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Jill Schlesinger
Real estate.
Mark
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Jill Schlesinger
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Jill Schlesinger
Learn more@americanexpress.com AmExBusiness welcome to the Jill on Money Show. It's Thursday, January 23rd and we are answering your questions now. Every single one of you has a distinct and interesting financial life. And so when we're talking to somebody who calls in or we're reading an email, I always want you to think, oh, how does that apply to my life? And if you have a follow up question to that, why don't you send us a note? For example, if you're someone listening and you're like hey, this sounds like a situation like mine, but I never thought of it that way, maybe you would like to get a little bit of guidance, or maybe you want a little bit of cheerleading, or maybe you're seeking almost like permission to go do something that you wouldn't normally do when it comes to your financial life.
Mark
If that's you, give us a Holler.
Jill Schlesinger
Go to jillonmoney.com, click the contact us button, write us a note, and if you want to come on the air live, just check the box and Mark will do everything else. Now, while you're on the website, don't forget, sign up for the free weekly newsletter comes out every single Friday. And you can also check out our subscription service. It's called Jill on Money Live. That is where you have access to quarterly live webinars, bonus audio and video.
Mark
Content, as well as our entire back.
Jill Schlesinger
Catalog, all for $45 for the next 12 months.
Mark
Jill on Money Live.
Jill Schlesinger
So check it out. All right, let's talk to Ed from Philadelphia. I just want to say one thing. We're recording this on the eve of a big Philadelphia Eagles game. So we have. We don't.
Mark
You will know the result when you.
Jill Schlesinger
Hear this, but, Ed from Philly, you say you're feeling confident.
Ed
I am feeling pretty confident, yes.
Mark
I guess the longer you say confident.
Jill Schlesinger
I could probably worm it out of you to say I'm not that confident. But okay. I mean, listen, we all want to make sure that we have certain amount of confidence and a certain amount of reality that bears down on us. So, Ed, I wish I could talk to you about football the whole time I'm with you. But let's talk about you. What brings you to us?
Ed
I'm 64 years old. I've been retired for the last three years. I do have a side job. The side job doesn't bring me much money. It's more to keep me out of trouble and to keep me busy. I've been called a super saver. I've saved for the last. I mean, big time. I've saved for the last 40 years. I'm a big believer in dividends, and I've saved over, over probably about $630,000 a year in dividends.
Jill Schlesinger
Wait, wait, wait, wait, wait. Are you kidding me?
Ed
No, I am.
Mark
Holy smokes.
Jill Schlesinger
Wait a sec. What did you. So when you were working, you retired three years ago. Were you making piles of money your whole career?
Ed
I made a lot of money, but I'm making more money now. I have more income now in retirement than I did when I was working.
Jill Schlesinger
Wow. So the income that you let me do a few other things. Are you married, single? What do we got going on?
Ed
I am married and have two older.
Jill Schlesinger
Children that live out of state, and they're fine Right.
Ed
They're fine.
Jill Schlesinger
And your spouse work?
Ed
Yes, but mainly as like, just like I am not bringing a lot of money just to keep busy.
Jill Schlesinger
Okay, so between the two of you and your little side hustles, how much money comes in from that?
Ed
Both of us combined, probably 25,000.
Jill Schlesinger
Okay, and then now tell us about the other income that is coming to you from all those dividends. Cause I imagine we're talking about a non retirement account because it sounds like there's, like it's. It's coming in and it's taxable, right?
Ed
Correct.
Jill Schlesinger
Okay, so first of all, what. What is the amount of income that's being spun off? About.
Ed
About $630,000.
Jill Schlesinger
How much is the actual investment account? Mark's laughing. So what is the account? This. It's probably a joint account or whatever. But what. What is the account value?
Ed
Just under 10 million.
Jill Schlesinger
Oh, boy. Well, that'll do it for you. He made a pile of money, Mark. Do you think he's pulling our leg? I feel like he's telling the truth.
Ed
I believe him.
Jill Schlesinger
Yeah. Why lie? He's a lot of other things you could lie about. Who cares? So is this where most of your money is, or do you also have retirement account income?
Ed
I have a little bit in retirement. I have a little bit in an ira, which I have not touched. And I also have a. Roughly about a $200,000 annuity, which I have not touched either.
Jill Schlesinger
Okay. And I presume that you are not claiming Social Security yet, because why do that?
Ed
Correct.
Jill Schlesinger
All right, what are we doing? So you're taking all these dividends and you're not living large.
Mark
You're not, you're not spending it.
Jill Schlesinger
I mean, I feel like if you're a super saver, I don't think that you're the kind of person who's like, yeah, you know what I'm going to do? I'm going to spend 200 grand to that every. Like, what do you guys spend on an annual basis?
Ed
Well, my biggest expense right now is health insurance. No, I take that back. Excuse me, I take that back. My biggest expense is taxes.
Mark
Right.
Jill Schlesinger
Of course.
Ed
My tax bill is just under $90,000 a year.
Jill Schlesinger
Hello. What do you need to live on, though? Like, do the, like. Okay, here's not just my tax bill, but I'm saying, like, cost of living my life without the tax bill.
Ed
Without the tax bill, I need probably roughly a little over 100,000.
Jill Schlesinger
Okay. The dividends that are being generated, are those dividends from individual stock holdings or are they from funds Mutual funds or exchange traded funds, individual stocks. So I presume that a lot of those individual stocks have very low cost basis, is that right?
Ed
Correct.
Jill Schlesinger
Does it really matter? You have piles of money, you're never going to spend it all. So what's the actual problem here? Is it like, oh my God, I have all this income and I don't really need it and what should I do with it? Should we, should we be thinking about doing some like aggressive gifting to your kids?
Ed
Well, I already, I already do that. I give each, each of my boys get about $15,000 a year from, from that 630. But my big question to you is, for the last 20 years I've been reinvesting my, the unspent dividends to create more income.
Jill Schlesinger
You can't help yourself. Geez Louise.
Ed
My question, my question is do I stop doing that and just save it or do I keep on reinvesting it and making it grow and grow and just give my sons a bigger inheritance?
Jill Schlesinger
Are they good kids? They like manage money. How old are they? I don't want to go crazy.
Ed
I got a start. But yes, I got a 30 year old and a 33 year old.
Mark
Married, single.
Jill Schlesinger
Are they any grandkids yet?
Ed
Not yet. The 30 year old lives in Nashville, he is married and the 33 year old lives in Fort Lauderdale and he is not married, but they are good kids.
Jill Schlesinger
Okay, so my next question is, and please, you know, you can answer truthfully, like do you, are you charitably inclined? Do you think about like I give, I'd like to give some money away to non family.
Ed
My wife gives a little bit to, to our church. But we could do more. I mean we could do a lot more. Currently we give about maybe 6,000 to our church.
Jill Schlesinger
So this is one of those crazy. First of all, you're going to get us all sorts of hate mail. Mark, we need a specific sounder for the hate mail that's about to come in. Right?
Mark
No hating from me.
No hate. This is amazing.
Jill Schlesinger
Okay, so a few things to consider and again, a lot of this is, I understand everyone listening, that this is one of those crazy situations that is like out of touch for most of us. Okay. But we're really trying to figure out when you have this big corpus, this big account that's driving so much income, what to do with it. So there's a few things to consider. One is that because this is low basis stock, if you were to just sell it, you'd get killed in taxes, right?
Ed
Correct.
Jill Schlesinger
Okay, so have you Heard the of something called a donor advised fund. Have you ever heard of that term?
Ed
No, I have not.
Jill Schlesinger
Okay, you're going to like this. So one thing that you can do is there is a way to set up a fund that is basically a charitable giving fund without. I'm not saying you should create some huge family foundation. This is literally like going to Vanguard or Fidelity or T. Rowe Price or wherever you have your money and saying, I want to open up an account. Do you manage all the money yourself, by the way?
Ed
Yes, I do.
Jill Schlesinger
Okay, so do you mind me asking where it's held?
Ed
It's all in Schwab.
Jill Schlesinger
Okay, great. Schwab has one also. So Schwab will have something called a donor advised fund. And the way it works is the government allows you to take a very big tax deduction today for whatever money you put into this fund. Okay, so I'm just going to make up some, some numbers here. Let's say that you were like, oh.
Mark
Jill, I bought Apple stock.
Jill Schlesinger
You know, and it has, you know, it's. I bought it for $10,000, and right now it's worth a half a million dollars, just for sake of argument. Right? So you know that if you sold that position now, you'd have a long term capital gain of $490,000, and you wouldn't want to take that gain. Right? But what you could do is you could say, I'm going to gift my Apple stock that $500,000 position. I'm going to push that into something called a donor advised fund. I'll open it up at Schwab and I will immediately get a $500,000 charitable deduction for this year. So we're in 2025. You get like right off the bat you're going to say, wow, I have a huge tax deduction. I made a charitable contribution, a half a million dollars. Now the money that goes into the donor advised fund, it does not go in as Apple stock. It goes in as Apple stock. They just sell it immediately, but that's it. There's no tax due on that.
Mark
When that money comes into the donor.
Jill Schlesinger
Advised fund, you can actually start investing it. Not in individual stocks, but, you know, some funds. And then you have a half a million dollars which you can then dribble out and give away. You could give it to your church. You could give it to, you know.
Mark
If you're worried about the LA fires.
Jill Schlesinger
You say, I'm going to give a bunch of money to the American Red Cross. I'm going to give some money to The California Fire foundation, whatever it is. But you don't have to do it all in one year. You have to give enough away that it's usually about, you know, you don't have to. But I think that the IRS is going to ultimately say you have to give 5% of it away a year, but you have to give a little bit of it away every year. And you've got that money and you get this big fat deduction. So you might say, hey, you know what, I want to give more to the church. I want to give, you know, 25 grand a year to the church. You can do it from the donor advised fund. And the cool thing is that the year that you make that contribution, you will get that tax deduction. So it's just that in the future years, you don't get to write off like what you're doing now is like six grand a year. Right. But you don't get that in the future. Anything that's gifted out of that donor advised fund, you don't take a deduction for. You take it all in on the way in for whatever goes into that account.
Ed
I can't carry it forward.
Jill Schlesinger
You can, you absolutely can. You can carry it forward for years. You don't have to give it all away in the year. It's just that you only get the tax deduction for that lump sum that goes in, in that first year. That's your tax deduction. It's cool.
Ed
It is. I've never heard of it. It's cool.
Jill Schlesinger
It's so a donor advised fund. The other thing I would suggest is, you know, if you have, you got, it sounds like you have good kids, right? You and your wife probably should give, give away a little bit more money to them. One thing that you could. Are they in a low tax bracket? The kids?
Ed
Yes.
Jill Schlesinger
Okay, so another idea is if you're writing a check for 15 grand, I would stop doing that. I would say you and your wife can give $18,000 a year to each kid. So you guys can give $36,000 a year to each kid. It's like basically it's kind of considered like a marital gift. Right. I would take $36,000 of some low basis stock and gift it to the kids. And either they can keep it or they can sell it, but they're going to sell it. The capital gain goes with the gift. But they're in such a low tax bracket, we might be able to have them make the transaction that you like. Let's say in my scenario of Apple stock Right. You give them something that you bought for a few thousand dollars and now it's $36,000. If they have that 30 or $40,000 gain, they can just sell it and it's taxed at their long term capital gains rate, which will definitely be lower than yours.
Ed
Okay.
Jill Schlesinger
Now, so that's another thing. I don't know. Mark, would you reinvest these dividends? At this point, I kind of feel like. Nah, let's try to. Let's try to maybe use those dividends and reallocate. Maybe it's time for us to start looking at some municipal bond funds for you because your tax bracket's so wacky.
Mark
Yeah. I mean, that's one aspect. Or like he said, you know, they don't need the money. Just let it continue to grow for the kids. You know, they'll eventually get a step up in cost basis when they inherit all this.
Jill Schlesinger
Yeah, but he's young.
Mark
I know he's a long ways to go.
Jill Schlesinger
I mean, you guys are in good health.
Ed
Yes.
Jill Schlesinger
Yeah. I'd be looking at trying to doing a little like. I would look for a little tax arbitrage right now. Meaning I would love it if the.
Mark
Kids can do some of the selling.
Jill Schlesinger
On your behalf every year. Not going to be huge. And I would love it if in that joint account that you have that, you know, eight figure income amount is there. Is it all stocks?
Ed
It's all stock. All. It's roughly about 22 individual stocks.
Jill Schlesinger
Did you. Were you in the business?
Ed
No, my father, who I learned a lot from, was also a big believer in dividends because of the low tax rate at 15% instead of paying this, you know, standard. Standard rate.
Jill Schlesinger
Yeah.
Ed
And I've just been pouring money into dividends and reinvesting it and re. And it's all big, big corporate corporations.
Jill Schlesinger
Right. It's not some fly by night.
Ed
We're talking like, like Merck and Verizon and, you know, Chevron, those kind of companies.
Jill Schlesinger
So what I think I might do is maybe you talk to someone at Schwab or maybe you just look for an Pennsylvania tax exempt bond fund. Might be someplace to throw some money. I mean, look, this is all like a silly problem. It's not even a problem. Right. You are in such incredible shape. All we're doing is we're not even dotting an eye. It's just like, we're like just waving a little fairy dust over this situation where you've already created so much wealth. I would just think about those couple of things. Have you guys Done estate planning yet?
Ed
We have an estate plan. The only thing I'm thinking about also doing, which I also wanted to talk to you about. I like the, I like the donor. The donor fund.
Jill Schlesinger
Yep. Donor advised fund.
Ed
I'm also thinking about getting a second to die policy to pay all the taxes on all this money once my wife or I die.
Jill Schlesinger
So my kids, I mean, here's what. But here's one thing. If you look at your total net worth, we just talked about your portfolio and you've got some other stuff here. You have, have a house. Do you have only one house or do you have a couple of houses?
Ed
Just one house and it's all paid off.
Jill Schlesinger
Okay, so do you guys have an estate together that's less than $13.6 million?
Ed
It's getting close. It's getting pretty close. It's about just over 12 million right now.
Jill Schlesinger
I mean, the only thing is you do have that. You have a weird situation in Pennsylvania because you have a state death tax. That's not great. If you've got a desire to push some money either into a donor advised fund to keep gifting some money, I have a feeling maybe you'll have some grandkids. You could Pre fund a 529 plan for those kids. You can put, you know, you can get money out of your estate and I think that will keep you under the estate tax exemption. So I don't think I would do unless like, if you had like a $25 million estate, then maybe I would say, yeah, maybe we think about a second to do die.
Ed
So what's the threshold amount?
Jill Schlesinger
It's 13,610,000 for 20. That was 24. I don't know what the, the new one is. And, but that's per person. You know, you can certainly talk to someone about it, but I wouldn't spend the money on a second to die policy for you. I really wouldn't.
Ed
Okay.
Jill Schlesinger
All right.
Ed
I'm glad I asked.
Jill Schlesinger
I saved so much money for you guys. Wow. Ed from Philly, wish you the very best and thank you so much for joining us today. What a crazy situation, huh, Mark? Like, I don't know if we've ever had. I mean, we've had people with a lot of money. Very rarely do we have people who come on and we're talking about like, I'm creating $600,000 of dividend income, taxable income. So if that's a problem that you have. But maybe it's not 600,000. Maybe it's 6,000, which is highly likely as opposed to 600,000 highly unlikely. Give us a Holler. Go to jillonmoney.com click the contact us button right and write us a note if you'd like to join us live. Mark will do everything else. You just have to check that box. And all of our content lives on the jillonmoney.com website. So you can see that we have another podcast, we have blogs, we've got resources all there for you. All right, you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review. Wherever you need listen and of course, lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. Real Estate.
Mark
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Ben Stiller
Hey, I'm Ben Stiller.
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I'm Adam Scott and we make a.
Ben Stiller
TV show called Severance. On January 17th, Severance is back for season two on Apple TV and we can't wait for you guys to see it.
Adam Scott
And before the premiere, Ben and I are going to be binging season one and putting out daily recap podcasts.
Ben Stiller
Yep, each weekday beginning January 7th, we'll be dropping an episode featuring exclusive behind the scenes tidbits and brilliant insights from our cast and crew and us, Patricia.
Adam Scott
Arquette, Britt Lauer, Zach Cherry, John Turturro, the list goes on.
Ben Stiller
All your favorite Lumen employees, their friends, families, enemies in your feed every single weekday.
Adam Scott
And here's the best part. After that, we're going to keep going. Tune in weekly as we recap Every episode of season two, the podcast drops on the same day the episode comes out.
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It's the Severance podcast with Ben and.
Adam Scott
Adam on Apple Podcasts, the Odyssey app, or wherever you get your podcasts.
Managing Massive Dividend Income: A Comprehensive Overview
In the January 23, 2025 episode of "Jill on Money with Jill Schlesinger", host Jill Schlesinger, CFP®, delves into the intricate challenges and strategic solutions surrounding substantial dividend income. This episode, titled "Managing Massive Dividend Income," features a compelling listener call-in from Ed, a retired individual grappling with the implications of significant dividend earnings. Below is a detailed summary capturing the essential discussions, insights, and conclusions presented during the episode.
Timestamp: [03:34]
The episode begins with Jill welcoming Ed from Philadelphia, a listener who presents an extraordinary financial scenario. Ed reveals that at 64 years old, he has accumulated a near $10 million investment portfolio, which generates approximately $630,000 annually in dividends. This amount surpasses his combined retirement and side job income, raising pertinent questions about tax implications and wealth management.
Notable Quote:
Jill Schlesinger [05:07]: "Wow. So the income that you let me do a few other things. Are you married, single? What do we got going on?"
Timestamp: [04:15] – [06:15]
Jill probes into Ed's financial structure, uncovering that aside from his substantial dividend income, Ed and his spouse earn an additional $25,000 annually from side jobs. Ed maintains minimal retirement accounts, including an IRA and a $200,000 annuity, and has not yet claimed Social Security benefits. The primary financial burden stems from taxes, with an annual tax bill of nearly $90,000.
Notable Quotes:
Ed [04:15]: "I've been called a super saver. I've saved for the last 40 years. I'm a big believer in dividends, and I've saved over, over probably about $630,000 a year in dividends."
Jill Schlesinger [07:21]: "So what are you doing? So you're taking all these dividends and you're not living large."
Timestamp: [07:38] – [09:08]
The conversation shifts to the tax consequences of Ed's dividend income. Jill emphasizes the substantial tax liability posed by selling high-basis stocks to generate needed income, highlighting the inefficiency of this approach. Instead, she introduces the concept of Donor-Advised Funds (DAFs) as a strategic tool to mitigate tax burdens while fulfilling charitable intentions.
Notable Quotes:
Jill Schlesinger [10:31]: "Okay, so have you Heard the of something called a donor advised fund. Have you ever heard of that term?"
Jill Schlesinger [11:07]: "So Schwab will have something called a donor advised fund. And the way it works is the government allows you to take a very big tax deduction today for whatever money you put into this fund."
Timestamp: [11:06] – [15:29]
Jill provides a detailed explanation of how DAFs operate, using a hypothetical example to illustrate the tax advantages. By contributing appreciated stocks to a DAF, Ed can receive a significant charitable deduction without incurring capital gains taxes. Additionally, Jill suggests reallocating dividends into tax-efficient investments, such as municipal bond funds, to further reduce tax liabilities.
She also discusses gifting strategies, recommending that Ed and his spouse increase annual gifts to their children. By transferring appreciated low-basis stocks to their 30 and 33-year-old sons, who are in lower tax brackets, they can minimize overall tax burdens while providing their children with opportunities to grow the inherited assets.
Notable Quotes:
Jill Schlesinger [12:35]: "So you could say, I'm going to gift my Apple stock that $500,000 position. I'm going to push that into something called a donor advised fund. I'll open it up at Schwab and I will immediately get a $500,000 charitable deduction for this year."
Jill Schlesinger [14:27]: "Another idea is if you're writing a check for 15 grand, I would stop doing that. I would say you and your wife can give $18,000 a year to each kid. So you guys can give $36,000 a year to each kid."
Timestamp: [17:00] – [19:28]
The episode further explores estate planning strategies to ensure the longevity and efficient transfer of wealth. Jill advises on pre-funding 529 plans for potential grandchildren and discusses the viability of second-to-die insurance policies. However, she cautions against unnecessary expenditures on such policies unless the estate significantly exceeds the exemption threshold.
Ed mentions having an estate plan totaling just over $12 million and considers a second-to-die policy to cover potential Pennsylvania state death taxes. Jill assesses that Ed is approaching the estate tax exemption limit and suggests leveraging DAFs and gifting strategies to remain within tax-advantaged boundaries.
Notable Quotes:
Jill Schlesinger [17:41]: "Do you have an estate together that's less than $13.6 million?"
Jill Schlesinger [19:09]: "It's the Donor Advised Fund. Another thing I would suggest is, you know, if you have, you got, it sounds like you have good kids, right? You and your wife probably should give, give away a little bit more money to them."
Timestamp: [19:28] – [20:45]
In wrapping up the discussion, Jill commends Ed for his impressive financial management and reiterates the importance of strategic planning in managing massive dividend income. She encourages listeners in similar situations to consider tax-efficient strategies, philanthropic endeavors, and thoughtful estate planning to optimize their financial well-being.
Ed expresses appreciation for the insights, acknowledging the unconventional yet commendable nature of his financial situation.
Notable Quote:
Jill Schlesinger [20:00]: "What we're really doing is we're not even dotting an eye. It's just like, we're like just waving a little fairy dust over this situation where you've already created so much wealth."
Donor-Advised Funds (DAFs): A powerful tool for reducing taxable income while supporting charitable causes. By contributing appreciated assets to a DAF, investors can receive immediate tax deductions without incurring capital gains taxes.
Gifting Strategies: Increasing annual gifts to family members in lower tax brackets can optimize tax efficiency and facilitate wealth transfer.
Tax-Efficient Investments: Allocating dividends into municipal bond funds or other tax-advantaged investments can help minimize tax liabilities.
Estate Planning: Proactive estate planning, including pre-funding education accounts and considering insurance policies, ensures the efficient transfer of wealth and adherence to tax exemptions.
Professional Guidance: Engaging with financial advisors and estate planners is crucial for navigating complex financial landscapes and implementing effective strategies.
Final Thoughts
This episode of "Jill on Money" underscores the significance of strategic financial planning, especially when dealing with substantial dividend income. Jill Schlesinger effectively navigates the complexities of tax implications, charitable giving, and estate planning, providing listeners with actionable insights to enhance their financial strategies.
For those facing similar financial scenarios or seeking personalized advice, Jill invites listeners to reach out via the jillonmoney.com website, encouraging engagement and further exploration of tailored financial solutions.
References: