20VC: Dropbox's Drew Houston on Leadership; Hiring, Firing, Breakpoints in Company Scaling, The Story of Nearly Getting Acquired by Steve Jobs and Apple, How Founders Should Think Through Potential Investors and Acquisitions

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 17 October 2022

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

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?

Items Mentioned In Today's Episode:

Drew's Fave Book: High Output Management by And

Transcript

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0:00.0	This is 20VC with me, Harry Stebbings, and the show state is a special one.
0:03.6	I listened to this guest on Tim Ferriss in 2018, and I loved their discussion,
0:08.2	but I did not know the best way to get in contact with them to have them on 20VC.
0:11.9	And so I recently tweeted that I'd love to have them on the show, and I tagged them.
0:15.5	And they responded, and this show is the result, which I'm so, so proud of and love doing, and so I'm thrilled to welcome
0:20.8	Drew Houston, co-founder and CEO at Dropbox, for over 700 million users and 600,000 teams.
0:27.6	Dropbox is the choice for storing and sharing their most important files.
0:31.7	Prior to their IPO in 2018, Drew raised funding from some of the best, including Sequoia,
0:36.7	Index, Greylock and IVP, to name a few. Drew also currently sits on the board of the best, including Sequoia, Index, Greylock and
0:37.8	IVP, to name a few. Drew also currently sits on the board of Meta and is a seasoned angel,
0:42.7	with a portfolio including the lights of gusto, scale AI, pilot and superhuman. And prior to Dropbox,
0:48.5	Drew founded Accolade, a bootstrapped online SAT prep company. He started while in college. And I want
0:54.0	to say a huge
0:54.6	thank you to the wonderful Doug Leoni at Sequoia and Sue J. Jaswa for many incredible questions
0:59.3	suggestions really did make the show so special. But before we dive into the show today, if you
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	...

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