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

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


Listen Later

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

...more
View all episodesView all episodes
Download on the App Store

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The PitchBy Harry Stebbings

  • 4.4
  • 4.4
  • 4.4
  • 4.4
  • 4.4

4.4

482 ratings


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

View all
This Week in Startups by Jason Calacanis

This Week in Startups

1,276 Listeners

a16z Podcast by Andreessen Horowitz

a16z Podcast

1,060 Listeners

The Official SaaStr Podcast: SaaS | Founders | Investors by SaaStr

The Official SaaStr Podcast: SaaS | Founders | Investors

176 Listeners

Invest Like the Best with Patrick O'Shaughnessy by Colossus | Investing & Business Podcasts

Invest Like the Best with Patrick O'Shaughnessy

2,283 Listeners

Equity by TechCrunch, Rebecca Bellan, Kirsten Korosec, Anthony Ha, Max Zeff, Theresa Loconsolo

Equity

338 Listeners

Capital Allocators – Inside the Institutional Investment Industry by Ted Seides – Allocator and Asset Management Expert

Capital Allocators – Inside the Institutional Investment Industry

792 Listeners

Y Combinator Startup Podcast by Y Combinator

Y Combinator Startup Podcast

226 Listeners

All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

All-In with Chamath, Jason, Sacks & Friedberg

9,263 Listeners

No Priors: Artificial Intelligence | Technology | Startups by Conviction

No Priors: Artificial Intelligence | Technology | Startups

125 Listeners

The Ben & Marc Show by Marc Andreessen, Ben Horowitz

The Ben & Marc Show

123 Listeners

BG2Pod with Brad Gerstner and Bill Gurley by BG2Pod

BG2Pod with Brad Gerstner and Bill Gurley

469 Listeners

AI + a16z by a16z

AI + a16z

32 Listeners

Lightcone Podcast by Y Combinator

Lightcone Podcast

20 Listeners

Training Data by Sequoia Capital

Training Data

43 Listeners

Uncapped with Jack Altman by Alt Capital

Uncapped with Jack Altman

34 Listeners