If the parents are paying, a college education is priceless. If they aren’t, it’s an investment—and the return better outweigh the cost.
BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?
He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.
The son decided to sell the house and paid about $430,000 in federal taxes.
$430,000 that could have been $0 instead…
How?
When you gift a property to someone, they receive a "carryover basis." It basically means the same price the original owner purchased it for.
The basis of that house was $50,000, so the son had to pay capital gains tax on the difference between the $2 million sale price and the basis, at rates reaching up to 23.8% on the top portion of the gain. But this is where a step-up in basis could come into play.
Assets such as a house or shares held in a brokerage account, when owned inside an estate rather than an irrevocable trust, receive a step-up in basis to their fair market value (FMV) at the time of the decedent's death, per IRC Section 1014. In our case, if Bob held that house in his own name, passed away, and his son received the house, he would've gotten a step-up in basis to the current value, or $2M.
At the time of the sale, if sold for $2M, he would pay $0 in federal taxes, though state tax might still apply. That's about $430,000 of "savings."
"But who cares, Bob is dead anyways?"
While true, many parents still want to make sure their children don't have to pay half a million in taxes. They want their children to enjoy the fruits of their hard labor.
Specifics
The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.
First, the step-up in basis typically adjusts to the market value, unless an election is made to use the value six months after the date of death, subject to certain rules.
The step-up in basis also doesn't apply to assets held in an irrevocable trust , though we will cover some strategies for that later, or to assets held in qualified retirement accounts, such as IRAs and 401(k)s.
In a community property state (Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin), the basis steps up whenever a spouse dies. You will typically need to complete a form to receive this step-up in a brokerage account.
For assets held in joint tenancy, the step-up applies only to the deceased partner's share. For example, Bob and Jenice have a house worth $300,000 with a $50,000 basis. After Bob passes away, Jenice will have a $175,000 basis in the house, calculated as ($300,000 minus $50,000) divided by two, plus $50,000.
There are also two additional things to keep in mind:
1. Living on the right assets
Bob, age 75, has two accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob's diagnosis isn't good.
From a tax-planning perspective, it might make a lot more sense to withdraw, say, $50,000 a year from the 401(k) to live on, $20,000 of which would be required minimum distributions (RMDs), and pass down the brokerage account to his beneficiaries.
This is because the brokerage account likely has a lot of gains. Bob bought many stocks in his 30s and 40s that could be stepped up now. But a more in-depth analysis might be needed if Bob has a lot of income and is in a high marginal tax bracket.
2. Selling the right lots
Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis, meaning a lot of capital gains, and some have a high basis, meaning fewer capital gains.
It's best to sell the high-basis stocks, which come with a lower capital gains tax, and pass down the low-basis stocks to the beneficiaries.
Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes. As always, make sure to consult a licensed CPA or estate attorney with your unique circumstances.
Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.NO. 21: A HIGH income makes it easier to grow wealthy. But no matter how much we earn, we’ll struggle to amass a healthy nest egg—unless we learn to spend less than we earn.
ANCHORING. Imagine the S&P 500 is up 20% over the past year. You might balk at buying stocks, because you’re anchored on the market’s old level and feel you’re overpaying at current prices. Or imagine your neighbors sold their home two years ago for $300,000. You might be reluctant to accept less for your home, even if property prices have since fallen.
NO. 30: WE underestimate the power of compounding. Most folks grasp that invested money should grow over time, while carrying credit-card debt can trigger interest charges. But studies suggest we fail to appreciate just how much our money can grow if left to compound—and just how costly our debts can be if we fail to pay them off in short order.
GAMBLER’S FALLACY. When the dice hasn’t come up six for a while, we think a six is more likely. Similarly, if a money manager has previously beaten the averages or a Wall Street strategist has a history of predicting the market’s direction, we assume they’ll continue to make winning calls. But what if it's random, like the dice, and these folks were just lucky?
NO. 21: A HIGH income makes it easier to grow wealthy. But no matter how much we earn, we’ll struggle to amass a healthy nest egg—unless we learn to spend less than we earn.
I’m booking flights at the moment. Suzie and I are heading to the South of England to visit my brother-in-law and family in a couple of weeks’ time. They’ve just recently hit a major life milestone by purchasing their first home together, and we’re looking forward to getting a tour by the proud owners. I’m very happy for them; I’m also very happy for myself because I’m getting free accommodation by staying with them.
My brother-in-law is in his mid-forties with a wife ten years younger and has expressed nervousness at taking on such a large debt at his age,
Hi,
I was encouraged to post here by my cousin, and HumbleDollar columnist, Ed Marsh so here goes – I’m considering a reverse 1031 exchange. I’d have preferred it be a straight 1031 exchange but timing hasn’t worked in my favor in that my wife and I found the replacement property unexpectedly and had not intended on selling the relinquished property so quickly. My question is twofold. First – can the QI take title to the relinquished property instead of the replacement property ahead of the sale of said property so that I don’t have title to both properties?
From the Wall Street Journal this morning: More than 1,000 families have lost a total of at least $190 million in 16 bankruptcies at continuing-care retirement communities since March 2020, according to a Wall Street Journal analysis. Chapter 11 filings rose during the pandemic period primarily because these facilities didn’t have enough new move-ins. And because of the way bankruptcy proceedings work, secured creditors get paid before residents.
I ended my online subscription to the WSJ a few months ago,
STOCKS, BONDS, CASH—and a house owned free and clear. For many, that’s the recipe for a financially successful retirement. Our homes represent a central pillar of middle-class status. With a paid-off mortgage, we have an affordable place to spend our old age.
Yet signing up for decades of house payments has become controversial for its high opportunity cost—what you give up to pay the mortgage. Has a home mortgage, with its long, slow road to payoff,
During his final months, my husband Jonathan worked tirelessly to complete his last book, Money and Me. The book is now available for pre-order and will be released in May 2026.
What’s so special about this book? This book features Jonathan’s best and most personal HumbleDollar articles. The articles are curated in such a way to teach everyone about personal finance through Jonathan’s own money journey. And sadly, his terminal cancer diagnosis is part of this journey about which he candidly writes.
There’s a world where I can go
And tell my troubles to
In my room, in my room
The Beach Boys, 1963
Alberta and I just returned from what for me was a restorative and emotionally powerful two-week trip to New York. No, not because she got to see seven movies at the International Film Festival in the Hamptons or four shows in the city. But she took pictures of me standing in front of five of the commercial buildings my family owned some fifty years ago.
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BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?
He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.
The son decided to sell the house and paid about $430,000 in federal taxes.
$430,000 that could have been $0 instead…
How?
When you gift a property to someone, they receive a "carryover basis." It basically means the same price the original owner purchased it for.
The basis of that house was $50,000, so the son had to pay capital gains tax on the difference between the $2 million sale price and the basis, at rates reaching up to 23.8% on the top portion of the gain. But this is where a step-up in basis could come into play.
Assets such as a house or shares held in a brokerage account, when owned inside an estate rather than an irrevocable trust, receive a step-up in basis to their fair market value (FMV) at the time of the decedent's death, per IRC Section 1014. In our case, if Bob held that house in his own name, passed away, and his son received the house, he would've gotten a step-up in basis to the current value, or $2M.
At the time of the sale, if sold for $2M, he would pay $0 in federal taxes, though state tax might still apply. That's about $430,000 of "savings."
"But who cares, Bob is dead anyways?"
While true, many parents still want to make sure their children don't have to pay half a million in taxes. They want their children to enjoy the fruits of their hard labor.
Specifics
The step-up in basis can be a bit nuanced, depending on how the assets are held and titled.
First, the step-up in basis typically adjusts to the market value, unless an election is made to use the value six months after the date of death, subject to certain rules.
The step-up in basis also doesn't apply to assets held in an irrevocable trust , though we will cover some strategies for that later, or to assets held in qualified retirement accounts, such as IRAs and 401(k)s.
In a community property state (Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin), the basis steps up whenever a spouse dies. You will typically need to complete a form to receive this step-up in a brokerage account.
For assets held in joint tenancy, the step-up applies only to the deceased partner's share. For example, Bob and Jenice have a house worth $300,000 with a $50,000 basis. After Bob passes away, Jenice will have a $175,000 basis in the house, calculated as ($300,000 minus $50,000) divided by two, plus $50,000.
There are also two additional things to keep in mind:
1. Living on the right assets
Bob, age 75, has two accounts: a traditional 401(k) worth $500,000 and a brokerage account worth $500,000. Bob's diagnosis isn't good.
From a tax-planning perspective, it might make a lot more sense to withdraw, say, $50,000 a year from the 401(k) to live on, $20,000 of which would be required minimum distributions (RMDs), and pass down the brokerage account to his beneficiaries.
This is because the brokerage account likely has a lot of gains. Bob bought many stocks in his 30s and 40s that could be stepped up now. But a more in-depth analysis might be needed if Bob has a lot of income and is in a high marginal tax bracket.
2. Selling the right lots
Say Bob has a $500,000 brokerage account. Some of the stock purchases have a low basis, meaning a lot of capital gains, and some have a high basis, meaning fewer capital gains.
It's best to sell the high-basis stocks, which come with a lower capital gains tax, and pass down the low-basis stocks to the beneficiaries.
Planning matters. These mistakes can cost thousands of dollars in unnecessary taxes. As always, make sure to consult a licensed CPA or estate attorney with your unique circumstances.
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