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Vol. II — No. 184Remarkable People · Exceptional CompaniesToday's Edition

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The Most Dangerous Second in AI
Ai · Saas · Enterprise

The Most Dangerous Second in AI

Operant AI is betting that the decisive moment in cybersecurity is no longer before software ships or after an alarm rings. It is the instant an AI agent decides to act.

ai-security · agent-securityRead →
Legend
Rick Caccia
Founder · Executive · Operator

Rick Caccia

Rick Caccia is CEO and co-founder of WitnessAI, the Mountain View-based AI security company that raised $85.5M total (including a $58M round from Sound Ventures and Ashton Kutcher in January 2026) and delivered 500%+ ARR growth in 12 months. A Silicon Valley native with multiple UC Berkeley degrees, Caccia spent two decades in cybersecurity product and marketing leadership at Palo Alto Networks, Google (founding CMO for Chronicle), Exabeam, Red Canary, ArcSight, and Symantec before pivoting to the CEO seat to build purpose-built security guardrails for enterprise AI.

ai-security · ai-governanceRead →