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Jill
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Mark
Welcome to the Jill On Money Show. It's Monday, October 13th and we are here trying to help you make better. It's sometimes less bad financial decisions now may not even be a decision that's going on. Maybe there is something in the ether of your life that impacts your money and you need a little guidance. You need a little, I don't know, coaching, mentoring, something like that if that's what is going on in your life. Mark and I are both certified financial planners and we would love to assist you in any way that you think we can help you out. So if something's going on, all you need to do is go to our website jillonmoney.com I know that so many of you have bookmarked it. Continue to bookmark it please. And in the upper right hand corner there is a Contact Us button. Click it. Write us a note. If you want to give us a lot of information because you're fraidy cats of coming on the air, no sweat, give us a lot of information. If, however, you would like to join us live, you don't have to go crazy. Just say, you know, give us the basic outline and Mark will Arrange to get you on the air. If you check that little box while you're on the website, don't forget to sign up for the free weekly newsletter. Comes out every Friday. It's such a great way to warm up for the weekend. You might have missed some stories. Check it out. Okay. Right now, let's go to Lisa, who listens to us in North Carolina. Hi, Lisa. How are you? Hi, Jill. How are you? Great. What's happening, girl?
Lisa
Just wanted to do a checkup to see if we're on track for some of our goals and to see if we can simplify life a little bit.
Mark
Do you think that maybe I should change our job descriptions, Lisa, to the primary care physicians for your finances? Nah, it doesn't. Sorry. But it's kind of what we're doing. Right. So tell us what's up. How old are you and what's happening?
Lisa
I'm 40 and my husband is 40. 40 as well. We've got three children, oldest being 11, youngest being 5.
Mark
Okay.
Lisa
And my husband works full time. I have a lot of side projects. We'll call it. We'll get into those.
Mark
Okay.
Lisa
Do you want to start with retirement.
Mark
Accounts or I want to know, first of all, how are you feeling right now? Like, let's just give the. Like, are you anxious about something? Are you feeling okay? Like, where are. Where's your head right now, before we dive in?
Lisa
Yeah, I'm feeling good financially.
Mark
Okay.
Lisa
I feel like we might be more complicated than we need to be at this moment.
Mark
Oh, I don't like complications. We like simplicity. Let's make it easier. Okay. So you're. Are you work. When you said you've got some side stuff, are you working and making money? Or are you primary caretaker for the kids and doing fun things like, what's happening? Are you earning money?
Lisa
But yes, both.
Mark
Okay. And so together, how much do you guys earn?
Lisa
I'm going to stick with saying that I make nothing, but that's not the case. But let's. Okay, pretend that for the beginning.
Mark
Okay.
Lisa
So my husband's the primary breadwinner in the family. He has. I think it's a little over 200, but let's just say a $200,000 base salary and he's at 50,000 in bonuses that might have gone up to 75 recently, but we haven't seen that play out yet. So let's just go with 50.
Mark
So. But. And that's been consistent. In other words, you're consistently seeing $250,000 of income, right?
Lisa
Yes, Correct.
Mark
Okay, great. Is he maxing out his retirement plan through work?
Lisa
He is.
Mark
Okay, great. And how much is in there?
Lisa
We've got between him and I combined in retirement accounts, we have 791,000.
Mark
Yowza. That's a lot. And it's all pre tax.
Lisa
130 is Roth. We're only doing Roth from this point forward. I think that's been a couple years.
Mark
Okay.
Lisa
And661 is traditional.
Mark
Incredible. That's great. Amazing. Is that it for your retirement savings, or do you have other retirement savings beyond that? 791 total.
Lisa
Are we talking about brokerage?
Mark
Yeah, give me whatever you got.
Lisa
Brokerage. We have 197,000 and savings. Just emergency high yield is 132.
Mark
Great.
Lisa
And we have an inherited IRA of 235,000.
Mark
Ooh, when did that person pass away?
Lisa
Three years ago. So we have seven years left.
Mark
Okay. Have you taken any money out yet?
Lisa
We already did 100,000 a couple years ago.
Mark
Okay, and what's the game plan for that? Do you want to draw, dribble it out?
Lisa
Have a game plan. And we need.
Mark
Okay, okay, so that's it for the. The money. What about the savings for kids? You got three kids, 529 plans, or any other money saved for them?
Lisa
Each kid we were hoping to have about $130,000 for in state tuitions. Roughly about 25 to 30 a year with housing. So that would give them their four years undergrad.
Mark
And what do you have now?
Lisa
They're all on track. If you look at the interest, like the potential growth from. They're all right. On track to be fully funded.
Mark
Great. Do you guys own a home?
Lisa
Three houses.
Mark
Oh, let's talk. Let's talk about the one you live in right now. What's that. What's that worth?
Lisa
That's worth 850.
Mark
Is there a mortgage outstanding?
Lisa
Yes. 250.
Mark
Is it at a reasonable interest rate?
Lisa
3.25.
Mark
That would be very reasonable to me. What about you? I think that's a good one.
Lisa
I like that one.
Mark
You like that one. Okay, now tell me about the other two. Are they vacation or are they rental properties or both?
Lisa
Both vacation rentals.
Mark
Okay, so what's the second one worth?
Lisa
So 330,000. And the mortgage on that is 125,000. And what's the 3.5?
Mark
3.5. Okay, third, tell me about that one.
Lisa
Yep, that one's 850,000.
Mark
Oh, okay. Mortgage?
Lisa
625.
Mark
Oh, yeah. Okay. What's the rate on that?
Lisa
7.25.
Mark
What, what would you. You know what? You had it so good, you really had to push it, didn't you?
Lisa
Yeah, you bought that one at the wrong time. The first one, cash flow is about $20,000 a year, and the second one breaks even, but we use that one.
Mark
A lot, so that's the one. When you think about your lives, you look at your primary, you're like, we love that house. And that's the third one. The $850,000 vacation. That's really the one you love? Yes.
Lisa
I don't love. Like I would be fine selling it, but the market where it is is not great.
Mark
So even not right now.
Lisa
Right. I think at this point we need to hold it.
Mark
Okay.
Lisa
For a little while. Enjoy it.
Mark
Okay.
Lisa
I mean, if we could refinance it, it's not gonna break even anymore. That would be a profitable house. So, I mean, sure. Kind of feels like maybe a short term pain.
Mark
Maybe. We'll see. Okay, this is all very interesting. When you look at your. Your lives, it's. You have a complication because you have three dwellings and you have three. Is there any other threesome that I need to know about that complicates your life further? Are there three other things going on in your life?
Lisa
There's two businesses.
Mark
Oh, come on. All right, tell me about two businesses.
Lisa
So the first business I purchased a couple years ago and that I probably make about $30,000 a year off of. What that does allow me to do, though, is potentially have my children putting money aside in Roth iras, which is something that's very intriguing to me because it's a business that they can work in. The oldest child actually does legitimately contribute in that business. And that's been something that's kind of.
Mark
Is this a very fancy lemonade stand that you've created?
Lisa
Don't tell me she was capable of doing a good amount of the work. And that business.
Mark
Okay. All right. So this is why you love this idea. Do you like the business itself?
Lisa
No, I feel as though it has taken away a lot of time for us.
Mark
Well, also because you're putting your children into forced labor.
Lisa
Yeah, that too.
Mark
You know. So besides that, what's the second business?
Lisa
The second business just started in July. That one still too early to really see any progression how this play out. But that one stands a strong chance of probably. I'm a partner on that one. That one stands a strong chance of probably me bringing home about 100k a year. Oh, going.
Mark
That's more interesting to me.
Lisa
Yeah. So that one I Have no plans on dropping out of that. But the first one, I just don't know if it's worth it.
Mark
Let me tell you something. To put money away for your kids Roth, I would say no way. Not even close. That. That is like the farthest thing from my mind right now.
Lisa
Okay.
Mark
Okay. So like, you know, if you want to put more money away for your kids, then put an extra $7,000 into their 529 accounts. But I would absolutely could not care less about that as an upside. Unless you're like, I love it. And you know what another upside is? In addition to loving it, I can put this money away. But other than that, if it's like this feels like a drain on my time and energy and you're looking to streamline some of your real life, that is like a goodbye and get your money out and move on.
Lisa
So let's say I sell that for maybe 175.
Mark
Wow.
Lisa
What would I do with that money?
Mark
Well, we're going to have a party, obviously, in your vacation home. Okay. So there's a couple of opportunities here. So one is that you can say, let me just take some of this money and put it into the 529s right now and get these plans up to date. And then you'll, you don't even have to pay it out of cash flow. You'll just say, like, I'll have all the money I need. Right.
Lisa
We already have that fully funded by the time. Like, it's funded to the point where it should grow to that amount.
Mark
All right? So over overfund it and later on you can move $35,000 into that, into that Roth that you Mark.
I was, I was totally going there with it. Like, you know, because the rule on the 529 plan now because of the Secure Act 2.0, is that you can overfund. And if you have up to $35,000 left over, then you can use that to fund a Roth. So you can overfund it a little bit and get the benefit of it. And also, by the way, it's great to invest it tax wise. It's such a great way to be. Now if you don't want to do that, two other opportunities is you take the 175. Will there be a tax on that? Will you have a capital gain on the business?
Lisa
We will. Maybe 40 or 50 of that will be taxable.
Mark
Okay. So we'll just make sure you'll have that set aside and then you can add the rest to your brokerage Account. The other thing you could do, not that I'm saying you should, but I'm just saying considering that you want to look at this vacation home, maybe there is a chance for you to refi the vacation home. And in doing so you might pay some of that money down that you have outstanding. Not all of it. I'm just saying that if you could get mark, what's a 30 year fixed rate now? 6.3. Okay, so let's say it's next year and you can get five, eight. Maybe this is a time where you're like, you know what, I have some of this extra cash from the business. I'm going to pay this mortgage down a tiny bit at five. Eight doesn't have to be a huge number, but you put a little, maybe you put 50 grand there and you buy it down a tiny bit. And now you're kind of in this great place with a vacation home where you don't owe as much. And of course you have the ability to lock that rate in. So that's another idea to just keep it, you know, on the side. I wouldn't touch anything else, obviously. And you know what's wrong. You could have the brokerage account. It's just a great way to have money growing forever essentially and see how things rock and roll with the new business. Now if you start getting if in the new business, are there many partners or is it just you and someone else?
Lisa
Just me and someone else.
Mark
So if this starts to cash flow, have you considered that you could each of you potentially put in a retirement plan for yourselves in this business?
Lisa
That's been a thought of mine potentially doing some more retirement. Do you think we're too heavy on retirement funds versus No.
Mark
I mean, I, I wouldn't put it this way. I would love to have that. I'm just going to call it like, you know, 140 grand. I'd love to have that. After you pay tax, you put whatever you need left over, you put it in the brokerage account. If you had 250, that would be great. That will grow. But if you have the ability, well, I'm not saying you should do this all at once. I'm just saying if you could put in a uni 401k and you and your partner are each putting money away, it's a nice way for you to build that up. And again, you don't have to put everything away. But if you're going to be able to cash flow and take this business and have, you know, upside of 100 grand a year. It'll be nice to take, you know, 23, 5 and pop it into a retirement account, use the rest of it and throw it into the brokerage. Okay, But I think you got, I mean, listen, you're in great shape. You got. I think you know that I'm very encouraged by this. I think the only thing that's funny about the inherited ira. Let's talk about that for a second. Because right now, if I looked at your tax returns, you're not showing that $100,000 in the business, right?
Lisa
No, no. This year has been, like I said, we just started this year, so it's been a slow start here.
Mark
So when I look at your top income tax bracket, because I'm not sure how the real estate, you're treating it on your taxes, but are you taking a loss when it comes to taxes on both properties?
Lisa
Yes.
Mark
Okay. So you're. Right now you're kind of locked into the 24% tax bracket. Okay. Now what might be interesting for you to do is in these years before, I mean, before this business starts chugging away and creating another hundred grand of income for you, maybe this is a time that you start taking some more money out of the inherited IRA. Like for this year, I might take like 50 or 100 grand out and stay in the 24% bracket and then do it again next year and then you're done. Like, get, get this thing. Let's get rid of this thing. Because it sounds like you're just going to keep making more and more money between the two of you.
Lisa
Yeah. What would you do with it then when you pull it out?
Mark
I would pay my tax and then I would put it into your brokerage account. And now you are really getting that brokerage account built up. And no longer will you feel like, oh, I don't have enough in brokerage. You're going to have a lot of money in brokerage.
Lisa
Okay.
Mark
Now the other thing is I think you're using all Roth. Now, I wouldn't necessarily convert what I have, but if you are going to put in a retirement plan through the new business, you may want to use a Roth. You can use a Roth 401K for one person or, you know, you can put something in, depending on what your partner's situation is. But usually when your partners, you know, you, you try to do the same ish kind of thing.
Lisa
Yeah, no, I think I feel like the traditional is a number that's going to grow substantially. Just, oh, yeah, time. And that kind of worries me a little.
Mark
Bit. Yeah. Well, don't worry. You're in great shape. Stop. Stop buying businesses and real estate, though. My God. Do you guys have your estate documents done? Because there's a lot going on here. We do.
Lisa
They probably need to be updated for some of these additional items that didn't exist at the time, though.
Mark
Yeah. And what about life insurance? Do you have that?
Lisa
Yes, we both are fully covered on life insurance. Let me ask you one more question. I mean, sometimes I just look at all this and I'm like, let's just completely simplify. If we were to take the business and sell it and to sell the $850,000 property and we were to put all that into brokerage, do you think between the 401k and the brokerage growing over time, that we're okay in the future if he doesn't continue to make at this level?
Mark
Well, let me ask you a question. How much money you're saving? A lot of money right now. What do you. What do you expect expenses to be? I'm not talking about the expenses associated with the house. I'm talking about your real spending month to month, year to year. What does that look like for you guys?
Lisa
Probably eight.
Mark
I mean, I think that you're in great shape. If that's the case. Now, is it that your husband hates his job or that he's like, kind of feeling like, oh, my God, I'm killing myself.
Lisa
He's not miserable in that way. I just feel like I've got the freedom at this point and it'd be nice to have somebody to share that with.
Mark
When you're 40 and you've got three kids and you've got properties and businesses, there's a lot going on. So if you said to me, I'm a little overwhelmed. We're a little overwhelmed.
Lisa
Yeah.
Mark
And we need to cut something out. Sure. That would make it a lot easier. You already have a million bucks, so this is just, you know, you'd be adding to that. And, you know, if you thought about him taking a step back, even if you said, like, he's going to work his butt off for 10 years and then at 50, he doesn't want to be in a go go kind of mode, but he would make maybe half as much.
Lisa
Yeah.
Mark
I would guess that you're in pretty good shape, Mark, Would you have that sense also, that, like, if Instead of making 250 in 10 years, remember that we'll have like, couple one of the two of the kids kind of done. They gotta, you know, go from 250 to 125. I think they got enough money, don't you?
Yeah, 100%. They're. And you can tell their hustlers are always going to be making some sort of income. Yeah, I'm not worried at all.
So I think like you said, there's.
A lot going on.
There's a lot going on, man. Mark just heard three kids and he stopped. You stopped him in his tracks right there.
Three homes, two businesses. No, thank you.
Yeah, there's probably a. There's a partridge and a pear tree there soon also. Anyway, I think that it's okay to consider that. And if something, you know, it's almost like I would ask yourself, is one of these things really bugging me or draining me? And it sounds like that $30,000 a year business, the custodial IRA business, is the one that's like kind of niggling at you. So why don't you start by selling that thing and see how things feel and maybe everything else will be fine. Maybe that one thing is bugging you enough that you say, let me get out of this.
Lisa
Right.
Mark
Yeah, you don't have to go wholesale. Let's just see how that feels and then go from there and. And otherwise keep doing what you're doing. They are hustlers. I like that. If you are like Lisa and her husband, a little bit overdone, like, there's a lot of stuff going on. You need some help. Want to walk through what's happening and maybe come up with some strategy or some priorities. Give us a holler. Go to Jill on money dot com. Click the contact us button. Write us a note if you want to come on the air. Check the box. Mark will do everything else. Hey, don't forget to check out our service called Jill on Money Live. That's where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content, all for 45 bucks for the next 12 months. Our next webinar will be doing year end tax and financial planning. So I'm going to try to hustle my guest up this week, as a matter of fact, and we'll announce the date shortly. So check that out. All right. You can subscribe to us on the Odysee app or wherever you find your favorite podcast. Try to do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.
Nancy Cartwright
Hi, I'm Nancy Cartwright. You may know me better as the voice of Bart Simpson on Simpsons Declassified we're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers, the celebrity guests? Be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.
Podcast: Jill on Money with Jill Schlesinger
Episode: Is Our Financial Picture Too Complex?
Date: October 13, 2025
Host: Jill Schlesinger (with co-host Mark)
Guest: Lisa (listener caller from North Carolina)
This episode focuses on a listener call with Lisa, who is navigating a complex financial life that includes multiple properties, a growing family, various retirement and investment accounts, and two businesses. Lisa seeks advice on whether her financial situation is unnecessarily complicated and how she might simplify things to promote peace of mind and long-term security. Jill and Mark dissect Lisa’s scenario, pose clarifying questions, and offer straightforward advice in their signature, jargon-free style.
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Jill and Mark walk Lisa through the tangled web of her finances and determine she is on solid footing, but encourage her to shed complexity where it causes personal burdens. Selling a draining small business—and possibly later a vacation home—are discussed as reasonable next steps. The hosts urge focus on balance: plenty in retirement, but don’t overlook the value of accessible brokerage for flexibility. Bottom line: Lisa and her husband are “hustlers” in strong shape, but simplification may bring them greater peace and more family time.
If your financial life feels overwhelming and you'd like tailored, plain-English advice, Jill invites you to submit a question or come on the air at jillonmoney.com.