founder
8:52 What are you running away from? Towards?
13:03 What does “high performance” mean to you?
15:53 Are there a few catalytic moments that caused your mindset to change?
19:45 Tips for Combatting Conflict Avoidance
22:30 Tips for Diplomatic Hand Grenades
25:33 What is the most difficult lesson you’re glad you learned?
32:37 How to Cope with Failure
35:16 Drew’s Biggest Lessons in Talent Acquisition
39:36 Drew’s Biggest Hiring Mistakes
41:22 How did you convince Sequoia to invest?
47:33 The Story of Nearly Getting Acquired by Steve Jobs?
53:42 Is Dropbox a Consumer or B2B company?
51:02 Whats the hardest element of your role at Dropbox?
51:28 What have you recently changed your mind on?
51:52 Who’s the best board member you’ve worked with?
52:39 Biggest Lesson from Joining the Meta Board
53:16 Where will Dropbox be in five years?


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In Today’s Episode with Drew Houston We Discuss:

1.) Entry into Startups and Y Combinator:

How did Drew make his way into the world of startups with an SAT prep planning startup?
How did Drew convince Paul Graham to accept him and Dropbox into Y Combinator?
If we are all a function of our pasts, what is Drew running towards and what is he running away from?

2.) Drew Houston: The Leader and CEO:

How does Drew define “high performance” today?
How would Drew describe his style of management? How has it changed over time?
How did taking an enneagram test change how Drew leads? What did he learn?
What have been Drew’s biggest hiring mistakes? What mistakes does he see others make?
What have been Drew’s biggest lessons in how to let people go the right way?

3.) Crucible Moments: Getting Sequoia, Acquisitions and Steve Jobs:

How did Drew convince the Sequoia team to invest in Dropbox? How did it all start in a rug shop thanks to Pejman Nozad @ Pear?
Has Drew had opportunities to sell the company? Why did he not take them? How does he advise founders on the decision to sell or not?
How did Drew come to meet Steve Jobs? How did the meeting go?

4.) Drew Houston: AMA:

Is Dropbox a B2B company or a B2C company?
What is the hardest element of Drew’s role with Dropbox?
What has Drew recently changed his mind on?
When press cycles were against him, how did Drew get through those tough times?
What is Drew’s biggest takeaway from joining the Meta board?


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Items Mentioned In Today’s Episode:

Drew’s Favourite Book: High Output Management by Andy Grove
https://www.amazon.com/High-Output-Ma...

Subscribe to the Podcast:
https://www.thetwentyminutevc.com/dre...

Follow Harry Stebbings on Twitter:
  / harrystebbings  

Follow Drew Houston on Twitter:
  / drewhouston  


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#DrewHouston #Dropbox #HarryStebbings #20VC #stevejobs #techhistory