Nirav Tolia: The Lonely Reality Of Being CEO l Trailblazers Podcast Episode 50

In this episode, we sit down with Nirav Tolia, co-founder and CEO of Nextdoor and a longtime Silicon Valley entrepreneur who previously co-founded Epinions, which became Shopping.com.

We discuss the lonely reality of being a CEO, building and rebuilding companies through failure, why Nirav returned to Nextdoor after years away, navigating fear and self-doubt as a leader, and how established technology companies can adapt in the age of AI. We also get into his time on Shark Tank, working alongside Mark Cuban and Kevin O'Leary, and what stepping away from Silicon Valley taught him about business and life.

If you're interested in entrepreneurship, startups, leadership, Silicon Valley, AI, Shark Tank, building companies, or understanding what it's really like to lead a business through its hardest moments, this episode is for you.

This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi

Sydecar: https://sydecar.io/partners/trailblazers

beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-14&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF)

Granola: http://granola.ai/trailblazers

*Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/55838edb-522f-4468-a139-fad215bab7ca-00b881l8

Kalshi: http://Kalshi.com/r/trailblazers

Wispr Flow: https://ref.wisprflow.ai/trailblazers

HEX: http://hex.ai/trailblazers

🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com