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Cyber Investing in the AI Exploit Era

Exploring what happens to security, and security investing, when vulnerability discovery becomes a continuous output of computation.

In this episode, I sit down with Founder and Managing General Partner at Rain Capital, Chenxi Wang, to discuss security investing in what she calls the AI Exploit Age.

Chenxi has seen this industry from the professor’s podium at Carnegie Mellon, the analyst seat at Forrester, the operator chair at Intel Security and Twistlock, and now the cap table, which makes her one of the most technical investors in security. She closed out my July run of conversations with security investors, and this one went deep on how AI is rewriting both the attacker’s economics and the investor’s.

We chatted about:

  • Her path from professor to analyst to operator to founding Rain Capital

  • The AI Exploit Age, where vulnerability discovery moves from scarce to continuous and exploitation windows compress from weeks to hours

  • The Guardian Agent thesis and whether it really takes an AI to govern an AI

  • How AI agent identity differs from the traditional non-human identity bucket of service accounts and API keys

  • The signals that tell an early-stage investor enterprises will actually buy

  • Capital concentrating at the extremes while Series B and C funding stays constrained

  • What security leaders should be doing differently over the next twelve months


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A big thanks to Chenxi for coming back on the show. You can follow her work through Rain Capital Insights, where she writes some of the sharpest monthly commentary on where AI and security are colliding.

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