# Investor Stories 464: Anti Portfolio Confessions: Missing Twilio, Zoom, DocuSign, MongoDB, and Solana (Austin, Simpson, Chaddha)

Page: https://stenobird.com/podcast/the-full-ratchet/investor-stories-464-anti-portfolio-confessions-missing-twilio-zoom-docusign-mongodb-and-solana-austin-simpson-chaddha
Text version: https://stenobird.com/podcast/the-full-ratchet/investor-stories-464-anti-portfolio-confessions-missing-twilio-zoom-docusign-mongodb-and-solana-austin-simpson-chaddha.md
Podcast: [The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified](https://stenobird.com/podcast/the-full-ratchet)
Published: 2026-03-09T08:00:00+00:00
Episode link: https://fullratchet.net/austin-simpson-chaddha
Audio file: https://traffic.libsyn.com/secure/fullratchet/Investor_Stories_464-_Why_I_Passed_Austin_Simpson_Chaddha.mp3?dest-id=204448
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Duration seconds: 412

## Resource

Top-tier venture capitalists share the stories behind their 'anti-portfolios'—the massive successes they failed to back. The discussion explores the psychological pitfalls of pattern matching and the importance of humility in correcting investment errors.

## Highlights
- Failure mode: Relying on the belief that a problem is 'already solved' can lead to missing category-defining platforms like Twilio
- Practical takeaway: Multi-stage firms have a unique advantage in 'fixing' mistakes by re-engaging with founders after initial concerns are resolved
- Main idea: Successful investing requires shifting focus from the validity of an initial idea to the execution capability of the team
- Failure mode: Over-reliance on past personal experiences (e.g., bad experiences with WebEx) can create blind spots for superior new technologies
- Main idea: Humility is a required trait for investors to admit when their initial thesis was wrong and pursue follow-on opportunities

## Topics

Venture Capital, Startup Investing, Anti-Portfolio, Decision Making, Founder Execution, Seed Funding, Investment Strategy, Twilio, Zoom, MongoDB

## Chapters
- 1:10 — The Cost of Missing Seed Rounds: Ethan Austin discusses the difficulty of backing early-stage founders when capital is constrained.
- 1:50 — Correcting Investment Mistakes: Arianna Simpson explains how to use humility to re-engage with founders after passing on them due to technical concerns.
- 3:00 — The Role of Multi-Stage Firms: A discussion on how investing across different stages allows firms to capture value even after an initial 'no'.
- 5:40 — The 'Solved Problem' Trap: Navin Chaddha reflects on passing on Twilio because his team believed the market was already saturated.
- 6:50 — Prioritizing People Over Ideas: A shift in investment philosophy from evaluating the strength of a product to evaluating the greatness of the founding team.
- 7:30 — The Hall of Fame Misses: A look at the recurring pattern of passing on massive successes like DocuSign and MongoDB.

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## Transcript

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