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
Drew Houston, the co-founder and CEO of Dropbox, shares his journey from a college SAT prep startup to leading a cloud storage giant. He reveals the early challenges of joining Y Combinator and securing Sequoia's investment. Drew discusses his evolving leadership style, the impact of self-awareness, and lessons learned from hiring and firing decisions. He even reflects on a near acquisition by Steve Jobs. The conversation also touches on Dropbox's ambitious plans to transform into a comprehensive digital workspace.
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question_answer ANECDOTE
YC Hustle
Drew Houston applied to Y Combinator in 2005 and got rejected, then later applied with Dropbox.
He hustled to get Paul Graham's attention, even showing up unannounced at YC (and getting kicked out).
volunteer_activism ADVICE
Co-founder Selection
Choose co-founders based on mutual trust and respect, like a serious relationship.
Ensure alignment on big questions and complementary skills for efficient work division.
question_answer ANECDOTE
Executive Coaching
Drew Houston's initial executive coaching revealed his strengths (creative, relationship-focused) and weaknesses (conflict-avoidant, disorganized).
He recommends the Enneagram personality test for better self-awareness.
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High Output Management is a seminal book by Andrew S. Grove that outlines his management and productivity concepts developed during his tenure at Intel. The book introduces the 'management by objectives' approach, also known as the objectives and key results (OKR) framework. It covers techniques for creating highly productive teams, methods of motivation, and the importance of measurable processes, performance reviews, and training. Grove emphasizes the role of managers in leading and motivating teams, and his book is praised for its practical advice and timeless relevance in various professions and industries.
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?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 
