#7: Investor Behind 45 Exits & 40,000 Jobs — AI, Karma, and How to Sell a Startup
Divot16 Huhti 2025

#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.


Follow Navin – X (Twitter): https://x.com/NavinChaddha

Follow Derek – X (Twitter): https://x.com/derekjandersen


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/


Follow Divot:

YouTube: https://www.youtube.com/@Divotpod

X (Twitter): https://x.com/divotdotorg

Instagram: https://www.instagram.com/divotdotorg

TikTok: https://www.tiktok.com/@divot.org

LinkedIn: https://www.linkedin.com/company/divotdotorg/


#VentureCapital #AirbnbMiss #StartupInvesting #NavinChaddha #MayfieldFund #MidasList #SiliconValleyVC #FounderAdvice #StartupEmpire #DivotPodcast

Jaksot(48)

#47: The 5 Types of Wealth & Why You’re Chasing the Wrong One | Sahil Bloom

#47: The 5 Types of Wealth & Why You’re Chasing the Wrong One | Sahil Bloom

Sahil Bloom grew up with one scoreboard: money. He worked his way into top private equity firms, built a career most would envy, and still felt hollow, until he started questioning what wealth actuall...

29 Huhti 1h 1min

#46: Elder Neil L. Andersen (Faith Conversation with a Latter-day Saint Apostle, My Dad)

#46: Elder Neil L. Andersen (Faith Conversation with a Latter-day Saint Apostle, My Dad)

Before becoming a global spiritual leader, Neil L. Andersen was a farm boy learning discipline, responsibility, and faith long before the world ever knew his name. For Derek Andersen, this isn’t just ...

22 Huhti 1h 19min

#45: The Mindset That Builds Champions | BYU Athletic Director Brian Santiago

#45: The Mindset That Builds Champions | BYU Athletic Director Brian Santiago

Brian Santiago is the Athletic Director at BYU, one of the most respected leaders in college sports. Over nearly three decades inside BYU athletics, he rose from the coaching staff to Athletic Directo...

15 Huhti 1h 20min

#44: Why You Feel Disconnected, How She Built a 25,000+ Global Community | Creative Mornings Founder

#44: Why You Feel Disconnected, How She Built a 25,000+ Global Community | Creative Mornings Founder

Tina Roth-Eisenberg is one of the most influential community builders in the world, founder of Creative Mornings (25,000+ people, 70+ countries), and the creator behind multiple iconic products like T...

8 Huhti 44min

#43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

#43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

Before leading a $4B company, Adam Edmunds spent years trying to prove he was good enough. From cold emailing CEOs as a student to building his first company, his journey started with uncertainty and ...

1 Huhti 1h 8min

#42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie

#42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie

Before building Crumbl, Jason McGowan was a tech founder focused on virality, creating products used by over 120 million people. He then made a bold move: leaving tech to start a simple cookie busines...

25 Maalis 1h 1min

#41: Stanford Negotiation Expert Reveals the Psychology of Winning Any Negotiation

#41: Stanford Negotiation Expert Reveals the Psychology of Winning Any Negotiation

Before teaching negotiation at Stanford, Stan Christensen spent decades advising leaders on high-stakes negotiations around the world. From corporate finance on Wall Street to the consulting arm of th...

18 Maalis 47min

#40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

#40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

Before building one of the fastest-growing legal technology companies in the United States, Ryan Anderson was a practicing lawyer frustrated by deadlines, paperwork, and systems that made it easy to m...

11 Maalis 1h 7min

Suosittua kategoriassa Liike-elämä ja talous

sijotuskasti
mimmit-sijoittaa
rss-rahapodi
psykopodiaa-podcast
hyva-paha-johtaminen
rss-oivalluksia-rahasta-elamasta
rss-rahamania
inderespodi
rss-lahtijat
ostan-asuntoja-podcast
rahapuhetta
oppimisen-psykologia
lakicast
rss-bisnesta-bebeja
rss-sisalto-kuntoon
rss-inderes
leadcast
mihin-sita-saastais
rss-rikasta-elamaa
rss-40-ajatusta-aanesta