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/

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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