Why High Earners Are Quietly Underinsured—and Don’t Find Out Until It’s Too Late with Tom Peterson

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Some of the most interesting insurance solutions are built after someone is told “no.” Tom Petersen shares stories from the specialty market that reveal how income protection works when traditional disability insurance falls short.

Traditional disability insurance wasn’t built for elite earners. In this episode of The Income Protection Podcast, Jamie Fleischner sits down with Tom Petersen of Petersen International Underwriters to explain how specialty disability insurance fills the gaps left by traditional coverage. They discuss income caps, excess coverage, and the unique challenges of protecting athletes, entertainers, ultra-high-income professionals, and those with complex or pre-existing health conditions. If your income is high, specialized, or performance-based, this conversation offers a clear look at how income protection really works at the highest levels.

In this episode of The Income Protection Podcast, host Jamie Fleischner sits down with Thomas Petersen, Senior Partner at Petersen International Underwriters, for an in-depth conversation on a side of insurance most people never see—but many high earners critically need. From professional athletes and entertainers to founders, executives, and ultra–high-income professionals, Petersen explains where traditional disability insurance quietly falls short and how specialty coverage steps in to protect both income and assets when the stakes are highest.

Drawing on nearly four decades in the industry and a career that spans underwriting, forensic investigation, emergency medicine, and entrepreneurship, Petersen offers rare insight into how risk is actually evaluated at the top levels. The discussion explores why income protection gaps begin appearing as early as the $150,000 income range, how Lloyd’s of London structures bespoke, short-term policies for complex careers, and why insurance is ultimately about preserving financial stability—not judging lifestyle or net worth. Listeners will also hear real-world examples involving athletes’ contracts, NIL income, entertainers’ tours, influencers, health-related underwriting challenges, and even some of the most unusual policies Petersen has ever written.

This episode is a must-listen for anyone whose income is specialized, performance-based, volatile, or far beyond what standard insurance models were designed to handle—and for anyone who wants to understand how wealth, risk, and protection intersect behind the scenes. Topics include: - Why high earners are often underinsured without realizing it - Specialty vs. traditional disability insurance - Protecting athletes, entertainers, and influencers - Insuring non-guaranteed contracts and performance income - Coverage options after medical declines or complex health histories - Lloyd’s of London and the bespoke insurance marketplace - Income protection as asset protection—not just replacement