#7: Investor Behind 45 Exits & 40,000 Jobs — AI, Karma, and How to Sell a Startup

What does it take to create $100B+ in value while staying grounded, humble, and deeply human?

In this episode of Divot, Derek sits down with one of Silicon Valley’s most respected VCs — a former founder turned long-term investor who’s helped build companies like Lyft, HashiCorp, and Poshmark, with more than 45 IPOs and acquisitions and over 40,000 jobs created across his portfolio.

As Managing Partner of Mayfield Fund, Navin Chaddha shares his journey from IIT Delhi to Stanford, from founding three companies to backing over 60, and how his core philosophy — bet on people, not markets — has guided him for over two decades in venture.

We talk about spotting great founders early, what it means to lead with compassion, and why long-term relationships and karma are the foundation of real success.

If you're a startup founder, investor, or just someone who wants to learn what truly great leadership looks like — this is one of the most insightful episodes we’ve ever done.

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Timestamps:

0:02 - Introduction to the Episode and Guest.

2:12 - Navin Chaddha’s Early Life and Education.

10:01 - Why Startups Fail and What Drives Success.

13:42 - Passion vs. Practicality in Business.

19:20 - Venture Capital as a Service and Learning.

25:42 - Embracing Failure to Learn and Improve.

36:08 - The Differences of Opportunities in India and the U.S.

39:49 - The Early Days of Tech Startups.

48:18 - The Benefits of Helping Others.

55:01 - How Navin Decides to Invest in a Company.

1:02:00 - Navigating Difficult Decisions as a Leader.

1:08:52 - Where to Start with Acquisitions and IPOs.

1:14:12 - Should a Founder Sell?

1:21:31 - Looking Towards the Future of AI.

1:36:01 - Final Piece of Advice.

Episode Partners:

Notion

Startups get up to 6 months free of Notion with unlimited AI. Use code SGXNotion: https://ntn.so/startup

Google Cloud

Accelerate your AI startup with Google for Startups Cloud Program: https://partners.startupgrind.com/partner/google-cloud/https://partners.startupgrind.com/partner/google-cloud/

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