Mark Annese

Co-Founder

Mark Annese is an IRMAA Certified Planner who specializes in the intersection of Medicare costs, Social Security timing, and retirement tax strategy. His work focuses on a blind spot in traditional retirement planning: the Income-Related Monthly Adjustment Amount (IRMAA), a Medicare surcharge that can add thousands of dollars a year to a household’s costs — and that most planning software ignores.

Through RetirementAdvisorPro, Mark builds planning and advisor tools that let financial advisors model how filing decisions, Roth conversions, and income timing ripple into Medicare premiums, IRMAA brackets, and lifetime taxes. His articles ground every recommendation in primary sources — SSA and CMS rules, current-year brackets, and published research.

Money Matters Episode 348-The Widow's Medicare Penalty: What Every Couple Needs to Plan For W/ Mark Annese

348

Aug. 17, 2026

Money Matters Episode 348-The Widow's Medicare Penalty: What Every Couple Needs to Plan For W/ Mark Annese

A reasonable retirement decision today could unexpectedly increase your Medicare premiums two years later. In Episode 348, Christopher Hensley speaks with IRMAA Certified Planner Mark Annese about the Income-Related Monthly Adjustment Amount and its impact on Medicare Part B and Part D costs. Mark explains how Roth conversions, required minimum distributions, investment sales, and other income events can trigger Medicare surcharges. The conversation also examines the “widow’s penalty”—the financial pressure a surviving spouse may face after moving from married to single tax and IRMAA thresholds. Listeners will learn how the two-year income lookback works, when an SSA-44 appeal may apply, and why Medicare planning should be coordinated with tax and retirement-income decisions before a costly surprise occurs.

Guest: Mark Annese

Listen to the Episode