Rob MichaelsonHosted by a 501(c)(3) nonprofitRob Michaelson
U.S. Retirement Education Association
Medicare 101Free 1-hour workshop hosted by U.S. Retirement Education · In person & online

Everything you need to know about Medicare

A plain-English session for anyone approaching 65 — how the parts work, what it really costs, and when to enroll. Educational only, free to attend, and never a sales pitch.

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No cost to attend. Choose a session, then complete the short form below.

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August 2026
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We don’t have any upcoming event dates scheduled just yet. Check back soon for new Medicare 101 workshops near you.

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What we cover

Rob Michaelson

No jargon, no slides full of fine print — just the parts that actually change what you pay and what you’re covered for.

1
What Parts A & B actually coverThe gaps most people don’t realize they have until they need care.
2
What Medicare really costs in 2026The premiums plus the surprise expenses that catch new enrollees off guard.
3
The enrollment windows that matterHow one missed deadline can trigger penalties that last for life.
4
How Medicare works with employer coverageSo you don’t pay twice or give up benefits you’re entitled to.
5
How to match coverage to your real needsInstead of a generic plan built for someone else’s situation.
6
Straight answers to your own questionsPlus the common misconceptions that trip people up.
Your presenter

Rob Michaelson

Rob Michaelson
Optimal Insurance Group · Boca Raton, FL
  • Limited Seats
  • Licensed Health & Life Agent
  • Serving Palm Beach County, FL
  • MBA · Nova Southeastern University

My name is Rob Michaelson, and I am the owner of Optimal Insurance Group in Boca Raton, Florida. I specialize in simplifying Medicare, helping people make informed choices that best meet their individual needs when selecting a Medicare Health Plan.

Born and raised in Ohio, I earned a Bachelor of Science degree in Psychology from the University of Cincinnati in 1992. After graduation, I worked with several Fortune 500 companies, achieving top management positions through dedication and performance. While working full-time, I pursued an MBA from the H. Wayne Huizenga School of Business and Entrepreneurship at Nova Southeastern University, graduating as a Dean’s List student.

My true passion emerged when I became a licensed Health and Life Insurance agent, where I have focused on helping people navigate their insurance options. Recently, the Florida Retirement Group recognized my commitment to the community by awarding me my own local territory, allowing me to provide educational workshops for seniors and expand my impact.

Outside of work, I enjoy spending time with my wife of 28 years and our three children, along with family and friends. I stay active through workouts, pickleball, and golf, embracing every opportunity to stay engaged and energized.

501(c)(3) nonprofit
We do not offer every plan available in your area. Currently we represent 6 organizations which offer 67 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.

This event is hosted by a 501(c)(3) nonprofit organization and is intended solely for educational purposes. It is not a sales presentation. No insurance products will be marketed or sold. The presenter is not affiliated with Medicare, CMS, or any government agency.

Workshops provided by U.S. Retirement Education Association.

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