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
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.
Explore the episode
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.
Follow Roelof Botha
LinkedIn: https://www.linkedin.com/in/roelofbotha/
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
Michael Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/
Amos Tversky: https://en.wikipedia.org/wiki/Amos_Tversky
Pat Grady on LinkedIn: https://www.linkedin.com/in/gradypb/
Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-52409b243/
Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred/
Elliot Jaques: https://en.wikipedia.org/wiki/Elliott_Jaques
Pik Botha: https://en.wikipedia.org/wiki/Pik_Botha
Matthew Rabinowitz on LinkedIn: https://www.linkedin.com/in/mattrverse/
Eric Yuan on LinkedIn: https://www.linkedin.com/in/ericsyuan/
Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor/
Joseph Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter
Niall Ferguson’s website: https://www.niallferguson.com/
Jess Lee on LinkedIn: https://www.linkedin.com/in/jesskah/
Alfred Adler: https://en.wikipedia.org/wiki/Alfred_Adler
Other resources
Sequoia: https://www.sequoiacap.com/
Sun Microsystems: https://en.wikipedia.org/wiki/Sun_Microsystems
Tandem Computers: https://en.wikipedia.org/wiki/Tandem_Computers
Oracle: https://www.oracle.com/
Cisco: https://www.cisco.com/
Gilt: https://www.gilt.com/
Rue La La: https://www.ruelala.com/
Roelof’s post on X about SPVs: https://x.com/roelofbotha/status/1895236567079530966
Paypal: https://www.paypal.com/
Airbnb: https://www.airbnb.com/
Otto von Bismarck’s quote: https://www.goodreads.com/quotes/294225-only-a-fool-learns-from-his-own-mistakes-the-wise
Adapting to Endure: https://www.sequoiacap.com/wp-content/uploads/sites/6/2022/06/Adapting-to-Endure_Sequoia-Capital-2022.pdf
The Sequoia Capital Fund: https://www.sequoiacap.com/article/the-sequoia-fund-patient-capital-for-building-enduring-companies/
Block: https://block.xyz/
Arab Spring: https://en.wikipedia.org/wiki/Arab_Spring
Time Span of Discretion by Alfred Lin: https://outlierspath.com/2023/06/25/time-span-of-discretion/
Natera: https://www.natera.com/
Sierra: https://sierra.ai/
Niall’s post on X about debt payments exceeding defense spending: https://x.com/nfergus/status/1893669468338815225
Sequoia Arc: https://www.sequoiacap.com/arc/
Iron Man: https://en.wikipedia.org/wiki/Iron_Man_(2008_film)
Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6
What is Kodawari?: https://exploringkodawari.blog/what-is-kodawari/
Jiro Dreams of Sushi on Prime Video: https://www.amazon.com/Jiro-Dreams-Sushi-David-Gelb/dp/B008ODZEQ0
What is Logotherapy?: https://viktorfranklamerica.com/what-is-logotherapy/
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