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This year I'm not missing opportunities. And it starts with not missing calls. Because a missed call is money out the door. Quo helps you and your team share one business number, reply faster and stay on top of every customer conversation so you never miss an opportunity to connect with your customers. That's why today's episode is brought to you by Quo, spelled Q U O. The smarter way to run your business communications. Quo isn't just a phone system. It's a smart system. AI automatically logs calls, generates summaries, highlights next steps, and can even qualify leads or respond after hours so your business stays responsive even when you're offline. Plus, it's easy to scale. Add teammates new numbers and sync your CRM in minutes. Your team can manage everything from one shared number, ensuring no messages are missed and no customer slips through the cracks. Try Quo for free plus get 20% off your first six months when you go to quo.com jillonmoney that's Q-U-O.com jillonmoney Quo no missed calls, no missed customers it's late at night and you finally spot it. That one product you've been looking for. You click the link, add it to your cart, and then it's time to check out. But then you realize your wallet's nowhere near you. And good luck remembering which password goes with which site. That's when you see it. The purple shop pay button. One tap and just like that, your payment information is already filled in. No wallet, no logging in, just a smooth checkout. Shopify is the commerce platform behind millions of businesses worldwide, from household names to brands just getting started. You can get started with your own design studio using hundreds of ready to use templates to build a beautiful online store. Shopify also makes it simple to get the word out with email and social media campaigns that reach customers wherever they are. Shopify's award winning 24. 7 support is always there to help. Plus you can manage everything in one place. See fewer carts go abandoned and more sales with Shopify and their Shop pay button. Sign up for your $1 per month trial today at shopify.com jillonmoney go to shopify.com jillonmoney that's shopify.com jillonmoney. Welcome to the Jill on Money Show. It's Thursday, February 12th. Lincoln's birthday I might add. We don't celebrate it on the day anymore, but old school people like me will know that. Mark. You probably know that, right? Honest Abe? Yeah, yeah, of course. A fine prezi. Okay, so listen, this is a program that takes the mystery out of your financial life. If you've got a question, give us a Holler. Go to jillonmoney.com, click the contact Us button, write us a note and, and if you'd like to come on the air, check the box. Mark will do everything else. He's the best executive producer in the whole wide world. While you're on the website, don't forget to sign up for the free weekly newsletter and also check out our subscription service. It's called Jill on Money Live. That's where you plunk down 45 bucks for the next 12 months. And you get to participate in four live webinars throughout the following 12 months. And you also get the back catalog of the webinars and bonus audio and video content. Again, 45 bucks for the next 12 months. Such a bargain. Our upcoming webinar is with the Fantastic Ed Slott, CPA Ira Roth, Ira expert. Thursday, February 26th. So just two weeks from today. And so you've got to be a subscriber to Jill on Money Live or, or, or if you want to watch the webinar after it actually has occurred, you can pay 15 bucks for it. So check it out. It's all on our website@jillonmoney.com today we are talking to Jason from upstate New York. That's what I'm going to call it.
B
Jason.
A
That's probably not exactly upstate, but I'm going to call it that because I know where you are, but I do not want to expose you too much. Welcome to the program. What can we do for you?
B
Hi. Well, thank you first to both you, both Jill and Mark, for including me. I'm grateful to have your wisdom and participate on the show. I have lived in the Hudson Valley and New York City for over a decade in the Hudson Valley and like 25 years in the city. And I recently sold my home in Woodstock, New York. And so what I'm looking at now is I'm going to end up with a lot of cash. I fixed this home up and sold it, became moving ready and found that there was a market for a move in ready home. And when it's all said done, I'm upwards of $900,000.
A
Wait, wait, 900 net to you?
B
Yeah.
A
Wow.
B
Yeah. I bought the least nice home on the nicest street. And you know, okay, so that's incredible.
A
So that's going to come when it's magic.
B
Probably February, March at the latest.
A
Okay.
B
And that's after, you know, so that's, you know, paying off the mortgage and the second mortgage. And so what my plan, my first plan is to pay off credit cards and my car. My car.
A
Okay. So how much debt do you have that's outstanding, other like that kind of stuff, consumer debt, credit cards and car loan or anything else, personal loan, anything like that?
B
That would be about one, about 125.
A
Okay. And that all accumulated because while you.
B
Were, or actually I should take that back. I'm including some things that don't really count. It's under 100, I'm sorry.
A
Okay.
B
Yeah.
A
All right. All right. And so it's, let's call it a hundred. And then anything else that you need to earmark from the 900 besides the 100 of debt payoff?
B
No, I've already earmarked the other stuff like, you know, solar panel loan and all that kind of stuff. So I, I, I, I, I suspect about 8 is what I have to buy a new house with. And my first very excitable moment was to buy a house and flip it, fix it up and flip it. And then I realized that since I don't have a place to live currently, that that's the wrong order.
A
Do you think?
B
Yeah, right. Yeah. I sold my home and I'm renting.
A
What's the rent? What's the rent? Wait, maybe this isn't the worst idea.
B
My rent currently is 2000amonth. Yeah, yeah, it's, you know, it's, I have a great deal and it's, and it's, you know, it's fine. But I really want to have my forever home.
A
Okay.
B
I like to landscape and garden and I really need to, you know, I'm creative and I like to be able to, you know, make a house, a home.
A
Okay.
B
But you know, I'm also willing to postpone that for a little while.
A
Okay.
B
And so I have.
A
How much would it cost you to buy that dreamy forever home in the area? Like will 800 do it or would you need to pay more?
B
I could do it for less than that, actually.
A
How come?
B
Well, because my plan, I'm working with a developer on building, on buying land and building a home. And from my experience buying a home and renovating it, I know, first of all, I'm not intimidated by renovation or building because I grew up in that environment and I have discovered that buying land and building a home is equal to just buying home.
A
Right. Because the rest of us are all lazy. We do want move in homes because it's scary and intimidating to have to go through permitting and do the whole thing. And all those choices.
B
Yes. And a big fat thank you to those of you who are. Because that's what created the bidding war on my house.
A
You're absolutely welcome. So how long will it take you to develop and build what you think you would want? You'll need to rent for a while longer. Like, you know, how long will this all take?
B
It's a wonderful ninth question and it's going to be a wonderful nine month journey, maybe, maybe a year even. And I'm comfortable with that. Renting while doing that.
A
Yeah, I mean, you have pretty cheap rent. What else do we need to know about you, Jason?
B
Well, it's important to know that I've started a new career in real estate and interior design and working with several clients on gut renovating their homes. And this career presented itself when I sold my house. I realized that everything that was happening around selling the house was what I wanted to do for a living. And it's what I enjoy the most is everything around homes and, and then sharing my experience in the Hudson Valley, Catskill area with people. So I got a real estate license during that process. And so I'm working in realtor and designer. And so that does present an interesting, you know, financial development because I no longer work with the structure of a regular corporate income.
A
And you're okay with that right now?
B
Right now I'm very okay with it.
A
You're like, why'd I wait so long?
B
Yeah, well, I think I waited so long because I'm also important to know that I turned 60 this year and so I would, the younger me wouldn't have been responsible enough to handle that kind of non structured.
A
It's hard. By the way, a lot of people who will say this to me, they'll be like, oh, you know, you know, I'm going to start my own business or I'm going to be a consultant. I said, you know, you have to go through periods that are kind of a little bit dormant and it kind of messes with your head a little bit, forgetting about the money part of it. So yeah, I think when you're 60, you have a little, first of all, hopefully you have not just this $900,000 influx, but other assets. So let's take a step back, Jason. So you're 60 and the, the premise of your call to us is what exactly? What are we solving for?
B
The premise of the call mainly is two things. One, first I want to mention that I was going to take about 60,000 out of this and pay myself a salary for this year while I earn for this year, for next year. So this is a plan that I.
A
Made up, I thought, meaning 60 grand out of my 900 is just like.
B
To live on, to live on. And then what I earn this year will be put into savings to live on next year.
A
Okay. All right.
B
My goal would be to match it, basically because I. I also have been used to living with less while after I got laid off and realized I don't need as much. And then that led me to think that as a premise of this call, is it wise for me to put the money that I make off of this house into just owning a house, clean and clear?
A
Okay. Okay, I got it. All right.
B
Or, by the way, or carrying a small mortgage, which, when rates go down, I would be willing to take out, you know, two. 250 mortgage, you know, to invest or something.
A
Okay, so, Jason, you're 60. Are you married, single, partnered?
B
I'm married and my husband owns a home, a townhouse in Brooklyn, so we have that space too. He works in the city and I work in Hudson Valley.
A
Do you keep your finances together or separate? No judgment here, just.
B
I know. No, I'm one of the, you know, Jill advised. We do not commingle our finances.
A
Okay, fine.
B
We basically each own a home and.
A
Run our home separately. That's fine. That's great. Again, as I said, no judgment. Okay, so you're 60. Tell us about the money that you accumulated in your prior life when you were working. I'm sure you have a retirement plan, so give us a little bit of the rundown of your assets.
B
Yeah, I do. I have. I have an IRA. There's about 240,000 in the IRA. I had more, but I took some of it out to finish the renovation during the pandemic because things got so expensive. So I did also want to replenish some of that. So I did talk to my financial advisor about taking at least a hundred thousand and giving that to him for investing. And I also for retirement. I don't know that this is wise to plan on, but I. I know a dependable inheritance that I'll be getting also from my mother.
A
What do you think about. Don't, don't go crazy. So give me the more conservative inheritance number, about 650. Okay, got it. Do you have any Roth assets?
B
No, I didn't. I had to move those. I wasn't qualified for that.
A
Okay, so 240,000 in an IRA. And you have a brokerage account as well? Just a plain, like, non retirement investment account. Because you mentioned A financial advisor. So I was just wondering.
B
No, he and I are going to talk about that when I get this.
A
Your windfall.
B
My windfall, as it were.
A
What do you think it takes you to live every month? Like, I know that you have separate dwellings, you have your rent, but what do you suspect is your monthly spend? Is it five grand a month? And that's where we came up with the 60,000.
B
Yeah, that's. And that's generous because I won't be paying. I won't have a car payment. And, you know, that's. That's. That's me using rent as. So here's an interesting thing. The amount of rent is the amount that I would run a household if my house was paid for.
A
Mm. Oh, okay.
B
Got making sure that I had money every month to run the house with.
A
But you wouldn't have your 800 grand. You know, you wouldn't have the. You wouldn't have the ability to hang on to it. So for right now, the assets you have are this 900, which we're going to whittle down to 800. Right. There's going to be 800,000 to buy a home, to invest, to do something. There's 240 in an IRA. There's a future inheritance of about 650. And right now, what are you earning in your new career? Approximately?
B
It's very early. I mean, as in four months.
A
Oh, that is early. Okay.
B
So currently it's around like $3,500 a month.
A
Oh, that's good. In four months. That's amazing.
B
Yeah, well, I'm planned on. I purposely planned to have something in addition to being a realtor, which is the design business. And so I have a couple of clients, and I'm. I get paid every month for this work that I'm doing, and I want to keep that balance because I think it solves two things. One, it solves my. Keeps my creative juices flowing, and it creates a steady income. And while being a realtor, do you.
A
Have just any money that's sitting in cash right now? A bank account, a cd, a savings account, anything like that?
B
No.
A
Okay, so let's just kind of go back in time for a second. So now I got your general. I got. I got a feel for what's going on. So of the 900, we know it's going to be really 800, because you're going to reduce your. You're going to pay off the debt. That'll be done. So now we have 800 of the 800 we want to make sure that you have money to live on. So you're going to take 60? Maybe. I don't know. Maybe. I think I want you to put 100 away. But just because. But let's just. I'm going to make it round.
B
I think 100 is a good idea.
A
So I think I'm going to say 100 there. So now we have 700 grand left. So the question I have for you is, you know, on one hand I want to say that, oh my God, we shouldn't do anything with that money. We should, you know, invest it, keep it liquid. You're still very young. We want the money working for you. But I hear what you're saying in that you have a knack and the ability to find a house, develop a house. Like, it sounds to me like you do know what you're doing and you've already been through it. So if I looked at that 700, what portion of that 700 would you need to buy the land, develop the land? Like, what do you need to really make sure you get this project done over the course of the next year?
B
I would, well, depend on the price of the land. I think the house is going to run between six and seven.
A
Okay.
B
I'm doing a pro forma with the builder right now.
A
Okay.
B
So the builder and developer, and that is the price range we're going to hit. So.
A
Okay, that's good.
B
Ideally what I would do is I buy land. Let's say I buy land for 150, 200.
A
Okay.
B
Then pay cash. Then I would take a mortgage for a small mortgage out, say for 200 later at the end. Yeah, an end mortgage to avoid a construction loan.
A
Yeah.
B
And also, I'm not qualified for a mortgage right now because.
A
Right, because you don't have enough income anyway.
B
Fancy corporate job with a, you know.
A
So should we make your husband co sign or not? No, I don't.
B
No, I don't want to do that. I think you can get cash out at the end.
A
Yeah, yeah, yeah, yeah. Because you've already put the money.
B
That's the direction I would.
A
So what. So I just. So we buy the land for 200. Now we have a half a million left. And what you're saying is you're going to use that 500 over time, you'll end up getting some. At some point you'll be. But that 500 will be gone in the process. Yes or no?
B
It would be gone in the process. Yeah.
A
Okay. And then at the. You might get a mortgage where you could, you know, Pull out a couple hundred grand, you will have improved it. It will be, you know, blah, blah, blah. So you'll have, you know, you'll spend the 500, but then eventually you have another 200 of, you know, probably mortgage proceeds. Okay.
B
Thinking at the end I'd have 200, because also when you buy land and then you improve it.
A
Yeah, yeah, yeah, I get you. Okay. So we still have. We would have your hundred in your emergency fund. You've got your inheritance to come. You've got your ira, and then you've got these more the mortgage proceeds. So my question to you is, you know, this is obviously incredibly risky. Can I just make assumptions? If something bad happened, would your husband be able to help you out?
B
Yeah, what I would do is. What I did. What I would do is I would just move into our place in Brooklyn and just.
A
Right, you'd sell this. You'd be done.
B
And I could sell it. I could rent it.
A
Yeah. Okay. Mark, how are you feeling about our game plan for Jason? Are you worried? No, I'm not worried. You know, Jill, you and I like things very simple, and we don't like a lot of moving parts. But Jason sounds like this is what he does. He knows what he's doing. He knows what he's getting into. He's already done it before, so, you know that that helps. And knowing that, you know, I hope your mother lives a long, long time, but knowing that that inheritance is coming, that also helps. Yes. And you're working, and you're probably going to ramp up my guess. Here's my goal for you, that if you do this, that by the time the house is sort of done, I'm hopeful that, like, basically, you're earning. You're. You're earning what you need to live on. Right. You're earning, you know, let's call it 100 grand a year, and then you're living on the 60, right. Because you need to earn 100, pay taxes, and then, you know, live on.
B
Pay taxes and do that.
A
Yeah, yeah, exactly. So, you know, you. I think it works. I think you have. If you're doing something really risky like this, Jason, then we must have, you know, your bailout plan. And you have it. You have it in the back of your head. You have it activated. Is your husband on board with this whole thing?
B
He is, yeah.
A
That does not sound like a resounding yes, absolutely.
B
My husband. My husband. My husband thinks that I should. Should wait till after the midterms to do anything. And I said, I don't really think that has anything to do.
A
Why does he think if he. Because if the midterms don't go a certain way, you're going to move to Canada.
B
Yeah. You know, I mean, it is a.
A
Bit of a going.
B
It is a bit of a doomed. Well, I'm not. So I said. I said, well, I'm not going to be moving. And by the way, this also, you know, developing building a house takes a really long time.
A
It does, it does.
B
But. But in that I renovated the home and made this big windfall, which was magic. And I don't expect it to be magical in the future. The worst thing that could happen is I built a house and it all and I needed to sell the house and then I would sell the house. So the house is going be worth a lot more than I put into it. And yeah, so be it.
A
I think in a weird way, like almost the fact that you're willing to do the work because the improving, starting from scratch is absolutely, you know, the, the way that you tend to extract more value. I know that. Right. And I was just having a conversation about this and with somebody who's like, you know, his parents were people who were able to buy, do gut renovations, flip, move, move. And he's like, I can't do that. Like, you have to know yourself and if you can do it. Okay. And as long as we have a plan B, and if the plan B is okay, Jill, I'll end up with a 7 or $800,000 house. Worst case scenario, I sell it, I pay off whatever mortgage there is. I got a half a million dollar proceeds I moved to back to Brooklyn, where, by the way, the food is obviously better than wherever you are. And, and then you go from there. And I'm okay with this now because you have separate lives, though. Do you have estate documents for the two of you?
B
No.
A
Oh, my God.
B
I know.
A
Come on. Did you hear the pause? He's like, oh, God damn it. I almost got off this, this conversation without her asking about it. Didn't you think you were almost free?
B
There are. We do have documentation for, you know, death benefits and all that tied to our, to our asset, to our assets, our investments and things like that. That's all recorded.
A
Yeah. You need a will, you need of a power of attorney and you need.
B
A. I don't have a will to my house. But it's also because it's about to not be mine anymore.
A
Yeah, but then, but you know what you're going to have is you're going to have to put this down on paper. Okay, I know that it's a pain in the neck. I don't want to. There is no way out of this. You cannot convince me otherwise. Right?
B
No. Well, we know better.
A
Okay? Exactly. And get a lawyer up there so you don't get one in, like, New York in the city where it's more expensive. So get a lawyer up there who can draft some documents. It's very simple. And. And make sure that your wishes are put down on paper. That's all I'm asking.
B
For the future, for the house that I build.
A
You mean for everything. Everything. A will. A will is a repository for every asset that is not actually passing by contract. Okay? So you must do this because I'm going to be a pain in the butt. I'm going to have Mark hunt you down and find you and say, did you do your estate documents? Why me? Why not you? You're in New York. Well, because you. You're more familiar with upstate things. Mark, remember, upstate is above White Plains for me. Yes. All right, we're letting you go, Jason. Good luck. Build a beautiful house and send us pictures. Hey, are you looking at doing some massive transaction like this? And by the way, Jason's doing, like, a couple of massive things. He is resetting his career. Sounds like he's very happy. He's doing this big housing transaction. It's incredible. So I'm so glad he got in touch with us. If you're in a position where maybe you're just doing one of those things, get in touch with us. Go to jillonmoney.com, click the contact us button. Let us know if you'd like to come on the air by checking the box. And of course, we are always so grateful that you listen to us every single day. So thanks for that. Subscribe to us on the Odyssey app or wherever you find your favorite podcasts. And as always, we ask that you do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. I'm Emma Greed, host of Aspire with Emma Greed, a podcast where I sit down with people who don't just dream big, they build big. From culture, shaping voices like Mel Robbins leaders, redefining success like Tracee Ellis Ross to game changing entrepreneurs like Mark Cuban. Aspire is about mindset, ambition, and doing the work that actually moves the needle. If you're ready to raise your standards and take charge about the life and career you're building, Aspire is where you start follow and listen to Aspire with me, Emma Greed, an audacy podcast available wherever you get your podcasts.
Date: February 12, 2026
Host: Jill Schlesinger
Guest: Jason from Upstate New York
In this episode, Jill Schlesinger speaks with Jason, a listener looking to reset his financial life after selling his home for a substantial profit. The conversation dives into Jason’s plans for his windfall, shifting careers at age 60, and big-picture questions about home ownership, investment decisions, and long-term planning. Jill provides actionable guidance on managing lump sum proceeds, risk management when building a custom home, and the crucial importance of estate planning.
On Leveraging Experience:
“The improving, starting from scratch is absolutely...the way that you tend to extract more value...if you can do it.” — Jill (19:59)
On Knowing Your Limits:
“You have to know yourself and if you can do it...as long as we have a plan B.” — Jill (20:09)
On the Importance of Estate Documents:
“There is no way out of this. You cannot convince me otherwise.” — Jill pressing Jason to create a will and related documents (21:34)
Humorous Spousal Dynamics:
Jason: “My husband thinks that I should wait till after the midterms to do anything. And I said, I don’t really think that has anything to do [with it].” (19:15)
Jill: “Because if the midterms don’t go a certain way, you’re going to move to Canada?” (19:25)
This episode is an engaging look at real-life wealth management questions and the balancing act between financial opportunity, risk, and personal reinvention at any stage of life.