Navigating Investment Valuations and Regrets in Venture Capital

This chapter explores the challenges of investment valuation in venture capital through the story of a company called Squirrel, later known as Square. It highlights the emotional and strategic dilemmas faced by investors as they navigate changing valuations and market dynamics.

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Episode notes

Sequoia Capital is synonymous with outstanding performance, backing companies like Apple, Google, Airbnb, and Stripe. In today’s episode, I chat with Roelof Botha, Sequoia’s Managing Partner, about what it takes to see the future first, capitalize on it intelligently once it arrives, and help founders build enduring companies.

Roelof is especially well-placed to discuss such matters. Not only has Sequoia navigated more than 50 years of market cycles, Roelof has personally spent more than 20 years helping shape the firm’s unique approach. From honing a philosophy rooted in clear thinking and long-term vision to asking the tough question of "What would you do with only 12 months of runway?" Roelof breaks down the mindset that’s helped Sequoia and its founders thrive, and what others can learn from it.

In our conversation, we explore:

• The psychological biases that most frequently derail investors

• Why the first-mover advantage is often a disadvantage in technology

• Why excess funding often undermines innovation

• The story of PayPal's near-death experience and how it sparked its most critical innovations

• How Roelof’s training as an actuary shaped his long-term thinking

• How Sequoia maintains investment discipline through market cycles

• Why they don’t use the word “deal” at Sequoia

• How the US can maintain the lead in the AI race

• The thinking behind the Sequoia Capital Fund and the firm’s organizational structure

• And much more

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