Ann Miura-Ko: Why Great Businesses Still Fail l Trailblazers Podcast Episode 41

In this episode, we sit down with Ann Miura-Ko, Co-Founding Partner of Floodgate and one of Silicon Valley's earliest investors in companies like Lyft, Twitch, Twitter, and Okta. After nearly two decades investing in founders at the earliest stages of company building, Ann shares how she identifies exceptional entrepreneurs long before the rest of the market. We discuss how Twitch almost never happened, the early rivalry between Uber and Lyft, why the best entrepreneurs are truth seekers, the future of AI-pilled organizations, what teaching has revealed about curiosity and character, and how Ann thinks about investing in the next generation of world-changing companies. If you're interested in startups, venture capital, AI, or understanding how the best investors think, 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-5&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF)

*beehiiv has a major announcement coming July 16 - can't say more, but you won't want to miss it. RSVP here: https://www.beehiiv.com/summer-release-2026

Granola: http://granola.ai/trailblazers

*Granola is the official notetaker of Trailblazers. Check out the episode show notes here: https://notes.granola.ai/t/d1fb3aec-f1c5-4681-b763-af05df15ac3d-008umkv4

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

🎧 Listen on Spotify: https://spotify.trailblazerspod.com