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Resilient Cyber w/ Ed Sim - The Intersection of Venture, AI and Cyber

In this episode, I sat down with Boldstart Ventures Founder and GP

. Ed is also the author of "What’s Hot in Enterprise IT/VC,” which I’ve been reading for some time and strongly recommend checking out!

We will dove into the intersection of Venture Capital, AI, and Cybersecurity.


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  • Ed and I started the conversation discussing boldstart ventures, their role as an inception fund and their recent announcement of a $250M fund for those building the “autonomous enterprise”

  • Ed and I explored how AI is having an outsized impact on the investment and venture landscape and why that is, with it poised to be the largest platform shift of our lifetimes.

  • Ed laid our his 5 P framework, for evaluating what teams/founders to bet on and back and what he’s learned through decades of investment experience and expertise.

  • One of his recent success stories was investing in Protect AI, which recently was acquired by Palo Alto for roughly $700M, with the news breaking around RSA. Ed discussed the origin story of Protect AI and what the acquisition signals for the cybersecurity and AI security market.

  • One paradigm unfolding right now is that between AI Native firms and Incumbents, and it is a race between speed of innovation and speed of distribution. We discussed how this race is and can play out and what will help determines who wins or loses.

  • We wrapped up the conversation discussing the rise of AI driven development with coding agents, copilots, and LLMs and the implications for the AppSec space.

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