Why Hackers Are Winning the AI War

Guest: Lee Rossey
Episode #246
Duration: 55:52 Mins
Release Date: 08-09-2026

Marc and Lee Rossey explore how artificial intelligence is lowering the barrier to entry for hackers, breaking down why building realistic cyber training ranges is the only way companies can survive.

About the Episode

Cybersecurity used to be a highly technical game played mostly by nation-states and elite military agencies. Today, artificial intelligence has completely lowered the barrier to entry, allowing amateur hackers to launch prolific, automated attacks against easy targets like hospitals and small businesses. Threat actors now operate like highly efficient corporations, using advanced tools to aggressively scale their offensive capabilities. This massive shift means defensive strategies must evolve just as quickly to keep up with the chaos.

To fight back, organizations can no longer rely on simple software updates or theoretical security protocols. They need to build realistic cyber ranges—essentially flight simulators for digital networks—to safely test how AI agents and security tools actually perform under heavy fire. We are rapidly entering an era where having an “AI proving ground” is a fundamental requirement to stay online. Companies that take the time to stress-test their systems today will be the ones left standing when these automated threats hit peak production in the coming years.

About the Guest

Lee Rossey is the Co-Founder and Chief Technology Officer at SimSpace, bringing over 15 years of experience from MIT Lincoln Laboratory to the frontlines of digital defense. Today, he is focused on exposing a dangerous disconnect in modern business leadership: while 78% of executives feel highly confident in their cybersecurity, actual defensive readiness scores often sit as low as 30%. Having watched AI rapidly lower the barrier to entry for amateur hackers, Lee actively challenges the outdated “we’ve always done it this way” mentality.

To close this massive security gap, Lee argues that AI defensive tools must earn trust through measurable outcomes in safe-to-fail simulations, rather than relying on polished sales demos. He helps organizations build rigorous “AI proving grounds” where security teams can safely find out what actually breaks before a live deployment. Through his work at SimSpace, Lee continues to push the industry away from assumed safety and toward a future of truly battle-tested cyber defenses.

Linkedin: https://www.linkedin.com/in/lee-rossey/     
Website: https://simspace.com/

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