Peter Settel (President and CEO, Bold Penguin): The "Structural Why" of Insurance Innovation

The Risks Nobody Is Pricing Yet | Amir Kabir

In this episode of Risk & Revolution, Evy Amira and Mike Gulla host Amir Kabir, Founder & Managing Partner at Overlook VC and author of The Weekly Dose of Risk. The discussion dives into one of the biggest unanswered questions in insurance and technology today: What happens when AI moves from recommendation… to action? Amir shares his perspective on: * AI operational risk * Silent AI exposure * Model dependency risk * Liability and governance challenges * Autonomous systems and accountability * Business interruption exposure * Capital markets vs underwriting * The future of insurance in an AI-driven world The conversation also explores how AI is changing decision-making across regulated industries and why today’s liability frameworks were originally built around humans — not autonomous systems. A thoughtful discussion on underwriting, AI, insurance, capital markets, and the future of risk. Follow Amir Kabir and subscribe to The Weekly Dose of Risk [https://overlookvc.substack.com/p/edition-45-2026-permissioning-machines] for more insights on emerging technology and risk.

What Happens After the Claim? The Missing Layer of Insurance | Joel Wish

What Happens After the Claim? | Joel Wish In this episode of Risk & Revolution, we host Joel Wish, Founder & CEO of Bright Harbor, for a conversation on one of the biggest blind spots in insurance: recovery after catastrophe. After a wildfire or flood, the claim payment may arrive — but survivors still face permits, government programs, rebuilding decisions, contractors, deadlines, and uncertainty. Joel explains why insurance is only one component of recovery, how technology can reduce friction, and why human trust remains essential during moments of loss. A timely discussion on climate risk, resilience, and the next layer of insurance. 👉 Follow Risk & Revolution [https://www.linkedin.com/company/risk-revolution-podcast/] on LinkedIn for more episodes.

AI in Insurance, Parametric Models & Climate Risk | Angela Grant (Palomar)

In this episode of Risk & Revolution, we sit down with Angela Grant, Chief Legal Officer at Palomar, for a thoughtful and practical conversation on how AI, parametric insurance, and climate change are reshaping the insurance industry. With over 30 years of experience, Angela brings a unique perspective at the intersection of technology, regulation, and real-world risk. In this episode, we discuss: * The role of AI in insurance - and why it should be treated as an “intern,” not a decision-maker * The importance of keeping a human in the loop to validate outputs and manage risk * How parametric insurance is transforming the claims experience * The growing importance of climate risk and community resilience We also explore Angela’s personal journey into insurance and the experiences that shaped her connection to the industry. 👉 Follow us on LinkedIn for more insights, clips, and upcoming conversations from Risk & Revolution. [https://www.linkedin.com/company/risk-revolution-podcast/]

Peter Settel (President and CEO, Bold Penguin): The "Structural Why" of Insurance Innovation

Welcome to the second episode of Risk & Revolution, the podcast where we peel back the layers of the insurance industry’s most complex mechanics. In this episode, Mike Gulla and Evy Amira sit down with Peter Settel, President and CEO of Bold Penguin. Peter is a cornerstone of the industry with a fascinating trajectory: from leading IT at the pioneering startup Homesite to serving as CTO and Chief Strategy Officer at insurance giant American Family. Peter provides a rare look at how major carriers make strategic decisions, why most startups fail when they try to "copy-paste" old models onto new tech, and what the future of distribution looks like in the commercial space. Key topics we explore: * The Carrier Foundations: Why underwriting profit requires years of patience and how to build a company with the right horizon. * Linear Improvement vs. True Innovation: Peter explains why "Digital Transformation" headlines don't always translate to bottom-line results. * The E&S and Specialty Market: An analysis of the structural shift in the market and the new opportunities for carriers and brokers. * Parametric Solutions: Why current market conditions (climate, infrastructure) are making parametric insurance a necessity rather than an alternative. About the Guest: Peter Settel is the President and CEO of Bold Penguin, the leading software solution for commercial insurance distribution. With over two decades of experience, Peter is a recognized leader in building technology-driven strategies for the US insurance market.

Rick McCathron from Hippo | Can Prevention Really Change Insurance?

In this episode of Risk & Revolution, we sit down with Rick, President & CEO of @hippo insurance, to explore one of the biggest questions facing the insurance industry today: 👉 Can insurance move from paying claims… to preventing them? Hippo has been at the forefront of rethinking homeowners insurance through technology, data, and IoT sensors. But beyond the headlines, we dive deeper into what prevention actually means in practice. We discuss the role of IoT and home data, the tension between innovation and underwriting discipline, and whether prevention can truly improve underwriting performance - not just customer experience. The real question isn’t whether prevention sounds good. The real question is: Can it be priced, capitalized, and sustained? If you care about the future of homeowners insurance and where insurtech is truly heading - this episode is for you. — Mike & Evy