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

What It Covers

Three VCs from Outside VC, Andreessen Horowitz, and Mayfield confess to passing on Twilio, Zoom, DocuSign, MongoDB, Solana, and Kin — revealing the cognitive patterns behind each missed investment.

Key Questions Answered

• •"Solved Problem" Bias: Naveen Chaddha passed on both Twilio and Zoom by categorizing them as already-solved markets. Investors should stress-test this assumption by asking whether existing solutions are genuinely good enough, not merely whether they exist.
• •Founder Conviction Over Idea Evaluation: Chaddha's framework evolved after missing multiple breakout companies — he now prioritizes identifying "black swan" founders and disregards initial ideas entirely, recognizing that exceptional operators pivot and adapt regardless of starting conditions.
• •Multistage Firms Can Correct Early Mistakes: Ariana Simpson notes that a16z re-entered Solana after initially passing, turning a missed seed into a still-early position. Multistage fund structures create a second-chance mechanism that single-stage seed funds structurally cannot access.
• •Humility as an Active Investment Process: Simpson frames mistake-correction as a deliberate discipline — investors must continuously reassess prior conclusions because being right about a specific concern at one moment can still produce the wrong long-term outcome if founders subsequently resolve that concern.