What if your AI startup could be destroyed in just fourteen days?

AI has changed the startup game. Small teams can now build sophisticated products in weeks, deploy autonomous AI agents, and scale faster than ever. But there is a dangerous side to this speed: many startups are building powerful AI systems without fully understanding what they have exposed.

Join Thomas Caldwell, technology executive, entrepreneur, and author of The Octopus Enterprise and the forthcoming The Octopus Startup, for a challenging exploration of a new reality: every AI startup is now also a cybersecurity startup .

Through “The Fourteen-Day Death,” Thomas will share the cautionary story of an AI-native startup that went from momentum and opportunity to collapse in just two weeks after serious weaknesses in its AI architecture were exposed. The story is based on real-world events, with facts and identifying details changed to protect those involved.

This session takes founders inside the new AI attack surface. How can prompt injection turn a helpful chatbot into an attack path? What happens when AI agents gain access to customer data and business systems? Who governs machine identities capable of taking autonomous action? And what happens when an AI knowledge base becomes a target?

This is not about slowing innovation. It is about building companies that can survive their own success.

Founders will leave with practical AI security priorities and a new perspective on using cybersecurity to build trust, accelerate enterprise sales, and create competitive advantage.

Who Should Attend

AI startup founders, SaaS founders, CTOs, product leaders, developers, investors, cybersecurity professionals, accelerators, innovation teams, and anyone building or supporting AI-enabled startups.