Ep. 102 - John Fees: The Insurance Founder Who Says His Own Company Shouldn't Have to Exist

What if the best measure of an insurance company's success isn't how many claims it denies, but how many it pays—and how many of those students re-enroll?

In this episode, host Jeff Dillon sits down with John Fees, co-founder and CEO of GradGuard, a fintech company that has protected more than two million students across 750 colleges and universities. John brings a rare perspective: he's a founder who built his first company in higher ed in 1999, sold companies to Viacom and JP Morgan Chase, and has spent three decades at the intersection of education, finance, and technology.

But here's the thing: John believes GradGuard shouldn't have to exist. He argues that the cost of college has become unsustainable, and that the student loan default crisis isn't about over-borrowing—it's about students leaving school without graduating. Health issues, mental health crises, and other disruptions are the primary drivers, and most schools don't even track how many students leave for legitimate medical reasons.

John shares how GradGuard flipped the insurance industry's scoreboard—measuring success by claims paid rather than claims denied, and tracking re-enrollment rates (currently around 75%). He also introduces the concept of "decision design," explaining how universities shape student outcomes through choices families don't even realize they're making.

For any enrollment leader, CFO, or student affairs professional thinking about retention, student risk, and the financial realities families face, this episode offers a deeply human perspective on a problem hiding in plain sight.

Key Takeaways

GradGuard Shouldn't Have to Exist: John believes the cost of college is the root problem. If education were more affordable and schools were more generous with refunds, tuition insurance wouldn't be necessary. But the reality is that most families can't afford the financial loss of a disrupted semester.

Student Loan Default Is About Dropouts, Not Over-Borrowing: The real crisis isn't that students borrow too much—it's that they leave school without graduating. If you don't finish, you don't get the ROI. That's the problem GradGuard was built to address.

Health Issues Are the Premier Reason Students Leave: According to Lumina and Gallup studies, health issues—including mental health—are at the top of the list of reasons students don't persist. Mental health isn't a "disorder" to be treated differently than physical health; it's a legitimate reason for withdrawal.

GradGuard Measures Success by Claims Paid, Not Claims Denied: The insurance industry traditionally tracks profitability by denying claims. GradGuard flipped that model. The real measure of success is: did the student re-enroll? Currently, about 75% of students who file a claim return to the same school.

Decision Design Is Hiding in Plain Sight: Universities shape student outcomes through forced decisions—living on campus, meal plans, health insurance—that families don't always realize are choices. CFOs and enrollment leaders are decision architects. Helping families make informed decisions benefits everyone.

Trust Has to Come Before the Transaction: In higher ed, trust is everything. The objection GradGuard hears most is: "We don't want families to think about bad outcomes." But ignoring the risk doesn't make it go away. Transparency builds trust.