Chalk Talk: Bridging the Gap to Medicare: Health Insurance Strategies for Early Retirement
on May 26, 2026
“Real Money Questions. Expert Answers”
When:
June 5th, 2026
3:00 pm Eastern; 12:00 pm Pacific
~45 minutes & Q/A included
How: Zoom Meeting
Recorded and able to retrieve for one week
Cost: Free to ongoing clients; $10 per session for guests
Buying Your Next Home Before You Sell
Hosted by: Anna Sergunina, CFP®
Guest commentator: Matt Allen
Founder, Iconic Insurance
Thinking about retiring before age 65? One of the biggest challenges early retirees face is navigating health insurance before Medicare begins. Join us for a practical conversation with Matt Allen, Founder of Iconic Insurance, as we break down ACA plans, COBRA, tax credits, private insurance options, and smart strategies to help manage healthcare costs and retire with more confidence.
Matt Allen is the Founder at Iconic Insurance, where he specializes in helping and educating self-employed individuals, small business owners, and early retirees navigate the complexities of health insurance. With over a decade of experience, Matt has developed a deep understanding of the challenges that come with securing health insurance coverage outside of employer-sponsored plans.
Iconic Insurance Mission Statement: “We empower people to confidently navigate the healthcare system.”
Some of the topics we’ll discuss:
- Understanding ACA marketplace plans and subsidies
- How COBRA works and when it makes sense
- Private insurance alternatives before Medicare
- Strategies to manage healthcare costs in early retirement
- Tax credit opportunities and income planning considerations
- Common mistakes early retirees make with health insurance
Disclaimer: This is a broad group session and certain strategies may or may not be appropriate for specific situations. MainStreet makes no claim that all member posted information is accurate or should be acted upon without professional and individual financial planning, tax and/or legal advice.
