Many people approaching Medicare feel overwhelmed by conflicting advice, stacks of mail, and uncertainty about what decisions actually matter. An inefficient transition can lead to higher premiums, unexpected prescription costs, loss of access to preferred doctors, or even permanent lifetime penalties that could have been avoided with proper planning.
Most of these issues don't show up immediately—they surface months or years later when your options are more limited. This masterclass will help you identify the hidden risks before they become expensive mistakes.
A clear understanding of how to transition from employer coverage to Medicare without costly mistakes.
How to compare Medicare Supplement (Medigap) and Medicare Advantage plans with confidence.
Strategies to reduce healthcare costs, prescription expenses, and unnecessary premium waste.
Insight into hidden Medicare traps, including IRMAA surcharges, COBRA issues, and HSA contribution rules.
A framework for building a Medicare strategy that aligns with your retirement income and tax plan.
The confidence to make informed Medicare decisions instead of relying on confusing mailers, sales pitches, or generic advice.
This is the most common transition people experience
Understanding the benefits you received as an employee, and how they change as you age
How you can run your numbers at home
What is Medicare?
The difference in Parts A, B, C, and D
What is Medicare Supplement (Medigap)?
Costs that might not be covered as a part of your Medicare plan
Income Related Monthly Adjustment Amount - IRMAA, and if you will be affected
COBRA // HSA
Why "Your Team" Matters Most

Zach has been helping folks 57-77 through some of their most important retirement considerations over the last decade. He still works with "the big company", while running a separate senior insurance practice . He'll be bringing his wealth of experience to share the top healthcare considerations turning 65 and beyond.