Medicare Open Enrollment comes around every year, but simply sticking with last year’s coverage may not always be the best decision. Don walks through the questions retirees should be asking as they review their Medicare options for 2027 and highlights several blind spots that can create unwanted surprises later. Open Enrollment isn’t necessarily about changing your plan, but it is a time to make sure the plan you have is still the right one.

Here’s some of what we discuss in this episode:

🛣️ Coverage Paths: Compare two Medicare approaches

💵 Plan Costs: Look beyond monthly premiums

🏥 Healthcare Access: Consider doctors and travel

📋 Supplement Options: Understand cost and exposure

⚠️ Switching Later: Know the long-term limitations

Get in touch with Don and learn more: https://doncashpodcast.com/

The fourth quarter is when a lot of financial planning opportunities start running out of runway. In this episode, Don walks through the year-end decisions retirees should be reviewing while there is still time to make adjustments. The bigger theme is focusing less on unpredictable headlines and more on the parts of your financial life you can actually control. Because January is a frustrating time to discover what you should have handled in December.

Here’s some of what we discuss in this episode:

📰 Market Headlines: Keep news from driving decisions

🧾 Tax Planning: Review opportunities before year-end

🔄 Roth Conversions: Evaluate multi-year tax strategies

💼 Retirement Contributions: Check progress before deadlines

📅 RMDs: Complete required distributions on time

❤️ Charitable Giving: Coordinate year-end giving strategies

🏥 Medicare: Review coverage before auto-renewing

Get in touch with Don and learn more: https://doncashpodcast.com/

Estate planning can feel “finished” once the documents are signed, but life has a way of changing the family faster than the paperwork. In this episode, Don uses the arrival of his first grandchild as a reminder that wills, trusts, beneficiaries, gifting strategies, and family wishes all need to evolve. A good estate plan shouldn’t just reflect what you owned years ago. It should reflect the family and priorities you have today.

Here’s some of what we discuss in this episode:

📜 Wills vs. Trusts: Understanding the different roles these documents can play

🔑 Trust Control: Using the “vault and key” analogy to explain revocable and irrevocable trusts

⚖️ Probate: Why the process isn’t always as frightening as people assume

👥 Beneficiaries: Making sure account designations match the rest of the estate plan

🧾 Gift Taxes: Understanding annual exclusions, Form 709, and lifetime exemptions

💍 Personal Property: Preventing family conflict over sentimental possessions

✉️ Legacy Wishes: Passing along values, stories, and personal instructions—not just assets

Get in touch with Don and learn more: https://doncashpodcast.com/