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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Thank you to the partners who make this possible

Brex: The banking solution for startups.

WorkOS: The modern identity platform for B2B SaaS.

Explo: Customer-facing analytics for any platform.

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For a full transcript of the episode, please visit: https://thegeneralist.substack.com/p/lessons-from-20-years-of-vc-roelof-botha

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Timestamps

(00:00) Intro

(04:50) Roelof on the AI bubble

(07:26) Sequoia’s Monday tracker and investment tools

(09:25) AI's role in business growth

(11:55) The challenge of spotting unicorns in a climate of rapid growth

(14:48) Roelof’s critique of capital-heavy AI startups

(19:30) A glimpse at how partners work at Sequoia

(21:43) A lesson from PayPal

(24:09) Roelof’s interest in decision-making and biases

(27:19) Two key biases: loss aversion and anchoring

(30:55) Examples of anchoring with Square and Twitter

(36:30) The case for long-term thinking

(41:00) Sequoia’s culture and commitment to winning

(48:38) What Sequoia looks for in founders

(51:39) How new technology enables less technical founders to succeed

(54:06) Why AI may favor incumbents over startups

(57:12) Where the US stands in the AI race

(1:01:16) The risks of government overspending

(1:03:54) Sequoia’s journey from idea to IPO

(1:10:44) How Sequoia uses AI

(1:15:05) Final meditations

Performance numbers shared in this interview are as of March 24, 2025. Past performance is not indicative of future performance.

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Follow Roelof Botha

X: https://x.com/roelofbotha

LinkedIn: https://www.linkedin.com/in/roelofbotha/

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Resources and episode mentions

—Books—

• Decisive: How to Make Better Choices in Life and Work: https://www.amazon.com/Decisive-Make-Better-Choices-Life/dp/0307956393/

• Leading: Learning from Life and My Years at Manchester United: https://www.amazon.com/Leading-Learning-Years-Manchester-United/dp/0316268100

• A Tale of Two Cities: https://www.amazon.com/Tale-Two-Cities-Penguin-Classics/dp/0141439602

• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807014273/r

—People—

• Don Valentine: https://en.wikipedia.org/wiki/Don_Valentine

• Daniel Kahneman: https://www.nobelprize.org/prizes/economic-sciences/2002/kahneman/facts/

• Brian Chesky on X: https://x.com/bchesky

...Episode resources continued at: https://thegeneralist.substack.com/p/lessons-from-20-years-of-vc-roelof-botha

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