Introduction & Hosts

Madison: Hello, everyone, and welcome to Not Just Numbers, Honest Conversations with a Financial Advisor and Lawyer. I am Madison Demora, and I am here with Mike Garry. Mike is a financial advisor and a CFP practitioner and the founder and the CEO of Yardley Wealth Management. He is also an estate planning lawyer, and his law firm is Yardley Estate Planning. Hey, Mike.

Mike: Hey, Madison. How are you this morning?

Madison: I’m good. How are you?

Mike: Good. Getting ready for this Memorial Day Weekend? Bright sunshine, warm temperatures. It probably is somewhere in the world, but not here.

What Happens First When a Windfall Arrives

Madison: Yeah, unfortunately. So, Mike, over the years you’ve worked with a lot of clients through major financial windfalls. Inheritances, business sales, bonuses, liquidity events. When someone suddenly comes into a large amount of money, what tends to happen first?

Mike: Well, Maddie, there’s almost always some kind of a splurge. Could be a little thing. It could be as big as a vacation home, renovations, trips that were never quite in the budget before. All kinds of things.

Madison: And honestly, I think a lot of people would hear that and say, well, of course. There’s nothing inherently wrong with enjoying some of it.

Mike: Well, exactly. People should enjoy a windfall. The issue is usually what happens in the months immediately after the money arrives. Because that window often determines whether the windfall becomes the foundation for something lasting, or whether short-term decisions quietly limit what could have been possible.

Madison: And something important to point out upfront is that a windfall can mean very different things for different people.

Mike: Oh, sure. You know, anything involving wealth and income is relative, right? I mean, for one family it could be a $5 million inheritance. For another it’s like a $20,000 or $50,000 bonus that is meaningfully larger than anything they’ve seen before. For others, the proceeds from selling a small business they spent 30 years building. You know, it really does differ.

Madison: It does. So it’s really less about the exact dollar amount and more about how significant it feels relative to that person’s life.

Mike: Yeah, that’s exactly right, Maddie. The emotional reaction and the advice we give are remarkably similar across the board. What feels like a windfall is relative to each family’s situation and what they define it as.

Madison: So whether the number on the wire transfer is six figures or eight figures, the patterns we are about to walk through tend to show up in the same way.

Mike: Yep. And the families who handle it well are not the ones with the biggest numbers. They’re the ones who paused, took a breath, asked the right questions, and made deliberate decisions before the money got committed.

The First 90 Days

Madison: One thing I’ve heard you say before is that the first 90 days after a windfall matter more than the next 10 years. That sounds kind of dramatic.

Mike: It does sound dramatic, but it’s true.

Madison: Why are those first few months so critical?

Mike: Because in those early weeks, emotion tends to outpace strategy. And we see it over and over again.

Madison: Can you walk us through what that looks like?

Mike: Sure. Lifestyle commitments made before any plan is in place. Loans to family members written under emotional pressure. Investment decisions made on a hot tip from a brother-in-law or a podcaster. Big purchases made in quick succession. A vacation, a renovation, a new car, and sometimes within the same six months.

Madison: And I imagine it’s not always overspending either.

Mike: No, sometimes it’s the exact opposite. Total paralysis. The money sits in a checking account because the number feels too big to touch. We probably have seen that one more often. You know, some inheritance often, and they come in and say, oh, yeah, it’s been sitting in a savings account earning nothing for two years. Yeah, that is quite common.

Madison: Yeah. That’s so interesting, because I think people assume everyone immediately starts spending.

Mike: Yeah. That analysis paralysis is especially real with inheritances. The money often arrives at the worst possible emotional moment, right, when someone’s just lost a parent or a loved one. And so nothing happens, sometimes for years.

Madison: There’s actually a behavioral finance concept tied to this, too. It’s called the house money effect. People tend to treat money they didn’t earn differently from money they did earn.

Mike: So, Maddie, five years ago, would you have ever thought you’d be discussing behavioral finance on a podcast? Come on, this was not in your bucket list, was it?

Madison: Maybe. Maybe.

Mike: But, you picked up the right thing. I mean, rationally, a dollar is a dollar, right? Like it doesn’t matter. But emotionally, people often treat windfall money like bonus money, which can lead to bigger risks and faster spending.

Madison: And the data supports that. Roughly 72% of Americans say they don’t feel confident managing a large financial windfall.

Mike: Right. But those same people feel confident giving chunks of it away in the first month.

Madison: Which probably leads into the patterns you’ve seen over the years.

Mike: It does. And after enough of these situations, you start recognizing the patterns very quickly.

Pattern 1: The Lifestyle Leap

Madison: Okay, let’s walk through those patterns. What’s the first one?

Mike: First one is what we call the Lifestyle Leap. The new house, upgraded cars, bigger vacation budget. None of it is inherently wrong. But we’ve seen clients commit to lifestyle expenses that require ongoing income to maintain, only to realize the windfall itself doesn’t generate enough return to support that lifestyle forever.

Madison: Can you give us an example?

Mike: Sure. A client received a three and a half million-dollar inheritance. It’s great, right? But then over the next 18 months, they committed to a vacation home, a boat, private school for three children, and a major renovation. Those kids probably aren’t going to go to cheap colleges either. None of it was reckless individually. But together it locked up more than half the principal and created annual carrying costs around $180,000 a year. Some serious money.

Madison: Yeah, I’d say so. So windfall that could have become generational wealth became more of a comfortable lifestyle.

Mike: Yep, exactly.

Madison: And to be clear, comfortable isn’t always a bad outcome.

Mike: No. Comfortable is great. But, you know, people should understand what the tradeoff is that they’re making, right?

Pattern 2: The Family First Impulse

Madison: That’s right. So what’s the second pattern?

Mike: The Family First Impulse. The pressure to share windfall can be intense. Adult children, siblings, parents, old friends. And generosity can be a beautiful thing. But there’s a real difference between strategic gifting, with proper documentation and tax awareness, and writing checks in the first few weeks because saying no feels uncomfortable.

Madison: And there are tax considerations here, too. The 2026 annual gift tax exclusion is $19,000 per person, and $38,000 for married couples giving jointly. Anything beyond that can start affecting lifetime exemptions, so it’s important to talk with a tax professional.

Mike: Exactly.

Pattern 3: The DIY Investor

Madison: So what’s the third pattern?

Mike: The DIY investor. Windfalls have a way of generating investment confidence. I don’t know why that is, but it is absolutely true. Someone receives, like, $800,000 and suddenly feels like they should manage it themselves.

Madison: Maybe because asking for help feels like admitting they don’t know what they’re doing.

Mike: Yeah, that’s probably it. And only about 20% of Americans say they would seek guidance from a financial professional after receiving a windfall.

Madison: Which is surprising considering these decisions are often much more complicated than managing regular monthly savings.

Mike: Exactly. It is really striking to think that only 20% of people who receive some sort of windfall, and most people have no real idea about how to manage something like that, wouldn’t even consider hiring a financial professional for it. It’s crazy to me.

Pattern 4: Sudden Wealth Syndrome

Madison: All right, so what’s the fourth pattern?

Mike: Sudden wealth syndrome. Term was coined by psychologist Stephen Goldbart in the 1990s. It describes the psychological and emotional distress that can come with an unexpected windfall. Anxiety, guilt, social isolation, difficulty trusting the people around you. So maybe they wouldn’t trust the financial professional either. I don’t know.

Madison: And I think inheritances make this even more emotional because the money is often tied directly to grief.

Mike: That’s right. The money arrives at the same moment someone is processing the loss of a parent or loved one. Making decisions can feel emotionally loaded, so people freeze.

Madison: But that paralysis has a cost too.

Mike: It does. Money sitting in a checking account is losing ground to inflation every single day.

Pattern 5: How People Navigate a Windfall Well

Madison: And then there’s the fifth pattern. The people who tend to navigate this really well.

Mike: Yep. Of course. I mean, some people just do stuff right. Right? Like, some people are great at everything. It seems clients who get it right usually do have a few things in common. Like they’re willing to talk honestly with their family about money. They’re curious rather than embarrassed by what they don’t know. As a quick aside here, that is a big skill set, like knowing… Like, being comfortable saying you don’t know something. It’s a huge thing. I first encountered that as a young guy with my now father-in-law, like 35, 36 years ago. He was like, the first adult back then that would confidently say, like, yeah, I don’t know anything about that. Whereas back then, a lot of adults would just, like, I don’t know, they would act as if they knew something or, like, would be so embarrassed. And it is actually, Bill’s way is so much better. Like, if you don’t know something, it’s okay. It’s a complicated world. There’s a lot to know. If you don’t know something, okay, be curious about it. If it’s something important to you, try to learn about it. Talk to somebody. All right. Anyway… Sorry about that.

Madison: I love that. That’s awesome. That’s good advice.

Mike: Yeah, it is so funny. It was striking to me, too, when he said, yeah, I don’t have anything. I don’t even know what it was about. But the way he said it struck me as surprising. And so I would have been in my 20s, right, because I started dating Rachel when I was 23, so sometime in my mid-20s, Bill said that. And, it has stuck ever since. Yeah. All right, let me get back to answering your question. You know, so it really helps to be curious rather than embarrassed. Like, you can learn a lot. And I think a lot of times we have people in the beginning of a relationship, you know, a lot of clients come to us because they really don’t know anything. And they learn a lot. And I think they actually enjoy that learning. So, you know, really think about, you know, money and ask questions and don’t be embarrassed. Right. And then those people that do that, so they start asking around, they talk about things and they become… They seem to have, like, a clear sense of what they want their wealth to accomplish. And, you know, they give intentionally and they invest strategically. And they’re careful not to let recurring lifestyle expenses creep up to match their new balance sheet. You know, some people really handle it well.

Madison: Yeah, that lifestyle creep piece is huge because once those expenses are in, they’re hard to pull back out.

Mike: Yeah. You put your kid in that private high school and then like, say like, you know what I don’t want that. Yeah. Trying to get your teenager to change high schools a second time. Yeah, that’s not going to go well.

The Great Wealth Transfer

Madison: Yeah, that’s true. So we mentioned windfalls show up in all sizes. But there is also a much bigger picture worth knowing about, because it’s shaping the next two decades for a lot of families.

Mike: Yeah, the whole wealth transfer has been talked about, my whole career in wealth management. But it’s out there like so Cerulli, which is a big consulting firm, is now projecting $124 trillion in assets will change hands through 2048, which is like 22 years from now. Nearly 100 trillion of that is expected to move from Baby Boomers and the Silent Generation to their heirs.

Madison: And a large portion of that is concentrated among high-net-worth households.

Mike: It sure is. Around 62 trillion is expected to come from high-net-worth and ultra-high-net-worth. Roughly $18 trillion is projected to go toward charitable causes.

Madison: And timing matters here, too. Gen X is expected to inherit the largest amount over the next decade.

Mike: Finally, Gen X gets something. Yeah, that’s around 14 trillion. And they will be receiving it at a complicated life stage. Many are already caring for aging parents while still helping adult children. You know, the oldest Gen Xers now are in their early 60s.

Madison: Millennials are the largest group of inheritors over the full 25-year window.

Mike: Yeah, millennials are a giant group, just like the baby boomers. So, yeah, I think for that Cerulli said like around 46 trillion by 2048.

Madison: So for people listening in their 50s or 60s with aging parents, this isn’t really a hypothetical conversation anymore.

Mike: Exactly. The question is not whether wealth will eventually transfer. It’s whether families are prepared for when it does.

Madison: And if someone is on the giving side of this equation, there are a different set of questions.

Mike: Right. Have you set your heirs up to receive your wealth wisely? Have you had the conversations? Have you structured your estate to reflect your values, not just your balance sheet? Have you structured your estate? We’ll make this real simple. Like, have those conversations. Talk to lawyers. Don’t try to draft it yourself. Like, take the time and spend a little bit of money that it costs to make sure things go right. Like, it’s really, really important. And you’ll be a huge, huge service for your kids and grandkids.

Madison: That’s right. And I think most families genuinely want to make life easier for their children.

Mike: They do. Right. But many haven’t done the work themselves to make sure you’re not unintentionally leaving behind confusion and conflict.

A Five-Step Framework for Windfall Decisions

Madison: Okay, let’s make this practical. If someone knows a windfall is coming, or one has just arrived, what’s the framework?

Mike: Well, we walk clients through five steps.

Madison: All right, so what’s step one?

Mike: Secure the funds before making decisions. Receive the money, park it somewhere safe, and don’t commit it to anything in the first weeks. Single most powerful financial decision you can make in those early days is no decision at all.

Madison: Basically, take a breath before reacting.

Mike: Exactly.

Madison: All right, what’s next?

Mike: Get the right professionals involved. Financial professional, tax, legal and or accounting professionals. Sometimes an estate attorney. Maybe an insurance specialist depending on the situation. Good strategy usually happens when those professionals are coordinating together. You need a team.

Madison: And I think a lot of people underestimate how many moving pieces there can be.

Mike: Yeah, they do. Many people try to handle everything through one advisor and unintentionally miss important pieces.

Madison: Right, so what’s step three?

Mike: Define the purpose. Like, what are you going to do with the money? What is this windfall actually for? Retirement? Helping your children? A legacy gift? A mix of all three? Clients who can clearly articulate the why behind the money tend to make much better decisions.

Madison: Otherwise, every opportunity starts feeling equally important.

Mike: Yep, exactly.

Madison: All right. And step four?

Mike: Cover the basics. Look at your full financial picture. Are there any high-interest debts worth paying down? Is the emergency fund where it should be? Are insurance coverages appropriate? Is the estate plan still aligned with what the family looks like today? These questions get skipped in the rush to make big moves.

Step 5: Build a Spending Permission Slip

Madison: And then the last step.

Mike: Build a spending permission slip.

Madison: Can you explain what that means?

Mike: Sure. We often encourage clients to intentionally carve out a small percentage of the windfall, you know, maybe 3 to 5% specifically for guilt free enjoyment. A trip. A renovation. Meaningful gifts. Whatever brings joy.

Madison: And why does that matter so much?

Mike: Yeah, Maddie, because if people don’t intentionally give themselves permission to enjoy part of the money, the pressure to enjoy all of it tends to build over time. That’s often when impulsive decisions happen.

Madison: So building enjoyment into that plan actually helps people stay disciplined.

Mike: Yep. It’s like, you know, it’s like a cheat day for a dieter. And it acknowledges something important. Windfall should create some joy, not just stress.

Conversations Inside the Family

Madison: All right. One piece we haven’t really talked about yet is the family conversation side of this. Because a windfall doesn’t just affect one person. It affects everyone connected to that person. And those conversations are some of the hardest to have.

Mike: They are. But, you know, we often always encourage clients to think intentionally about who needs to know what, and when. Aging parents may need to know that their adult child is now in a different financial position. Siblings may need clarity if there’s a shared family money in play.

Madison: And avoiding those conversations can create issues later.

Mike: Yep, all the time. Adult children may structure their lives assuming more money is eventually coming. Siblings who feel blindsided by gifts that went one direction. Parents who hear about a windfall through someone else.

Madison: And often these problems could have been avoided with a few intentional conversations early on.

Mike: You know, and importantly, those conversations do not have to include every exact number. Sometimes it’s simply acknowledging that something has changed and opening the dialogue.

Final Thoughts

Madison: So if someone listening today knows a windfall may be coming, or one has already arrived, the biggest takeaway is probably this: slow down.

Mike: Yep. Receive the money. Get the right professionals involved. Define the purpose of the money. Cover your basics. And give yourself permission to enjoy part of it.

Madison: Because a windfall is one of those few moments where the decisions you make in a short window can genuinely alter the trajectory of your family’s financial story. For better or worse.

Mike: Yeah, we’ve seen that play out both positively and negatively many times.

Madison: And if you want help thinking through what this could look for you and your family, that’s exactly the kind of work we do.

Mike: Reach out anytime.

Closing & Contact Information

Madison: Thanks for listening. For more information on Yardley Wealth Management or Yardley Estate Planning, you can visit our websites at yardleywealth.net and yardleyestate.net. You can also follow us on socials at Yardley Wealth Management. Don’t forget to subscribe to our YouTube channel. This podcast has been produced by Madison Demora and Mike Garry, with technical and artistic help from Poe Productions.