AI is moving from helping people do their jobs to performing more of the work itself. That creates a new question for insurance: when AI takes an action, makes an error, or produces an outcome that causes harm, who owns the risk? Jeremy Epstein, Founder & CEO of Mayflower Specialty, joins the Age of the MGA to unpack how his team is approaching that problem. The conversation goes well beyond whether AI is simply another cyber exposure. Jeremy explains how Mayflower thinks about underwriting AI based on what the technology is actually being allowed to do, the authority it has, the humans and controls surrounding it, and how consequential a failure could become. The discussion also gets into coverage ambiguity, D&O, professional liability, employment-related exposures, regulation, distribution, claims, and what it takes to build a new insurance category while the underlying technology is still changing. IN THIS EPISODE: ✅ How Mayflower thinks about underwriting what AI actually does inside a business ✅ Why AI liability is not simply another version of cyber risk ✅ How authority, human oversight, controls, models, and consequentiality affect the exposure ✅ Where D&O, professional liability, and employment-related risks can intersect with AI ✅ Why existing policies can create ambiguity over which coverage responds to an AI-related loss ✅ Why stronger AI capabilities may require stronger controls ✅ How brokers and insurers are navigating a category that is still being defined ✅ Why Jeremy is deliberately selective about the risks Mayflower takes as the MGA grows For serious MGA founders, operators, investors, and ecosystem partners, this episode matters because Mayflower is building around a risk that is already developing but is far from fully understood. That means making decisions about underwriting, coverage, distribution, controls, appetite, capacity, and growth without waiting for the market to become perfectly clear. Jeremy's approach is not to try to insure every possible AI exposure. It's to define where Mayflower believes it can underwrite responsibly, work with the right risk partners, and build from there. GUEST INFORMATION Jeremy Epstein Founder & CEO of Mayflower Specialty LinkedIn: https://www.linkedin.com/in/jaepstein00002/ Website: https://mayflowerspecialty.com/ CONNECT WITH THE HOSTS Doug Ver Mulm CEO, Turris https://www.linkedin.com/in/douglasvermulm/ Dylan Brand President, Typhoon Risk https://www.linkedin.com/in/dylanbrand/ Peter Tilbrook CEO, Loro https://www.linkedin.com/in/peter-tilbrook-50832336/ 🎧 Subscribe to Age of the MGA on Spotify, Apple Podcasts, and YouTube. 📲 Follow Age of the MGA on LinkedIn: https://www.linkedin.com/company/age-of-the-mga/ THANK YOU TO OUR SPONSOR, TURRIS Turris helps insurance carriers, MGAs, brokers, and agents automate producer onboarding and appointments, compliance, payments, and other back-office workflows. The platform is being built to bring financial and compliance infrastructure together in one place: helping insurance teams reduce manual work while creating a better experience for their distribution partners. Learn more about Turris: https://www.turrisfi.com/ CHAPTERS 00:00 — Introduction 07:22 — Jeremy’s Path From Underwriting to Mayflower 11:45 — Why Mayflower Is Building Around AI Risk 14:16 — Creating a New Insurance Category 19:25 — How Do You Underwrite AI? 22:38 — Why AI Risk Is Different From Cyber 28:10 — Where Existing Coverage Meets AI 32:07 — Coverage Gaps, Claims & Controls 46:18 — Where AI Risk Goes Next 51:57 — Choosing Which AI Risks to Underwrite 01:04:33 — The Legacy Jeremy Wants Mayflower to Build