Flight #108: Understanding Medicare, Early Retirement & Health Insurance with Cole Craven

Is Medicare more confusing than it should be? If you’re nearing retirement or thinking about leaving your job early, the healthcare piece can feel overwhelming and expensive. In this episode, we sit down with Cole Craven, co-founder of Move Health, to demystify the complexities of Medicare, healthcare costs, and early retirement planning.

Listen in to learn the difference between Medicare Advantage and Medigap, how to time your enrollment correctly, and what your healthcare options are if you want to retire before 65. Plus, we dive into how Tricare works with Medicare, when to appeal IRMAA, and why bad advice about healthcare costs might delay your retirement.

What You’ll Learn In Today’s Episode:

  • The basics of Medicare Parts A, B, C, D, and Medigap plans.
  • Pros and cons of Medicare Advantage vs. Medicare Supplement.
  • How your income affects your Medicare premiums.
  • Steps to take if you want to retire before 65.
  • How financial advisors and Move Health work together to simplify coverage.
  • Why pilots may be surprised by Medicare’s benefits compared to their employer plans.
  • What military retirees with Tricare need to know before enrolling in Medicare.
  • Real-life stories that highlight what not to do and how to do it right.

Ideas Worth Sharing:

  • “Medicare is boring as heck for almost all individuals. And then you turn 64, and then it becomes super interesting because it’s now your life.” – Kevin Gormley
  • “Healthcare changes are at an all-time high, and healthcare literacy is at an all-time low.” – Cole Craven
  • “Don’t let healthcare be the one that stops you from retiring early.” – Charlie Mattingly

Resources In Today’s Episode:

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