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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.

EP 1The Hardest Part of Passing On Wealth Isn't the Money

The Hardest Part of Passing On Wealth Isn't the Money

The families who keep wealth aren't the ones with the best investments. They're the ones who prepared their children for it.

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EP 2The Inheritance You Can See Coming

The Inheritance You Can See Coming

Most people are blindsided by an inheritance. A lucky few can see it coming — and that window is where nearly all the planning value lives.

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EP 3When the Problem Isn't Growth, It's Coordination

When the Problem Isn't Growth, It's Coordination

Once you have enough, the biggest threat to your money is no longer a bad return. It's the gaps between advisors who never talk to each other.

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EP 4The Tax Bill Hiding in a Good Year

The Tax Bill Hiding in a Good Year

A single big-income year can quietly trigger four different taxes at once — and raise your Medicare premiums two years later.

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EP 5Layering a Windfall Onto an Already-Full Plan

Layering a Windfall Onto an Already-Full Plan

When you already have enough, an inheritance isn't about security anymore. It's about purpose — and deploying it deliberately.

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EP 6Giving While You're Alive to Watch It

Giving While You're Alive to Watch It

Most wealth passes at death, when heirs are in their sixties and need it least. There's a strong case for giving sooner — with surprisingly generous tax rules.

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EP 7Build the Team Before You Need It

Build the Team Before You Need It

The worst time to assemble a coordinated team is in the middle of a crisis. The best time is now, while everything is calm.

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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.

EP 1Do I Need Life Insurance in Retirement?

Do I Need Life Insurance in Retirement?

The honest answer: it depends on the job you need it to do — and for some people, it's no. Here's how to tell which side you're on.

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EP 2Be Your Own Bank: The Cash Value Most People Never Touch

Be Your Own Bank: The Cash Value Most People Never Touch

Some life insurance quietly builds a pool of money you can borrow against, tax-advantaged, for anything you want.

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EP 3The Policy That Helps You While You're Alive

The Policy That Helps You While You're Alive

Almost 70% of people turning 65 will need long-term care, and Medicare won't cover most of it. Some life insurance can step in while you're still here.

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EP 4The Tax-Free Bucket Most Retirees Are Missing

The Tax-Free Bucket Most Retirees Are Missing

Most people retire with nearly all their savings in accounts the government still gets to tax. There's a third bucket it doesn't.

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EP 5The Nine-Month Problem That Forces Families to Sell What They Love

The Nine-Month Problem That Forces Families to Sell What They Love

When a large estate owes federal tax, the bill is due in cash within nine months. Here's how families keep the ranch, the business, the lake house.

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EP 6Your Own Life Insurance Could Be Adding to Your Tax Bill

Your Own Life Insurance Could Be Adding to Your Tax Bill

A policy you own is counted in your taxable estate — quietly adding to the very tax bill you hoped it would cover. A special trust fixes that.

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EP 7The Family Bank: Setting Up the Next Generation While It's Cheap

The Family Bank: Setting Up the Next Generation While It's Cheap

A policy on a young grandchild can lock in lifelong insurability and quietly build a pool the next generation can borrow against.

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Tax Window Series

The Gap Years4 Episodes

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

EP 1The Gap Years: Often the Lowest-Tax Window of Your Life

The Gap Years: Often the Lowest-Tax Window of Your Life

Most retirees coast through the years between their last paycheck and age 73 — and pay for it later. This window is worth planning around.

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EP 2Filling the Bracket: The Roth Conversion Window Before Age 73

Filling the Bracket: The Roth Conversion Window Before Age 73

During the gap years your tax bracket has room in it. A Roth conversion lets you fill that room on purpose, at today's low rate.

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EP 3Meet IRMAA: The Medicare Surcharge With a Two-Year Memory

Meet IRMAA: The Medicare Surcharge With a Two-Year Memory

IRMAA raises your Medicare premium based on income from two years ago. Here's how it works and how to see it coming.

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EP 4The Social Security Tax Surprise: How Much of Your Benefit Is Taxable

The Social Security Tax Surprise: How Much of Your Benefit Is Taxable

Most retirees are surprised to learn their own Social Security can be taxed — up to 85% of the benefit can land in taxable income.

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Estate Series

Passing It On3 Episodes

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

EP 1You Have a Will. So You're Covered, Right?

You Have a Will. So You're Covered, Right?

A will is the floor, not the finish line. Three things it quietly leaves out — and the one part no document can cover.

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EP 2The Conversation No Family Wants to Have First

The Conversation No Family Wants to Have First

Most families wait, each side hoping the other brings it up. Here's how to actually start the talk about your parents' plans.

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EP 3You Just Inherited. Now What?

You Just Inherited. Now What?

The biggest mistake people make with an inheritance is moving too fast. Here's the calm, in-order list.

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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.

EP 1The Fourth Color: When Real Estate Is Part of Your Retirement Income

The Fourth Color: When Real Estate Is Part of Your Retirement Income

Green, yellow, red. For years those three colors of money covered nearly everything.

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EP 2The Tax Bill Hiding in Your House: Capital Gains on a Home Sale After 65

The Tax Bill Hiding in Your House: Capital Gains on a Home Sale After 65

Many sellers still believe there is a special capital gains break once you turn 65.

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EP 3Passing On the House: Step-Up in Basis, Gifting Rules, and the Estate Tax Most Families Will Not Pay

Passing On the House: Step-Up in Basis, Gifting Rules, and the Estate Tax Most Families Will Not Pay

Give the kids the house now, or leave it to them later? The tax code treats those two acts completely differently, and the difference can be worth six…

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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.

EP 1Widowed at 55: What Happens to Social Security, Health Coverage, and the Plan You Built Together

Widowed at 55: What Happens to Social Security, Health Coverage, and the Plan You Built Together

Losing a spouse in your fifties comes with a rulebook most people never open until they need it. Survivor benefits that cannot start until 60.

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EP 2Widowed in Your 60s: The Qualifying Surviving Spouse Tax Status and the Social Security Choice Almost Everyone Gets to Make

Widowed in Your 60s: The Qualifying Surviving Spouse Tax Status and the Social Security Choice Almost Everyone Gets to Make

The sixties are when the widow's penalty does most of its quiet work. A tax filing status with a two-year clock. A first April filing alone.

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EP 3Widowed at 75: How to Appeal a Medicare IRMAA Surcharge After the Death of a Spouse

Widowed at 75: How to Appeal a Medicare IRMAA Surcharge After the Death of a Spouse

Two years after a loss, a letter from Social Security can raise a widow's Medicare premium based on income from a life that no longer exists.

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EP 4Inherited IRA Rules, Step-Up in Basis, and What Your Kids Actually Receive When Everything Passes to Them

Inherited IRA Rules, Step-Up in Basis, and What Your Kids Actually Receive When Everything Passes to Them

Seven rental properties, one grieving widow, and no structure holding any of it.

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EP 5What to Do Financially When Your Spouse Dies: The First 90 Days

What to Do Financially When Your Spouse Dies: The First 90 Days

She started over from zero and built a seven-figure retirement on her own.

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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.

EP 1The Call Your Kids Will Get: Inheritance From the Other Side of the Table

The Call Your Kids Will Get: Inheritance From the Other Side of the Table

You spent forty years building it. It will land in your kids' lap during the most expensive decade of their lives.

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EP 2The Ten-Year Tax Bomb: What Your IRA Looks Like From Your Kids' Side

The Ten-Year Tax Bomb: What Your IRA Looks Like From Your Kids' Side

Your IRA statement says $900,000. Your kids will not inherit $900,000.

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EP 3The House They Grew Up In: What Really Happens When Kids Inherit Property

The House They Grew Up In: What Really Happens When Kids Inherit Property

Day three of our series from the heir's side of the table. The quiet tax gift buried in an inherited home, the twenty-minute deed that skips the…

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EP 4The Folder: What Your Kids Will Need to Find in the First Thirty Days

The Folder: What Your Kids Will Need to Find in the First Thirty Days

Someday your family will open a folder. What they find inside is up to you.

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EP 5The Gift of a Plan: What the Luckiest Heirs All Have in Common

The Gift of a Plan: What the Luckiest Heirs All Have in Common

The finale of our week on the receiving end of inheritance. After the IRA, the house, and the folder, one pattern is left standing: the inheritances that…

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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.

EP 1The Word That Held Off Medicare for 53 Years

The Word That Held Off Medicare for 53 Years

In 1912, a former president put health insurance for the old and the sick on a national ballot. It did not become law until 1965.

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EP 2The Record Album That Almost Stopped Medicare

The Record Album That Almost Stopped Medicare

In 1961, the campaign to stop Medicare did not run on television.

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EP 3The Man Who Blocked Medicare for Years, Then Built It in One Night

The Man Who Blocked Medicare for Years, Then Built It in One Night

By 1965 there were three rival health bills in Congress, and two of them existed to make sure Medicare never happened.

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EP 4Sixty-One Years Ago Today, a President Flew to Missouri to Finish Someone Else's Fight

Sixty-One Years Ago Today, a President Flew to Missouri to Finish Someone Else's Fight

On July 30, 1965, Lyndon Johnson did not sign Medicare in Washington.

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EP 5The Three Things Medicare Did That Almost Nobody Gives It Credit For

The Three Things Medicare Did That Almost Nobody Gives It Credit For

In the spring of 1966, roughly seven hundred federal workers fanned out across the country to inspect two thousand hospitals in three months.

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EP 6The Door That Closes at 65, and the Gap Sixty-One Years Never Filled

The Door That Closes at 65, and the Gap Sixty-One Years Never Filled

All week we followed a promise that took fifty-three years to win.

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EP 7I Have Been Reading the Mail the Carriers Send Us. You Should See It Too.

I Have Been Reading the Mail the Carriers Send Us. You Should See It Too.

Four things happened in the last ten days that change what your 2027 Medicare decision looks like. All of them are public.

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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.

EP 1The First Life Insurance Policy Ever Sold Ended in a Lawsuit

The First Life Insurance Policy Ever Sold Ended in a Lawsuit

June 18, 1583. A London salt merchant named William Gybbons becomes the first person in recorded history covered by a life insurance policy.

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EP 2The Math That Made the Promise Fair

The Math That Made the Promise Fair

In the 1750s, London's only life insurance society turned a man away for being too old.

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EP 3Every Tool in the Life Insurance Box Was Invented for a Problem

Every Tool in the Life Insurance Box Was Invented for a Problem

Term, whole life, the policy your employer hands you, and a product born because the 1970s broke everything. None of them were invented to be sold.

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EP 4How Are Your Assets Actually Taxed? The Three-Bucket Diagnostic

How Are Your Assets Actually Taxed? The Three-Bucket Diagnostic

Two households, identical incomes, very different tax bills. The difference is not luck and it is not loopholes.

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EP 5The Three Plays the Pros Run

The Three Plays the Pros Run

Yesterday you learned the three tax buckets. Today, the playbook.

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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.

EP 1Seven Ways In, Part 1: He Turned 65, Kept the Company Plan, and Medicare Was Already First in Line

Seven Ways In, Part 1: He Turned 65, Kept the Company Plan, and Medicare Was Already First in Line

There is a line in the Medicare rules drawn at twenty employees. On one side, your group plan pays your bills first.

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EP 2Seven Ways In, Part 2: She Had Two Years of COBRA Left. She Had Two Months of Medicare Left.

Seven Ways In, Part 2: She Had Two Years of COBRA Left. She Had Two Months of Medicare Left.

She was let go at 68 after decades with the same company. They handed her two years of COBRA, which felt generous, and it was.

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EP 3Seven Ways In, Part 3: He Was Told He Did Not Need Part B Because He Had the VA

Seven Ways In, Part 3: He Was Told He Did Not Need Part B Because He Had the VA

It is some of the most common advice a veteran hears, it is offered kindly, and it quietly assumes something that is not true. The VA covers care at the VA.

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EP 4Seven Ways In, Part 4: Everyone Called It Excellent Retiree Coverage

Seven Ways In, Part 4: Everyone Called It Excellent Retiree Coverage

He retired from a city job with the retiree health plan everyone in the building envied.

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EP 5Seven Ways In, Part 5: He Turns 65. She Is 62 and on His Plan. Nobody Asks About Her.

Seven Ways In, Part 5: He Turns 65. She Is 62 and on His Plan. Nobody Asks About Her.

Medicare is an individual program. There is no family plan and no spouse rider.

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EP 6Seven Ways In, Part 6: She Picked Advantage Three Years Ago. Nobody Mentioned the Door Locked Behind Her.

Seven Ways In, Part 6: She Picked Advantage Three Years Ago. Nobody Mentioned the Door Locked Behind Her.

There is exactly one window in your life when an insurance company cannot say no to you on a Medicare supplement.

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EP 7Seven Ways In, Part 7: A Bill Arrives for Income You No Longer Have

Seven Ways In, Part 7: A Bill Arrives for Income You No Longer Have

You retire in the spring. Your income drops by two thirds. And the following January, Medicare bills you as though you are still earning what you earned…

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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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