Episode 70: Why Giving Money Can Do More Harm Than Good
Episode 70
Host: Jill Mastroianni
Why Giving Money Can Do More Harm Than Good
A viral GoFundMe campaign for a DooDash delivery driver reminds us that generosity, while beautiful, can have unintended consequences. In this episode, Jill walks through real-life examples from her law practice to explain how giving money, especially to someone receiving government benefits, can sometimes do more harm than good. Thoughtful generosity often requires slowing down and understanding the full picture.
What You’ll Learn in This Episode
Why good intentions aren’t always enough. Even well-meaning financial help can create serious legal and financial consequences when government benefits like Medicaid are involved.
What “means-tested benefits” actually means. Programs like Medicaid require recipients to stay below strict income and asset limits to qualify and remain eligible.
How a financial gift can backfire. A lump sum (like GoFundMe proceeds) count as income in the month received. If retained, the lump sum becomes a resource in the following month. Both an increase in income and an increase in resources can push someone over eligibility limits and cause a loss of government benefits
The real cost of “help.” A $10,000 gift could trigger loss of coverage and result in tens of thousands of dollars in out-of-pocket medical or nursing home costs.
Why Medicaid eligibility is not “set it and forget it.” Eligibility is reviewed regularly, and changes in income or assets can trigger reassessment or penalties.
How small details can cause big problems. Even something like a life insurance policy structured incorrectly can jeopardize benefits eligibility.
The hidden questions behind sudden wealth. When someone receives a large sum of money: (i) Can they manage it responsibly? (ii) Are they protected from scams or pressure to give or loan money? (iii) Do they have an estate plan in place?
The core principle: “First, do no harm.” Sometimes the most compassionate action is to pause, ask questions, and ensure your help actually helps.
Resources & Links
Brittany and Richard’s News Clip on YouTube: https://www.youtube.com/watch?v=wnYmQH4Ivv4
Brittany’s GoFundMe campaign for Richard’s benefit: https://www.gofundme.com/f/give-richard-a-chance-to-rest-again
Episode 20: What You Need to Know about Medicaid and Protecting Your Mom’s House: https://www.deathreadiness.com/podcast/episode-20-what-you-need-to-know-about-medicaid-and-protecting-your-moms-house
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A viral GoFundMe raises nearly a million dollars for a struggling DoorDash driver. It feels like a beautiful story of generosity, and hopefully it is. But situations like this can be more complicated than they appear, especially when government benefits are involved. Today, I explain how well-intentioned financial help can sometimes create serious legal and financial consequences. Often, the most compassionate thing we can do is pause long enough to make sure our help truly helps.
Welcome to The Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni — estate planning attorney, death readiness guide, and your translator for wills, trusts, probate, and the conversations most families avoid. If you’ve been wondering things like, ‘Can a trust protect what I leave to my children?’ ‘What happens if I give someone power of attorney over me?’ and ‘How can I help my parents while respecting their independence?’ You’re in the right place.
Before we get started today, I have a quick update. The second edition of The Death Readiness Playbook is heading to the printer this week, and I’m expecting it to be available in early April.
The first edition sold out, which was incredibly encouraging, and it inspired me to make this new version even better. The second edition includes new ways for people to stay connected and collaborate around Death Readiness.
I’ll also be offering a co-branding option for law firms, wealth advisors, and funeral homes who want to share the Playbook with their clients and communities. Co-branding is the Playbook with your brand, your team member profiles and your contact information.
Stay tuned for more details in my weekly email newsletter. If you’re not already subscribing, check it out at deathreadiness.com/subscribe. That’s deathreadiness.com/subscribe
Now, let’s get into today’s episode.
For the past few days I’ve been down with some sort of bug. According to the test my husband picked up from CVS, it’s not the flu and it’s not COVID, but I definitely feel pretty wiped out.
On Saturday, my daughter and I still showed up at a Detroit Dog Rescue adoption event in Livonia, Michigan, with our foster puppy, Boots. Four puppies were adopted that day. Boots, unfortunately, was not one of them.
So that night I took some Mucinex, crawled under the covers, and started scrolling through YouTube while drifting in and out of sleep. And that’s when I came across a story that reminded me of something I’ve seen a few times in my law practice.
The news clip, which I’ll link to in the show notes, was about a 78-year-old DoorDash delivery driver named Richard and a GoFundMe campaign that raised close to a million dollars for him.
The story started when a woman named Brittany received a Starbucks delivery at her home. When she watched the footage from her doorbell camera, she saw Richard, an older man, slowly making his way up her walkway and struggling to climb the few steps to her porch to complete the delivery.
She was concerned, tracked him down via Facebook, and set up a GoFundMe campaign to help him. Within just a few days, the campaign has raised close to a million dollars.
From everything I could see, Brittany acted with the very best of intentions, and Richard appears incredibly grateful. In one clip I saw, he said, “In three days, she’s turned the world around for me.”
And I hope that’s exactly what happened.
But this story also reminded me of something important that I’ve encountered more than once in my work as an estate planning attorney.
Tuesday Triage episodes usually answer listener questions. But sometimes I like to talk about the questions people don’t even realize they should be asking because unless you work inside an estate planning practice, you don’t always see the situations that bring those questions to light.
Early in my career, a woman came into the law office where I worked very worried that she had tried to do the right thing but had accidentally gotten herself in over her head.
Let’s call her Kate.
Kate had noticed that a woman in her community — we’ll call her Amanda — was struggling to support her grandchildren while her son and his girlfriend, the children’s parents, were dealing with substance abuse issues.
Kate wanted to help. So she set up a fundraising account for Amanda.
What Kate didn’t realize was that Amanda was receiving means-tested government benefits to help support herself and her grandchildren.
A means-tested benefit is one that you only qualify for if your income and assets stay below certain limits. In other words, the government looks at your financial resources, what you earn and what you own, to decide whether you qualify.
From what I remember, Kate raised somewhere around ten to fifteen thousand dollars. So we’re not talking about the nearly one million dollars that Richard received through the GoFundMe campaign. This was a much smaller amount.
But Kate was incredibly frustrated when she came to see us. She just wanted to help Amanda. She didn’t expect that trying to help someone would lead to meetings with lawyers and the possibility of spending even more money just to give Amanda a modest financial boost.
We explained that if she wanted to move forward, we first needed to understand exactly what types of government benefits Amanda was receiving. Only then could we determine whether there was a way, possibly through a trust, to structure the gift without jeopardizing those benefits.
The money Kate raised for Amanda could actually have created a bigger problem than it solved.
Depending on the benefits Amanda was receiving, that extra money could have caused her to lose those benefits, including something as critical as health insurance. And that’s a very big deal.
Unfortunately, I never learned how the situation turned out, because Kate never came back to us.
The description on Richard’s GoFundMe page is very simple. It says:
“With the help of social media [Brittany] was able to track down Richard and learned he does DoorDash due to his wife being fired from her job (at no fault of her own) and by the time they pay their monthly expenses plus purchase their medication there is nothing left. Let’s help Richard go back into retirement!!”
And I suspect many people who gave to that campaign felt the same way Kate did when she tried to help Amanda.
I also worked with another family that I knew personally who was the recipient of GoFundMe campaigns.
The wife experienced a sudden medical event that left her with severe physical limitations. Her daughter started a GoFundMe campaign to help cover care that wasn’t paid for by insurance.
My husband and I contributed. And then we contributed again.
Each campaign raised about ten thousand dollars, similar to the amount Kate had raised for Amanda.
Later, the couple, who we’ll call Hal and Pam, became clients of mine.
They came to me because Pam needed long-term care. At the time, Hal and Pam were insured through the Affordable Care Act, but their coverage was ending and they could no longer afford to continue it. Meanwhile, Pam needed significant medical care.
So we made the decision to apply for TennCare for Pam, which is Tennessee’s implementation of Medicaid.
If you’d like a deeper dive into Medicaid, I’ll link to Episode 20 in the show notes, What You Need to Know about Medicaid and Protecting Your Mom’s House.
Pam also signed powers of attorney so that Hal could make both financial and medical decisions on her behalf. That step was incredibly important. Even though Pam had serious physical limitations, she was still mentally competent and able to sign those documents herself. She was tired, and she wanted Hal to step in and take the reins where he could.
Applying for TennCare turned out to be an arduous process. It wasn’t particularly complicated legally, but it was administratively exhausting. We submitted documentation, followed up, submitted more documentation, followed up again… and then followed up again and again.
Eventually, we got everything in place and Pam was approved for TennCare.
After the approval, I sat down with Hal, Pam, and their daughter and explained something very important.
TennCare is a means-tested government program, which means the person receiving the benefit has to stay within certain income and asset limits in order to keep qualifying.
The fundraising campaigns had helped their family tremendously in the past. But now that Pam was receiving TennCare, they could not run additional fundraising campaigns. If they received more money, it could push them over the program’s income or asset limits and cause Pam to lose her coverage, including the caregivers who were coming to their home every day to help with her physical needs.
If they needed additional financial help, we would have to talk about ways to raise and distribute those funds without jeopardizing Pam’s eligibility.
Now, I know that conversations about Medicaid eligibility can start to sound like “blah, blah, blah, blah, blah.”
And I really don’t want this podcast to sound like that for you.
So instead of leaving it abstract, let’s walk through some real numbers.
We’ll use the 2026 TennCare numbers as an example. Other states vary a little, but the general framework is very similar across the country.
In Hal and Pam’s situation, we have a married couple where one spouse, Pam, is applying for TennCare.
I don’t remember the exact eligibility category we applied under at the time, so I’m going to use a long-term care level example with the largest possible income and asset limits. Just keep in mind that the limits can sometimes be lower depending on the specific type of TennCare coverage.
In one common scenario, where the spouse applying for TennCare requires nursing home–level care, the applicant spouse, Pam, in our situation, is limited to about three thousand dollars per month in income and an asset limit of about two thousand dollars.
Now, there are some important exceptions to those limits.
For example, if Pam needed to live in a long-term care facility but Hal was still living at home, the house would usually be considered an exempt resource. In other words, the value of the home would not count toward Pam’s two-thousand-dollar asset limit.
Hal, as the community spouse, the spouse still living at home, is allowed to keep more resources in his own name.
Depending on the situation, Hal could keep roughly one hundred sixty thousand dollars in assets.
At first glance, that might sound like a lot of money. But if two retired people need to live on that for the rest of their lives, especially while one spouse is dealing with serious health issues, it’s actually not that much.
So at this point you might be wondering: once someone is approved for Medicaid, who’s really going to notice if they receive a little extra money?
Well, first, failing to report income or assets to your state’s Medicaid program is fraud, and that’s illegal.
But even setting that aside for a moment, fundraising campaigns are very public. They circulate online and throughout a community. It’s risky to assume that something that visible would never come to the attention of TennCare.
And there’s another important piece to understand.
Eligibility for TennCare doesn’t get approved once and then forgotten about. It’s reviewed regularly.
Typically, TennCare reviews eligibility about once every twelve months. But if there’s a reported change in income or resources, they can review eligibility sooner.
During those reviews, the agency looks again at income, assets, and any other factors that might affect whether someone still qualifies for coverage.
And with that eligibility review in mind, I want to share another story from early in my career.
I once helped someone who cleaned the home of a friend of one of the partners at the law firm where I worked. She didn’t have much money, and she was caring for her adult brother, who had an intellectual disability and was unable to work. He relied on means-tested government benefits.
At one point this woman received a notice from the government saying that she owed thousands of dollars because her brother’s benefits had been overpaid.
The issue turned out to be a small life insurance policy she had purchased on his life. She bought the policy so that she would have the funds to bury him when the time came. She paid the premiums herself. She was simply trying to do the responsible thing.
But when she set up the policy, she listed her brother as the owner.
That meant the policy counted as his asset.
She wasn’t hiding anything or trying to cheat the system. She was just trying to do the right thing. But because that life insurance policy counted as a resource, it affected his eligibility for benefits.
Most of the time the government feels incredibly inefficient. And then suddenly they discover a piece of information that I have no idea how they even found.
So yes, you shouldn’t try to hide anything because it’s illegal.
But moreover, if the government was able to discover that a person receiving benefits owned a small life insurance policy, it’s not a huge stretch to imagine they could discover a very public fundraising campaign for that same person.
Now let’s go back to Hal and Pam.
Let’s say one of their friends knows they’re struggling financially and decides to start a GoFundMe campaign to help them out.
If you’re not familiar with GoFundMe, each campaign lists an organizer and a beneficiary. In this case, the friend would be the organizer and Pam would be listed as the beneficiary.
And let’s say the campaign raises ten thousand dollars.
In the month Pam receives that ten thousand dollars, it counts as income.
But remember, Pam’s monthly income limit to remain eligible for TennCare is about three thousand dollars.
So in the month she receives that money, she becomes ineligible for TennCare.
Then let’s say she still has that money the following month.
At that point, it no longer counts as income, it counts as a resource.
And Pam’s resource limit is about two thousand dollars.
So now she’s over the resource limit.
Now imagine TennCare discovers this during her annual eligibility review.
Let’s say Pam is living in a nursing home and TennCare has been paying for that care. TennCare determines that Pam was ineligible for two months while she had that extra ten thousand dollars.
That means TennCare can require Pam to pay for those two months of care out of pocket.
The average cost of nursing home care in Tennessee is about ten thousand dollars per month.
So now, assuming Pam was ineligible for two months, she owes roughly twenty thousand dollars for those two months.
And all of that started with someone trying to help.
One of my dad’s favorite sayings is, “No good deed goes unpunished.”
And unfortunately, that’s exactly what can happen in situations like this.
Someone tries to help Hal and Pam with a ten-thousand-dollar gift, and it ends up costing them twenty thousand dollars in lost TennCare coverage.
And Hal and Pam aren’t the only ones affected in a situation like this. Of course they’re affected, but so are the people who gave generously to try to help them. All of that generosity, given with the very best intentions, could actually leave Hal and Pam worse off.
Now, I’m not going to go into all the ways you can give in a way that avoids these problems. That’s more than we can cover in today’s Tuesday Triage episode.
But before you give money to someone who may be receiving government benefits, it’s worth pausing, learning a few basic facts, and bringing in a professional if needed.
Now let’s go back to Richard, the older gentleman who became the focus of that viral GoFundMe campaign.
When I looked at the campaign, I noticed that the largest donation was five thousand dollars, and there were many others in the one-thousand-dollar range.
And I want to be very clear: I don’t know anything about Richard or his wife, and it’s entirely possible that either they are making responsible decisions with that money or that there are people working behind the scenes helping them make good decisions.
But situations like this raise important questions.
Are Richard and his wife comfortable managing that amount of money?
Is there a trusted person in their lives who can help them invest it wisely?
Do they have children or other family members who might create pressure around that money?
Now the entire internet knows that this couple has received close to a million dollars. Older adults are already frequent targets for financial scams and now the world knows exactly how much money they have.
And let’s imagine that everything goes perfectly. They invest the money wisely, they manage it carefully, and no one pressures them to lend or give it away.
But what happens if Richard and his wife pass away in a few years?
Did they create an estate plan? Did they think about where that money should go? Did the thousands of people who donated think about the possibility that the money might ultimately benefit someone other than Richard and his wife, or whoever the state determines should inherit it if no planning was done?
Situations like this can raise a lot of questions. The answers to these questions in Richard’s situation are none of my business. I don’t know Richard and I’m not donating to his GoFundMe campaign.
So, let’s come back to where we started.
A woman saw an older man struggling to deliver a cup of coffee. She felt compassion, she took action, and thousands of people joined her in trying to help. In a world that can feel pretty heavy sometimes, that kind of generosity is actually something beautiful.
But stories like this also remind me of something I see again and again in my work as an estate planning attorney.
Good intentions are powerful. But good intentions don’t always come with the full picture.
Sometimes the most compassionate thing we can do isn’t to act immediately. Sometimes it’s to pause for a moment, ask a few questions, and make sure the help we’re offering actually helps.
There’s a phrase that comes from medical ethics that I think applies just as well to situations like this: first, do no harm.
That doesn’t mean we stop being generous. It just means we slow down long enough to make sure our generosity lands in the way we hope it will.
If today’s episode made you realize that legal and financial decisions can have consequences you might not see right away, that’s exactly the kind of situation estate planning is designed to help with. If you live in Tennessee and want thoughtful guidance to create or update your estate plan, I can help. You can learn more at DeathReadiness.com/solutions. That’s DeathReadiness.com/solutions. I’ll include the link in the show notes.
Thanks for listening today.
This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.
Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast. While my mom is an attorney, she’s not your attorney. The Death Readiness Podcast is for educational and entertainment purposes only. It does not provide legal advice. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state. To learn more about the services my mom offers, visit DeathReadiness.com.
