Sizing Checks and Asymmetric Risk

Two decades ago, Aydin Senkut was a first-time fund manager with a thin track record to show prospective backers. LPs didn’t believe a solo GP, especially one without experience at a legacy firm, could build a lasting franchise. They were wrong. Today, Felicis is a Silicon Valley mainstay on its 10th fund, a $900M vehicle. Across its history, Felicis has backed a slew of winners, including Shopify, Canva, Crusoe, and dozens of other billion-dollar outcomes. Rather than specialize over time, Aydin has remained a true generalist, investing across markets and cycles. In this conversation, we dig into the frameworks, stories, and philosophies that shaped Felicis into what it is — and where Aydin believes the next decade of technology is heading.

We explore:

• How growing up in Turkey with entrepreneur parents shaped Aydin’s approach to risk and investing
• Lessons from working alongside Larry Page and Sergey Brin during Google’s early days
• Why Felicis deliberately chose a generalist strategy when most VCs were specializing
• How international experience became a competitive advantage in finding global winners
• The mathematical case for portfolio diversification (50-70 companies per fund)
• Why valuation concerns are often overblown when revenue growth is exponential
• Felicis’s aggressive AI investment strategy and what other investors are missing
• The future of robotics and physical AI through companies like Skild AI
• Why learning and adapting rapidly is Felicis’s constitutional principle

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Transcript: https://www.generalist.com/p/why-being-a-generalist-vc-is-a-competitive-advantage

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Timestamps

(00:00) Introduction

(03:09) How Aydin made his way to Silicon Valley

(06:15) What he learned from his entrepreneurial parents

(08:55) Learnings from the early days at Google

(15:05) The childhood roots of his investing philosophy

(16:31) Why rejection became a catalyst for his venture career

(19:28) Strategy behind Felicis's first $41M fund

(25:44) How his international background became an investing edge

(28:17) How Aydin approaches diversification at scale

(32:08) How he sizes investments based on conviction

(33:15) Generalist vs. specialist investing

(38:23) Why founders are the foundation

(42:48) Why success may look different than expected

(43:46) The Felicis journey

(48:18) Why Felicis is going all in on AI

(54:54) Why entry point matters less than potential

(57:33) How the AI bubble debate misses the point

(59:47) What makes Skild AI a standout company

(01:04:58) The AI bets Felicis missed

(01:07:55) How missing Airbnb and Uber led to backing Adyen

(01:11:20) Final meditations

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Follow Aydin Senkut

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

X: https://x.com/asenkut

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Resources and episode mentions

—Books—

• Antifragile: Things That Gain from Disorder: https://www.amazon.com/Antifragile-Things-That-Disorder-Incerto-ebook/dp/B0083DJWGO
• Clear Thinking: Turning Ordinary Moments into Extraordinary Results: https://www.amazon.com/Clear-Thinking-Turning-Ordinary-Extraordinary/dp/0593086112

—People—

• Larry Page: https://en.wikipedia.org/wiki/Larry_Page
• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin
• Eric Schmidt: https://en.wikipedia.org/wiki/Eric_Schmidt
• Brian Chesky on X: https://x.com/bchesky
• Shane Parrish’s blog: https://fs.blog

—Other resources—

• Felicis: https://www.felicis.com
• Mastering Portfolio Construction: https://www.generalist.com/p/mastering-portfolio-construction
• Steve Jobs’s quote on focus: https://www.goodreads.com/quotes/629613-people-think-focus-means-saying-yes-to-the-thing-you-ve
• Angry Birds: https://www.angrybirds.com
• Rovio: https://www.rovio.com
• Adyen: https://www.adyen.com
• Canva: https://www.canva.com

...Resources continued at: https://www.generalist.com/p/why-being-a-generalist-vc-is-a-competitive-advantage⁠

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