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
10 snips
Oct 17, 2022 
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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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).
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.
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.
