Matthew Claassen, CMT and CEO of Medigap Seminars Insurance Agency

I genuinely enjoy assisting people with their Medicare, though I didn’t always recognize the value in my work. I began my career in insurance in 1984 as a captured agent with The Guardian, selling Life Insurance, Annuities, and Group Health. It was a solid company, but I craved more meaning. At 24, single and healthy, insurance felt irrelevant to me. So, in 1987, I earned my Series 7 license and shifted to investment management, though I still handled personal insurance. By the late 1990s, I hosted the #1 AM financial talk-radio show in the Washington-Baltimore area, leveraging rush-hour audiences to grow a thriving business.

In 1998, I became a financial analyst, advising hedge funds and mutual funds with a focus on intermarket analysis. Soon, I launched my own Hedge Fund Advisory, serving clients globally. Yet, working with the ultra-wealthy taught me a harsh truth: value was tied solely to profits, not loyalty or individuality. Seeking purpose, I left that world, took time off, and became a Master Gardener, specializing in tropical fruit and medicinal herbs. I now tend 2 ½ acres of my own. Helping fellow gardeners in South Florida was fulfilling, but assisting friends with Medicare revealed a deeper reward—personal gratitude. That inspired me to start Medigap Seminars, offering free, expert guidance to help people navigate Medicare, ensuring they’re never alone in facing its challenges.