Too Much in a Single Stock?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger Episode: Too Much in a Single Stock?
Date: March 20, 2026

---

Episode Overview

In this episode, host Jill Schlesinger, CFP®, takes a listener call from Katrina in Long Island, New York, for an in-depth financial "gut check." The main focus centers on whether Katrina’s family is overexposed to a single company stock—constituting a significant portion of their net worth—and explores the implications, risks, and strategies for diversifying those holdings. The episode also covers retirement savings strategies, questions on Roth vs. traditional IRAs, long-term care insurance, and estate planning, all discussed in Jill’s signature straightforward and candid style.

---

Key Discussion Points & Insights

1. Listener Background and Financial Situation

• Katrina & Family: Early 50s, married, two kids (college sophomore and high school freshman) [04:19].
• Income: Husband just switched jobs with projected earnings (salary, bonus, and stock) $400K-$450K/year. Katrina is self-employed, netting about $40K/year [06:17].
• College Funding: Approximately $137K (older child) and $113K (younger child) in 529 plans, contributing $6K per child per year [05:00]. Looking at paying $45K out-of-pocket for one semester [05:51].

2. Over-Concentration in Company Stock

• Company Stock Position: $1.3 million in vested company stock, about 80% long-term gains [07:33, 08:19].
• Katrina's Concern: Worries about triggering a large tax bill if selling, though also aware of "over investment" risk [07:44].
• Jill’s View: Urgent recommendation to diversify. “It is so scary to have that much money, that big part of your net worth in one holding.” [20:17]
• Strategy Suggested: “Even if you just said to the accountant, we’re going to sell a quarter of this every year for the next four years. Count on it.” [20:15]

3. Retirement & Investment Assets Summary

• Retirement Accounts:
  • Katrina’s IRA: $479K [08:45]
  • Husband’s IRA (rollovers): $940K [08:55]
  • Katrina’s Simple IRA: $335K [09:03]
  • Husband’s old 401k: $281K [09:13]
• Brokerage/Investment Accounts:
  • Cash equivalent/emergency fund: $50K [09:35]
  • Mixed allocation brokerage: $360K [09:46, 09:58]
• Home Value & Mortgage: House worth ~$1.4 million; just $54K left on a 2.75% mortgage [10:27-10:54].

4. Spending Estimates and Retirement Projections

• Expenses: Katrina estimates $5–6K/month, but Jill presses for accuracy, settling on ~$10K/month including taxes and all-in housing costs [11:53–12:16].
• Retirement Horizon: Planning to work until mid-60s, so roughly 12 years to go [12:43–13:14].
• Retirement Savings Rate: Both maximizing retirement contributions, including catch-ups and 529s [13:11–13:58].
• Gut Check: With current and projected savings, “100%...they’re good to go” to generate $10K/month in retirement, per Mark and Jill [15:55].

5. Traditional vs. Roth IRA/401k Debate

• Roth Option in New Job: Available to husband [16:34].
• Tax Bracket Analysis: 32–35% (married, NYC) [16:35–19:20].
• Jill’s Priority: “If I were doing triage, I don’t think Roth is the most important. I think your allocation to the company stock is far more important to deal with.” [17:39]
• Advice: Focus primarily on reducing single-stock exposure, then consider Roth contributions, possibly scaling into Roth as stock risk reduces [18:56, 23:53].

6. Estate Planning & Insurance

• Estate Docs: Will, power of attorney, healthcare directives are in place; Jill confirms that’s adequate (no trust needed under NY thresholds) [22:20–22:46].
• Life Insurance: Term policies for both [22:20].
• Long-Term Care Insurance: Jill’s advice: “Generally speaking, they are very expensive and at your level of assets, like... you should be able to self-finance a chunk of it. But if there were a corporate benefit, I’d look at it...” Recommends getting a quote and reconsidering if premiums are astronomical [26:48–28:46].

7. Notable Advice on Fees & Diversification

• Investments at Chase: Managed at a 0.41% fee, which Jill considers reasonable [23:09, 23:36].
• Single-Stock Exposure Limits: Jill’s rule: “The maximum that should be in any one single stock...is 5 to 10% of your invested assets” [25:21–26:14].

---

Memorable Quotes & Moments

• On Concentrated Stock Positions
  Jill: “It is so scary to have that much money, that big part of your net worth in one holding... I would sell at least a third of that and...come up with a strategy for like scaling out.” [17:19–18:55]

• On Letting Taxes Delay Action
  Jill: “Are we letting the tax tail wag the investment dog?” [20:17]

• Financial Outlook Assessment
  Jill (to Mark): “Will they be able to generate what they need...in their early to mid-60s? 100%—you think they're good? They're good to go.” [15:34–15:55]

• Tough Love on Diversification
  Jill: “You know, I could find the best stock in the world and I wouldn't put 30% of my net worth down on it. Yeah, there's no way.” [24:41]

• Reframing Tax Payment
  Jill: “Isn't that terrible? Wouldn't it be worse...if it's only worth $300,000?” [25:22]

---

Important Timestamps

• [04:19] Introduction of Katrina and overview of her family’s financial questions
• [07:33] Discovery of the $1.3 million in company stock
• [11:17–12:16] Deep dive into family’s expenses
• [15:34–15:55] Retirement outlook is solid—"good to go"
• [16:34] Introduction of the Roth 401k question
• [17:19–18:55] Jill’s urgent advice on over-concentration in single stock
• [20:17] Discussion on not letting taxes control the investment decision
• [22:20–22:46] Estate planning review
• [23:09–23:36] Fee structure of investment accounts at Chase
• [24:41–26:14] Tough love on stock concentration limits
• [26:48–28:46] Long-term care insurance guidance

---

Action Steps/Recommendations

• Immediately address over-concentration in single company stock. Develop a structured, multi-year selling plan in concert with a tax advisor.
• Primary focus should be risk reduction—not minimizing near-term taxes.
• Once portfolio is diversified, re-evaluate eligibility and value of Roth contributions.
• Insurance and estate plan: Maintain current term policies and estate docs; review long-term care options offered through employers before considering private policies.
• Keep up the good habits: Retirement savings, targeted 529 funding, and low investment fees.

---

Tone and Style

Jill is direct, humorous, and unapologetically practical throughout (“tough love today,” “bathe myself in my tax liability”). She emphasizes actionable steps, risk management, and financial sanity over chasing tax advantages or speculative returns.

---

This summary covers the substance and unique flavor of the episode, providing a complete picture for listeners who missed it or want to revisit the key discussion points.

Transcript

[A]

You know, when Mark and I first started this podcast, we had no idea how many hats we would be wearing. Host, Producer, Editor Social Media Manager it was exciting but also intimidating. We really wish that we had had a built in business partner from day one. A partner like Shopify. It's the commerce platform behind millions of businesses worldwide and powers 10% of all E commerce in the US you can build a beautiful online store with hundreds of ready to use templates that match your brand's style and their AI tools help write product descriptions, create headlines, even enhance your product photos. Plus you can run email and social campaigns and manage inventory, payments and analytics all in one place. Start your business today with the industry's best business partner, Shopify and start. Sign up for your $1 per month trial today at shopify.com jillonmoney go to shopify.com jillonmoney that's shopify.com jillonmoney hey gang, you I'm all about not missing opportunities. And that starts with not missing calls. Because a missed call is money out the door. 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 makes it easy for your team to stay on top of every customer conversation. Everyone can call, text and reply from one shared number. No more missed messages, no more disconnected threads. Plus it works wherever you are right from your phone or computer and you can even keep your existing number, add teammates new numbers or sync your CRM in minutes. It's built to scale as your business grows. And here's the kicker. Quo isn't just a phone system. It's a smart system. AI automatically logs calls, summarizes conversations, highlights next steps, and can even handle after hours messages or qualified leads. Everything lives in one clean view so your team communicates faster, stays aligned and gives customers that personal touch that actually sticks. Make this where no opportunity and no customer slips away. 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 Foreign welcome to the Jill on Money Show. It's Friday, March 20th and we are here trying to provide you with unconventional and entertaining insights on your money and your life. I'm Jill Schlesinger, your host. S Sometimes I forget to say who I am. Mark I think they probably know by now, but anyway, that's who I am and I love answering your questions. I'm a certified financial Planner. So is executive producer Mark. You know, sort of my day to day job is I'm the business analyst at CBS News. But I love these conversations with you guys because I think that they inform so much of what's relevant in people's lives, which is I want to do what I want to do when I want to do it. And so if you can relate to that and you've got a question, get in touch with us. Go to jillonmoney.com and in the upper right hand corner of our website there is a contact us button. When you click that button, a form will pop up and that's the email that we receive. Give us a bunch of detail if you don't think you'll want to come on the program. If you want to come on the show, however, just check the box Mark will arrange to get you on. While you're on the website, check out all the stuff that lives there. We've got another podcast, it's called Money Watch that's on the weekend. So if you can't get enough of us Monday through Friday and you want a little more Jill and Mark, then check out the Money Watch podcast. We go a little bit deeper in particular topics usually and we try to highlight all sorts of different kinds of people because you guys tell us that on this show we only talk to rich people, which is not true. But we try to give you a wider range on the Money Watch show. We also have a blog and we have a radio show and videos and resources. All that right [e-mail] today we are talking to Katrina who joins us from Long Island, New York. Hello Katrina, how are you? What can we do for you?

[B]

Hi, Jill. I'm great. So I, or me and my husband were a couple in our early 50s, two kids and basically reached out because I want to get a financial gut check based on where we are right now, specifically. Also asking about if we should, if I should switch to a Roth ira. I've kind of got a lot of different questions going on.

[A]

All right, that's good. So you're in your early 50s. So you're married. How old are the kids?

[B]

I have a almost 20 year old who's a sophomore in college and a 15 year old who's a freshman in high school.

[A]

Okay, so you spaced it out. You gave yourself a little break. Well done. How are you paying for college?

[B]

So we've been contributing to A529 basically since they were born. For my older one who's in college currently, I have about 137 left in his 529.

[A]

Okay.

[B]

And for the freshman, it's about 113 in his 529. And we contribute annually, 6,000 a year into each of them.

[A]

Okay. Is the sophomore in college in a reasonably priced school or a very like. When is this fund going to get drained, do you think?

[B]

He may try to graduate in three and a half years, but assuming I know, assuming he doesn't, the fund would probably get drained by. I'd have six months that have to pay for out of pocket.

[A]

So one semester out of pocket. Correct. How much will that be, that one semester?

[B]

Probably around 45,000.

[A]

Oh, my God. No, it hurts, it hurts. 40. I'm sure a $45,000 keg party was well worth it. Okay, and. Okay, so that's good. You're both working full time, Both you and your spouse.

[B]

My husband works full time. I am self employed.

[A]

Okay, and how much does your husband earn working full time?

[B]

Well, he's actually just switching jobs. So based on this new job, I'm going to reproject it between his salary, potential bonus in stocks, somewhere between 4 and 450 a year.

[A]

Wow. And you being self employed, Katrina, how much do you earn?

[B]

Mine is very low. I, I net maybe about 40,000. So basically I figure like, what I do is more for our everyday expenses

[A]

that we cover or perhaps to think about that last semester of college. But so the new job for your husband, how much more is he earning in this new position?

[B]

Well, it's a little tricky because the job he's leaving was very heavily based on salary and then plus stocks. So that was kind of another part of my question. And we sold part of the stocks based because the stock price was very high in the last vesting period, but we pretty much have those remaining stocks on a hold pattern.

[A]

How much money is in the company? You don't have to tell me the name of the company. How much money is in the company stock right now that he could sell? Like what's vested?

[B]

Okay. Last time I looked, it was about a million three.

[A]

What? Dude. Oh, my God. Okay, so that's out there. I know the stock went down. I understand. I.

[B]

Well, the thing is, when he vested it, the stock was pretty low. So that was kind of my question is I've talked to other people saying we're probably over invested in this particular stock.

[A]

Yeah.

[B]

But if I sell it, if I sell it, I feel like there's going to be a high tax liability because they're all gains.

[A]

Okay. No Good problem to have. What's a what? What's so bad? Oh, my God, I Wish it were 300,000, not 1 3. And you'd have a lower tax bill. Come on now. And is this. When did this vest? In other words, is this long term capital gain or short term?

[B]

Probably 80% is long term.

[A]

Okay, great. That's awesome. That's huge. Okay. All right. I'm keeping that over there on the side. So, ready for your financial gut check? We're going to go through some of the stuff that you have. All right, so you're going to be making a lot of money. Let's talk about how much you've already saved. We know about the company stock. That's 1.3 million. What else have you saved? What's in retirement? What is in brokerage? What's out there?

[B]

Okay, I'll start with the retirement. So I have an IRA, and that's about 479. My husband's IRA is about 940 thousand.

[A]

And that. Is that a rollover from his old workplace? Yes. Okay.

[B]

Yes.

[A]

So you've got. And yours is traditional. His is traditional. Okay. Correct. Got it. Yep.

[B]

In addition to that retirement savings, I have a simple IRA since I'm self employed and that has about 335.

[A]

Great.

[B]

And then a 401k from his previous job is at 281.

[A]

So the old, the traditional IRA, that 940 in his name, was that also from a different job or where, where did that come from?

[B]

It's from a different job. Like rollovers from 401ks.

[A]

Okay, gotcha. Okay, so Ira, Ira, simple Ira, old 401k. What else?

[B]

Yes, then we have our investment accounts. Brokerage 1 is a fixed. Yeah, thank you. Brokerage, fixed income, cash brokerage account. That has about 50.

[A]

That's like.

[B]

That's kind of like my emergency fund. Yes, exactly. Great. And then we have another investment count. That's 46% equity, 54% fixed income, and that has about 358.

[A]

I'm going to call it 360 because I can do that. Okay, so brokerage account, 360. Little bit more moderately invested, I guess to make up for the fact that you have one stock worth $1.3 million. I'm teasing you, you know that. Okay, so is that it for the assets? Is there anything else? Is there rental property? I'll get to your house in a second. Anything else?

[B]

Nothing else.

[A]

Okay. How about your house? I know you live in a, a high cost of living area. What is your House worth, I'm gonna

[B]

say, based on, as we know, the real estate market, especially where I live, is pretty strong. Maybe 1.4.

[A]

Okay, and do you have a mortgage that's still outstanding?

[B]

So the unpaid principal is $54,000.

[A]

54. That's it?

[B]

Yes.

[A]

This thing's going to be gone in two minutes.

[B]

My maturity date is 11:28. I've always talked about paying it down, but My rate is 2.75%.

[A]

Jesus. Oh, my God. Okay, whatever. It's going to get paid down in a couple years, so that's done. Okay, so that's done. No rental property, no vacation homes, right? Correct. All right, you ready for your magic question, which is always the hardest one to answer, which is, how are your expenses? What do you. What are you spending to live this life?

[B]

So other than our mortgage.

[A]

No, how much is the mortgage right now? It's got to be piddly.

[B]

It's like. Well, with the insurance, it's about 5,000amonth.

[A]

Do you know what the principal and interest is? A couple thousand.

[B]

I want to say the okay of the 5050% is. Is not the taxes and.

[A]

And insurance. Okay, so. So, yeah, so. Okay, so 2500 added to, like, what else are you spending then?

[B]

Just like, every day?

[A]

Yeah, everything. Not even every day. Like, going away and, like, your life. What's it cost?

[B]

So I'm going to say monthly expenditures would be about five to 6,000.

[A]

No way. That's it. No possible. Way too low. Way too low. You mean it? Yeah, I know where you live. On the 2500. Yeah, maybe, like I'm saying, 10 grand a month. With our. With our taxes and the homeowners insurance, your taxes have to be 20 grand a year, right?

[B]

Oh, my taxes are. No, 27.

[A]

Yeah. Okay, so, like, your expenses have got to be ten grand a month is what I'm going to put in here as your placeholder, because there's no way it's that low. But sweet that you would imagine. I. It's aspirational. Okay. How much longer are you and your husband going to work? That's a big question to try to answer before we figure out kind of where you are in the process.

[B]

I mean, I. I would guess till our mid-60s.

[A]

Okay, so you would work and. And he's not going to be entitled to a pension. Right. No other job or no military service. Correct. Okay, so if we said, like, 65, does that seem horrendous to you, or does that seem realistic?

[B]

That seems realistic.

[A]

Okay, so. And you said you're in your early 50s, like 52 or 54. Did you, did you kind of do that thing, that cheat thing? I did. How old are you?

[B]

Actually I'm 53. He's 54.

[A]

Okay, there you go. Early 50s. Nice. Nicely done. Okay, so the reason why I want to know that is we've got a dozen years here. Okay. That's what we want to look at. We got, let's even say for your husband got 10 years to go. Okay. And you're, I imagine he's putting, he is maxing out his retirement contribution, right?

[B]

Yes.

[A]

Okay, you're maxing out at your simple, right?

[B]

Yes.

[A]

Is there any other money you're putting away proactively like in that brokerage account? Is that, are you putting money into that? No. Okay, so most of the saving that is happening is either retirement or the thousand dollars a month into the 529 accounts, right?

[B]

Yes.

[A]

Okay, good. I just want to get, there's no, see no judgment. And when you say maxing out for your husband, is he making the catch up contribution because he's over the age of 50?

[B]

Yes.

[A]

Okay, so it's 32,5. And then you're simple on top of that. So it's like 40. Okay. So what's interesting about this is you are, you are certainly socking away a good chunk of money, right? Like it's fifty something thousand dollars into retirement and you've got your 529. And then you know, the reason why, I know your expenses are probably more than you think is that you're doing a great job saving for retirement, but you've got these kids and you live in an expensive area. And so all of this put together is like cash flow heavy, right? You just, you have a lot of drain on your cash flow. So it all makes sense to me now. Let's say are you the gut check part of it, Are you on track to be able to produce $10,000 a month at age 65, Mark, do you think, based on what they've accumulated already, and we'll deal with the old company stock in a second, but just let's presume that the company Stock that's worth 1.3 is not 1.3, we're going to pay some tax. Let's just say that to the brokerage account which now has 360,000, let's just pretend we added a million to that. So let's just say we had $1,400,000 in brokerage and then we have retirement assets. I don't know if you got these numbers, mark, but let's say 480 for her, 940 for him, 335 in. That simple. And 281. So there's a lot of money that is saved. Plus now we know there's about $1.4 million that will be in the brokerage once we get rid of this concentration in this one stock. How do you think the financial gut check is going for Katrina and, and the wave? That's just an old musical. Musical joke. Katrina on Long Island. How are, how are they doing? Will they be able to generate what they need in 10 years from now? They're early to mid-60s, 100%. You think they're good? They're good to, they're good to go. Okay. Especially, especially if he's gonna be making more money and they're able to save even more than they have been saving 100%. I think they're going to end up saving more because I think once the kids are, you know, like, we're going to be done with college, it's going to be okay, you know, no problem here. The thing that's going to be tough for you guys is, you know, you make a bunch of money, you're in a high cost state. And so Mark's going to try to make an argument that you should be using, or your husband should be using a Roth option through work in his new job. Will he have a Roth 401k option?

[B]

Yes.

[A]

Okay, so Mark, just to be clear, they are in the 32% tax bracket. They're going to lose a lot of the, some, some of the benefits that you would have of, you know, kind of defraying your taxes a little bit. You know, you'll lose that. And New York's an expensive state to live. So Mark, are you going to advocate to Katrina and her husband that they start using the Roth option? I don't preach what I don't practice. Yeah, I live in the same general metro area also high tax bracket. You guys have a lot of pre tax money. That's the issue. That's the real issue to me that I see. You don't have to do it all at once. You can kind of scale it in. But you know, you guys do have a lot of money that is sitting, not taxed. Right. And we want to make sure that when you, 10 years from now, that problem isn't compounded more than it needs to be. Now, I'm not saying you made a mistake. Like this is how most people who are 50 years old kind of look, they're overly invested. So you got $2 million that has not been taxed but in 10 years it's going to be 4 million and change. And we'd rather try to defray some of that into the Roth now. So here is what I think like in the. If I were doing triage, I don't think Roth is the most important. I think your allocation to the company stock is far more important to deal with. So if you would like to maybe deal with that first and create that horrible tax liability right now, which you know you're going to have to deal with at some point, you're going to end up spending about, you know, 20 something. Let's just say a quarter of the money. That is, let's even say a third. If you sold the whole company stock now you don't have to do it all at once. I'm just saying I would sell at least a third of that and, or talk to an accountant and come up with a strategy for like scaling out and getting out of that company stock. That money needs to be reallocated and diversified. It just does. And you know, I, if you do it all at once, you're going to get whacked like crazy. You're going to be in a very high brackets. Do you work with a tax preparer?

[B]

Yes, they do.

[A]

I think you should talk to the tax preparer. I think you should. They do they know about the 1.3 in the company stock?

[B]

Yes.

[A]

What do they say? Don't do it because you're going to pay taxes. Say we're doing it. Like just say we are doing it. What's the, what's our game plan? That's what you should be like. Be very direct.

[B]

Well, you mentioned that I'm in the 32% tax bracket. I actually asked him, I emailed him what tax bracket for, you know, it's 2025.

[A]

He said at 35% maybe because did you get some sort of. I mean he makes 450. You just, it's just a tip. So married filing jointly. The top bracket is 512 to 768. So 500,000 to 770 is okay. You know, most of your money looks like it's coming in at the 32% bracket. Is he including?

[B]

I think because the numbers I gave you for the current job is less than what the prior. Oh, because of the stocks.

[A]

Interesting. Okay, so this year you actually. So this job is going to be much more salary based or this is like this. Did he take a Cut.

[B]

He took an even salary, I would say is lateral. And then there's a bonus, 30% potential bonus. And then there's a stock vesting over four years based on what the annual salary is. I say it's a little complicated.

[A]

Yeah, I get it.

[B]

So it's hard to kind of.

[A]

But even at 35%. Okay, let's say that, you know, hey, you're making for half a million or 600,000. Let's just put it out there. Even so, shouldn't we be more concerned with the risk of having $1.3 million in one stock? Are we letting the tax tail wag the investment dog? In other words, if you had just said, you know, we sold some, we paid tax. Like, even if you just said to the accountant, we're going to sell a quarter of this every year for the next four years. Count on it. It is so scary to have that much money, that big part of your net worth in one holding. And even if it goes. Even if it goes up, up, up, and you've missed some, maybe the way to make yourselves feel better is to have a plan to do this on an annual basis. It just feels so. Well, okay, I'm gonna say it feels anxiety provoking to me as someone who has lived through many ups and downs with people in my life who have taken on this kind of risk. Even if you feel like, oh, we can assume the risk, or, you know, oh, we'll just wait, well, what if the company doesn't do as well? I'm sure you've lived through cycles where you've seen that stock go up and down. I just feel like it would. It would really behoove you to just say, look, I'm going to pay some of the taxes. Even if you had to skip the Roth, even if that were the case, I'd rather you sell the stock and keep getting your tax deduction for the Roth and I'll deal with your untaxed assets later. I am much more concerned about that company stock. To me, that's the risk that sits on the balance sheet. That 1.3 million bet on, you know, Red 21 or whatever it is, you know, whatever the stock is, it doesn't. It could be the best stock in the world. Maybe it's like, oh, I own. If you worked at Nvidia and you said, why, God? The stock was, you know, we. We acquired it, it was 200, 000. Now it's 1.3. Great, let's take that money off the table and ensure that you're 65 or 62 looks like a reality. Let me ask you a few more questions. Do you guys have life insurance?

[B]

We do.

[A]

Okay. And it's term life insurance.

[B]

Yes.

[A]

Okay, great. How about estate planning? You have kids who are kind of in a interesting situation. A 20 year old is almost 21. So do you have the estate docs done?

[B]

Well, that's my other question. We have a living will and testament, power of attorney and advanced healthcare directive.

[A]

Okay, a living will you don't have just a plain old will.

[B]

Oh, and a living will.

[A]

Yeah. Okay. Okay. So you have a will, a power of attorney and the living. Yeah, that's all good. You don't need a trust. You don't need a trust because you're. Even for New York state death tax, you're under the limit, so you're good. Anyway, I got to spend some of this money down, you know. Is your brokerage account held? Where? Where? That 360 that you said, where is that held?

[B]

At Chase.

[A]

At Chase? You're in JP Morgan Chase as like an investment.

[B]

Yes.

[A]

Okay, no shade throwing at Jamie Dimon if he's listening, but how are they doing for you and what do they charge you?

[B]

I knew you were going to ask me that question. So I did actually text my advisor to find out because I know at one point it was 1%, but because we've combined assets and whatnot, it is at 0.41.

[A]

0.41, that's it. Geez, it's cheap. Okay, keep doing what you're doing. I think it's more important to take the tax hit on the sale of the stock than doing a Roth. But I think a Roth is possible in the future once we get that stock situation managed.

[B]

Okay. So as he starts his new company, start off 100% doing a traditional IRA.

[A]

Yeah. As long as you're going to sell the stock. If he's not going to do the stock, if he. If you guys are like holding your breath and saying, no way, we're not doing it, then use a Roth for him.

[B]

Okay, what about splitting? Could one split like partial Roth, partial traditional?

[A]

Well, yeah, sure you could, but you know, again, you're going to feel the tax hit at a time when you're going to pay a lot in when you sell the stock. You should. So I'm happy to feel if you're willing to do that. Absolutely. It sounds like you're more willing to do the Roth and take the tax hit on the sale of the stock.

[B]

My husband would like to.

[A]

Market time.

[B]

No, sell the sell more of the stock. Yeah, I think I'm a little bit more holding that. It's a strong stock.

[A]

So what you got? You got. Are you kidding me? I could find the best stock in the world and I wouldn't put 30% of my net worth down on it. Yeah, there's no way. The most I would ever. Mark is laughing at me now. So the most that I would ever have in that stock. Like right now, if we think about your net worth being, let's just say your invested net worth is $3 million. You could have like 300 grand at most in that stock. The rest should be sold. Having more than two diversified portfolio. Let your broker, Chase, JP Morgan Chase reallocate and put that money in the brokerage account.

[B]

Yeah, that's what we're thinking.

[A]

Yeah, totally. Okay. And like suck it up, girl. You know you're going to pay some taxes. Isn't that terrible? Wouldn't it be worse? Literally. Would you rather be in the situation where like, well, it's only worth 300,000. No, you want it to be more. So pay the tax. You don't do it all this year, but you have to get out of this thing. The maximum that should be in any one single stock or any single loopy idea like gold crypto. Like One thing is 5 to 10% of your invested assets. You got $2 million in investments right now. I'm not even including the, the 360 that's in the brokerage. $2 million there. You got another million dollars. It's 3 million. You know, like you really shouldn't have more than 300 grand in this stock.

[B]

Okay. All right. Yeah.

[A]

It's your tough love today that you're doing great. You're your financial gut check. I think, I think, Katrina, you look good. You really do. But let's get, let's, let's clean some of this mess up. It's not a mess. Let's clean up some of these great opportunities you have. Let's convert this great opportunity into more freedom for you in the future. How does that sound?

[B]

That sounds great.

[A]

See, I did it with a little bit of a salesmanship. I have that in me still. I really do. Is there anything else that we can do for you, Katrina from Long Island?

[B]

Yes. There's one more question regarding life insurance. I'd love to get your thoughts on getting a law long term care policy.

[A]

Well, that's an interesting question. If your husband has that as a benefit through work, it might be worth looking into. It might be. But Generally speaking, they are very expensive and at your level of assets, like, and I look at everything together here, right. So now I'm saying that you'll have $3 million invested and you'll have a, you know, one and a half million dollar house. You should be able to self finance a chunk of it. But if there were a corporate benefit, I'd look at it and maybe if you want to take a look and see what the cost would be because you're young, you know, you're under the age of 55, what would it be to get some partial coverage? That would be interesting for me to find out because you know, obviously if one, if something bad happened to one of you, then the other one is going to plow through the money pretty quickly.

[B]

Right, right.

[A]

And so I would look into it.

[B]

Okay.

[A]

Kind of like this donut hole. It's like if you had, if you had all that money from your investment reallocate. No, I'm just kidding. If you had, if you had more like $5 million invested and a million and a half dollar house, then yeah, then I'm like, okay, you can self fund, but at this level, at this point in your life, there is risk. There is certainly risk here that again, you live in a very high. If you had to go into one of your places out on Long Island, I happen to know, because my mother in law was in one, so I know how much it costs. And you know, 200 grand a year can get eaten up pretty quickly with one person needing care. Now it wouldn't be forever, but it would be like you'd eat up $1 million. It leaves the other one short when it comes to retirement. If it happens too early in your life, that's, that's the downside. So maybe get a quote and if it's so expensive or you get a quote, come back to us and we'll give you an opinion about whether we think that's too expensive or not.

[B]

Okay, that sounds great.

[A]

Good.

[B]

Yes.

[A]

My God, this is fantastic. What? What, What a joy. I love it. I love when other people have to pay taxes. I would love to pay taxes. I wish I had stock worth $1.3 million. And I would love to take that whole thing and just like have bathe myself in my tax liability because it's a million dollars, Mark. That's a check I would love to write. I'm. Me too. I'm happy. I'd be the most patriotic girl in the world. Okay, gang, are you sitting on a big position that is kind of bugging you. You know you should sell it, but you just need a little nudge. We are happy to nudge you, we're happy to coach you, and we're happy to show you that this unpaid tax liability is going to give you freedom in the future. You just have to unleash it. So go to jillonmoney.com, click the contact Us button, Write us a note. Please come on the air so we can talk at 3. And don't forget to sign up for the free weekly newsletter which comes out today Fridays. And because it is Friday, we like to tell you that our music is composed by Joel Goodman. Mark Tularcio is our executive producer and king of all things Web. We are distributed by Odyssey, which is where you can subscribe to this show and our Money Watch program. Try to do something nice for someone else today. Change your work, Change your wealth, change your your life. Thank you for listening and we'll talk to you on Monday. You know, everyone has their own reason for giving. For some, it's something personal, like honoring a loved one's memory. For others, it's about paying it forward after someone helped them through a tough time. And sometimes it's just a quiet belief that things should be better than they are. There are a million reasons to give, but now there's one way to do it better. It's called DAF Giving360 and it's a public charity that offers the giving solution of a donor advised fund that makes charitable giving simple, tax smart and more impactful. So how does a donor advised fund from DAF giving 360 work? First, you open an account and contribute. Contributions can be anything from cash, stocks and securities or even non cash assets like real estate, life insurance and crypto. And you may qualify for a current year tax deduction even if you don't make your grant decisions right away. Next, you can choose to invest that contribution. You can select from a variety of investment pools, or if your account is over $100,000, you can recommend your own investment advisor to manage the funds. And then when you're ready, you recommend grants to the causes and charities you care about and and you do it on your timeline. Could be this week, could be next year. There's no rush. You just log into the Daft Giving360 client center. Then you can grant in just a few clicks. Daft giving360 takes care of the rest. They verify the charity, send the check and include a personalized grant letter with your name and custom letterhead. And when tax season rolls around, you've got a simple, personalized annual report ready to go. What's also great there's no minimum contribution to open an account, but once you do contribute, you can grant to charity right away or invest and potentially let those charitable dollars grow tax free until you're ready to grant. So whether your reason for giving is deeply personal, practical, or somewhere in between, daft giving360 helps you make a greater impact with less hassle, more flexibility, and more strategy. There are a million reasons to give. There's one way to do it better. Daft giving 360. Want to learn more? Visit daftgiving360.org have you ever felt like you are living just a B or B plus life?

[B]

It's so dangerous to live that.

[A]

More dangerous than a B or a C plus life?

[B]

Because when you're living a B or B plus life, you don't change it.

[A]

You think it's good enough. Is it? I'm Susie Welch.

[B]

I hope host a podcast called Becoming youg People Think okay, an A plus

[A]

life is not available to me, but

[B]

there is a way. We are all in the process of becoming ourselves. Listen to Becoming youg wherever you get your podcasts.