Investor Stories 471: Missing Great AI Bets, Losing Conviction, and Overweighting Founders — Lessons from Redpoint, a16z, and Outside VC (Effron, Austin, Simpson) episode artwork

EPISODE · Apr 16, 2026 · 6 MIN

Investor Stories 471: Missing Great AI Bets, Losing Conviction, and Overweighting Founders — Lessons from Redpoint, a16z, and Outside VC (Effron, Austin, Simpson)

from The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

On this special segment of The Full Ratchet, the following Investors are featured: Jacob Effron of Redpoint Ethan Austin of Outside VC Arianna Simpson of Andreessen Horowitz We asked guests to tell the most important lesson they've learned in their career. The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area. We're proud to partner with Ramp, the modern finance automation platform. Book a demo and get $150—no strings attached.   Want to keep up to date with The Full Ratchet? Follow us on social. You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter.

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Investor Stories 471: Missing Great AI Bets, Losing Conviction, and Overweighting Founders — Lessons from Redpoint, a16z, and Outside VC (Effron, Austin, Simpson)

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This episode was published on April 16, 2026.

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On this special segment of The Full Ratchet, the following Investors are featured: Jacob Effron of Redpoint Ethan Austin of Outside VC Arianna Simpson of Andreessen Horowitz We asked guests to tell the most important lesson they've learned...

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