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Episode 9

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

December 19, 2025
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About the Guest

Rakesh Loonkar

Co-Founder & General Partner at Picture Capital
Rakesh Loonkar is the founder and general partner of the venture capital firm, Picture Capital, based in Boston, and founded in 2024 with other leading figures in cybersecurity. Backed by leading Ivy League endowments, Sequoia, and Accel, Picture Capital invests in and develops the next generation of industrial leaders. As an angel investor, Rakesh has backed companies, including Palo Alto Networks, Zscaler, Wiz, Trusteer, Abnormal Security, Island, Armis, and McAfee Investments, that together have created more than $290 billion in enterprise value. Rakesh is also the president and co-founder of Transmit Security, a market leader in online identity and fraud prevention. Transmit was bootstrapped by its founders before raising $543 million in its Series A, the largest in cybersecurity history. Prior to Transmit, he co-founded Trusteer, growing it from inception to a market leader in web anti-fraud. IBM acquired the company in 2013 for roughly a billion dollars. Earlier here, he co-founded OneSecure with Nir Zuk, the founder of Palo Alto Networks, which was acquired by Juniper Networks.

Episode Overview

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

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