Gokul Rajaram is an early stage technology investor. As a product leader, operator and board member, he’s helped build seven generational technology companies, including Alphabet, Block, Coinbase, DoorDash, Meta, Pinterest, and The Trade Desk.
We talk about lessons learned from Zuck, Sergey Brin, and Jack Dorsey, when big acquisitions can go well, how to define your ICP, why you should always size markets bottoms-up, having a fast response time, how seed investing has changed since 2007, and Gokul’s hot takes on titles at a startup. Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at ⁠https://bit.ly/WorkOS-Turpentine-Network⁠.

Timestamps:
(00:00) Intro
(02:14) Common thread of success between the founders of Google, DoorDash, Facebook, and Square
(05:50) Gokul’s first job in Silicon Valley
(07:46) How Serendipity led to PMing Adsense, one of Google’s biggest products
(12:20) Lesson from Sergey Brin on reducing friction before a products magic moment
(18:50) How Zuck used founder mode to beat Google Plus in 2011
(22:51) When big acquisitions can go well
(24:47) How Gokul switches from startup helper to public company board member
(28:09) The evolution of Seed investing since 2007
(33:27) How to have a fast response time
(37:40) Lessons from Jack Dorsey always selling
(39:54) How to define your ICP
(42:40) Using bottoms-up to size a market
(44:05) Why Director and VP titles are bad for startups

Referenced:
Who’s Got the Monkey? https://hbr.org/1999/11/management-time-whos-got-the-monkey
Getting Things Done: The Art of Stress-Free Productivity https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280
How to Size a Market in 30 Minutes https://blog.blingcap.com/2023/02/13/How-to-Size-a-Market/
Follow Gokul:
Twitter: https://x.com/gokulr
LinkedIn: https://www.linkedin.com/in/gokulrajaram1
Follow Turner:
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LinkedIn: https://www.linkedin.com/in/turnernovak
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Alex Jones 2025-Feb-09 Sunday