About Toby
Toby has spent over 20 years in disability insurance, working with physicians, CRNAs, dentists, technologists, and other high-income professionals to protect the careers they've built. He co-founded Seaworthy Insurance on a simple premise: the analysis should come before the recommendation, and the client's contract matters more than the carrier's commission schedule.
Today, Toby operates on the business side: strategy, marketing, systems design, and the technology infrastructure that keeps the agency running. He's the one building the tools, tightening the processes, and making sure the client experience is as sharp as the contract analysis. He doesn't work directly with clients anymore, but the team and systems he's built do, from Jack Howard on coverage analysis to Chawna Dill on case management.
Before insurance, Toby studied liberal arts, which turns out to be surprisingly useful when your job involves making complex financial products actually make sense to people. He lived in Spain for three years, speaks Spanish, and has traveled to 42 countries. He spent a decade doing CrossFit at a competitive level, reads The Economist cover to cover, and has a real fascination with economic systems, geopolitics, and how the world actually works.
Originally from Tucson, Arizona, and still a devoted Wildcats basketball fan. When he's not designing systems or reading about global macro trends, he's at the beach, on a trail, or playing with his kids.
What Toby does at Seaworthy
Toby leads strategy, systems, and the editorial standard for everything Seaworthy publishes. He is the sole author of the site's educational content, which means every carrier comparison and specialty guide carries his name because he wrote or reviewed it. Client-specific recommendations stay with the advisory team. The published content is educational, built to explain how disability insurance actually works to a reader who is smart, time-pressed, and skeptical of insurance sales copy.
He also owns the agency's placement methodology and editorial policy, the two documents that set how carriers get ranked and how claims about contracts get sourced before they go live. When the site cites a book statistic or a contract provision, it traces back to those standards rather than to marketing convenience. His original writing runs in the Insights series and the agency research pages.
Licensing and credentials
Toby is a licensed insurance producer. Seaworthy Insurance is the brand name of Physician's Disability Insurance Agency LLC, a California-licensed agency operating since 2011 (CA license #0H52962), with the full state-by-state record on the licenses page. He is also working toward the Chartered Life Underwriter (CLU) designation through The American College of Financial Services. As surface-level product knowledge became free to anyone with an AI assistant, verifiable expertise became the thing worth having, and the credential holds that expertise to a standard a client can verify. He wrote about that decision in AI Sent Me Back to School at 43.