Show Notes
Amir Kabir, Founding & Managing Partner at Overlook Ventures, joins hosts James Benham and Rob Galbraith to reimagine risk in the age of AI — what the last decade of insurtech got wrong, where the next wave of opportunity actually lives, and why "liability is getting weird" is an understatement.
Amir spent the first chapter of his career in Germany, building enterprise software at a Karlsruhe startup that was eventually acquired by a Silicon Valley company. In 2013 he immigrated to the US for an MBA at Georgetown, became the third person on the founding team at Munich Re Ventures, and helped grow that fund from $50M to over $1B. He later served as General Partner at AV8 Ventures leading the financial services practice before launching Overlook Ventures to invest full-time at the intersection of risk and frontier technology.
In this episode: • Why the early insurtech era mistook insurance for a scalable SaaS business • "Insurance is a get-rich-slowly business" — and what that means for exit math • The Overlook thesis: investing in the infrastructure of risk across every tech cycle • Where AI is real in insurance today (claims, underwriting data extraction) — and where regulation still slows it down • The emerging risk categories that don't fit today's policy structures: autonomous systems, longevity, and reputational narrative risk
Key Quotes: "Insurance is a get-rich-slowly business." "Technology moves in cycles. Risk always evolves through them." "Liability is getting weird." "Try to find a problem before you find a solution." "A brand can be destroyed in 48 hours by a viral moment."
🔗 Connect: Amir Kabir: https://www.linkedin.com/in/amirkabir/ Overlook Ventures: https://www.overlook.vc | https://www.linkedin.com/company/overlookvc/
👤 Hosts: James Benham: https://www.linkedin.com/in/jbenham Rob Galbraith: https://www.linkedin.com/in/rob-galbraith/
🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software. Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/
📌 Find InsurTech Geek: LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/
Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓
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