96 Stories · 15 Series · Read or Listen

Retirement Insights

Free articles and podcasts on income, inheritance, and healthcare planning. Pick a series and dive in.

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New products. New rules. New headlines. But the fundamentals of a secure retirement have not moved in 100 years — and here are the receipts to prove it.

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High-Net-Worth Inheritance Series

Both Ends of the Table7 Episodes

A seven-part series on the largest wealth transfer in history — for the families on both sides of it.

Go deeper: Generational Wealth Strategies and Before Death Do Us Part

Life Insurance Series

More Than a Death Benefit7 Episodes

Seven honest answers about what life insurance can actually do for you while you're alive.

Go deeper: Life Insurance and The Long-Term Care Planning Guide

Tax Window Series

The Gap Years4 Episodes

The years between your last paycheck and age 73 — often the lowest-tax window of your life.

Go deeper: The Roth Conversion Playbook and Required Minimum Distributions (RMDs)

Estate Series

Passing It On3 Episodes

The estate conversations every family needs — before, during, and after.

Go deeper: Before Death Do Us Part and Your Trust Is Just the First Step

Real Estate & Retirement Series

The Fourth Color3 Episodes

David's Three Colors of Money just got a fourth — Purple, for real estate. The house on your balance sheet carries a tax bill most people never see coming.

Go deeper: Your Home, Your Legacy

Surviving Spouse Series

The Widow's Penalty5 Episodes

The year you lose a spouse, the tax code, Medicare, and Social Security all quietly change the rules on you. Which rules bite depends on your age: this series walks the three ages of widowhood, what the kids actually receive, and the first 90 days.

Go deeper: Before Death Do Us Part and The IRMAA Trap

Family Inheritance Series

When the Kids Inherit5 Episodes

You spent forty years building it. It lands in your kids' lap during the most expensive decade of their lives. This series sits in their chair, because the best inheritance plans are designed from the receiving end.

Go deeper: Generational Wealth Strategies and Required Minimum Distributions (RMDs)

Medicare History Series

The Promise They Called Socialism7 Episodes

Health coverage for the old reached a national ballot in 1912 and did not become law until 1965. In between sits a fifty-three year argument, a record album mailed to doctors' wives, and a president who flew across the country to hand the man who lost the fight the very first card. This series tells how the card in your wallet was won, and what it still does not cover.

Go deeper: Leaving Your Employer's Plan

Life Insurance History Series

The Evolution of a Promise5 Episodes

In 1583 a London merchant insured another man's life, and eleven months later the underwriters tried not to pay. A court made them. This series follows that promise across four and a half centuries: how it became fair, how it grew new tools for new problems, and what it quietly does for families now.

Go deeper: Life Insurance

Medicare Enrollment Series

Seven Ways In7 Episodes

Almost nobody arrives at Medicare the same way. A business owner turning 65 whose group plan was quietly paying second. A woman handed two years of COBRA who did not know the clock had already started. A veteran told he did not need Part B. Seven real doors into the same program, and the one detail inside each that decided everything.

Go deeper: Leaving Your Employer's Plan and The IRMAA Trap

Financial Checkup Series

The Whole Chart6 Episodes

You would never start a new medication without checking it against everything you already take. Yet most people buy annuities, life insurance, and funeral policies one salesperson at a time, and nobody ever reads the whole chart. Seven days on what those products do to each other, and what changes when someone finally sees everything in one place.

Go deeper: Not All Annuities Are Created Equal and Life Insurance

EP 5The Steak Dinner

The Steak Dinner

You know the invitation. Heavy cardstock, a nice restaurant, a free dinner, and a presentation about an exciting financial opportunity. Go. Enjoy the steak.

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EP 6The Box They Named Bob

The Box They Named Bob

A couple we work with gave their beneficiary planning box a name, and somewhere along the way, Bob became part of the family.

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Estate Planning Series

The Fridge List5 Episodes

The attorney's number has been on the refrigerator for three years. The trust is still a question. The kids still do not know where anything is. Most people say estate planning matters; more than half have nothing in writing, and the number one reason is simply not getting around to it. Five tasks people put off for years, each finished in one afternoon — the call, the meeting, the talk, the box, and the day you finally show up.

Go deeper: Your Trust Is Just the First Step and The BeneficiaryBox™ Program

Healthcare in Retirement Series

Healthcare in Retirement20 Episodes

An open-ended series on the tricky corners of Medicare, one real situation at a time, and what a Certified Medicare Planner does about each.

Go deeper: Leaving Your Employer's Plan and The IRMAA Trap

Medicare Workshop Series

Take-Home Notes6 Episodes

The Medicare workshop, in print. Every section of the live show, one at a time and just as fun: the two paths, the words that decide your bill, the calendar, Medicare.gov step by step, and which one you are.

Go deeper: Your plan letter came: what to do before December 7 and Leaving Your Employer's Plan

Annual Enrollment Series

What the Letter Leaves Out5 Episodes

Your plan's Annual Notice of Change is supposed to tell you what changed. It leaves things out. One gap a day before the Annual Enrollment Period: deductibles, your worst-case year, your drug plan, your doctors, and the extras, and where to find the real answer for each.

Go deeper: Your plan letter came: what to do before December 7

Have Questions About Your Own Plan?

These series come from real conversations in our office. If something here sounds like your situation, our advisors are glad to walk through it with you, at no cost to you, on the phone or over Zoom.

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