Episode #100: 300 Reads Later, Are VC Skills Obsolete?, Making Venture Exciting Again
For our 100th episode, we turn the mic on Charles to reflect on the state of venture, using the themes that have come up again and again across roughly 300 good reads since we started the show. We dig into whether the skills that made investors great still matter in an AI-first market, drawing on pieces like Alberto Romero's "You Spent Your Whole Life Getting Good at the Wrong Thing" and Sarah Guo's "Relevance Decays." Charles looks back on what surprised him most over the last two years, from the seed squeeze and the bubble debate to founders who now say they work for their AI agents. We close on where venture needs to go to feel exciting again, and the one line summary of venture in 2026 Charles would leave for someone reading it in 2036.
Key Points
- Venture has become increasingly squeezed into a narrow set of consensus trades, making it harder for firms and founders outside the hottest areas to stand out or get funded.
- The skills that matter most in venture are shifting toward brand, judgment, and the ability to be chosen by founders, while old assumptions about capital scarcity and platform support matter less than they used to.
- AI is changing how companies are built and how investors think about outcomes, but the pace of change is creating both new opportunities and a lot of uncertainty about which behaviors and business models are here to stay.
[You Spent Your Whole Life Getting Good at the Wrong Thing, Alberto Romero](https://www.thealgorithmicbridge.com/p/you-spent-your-whole-life-getting)
[Relevance Decays, Sarah Guo](https://www.linkedin.com/pulse/relevance-decays-sarah-guo-ps0lc)
[No Country for Old Founders, Euclid Ventures](https://insights.euclid.vc/p/no-country-for-old-founders)
[Everyone Wants to Be AI-Pilled. Most Companies Are Still Level 1, Ann Miura-Ko](https://x.com/annimaniac/status/2050225284277026990)
[A Crisis Moment for Seed VC, Rob Go](https://nextview.vc/blog/a-crisis-moment-for-seed-vc/)
[VCs Are Cockroaches, Micah Rosenbloom](https://www.linkedin.com/posts/micah-rosenbloom-a0350_%F0%9D%97%A9%F0%9D%97%96%F0%9D%98%80-%F0%9D%97%AE%F0%9D%97%BF%F0%9D%97%B2-%F0%9D%97%96%F0%9D%97%BC%F0%9D%97%B0%F0%9D%97%B8%F0%9D%97%BF%F0%9D%97%BC%F0%9D%97%AE%F0%9D%97%B0%F0%9D%97%B5%F0%9D%97%B2%F0%9D%98%80-%F0%9D%98%81%F0%9D%97%B5%F0%9D%97%B2%F0%9D%98%86-activity-7372386276894724097-hJhP)
[I See Dead VCs, Beezer Clarkson](https://www.linkedin.com/pulse/i-see-dead-vcs-elizabeth-beezer-clarkson-uc4xc/)
[Hey There's a Bubble, M.G. Siegler](https://spyglass.org/ai-bubble/)
[Bubbles and Balloons, Kanyi Maqubela](https://x.com/km/status/2021831071617495415)
[The AI Wildfire Is Coming, Dion Lim](https://ceodinner.substack.com/p/the-ai-wildfire-is-coming-its-going)
[Patient Capital Will Eat the World, Will Manidis](https://x.com/willmanidis/status/2018318844247347308)
[Startup Founders Are Working Harder Than Ever to Keep Up With Their AI Agents, WSJ](https://www.wsj.com/tech/ai/ai-agents-startup-work-culture-fa10494d)
[VC-Backed Startups Are Low Status, Michael Dempsey](https://mhdempsey.substack.com/p/vc-backed-startups-are-low-status)
[Build What's Fundable, Kyle Harrison](https://investing101.substack.com/p/build-whats-fundable)
[Tool Shaped Objects, Will Manidis](https://x.com/WillManidis/status/2021655191901155534)
[What Capital Wants, Yoni Rechtman](https://99d.substack.com/p/what-capital-wants)
[The Changing Math Behind Seed Investing, Micah Rosenbloom](https://www.linkedin.com/posts/micah-rosenbloom-a0350_if-you-invested-500k-in-a-startup-in-2025-activity-7449485836909195264-QOMT)
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Transcript
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