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Jill Schlesinger
Real estate.
Mark Teo
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Jill Schlesinger
Welcome to the Jill on Money show. It's Thursday, January 16th and we are here trying to help you make better financial decisions. Or maybe just walk through what's going on in your financial life and lay out the different options that are available to you. If you've got a question, go to our website jillonmoney.com click the contact us.
Mark Teo
Button and write us a note. And if you'd like to join us live, check the box and Mark will do everything else.
Jill Schlesinger
While you're on the website, check out all the great content including Mark's bio where which is up there now. Mark, nice Job. Where did you get that picture done? Let's be honest now. You cannot. Don't. Don't make fun of this, but I'm just going to say that the picture of Mark, I don't know. It's not the best picture of you, man. I got to be honest.
Coco
Well, that's the only one. So there are no other options.
Jill Schlesinger
So why are you half in shape? You're like half in shadow?
Coco
I don't know. I didn't take the picture. You know. You know who took that picture is our old. Well, maybe he's still your current colleague at CBS radio. Remember good old Dwayne?
Jill Schlesinger
Oh, Dwayne is there. It looks like you haven't shaven. I don't know. It's like a very. It's not a great picture of you. I just want to say that. And so I would like you to think about potentially getting a new headshot. I'll pay for it. Maybe the next time Carrie Kehoe, photographer extraordinaire, is in town, I will send her to Brooklyn and there you go. Do that for you. I will do that. I would pay for it. This does not. It's not the best picture of you, man. It's just not the.
Mark Teo
The bio. Fantastic.
Jill Schlesinger
Mostly because I wrote it. I don't know. Everyone, let's. Let's give a little opinion on Mark's about section. Mark Teo, executive producer extraordinaire, king of all things Jill on money web. So, Mark, well done. It's only like a year late, but thank you.
Coco
The picture will be updated in two years.
Jill Schlesinger
Maybe by the end of this year. I might.
Mark Teo
Well, we.
Jill Schlesinger
We're going to have to figure that out. All right, gang, take a look at everything that lives on the website because right now we have to go and do some business. We are talking to Coco, who's on the line from Washington state. Hello, Coco.
Mark Teo
How are you?
Jill Schlesinger
What can we do for you?
Caller (Coco's Husband)
Oh, very good. Thank you so much for taking my call. I'm so excited.
Jill Schlesinger
So good. Yay. What's happening? How can we help you out?
Caller (Coco's Husband)
Yes. So I. Your age, Jill and I are same birth.
Jill Schlesinger
Oh, really?
Caller (Coco's Husband)
Maybe. And I have one husband.
Jill Schlesinger
Just one.
Caller (Coco's Husband)
Just one. One human child and two canine children.
Jill Schlesinger
What kind of canine children?
Caller (Coco's Husband)
One is a black lab and then the other is a weenie dog.
Jill Schlesinger
Oh, my God. A big and a little. It's so cute.
Caller (Coco's Husband)
One is a runner, the other one is a schooner.
Jill Schlesinger
I love it.
Mark Teo
I love it.
Jill Schlesinger
Okay, so how old's your husband?
Caller (Coco's Husband)
62.
Jill Schlesinger
And how old is the kid?
Caller (Coco's Husband)
Kid is high school.
Jill Schlesinger
Oh, okay. Later. A little bit of an older mom and dad, right?
Caller (Coco's Husband)
Maturing.
Jill Schlesinger
Okay, Maturing. Thank you. So what brings you to us? What's going on?
Caller (Coco's Husband)
So we both are not working. We. We. How do you say? Retired? Done working.
Jill Schlesinger
Okay. I like not working. Is also retired. I like that.
Caller (Coco's Husband)
And now you feel like it's a great time to start doing the Roth conversions because we, we just don't have income to claim for. So.
Mark Teo
Great.
Caller (Coco's Husband)
We have about 2 million in tax deferred. Both are roll over IRA. Roughly 1 million each under each name.
Jill Schlesinger
Okay.
Caller (Coco's Husband)
I'm just thinking how I could do the conversion with how much and what speed.
Jill Schlesinger
Okay, here's my question to you. You got this 2 million in retirement accounts that hasn't been taxed. What other money do you have?
Caller (Coco's Husband)
Good question. And I printed out my spreadsheet.
Mark Teo
Oh yes.
Jill Schlesinger
I love a woman with a spreadsheet. Very attractive.
Caller (Coco's Husband)
Sexy. Very sexy. Yep.
Jill Schlesinger
At least to me.
Caller (Coco's Husband)
At least to me too. Taxable? About 6 million.
Jill Schlesinger
6 million. The $6 million couple. Okay.
Caller (Coco's Husband)
And tax free or Roth. About half a million and another hundred thousand in hsa.
Jill Schlesinger
Okay, great. What about this high school kid? College bound.
Caller (Coco's Husband)
College bound. We send, set aside about 300,000 in 529.
Mark Teo
Great.
Caller (Coco's Husband)
Just in case.
Jill Schlesinger
Okay.
Caller (Coco's Husband)
All right.
Jill Schlesinger
That's great. House you were about to say is paid off?
Caller (Coco's Husband)
Yep, it's about a million. And we have another property in overseas which is about 200,000.
Jill Schlesinger
And you're going to keep both of these properties? No changes?
Caller (Coco's Husband)
No, no.
Jill Schlesinger
Oh, tell me more.
Caller (Coco's Husband)
We are selling that.
Jill Schlesinger
You're like the kids graduating. It's like the day after graduation. Houses on the market, basically.
Caller (Coco's Husband)
Correct, Correct.
Jill Schlesinger
What happens then?
Caller (Coco's Husband)
Think that we want to rent for a while and we want. I'm. I'm dreaming of tiny homes. That's my dream. I don't know if that dream you shared, but I am done with the ownership, to be honest.
Jill Schlesinger
It's a drag, isn't it?
Caller (Coco's Husband)
Drag. So I. I think we would be perfectly happy with renting and moving around.
Jill Schlesinger
Okay, that sounds great. Okay, so what is, what is the income currently? You're not working, so do either of you receive a pension?
Caller (Coco's Husband)
So my husband has a small pension. Doesn't start until 65, which is about 20,000 a year. So we're just kind of taking appreciated stock. Try to offload some of them and then just paying a capital gain, long term capital gain. So that's what we have done in the last couple of years to just.
Jill Schlesinger
Create cash flow for yourselves.
Caller (Coco's Husband)
Right. And Then we do hope that taxable about 300,000 is in cash, so we have cash flow.
Mark Teo
Oh, yeah.
Caller (Coco's Husband)
Another three to five years. Yeah.
Jill Schlesinger
So what three to five years, you spend like 100 grand a year or 80 or 100, what do you got?
Caller (Coco's Husband)
Somewhere between 75 and 80,000 a year.
Jill Schlesinger
Oh, my God. You don't spend any money.
Caller (Coco's Husband)
But we travel, so.
Jill Schlesinger
Okay, that's good. I'm game. Were you fully retired in 2024?
Caller (Coco's Husband)
Yes.
Jill Schlesinger
What do you think is the tax liability from the taxable account, that $6 million account, what does that throw off in terms of tax liability for you?
Caller (Coco's Husband)
So last year I sold a lot of stocks about up to 60,000 in capital gain. But that was just last year. I could be doing that.
Jill Schlesinger
But you pay. But wait a second. Just so I'm clear that would that keep you in a 0% capital gains rate for married filing jointly? Because isn't that, doesn't that go up to like 90 something thousand?
Caller (Coco's Husband)
Yes, except I did $100,000 conversions last year.
Jill Schlesinger
Oh, okay. Okay, okay. All right. So you're basically in the 22% tax bracket, right? Okay. And then, and then a 15% long term capital gains, right?
Caller (Coco's Husband)
Okay. Yeah. So I had looked into this financial planning tools to see if I can get some kind of idea as to how, how much I should shoot for in terms of conversion sort of picture. So I wanted to throw some ideas to you. Maybe you can tell me. This is, this is good.
Jill Schlesinger
All right, let's do it.
Mark Teo
Give me those ideas.
Jill Schlesinger
I love. I'm doing all the work for me, so I feel good about this. Hit me up, girl.
Caller (Coco's Husband)
Option one, convert steadily up to 22% tax. Block it however many years it takes.
Jill Schlesinger
22% for however long and get it done.
Mark Teo
Okay.
Caller (Coco's Husband)
Just the caveat is we're thinking my husband will start Social Security at 67. I would be 70. 70. So that would be about 40,000 a year for him, 48,000 for me, and then we have 20,000 a year pension. So.
Jill Schlesinger
Wait a minute, why are we starting at 67 for him?
Caller (Coco's Husband)
I don't know, maybe.
Jill Schlesinger
Well, I mean, it gives you a few more years before you've got that extra income. Is he in good health?
Caller (Coco's Husband)
Relatively speaking? Yes.
Jill Schlesinger
Yes, except I just heard him sneeze like a big time sneeze. Tell him he's messing up our recording. I'm just kidding. Okay, so 22% and do it for as long as it takes, which would take a while, obviously you probably wouldn't get there. I, I would imagine if the money.
Caller (Coco's Husband)
Is left in Ira. Don't worry about it. Just donate once.
Jill Schlesinger
Okay. RMD kicks in, right? That's a possibility. Also.
Caller (Coco's Husband)
And also I order, I, I opened donor advised fund.
Jill Schlesinger
Yeah.
Caller (Coco's Husband)
And I can put appreciated stock to push the block it up, so to speak. So yes, I put fifty thousand or a hundred thousand that just itemize it so that I would have a higher ceiling to get up to the conversions.
Jill Schlesinger
I love that. Okay, that's kind of. So what I'm thinking is to how much money did you guys make during your, your work lives? What was it? What was are you used to paying tax wise?
Caller (Coco's Husband)
I used to pay somewhere between 22 and we made about 350 to 400,000 a year.
Jill Schlesinger
All right, so you're 24% kind of people, right? Yeah.
Caller (Coco's Husband)
Yeah.
Jill Schlesinger
Okay, here's my idea. Let's see if you're, you're game for it.
Caller (Coco's Husband)
Yeah.
Jill Schlesinger
I think you convert up to the 24% bracket, which I don't have the new brackets yet, but it would allow you to make have earned income of 3, 383,000. Okay. And I would do that plus the gifting the low basis stock into a donor advised fund. I would do the combination of that and I would do it for as long as, you know, tax brackets and tax rules are as they are.
Caller (Coco's Husband)
Okay.
Jill Schlesinger
And I think that takes you, I mean you listen we can determine what would happen at age 67 if you guys really are desperate to like I really want some income from Social Security and your husband really wants to claim, you know, you could do that. However, you're in great shape and you know, financially we're just talking about you're going to have lots and lots of money and we just want to be smart about it. I think some combination of pulling more money out at the 24% bracket, using the low basis stock to put money into a donor advised fund, that 50 grand a year, that's going to get a lot of the work done for you.
Caller (Coco's Husband)
Right.
Jill Schlesinger
I'm just going to ask Mark to, to hop in here and see if he has any different opinion about this.
Coco
I was just going to say, I mean why not just pull it out instead of converting it? I mean they can pull it out now.
Jill Schlesinger
Either way would be fine. But it doesn't seem like they're going to have any need for real. They just don't have a lot of need for income right now.
Caller (Coco's Husband)
No, we have saved enough in a cash bucket so that we would continue. And then the, and then of course.
Jill Schlesinger
By the way, when your daughter Graduates. It was a daughter or a son. I don't remember what you said.
Caller (Coco's Husband)
Yeah.
Jill Schlesinger
Okay. When your daughter graduates, there's also going to be a million dollars of equity, but you're going to have higher expenses because of rent.
Coco
The 300,000 in cash. You're not thinking of using that to pay the taxes on any conversions, are you? That's more of like your living expenses, right?
Caller (Coco's Husband)
Living expenses, yes.
Coco
So if you do these conversions, you're gonna have to pull the cash from somewhere to pay the tax due. So you'd be pulling money out of the brokerage account, which is a taxable event. I would just take it from the ira and then you don't have to have the taxable event of freeing up money from the brokerage account.
Jill Schlesinger
But I don't think that there's. I don't think that. I think there's still going to be a compounding tax problem that is lining up for us. Well, let's just say this. What if you pulled out enough to live on and then at the same time use the money to pay the taxes that are due? Between the. What pulling out to live on and converting something up to the 24% bracket, that's I guess, what I would say.
Caller (Coco's Husband)
Right. And I have high concentration of some stocks that I would love to offload.
Jill Schlesinger
Well, then let's. Yeah, so let's do that. That's.
Caller (Coco's Husband)
That do to pay tax.
Jill Schlesinger
That makes sense to me. What's the. What's the cost of rent in your area for a tiny little house that we want for.
Caller (Coco's Husband)
I'm thinking somewhere between 2 and 3,000amonth.
Jill Schlesinger
That's it.
Caller (Coco's Husband)
Well, it's not Seattle downtown. It's a different part of Washington state.
Jill Schlesinger
Okay.
Caller (Coco's Husband)
Yeah.
Jill Schlesinger
All right. Okay. It's such a great problem to have.
Coco
Lucky kid.
Jill Schlesinger
Yeah. Is this a good kid? Is a kid gonna go to a good school going to like Washington State? What do you think?
Caller (Coco's Husband)
I don't know. She likes to. I'm leaving up to her to. To just make sure that she. She doesn't mess with. Mess up with it. But the thought behind this, creating this Roth conversion, is that would be for her to inherit.
Jill Schlesinger
And then I know it's much better to inherit a Roth asset than any other asset.
Caller (Coco's Husband)
Yes. I feel like I'm going to give it to charities.
Jill Schlesinger
Well, that's very nice of you. I love this. I think it's a great game plan. Mark, are you mad for the daughter? Poor daughter, she's not going to get all the money. Are you mad?
Caller (Coco's Husband)
You have to have A skin in the game, right?
Jill Schlesinger
Yeah. Mark just can't give the kid everything.
Caller (Coco's Husband)
True.
Jill Schlesinger
I was with Mark's son over the weekend and he is just absolutely adorable. I would completely roll over and give him everything. I got to be honest with you. It's a good thing I'm not a parent. It'd be very bad. I think you're in great shape, Coco.
Mark Teo
Do you have your estate documents done?
Caller (Coco's Husband)
Yes.
Jill Schlesinger
All right, well, you got a lot of money. Everyone's going to be able to be fine. I like some com, some combination of converting, pulling money out using the donor advised fund all up into the 24% bracket. If for some reason five years from now, we're like, oh, change in administration, taxes are going up, we might have give us a holler back, you know, we'll have to figure out what happens next. But for today, I love this game plan. It's a wonderful problem to have and you know that. But you're in great shape. So I think unless there's anything else on your mind, I would go ahead and start running your spreadsheets at the 24% bracket. Yes, a donor advised fund for sure will really, really help that low basis stock situation.
Caller (Coco's Husband)
That's good. And just the one word, that decumulation is much harder than I. I can't.
Jill Schlesinger
Wait to have that problem. I'm not going to have a problem with this. I'm going to tell you that right now. Oh, you know why? Because you guys are all teaching me about how nice it is to be lucky enough to be like, oh, I'm worried about decumulation. I'm not going to worry about this.
Caller (Coco's Husband)
You will have that problem too, Jill.
Jill Schlesinger
You think?
Caller (Coco's Husband)
I think so.
Jill Schlesinger
And Mark's like. Mark says to me over the weekend, he's like, oh, you gotta work for 10 more years. So I get home and my wife says to me, you're not working for.
Mark Teo
10 more years, are you?
Jill Schlesinger
You better make sure that Mark knows that you're not working for 10 more years. So literally, he said this to me and she said this to me. And I'm like, he knows that. He's just teasing. And she goes, I didn't hear teasing in his voice. So Mark, I'm on the record here with everybody. You're not getting 10 years. According to Jackie, I got to worry about my decumulation phase, remember?
Caller (Coco's Husband)
Yeah, it's just a different mental game, I feel.
Jill Schlesinger
Yeah, I know, I know.
Caller (Coco's Husband)
But not to get anxious as I think I'm working best. Try not to get.
Jill Schlesinger
Yeah. You know how I. I diffuse anxiety about money in the way that you do, which is I create a spreadsheet. I look at different scenarios. Hey, what would happen if I pulled out this much money? What would happen if this much money? And that gives me a lot of peace because I think when I understand, like I trust the numbers, it doesn't mean they work a hundred percent of the time, but I do generally trust the numbers. So I feel like that is a good way to try to help yourself take a little control and feel better about these transitions. So congratulations on getting there. I look forward to being as smart as you, Coco. Although, Mark, let me be clear about the difference between me and Coco. While she has a problem with decumulation, wait until she sees if I sent her my spreadsheet on my monthly spend.
Coco
Ha.
Jill Schlesinger
It would not be what she's looking at. So I have to keep working a little bit longer because I have a little bit of a larger monthly spend. Thank you for getting in touch with us. Hey, if you're running through your financial priorities and you're just getting stuck somewhere, maybe you don't have to have as much as Coco and her husband.
Mark Teo
They're really in great shape.
Jill Schlesinger
But maybe you have the similar kind of idea, like maybe I should get some of my money out of this traditional retirement environment. How can I do that without blowing up my taxes? Maybe you're working for a single company and you have a very low basis stock. All of these things can really come together in those years before you claim Social Security. So give us a Holler. Go to jillonmoney.com, click the contact us button, write us a note and check the box. If you'd be willing to come on the air, don't forget to sign up for the free weekly newsletter comes out every single Friday. You can subscribe to us on the Odysee app or wherever you find your favorite podcasts. And don't forget to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. Real estate.
Mark Teo
It's been a cornerstone of wealth building for generations, but it's also often a major headache for investors. 3:00am Maintenance calls, tenant disputes, property taxes. Enter the fundrise flagship real estate fund, a $1.1 billion real estate portfolio built for you. We're Talking more than 4,000 single family homes in thriving Sunbelt communities, 3.3 million square feet of in demand industrial facilities, all professionally managed by an experienced team. With the flagship fund, you're tapping into real estate's most attractive qualities Long term appreciation potential a hedge against inflation diversification beyond the stock market Check, check, check. All without complex paperwork, massive down payments or soul sucking landlord duties. Visit fundrise.comjillonmoney to explore the portfolio. Check out historical returns and see just how easy it can be to add real estate to your investing strategy. Carefully consider the investment objectives, risks, charges and expenses of the Fundrise Flagship fund before investing. This and other information can be found in the Fund's prospectus@fundrise.com Flagship this is.
Jill Schlesinger
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Podcast: Jill on Money with Jill Schlesinger
Host: Jill Schlesinger, CFP®
Guest: Mark Teo, Executive Producer
Release Date: January 16, 2025
Episode Topic: Strategies for Roth Conversions – Determining the Appropriate Amount and Pace
In this insightful episode, Jill Schlesinger delves into the complex world of Roth conversions, addressing the critical questions of "How Much?" and "How Fast?" to convert traditional retirement accounts into Roth IRAs. Joined by her executive producer, Mark Teo, Jill navigates the intricacies of tax implications, financial planning, and strategic decision-making to help listeners optimize their retirement savings.
The episode features a detailed consultation with a listener, Coco’s Husband, who presents a comprehensive financial scenario:
Key Concerns: Coco’s Husband is considering initiating Roth conversions due to a lack of current income and seeks guidance on the optimal amount and conversion rate to minimize tax liabilities while ensuring financial stability.
1. Assessing Tax Brackets and Conversion Amounts Jill begins by evaluating the listener’s tax situation, noting that with an annual capital gain of $60,000 and previous conversions, the couple is likely in the 22% tax bracket.
Jill Schlesinger [09:17]: "But you pay. But wait a second. Just so I'm clear that would keep you in a 0% capital gains rate for married filing jointly? Because isn't that, doesn't that go up to like 90 something thousand?"
Recognizing the goal to stay within a favorable tax bracket, Jill proposes converting funds up to the 24% tax bracket. This approach allows the couple to convert significant amounts each year without crossing into higher tax brackets.
2. Leveraging Donor-Advised Funds To mitigate the tax impact further, Jill suggests utilizing donor-advised funds (DAFs):
Jill Schlesinger [12:11]: "I think you convert up to the 24% bracket, which I don't have the new brackets yet, but it would allow you to make have earned income of 3, 383,000. Okay. And I would do that plus the gifting the low basis stock into a donor advised fund."
By donating appreciated low-basis stocks to a DAF, the couple can both reduce their taxable income and create additional room for Roth conversions, effectively lowering their overall tax burden.
3. Managing Required Minimum Distributions (RMDs) Jill highlights the importance of considering future RMDs, which could impact the couple’s tax situation:
Jill Schlesinger [12:40]: "Requires some planning around RMDs kicks in, right? That's a possibility. Also."
Strategic Roth conversions can help manage RMDs by reducing the size of traditional IRAs over time, thereby decreasing the mandatory withdrawals that are subject to income tax.
The discussion further explores balancing the couple’s retirement income needs with tax-efficient strategies:
Living Expenses vs. Taxes: Ensuring that the couple has sufficient cash flow ($300,000 in taxable accounts and annual expenses of ~$80,000) to cover living expenses without needing to tap into converted Roth funds for tax payments.
Estate Planning: Emphasizing the benefits of Roth IRAs in estate planning, as Roth assets are typically more advantageous for heirs due to their tax-free growth and distributions.
Jill Schlesinger [15:17]: "Is this a good kid? Is a kid gonna go to a good school going to like Washington State? What do you think?"
The goal is to create a sustainable and tax-efficient financial plan that secures the couple’s legacy while minimizing tax liabilities.
Jill synthesizes the conversation into actionable steps:
Jill Schlesinger [17:24]: "I create a spreadsheet. I look at different scenarios. Hey, what would happen if I pulled out this much money? What would happen if I pulled out this much money. And that gives me a lot of peace because I think when I understand, like I trust the numbers, it doesn't mean they work a hundred percent of the time, but I do generally trust the numbers."
Jill underscores the importance of detailed financial planning and forecasting to navigate the complexities of Roth conversions effectively.
In wrapping up, Jill encourages listeners facing similar financial scenarios to reach out for personalized advice:
Jill Schlesinger [19:31]: "But maybe you have the similar kind of idea, like maybe I should get some of my money out of this traditional retirement environment. How can I do that without blowing up my taxes?"
By leveraging expert strategies and personalized planning, listeners can make informed decisions to optimize their retirement savings through Roth conversions.
Notable Quotes:
Jill Schlesinger [09:17]: "But you pay. But wait a second. Just so I'm clear that would keep you in a 0% capital gains rate for married filing jointly? Because isn't that, doesn't that go up to like 90 something thousand?"
Jill Schlesinger [12:11]: "I think you convert up to the 24% bracket, which I don't have the new brackets yet, but it would allow you to make have earned income of 3, 383,000. Okay. And I would do that plus the gifting the low basis stock into a donor advised fund."
Jill Schlesinger [17:24]: "I create a spreadsheet. I look at different scenarios. Hey, what would happen if I pulled out this much money? What would happen if I pulled out this much money. And that gives me a lot of peace because I think when I understand, like I trust the numbers, it doesn't mean they work a hundred percent of the time, but I do generally trust the numbers."
For personalized financial advice and to explore strategies tailored to your situation, visit jillonmoney.com and reach out through the contact form.