The Real Drivers of Cyber Spend: Risk, Compliance, and AI Disruption

What really drives cybersecurity investment and why is “threat” often the last reason?

In this episode, Rakesh Loonkar, co-founder of Transmit Security and general partner at Picture Capital, shares a contrarian take on how cybersecurity product categories emerge and why compliance and platform shifts often matter more than actual threats. Drawing on decades of experience as both operator and investor, Rakesh explains how he evaluates risk timing, founder mindset, and market inflection points.

Key highlights from the episode:

• Why most cyber spend starts with compliance, not attacks

• How to invest ahead of platform shifts like AI and cloud

• A three-part model for understanding cyber spending behavior

• The risks of financial-only boards in technical startups

• Lessons from building Trusteer, Transmit, and Picture Capital