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26th May 2023
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. As for Doug, he joined Sequoia over 33 years ago and has led investments in Nubank, Meraki, ServiceNow and TradeRepublic to name a few.
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1.) How a 5PM Monday meeting with Don Valentine led to Doug joining Sequoia over 33 years ago? What did Don ask Doug in the meeting? What does Doug believe led Don to offer him his first role at Sequoia?
2.) The Leader: How did Doug change when he made the transition from a “COO” role to more of a “CEO” role with Sequoia? Doug has previously said, “Sequoia is a team, not a family”. What does he mean by this? How do Doug and Sequoia do to give the team an unwavering sense of duty to the Sequoia brand? What does Doug believe Sequoia have done so well to allow them to move seamlessly from generation to generation?
3.) The Investor: Doug’s first 3 investments all went on to successful IPOs, how did this impact his mindset at the time? What does Doug mean when he discusses “the abyss” he went through post this time? How does Doug advise others going through the abyss? What are the signs certain people will make it through vs not?
4.) The Landscape Today: How does Doug think about and react to newer entrants like Tiger and Softbank? How does Doug think about and assess his own price sensitivity today? How does Doug determine when to be disciplined vs when to pay up? Through what lens does Doug assess the compression of deployment cycles in venture today? Should we “play the game on the field”?
5.) The Expansion: In 2005, Sequoia expanded to China. Why was this the right time? What was the decision-making process for the Sequoia China team? Why does Doug believe, “when you lose pre-seed, you become private equity”? How does Doug react to the notion that success in venture is cyclical and compounds?
Doug’s Favourite Book: The Fountainhead: Ayn Rand, Antifragile: Things that Gain from Disorder