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

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Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday.

Timestamps:

0:00 Intro 

0:41 The AI Pilled Organization 

6:09 The Biggest Barrier to AI Adoption

8:41 The Rise of the Non-Technical Founders

10:32 How To Find Super-Thinkers

12:30 Why Ann Loves Teaching 

13:36 Stanford Mayfield Program

16:25 Getting Pitched By A 14-Year-Old

18:52 Different Types Of Leadership 

23:29 Early Investment In Twitter 

24:42 Why Twitch Never Should Have Worked

27:01 Ann’s 10,000x Return From Lyft Investment 

30:00 Inside the Uber vs. Lyft Rivalry

33:25 Ann’s Investment Philosophy  

35:52 Investing In Lyft At $5M Valuation 

39:10 Staying Disciplined On Fund Size 

47:49 Evaluating Companies After The Investment

51:29 Ann’s Partnership With Mike Maples 

1:03:27 Rapid Fire Questions