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Too Much in a Single Stock? - Jill on Money with Jill Schlesinger | Wave AI Podcast Notes

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Too Much in a Single Stock?

Jill on Money with Jill Schlesinger

Fri Mar 20 2026

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.

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Transcript

A (0:00)

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 there@jillonmoney.com 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?

A (14:11)

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?

A (16:35)

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?

A (20:17)

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?

A (28:49)

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?