In this Episode of the Secure Your Retirement Podcast, Radon and Murs discuss Concentrated Stock Positions and why so many pre-retirees and retirees are sitting on a mountain of Appreciated Stock without a plan for it. Whether it came from Company Stock Options at a long-time employer or from riding a big name higher over the past few years, a single stock that grows into half a portfolio changes the entire risk picture heading into retirement. Radon and Murs break down why Stock Diversification matters more now than it did during your working years, and why Capital Gains Taxes are usually the real obstacle keeping people stuck.

Listen in to learn about the Tax-Efficient Investing strategies Nick Hyman is using with clients to unwind large positions without triggering an unnecessary tax bill. You’ll hear how Tax-Loss Harvesting through Direct Indexing can offset gains, how a Donor-Advised Fund can move highly appreciated shares to charity with zero tax on the gain, and how bracket-aware selling fits into a coordinated Retirement Investment Strategy. If you’re building a Retirement Financial Plan and Company Stock Options or one big winning stock are part of the picture, this episode lays out exactly where to start.

In this episode, find out:

• Why holding a large Concentrated Stock Position is a different risk in retirement than it was while you were working
• How Tax-Loss Harvesting and Direct Indexing can help offset gains when you sell Appreciated Stock
• Why bracket-aware selling, year by year, is central to smart Retirement Tax Planning
• How a Donor-Advised Fund lets charitably inclined retirees give appreciated shares without paying tax on the gain
• Why doing nothing about a concentrated position only compounds the problem instead of solving it

Tweetable Quotes:

“When we’re working and we have a salary and income coming in, if a stock goes down 20, 30, 40 percent, it’s not as big of a deal because there’s still income coming in the door.” – Murs Tariq

“If you just stay in this place of doing nothing, you only are compounding the problem. It’s not getting better.” – Radon Stancil

Resources: If you are in or nearing retirement and you want to gain clarity on what questions you should be asking, learn what the biggest retirement myths are, and identify what you can do to achieve peace of mind for your retirement, get started today by requesting our complimentary video course, Four Steps to Secure Your Retirement! To access the course, simply visit POMWealth.net/podcast.

Here’s the full transcript:

So, Nick and Murs, we’ve been talking a little bit about this idea of this appreciated stock. 

And I guess we could just, first of all, just to kind of catch everybody up on our conversation. 

When we talk about highly appreciated stock, what we’re talking about in very simple terms is 

somebody who has owned a stock that was valued at Let’s just say if I had a stock that was valued 

at $100 and now it’s worth $2,000, that would be considered a very highly appreciated stock. 

And there are issues with that that we have to deal with, especially when it comes to 

diversification as well as when it comes to tax ramifications. And I know, 

Nick, you’ve been working with some clients here recently where you’re seeing this kind of… 

I guess, more commonly. And I’m curious, could you just share kind of some of those cases that 

you’re seeing and what that looks like? Yeah. So, it has been a very common conversation over the 

in the last few months, I would say. And so, one case in particular is a situation where someone’s been 

working at a company. Typically, lately, it’s been large tech companies like IBM, Cisco, 

Intel, and they’ve been granted company stock for many years. 

Most of the time, that’s due to their position at the company. And so, as those stocks have 

restricted stock units have vested, they’ve been able to save those stocks and basically watch them 

grow over the last few years. And so, what’s happened more recently is that so many of these stocks 

like IBM, Cisco, Lenovo have all just skyrocketed in the last few months and especially since the 

beginning of this year. So, the conversation has been. How do we strategically diversify, 

keep the portfolio diversified and make sure that we’re not running into huge tax ramifications? 

Because now a lot of the situations are while that stock, that company stock used to be a smaller 

portion of someone’s retirement plan. Now it’s a lot larger of a portion. So, the ramifications, the 

risk has gone up for many of our clients. And so, we’re having conversations around that. Yeah, 

Nick, I think that’s a very common thing. Even those companies you mentioned being local to here in 

this area, but I think there’s quite a few investors that are, whether they were granted it, 

like you were saying, or they just bought it, hopped on whatever bandwagon, and those big names 

like the NVIDIAs and the Tesla’s and all of that, it’s a similar boat that a lot of people are in. 

where they bought it low it grew especially over the last four or five years it grew significantly 

and now you’re like well what do I do and we often call that the golden handcuffs of hey I’ve 

got a stock that’s been really good to me but now i feel stuck with it and i may still like 

the company but I’m starting to do you see that they’re starting to realize that that number that 

they had five years ago has gotten maybe too big and what are they feeling how are they 

what are they saying to you Yeah, absolutely. So it was, I would say, 

a slower move in terms of the stock over the last few years. But then more recently, 

it’s been a lot quicker of a move. We have gotten into conversations where some of our clients have 

been working for these companies for 10, 20, 30 years. And they say, hey, I’ve had this stock here 

and I’ve been holding on to it mostly as kind of a hedge against everything else, I’m doing. 

And I know the company and I’m very familiar with it, but it wasn’t necessarily anything that was a 

huge part of the portfolio. So now it’s one of those things where sometimes it’s emotional 

decision to sell the stock because. We’ve been working there for so long, but other times it’s more 

of a situation of we don’t want to run into a huge tax bill. So that is the biggest concern. 

How do we strategically start to diversify this stock? It’s great that it’s done well, 

but the tough part is now there’s taxes that may be incurred. So how do we do that from a tax 

standpoint? Yeah, I think what I’ve seen in this case, and I’m thinking right now of a couple of 

families. You mentioned IBM, and it could be any company. But sometimes the story is, 

I went to work for IBM. I worked for them for whatever, 30 years. And honestly, 

a lot of my net worth right now came from this IBM stock. And so, it starts to kind of feel like it 

got me here. Why would I now give up on it? And so sometimes I think people get in this emotional 

things like, well, wait a minute, I wouldn’t be worth what I’m worth right now if it wouldn’t have 

been for this IBM stock. And so, what we’re talking about there is the difference between growing 

money when I’m younger and then making it last throughout retirement. 

How do you talk to somebody when, when, let’s just say that I, if I’ve got a portfolio and we can 

make up numbers here, but I got a portfolio, let’s say it’s $2 million and 1 million of my 2 

million is in an individual stock, which we see that all the time where they’ve got half their net 

worth half of their assets in one stock. You know, what’s the difference or how do you explain the 

difference to somebody about the, the, that concentrated risk? when I’m at retirement age compared 

to when I was 30, 40, even maybe in my early 50s, now here I am, I’m 60. 

What is the difference? How do you explain to them that this is a different story today than back 

when you were building this because you could have lived through the downturn back then? Right, 

right. When we’re working and we have a salary and income coming in, if a stock goes down 20, 

30, 40 percent, even though it is a large portion of the portfolio, it’s not as big of a deal 

because there’s still income coming in the door. That’s the biggest thing when it comes to 

retirement, making sure there’s still an income plan there. So, when it comes to actually being 

retired and relying on that money, well, that’s a whole different story. 

So now it’s a matter of… intelligently investing the funds but making sure that they can last and 

so, these are big companies you know a lot of the times we’re not concerned about them going out of 

business but what we are concerned about is a big fast run-up in the market and not taking 

advantage of that opportunity so there are significant opportunities that come up and then there 

are other situations where there could be bad times down 20 or 30 percent so it’s just wrapping our 

heads around Maybe we take advantage of this good opportunity now because it will help in 

retirement in the long run and essentially make those assets last. I know you might have something, 

Murs, but before we get to that, I got another thought that I just wanted to add to this 

conversation about this concentrated stock and I think what’s different. So, let’s go back to what 

you said, Nick. You said, you know, when I’m younger, I could have let it go down 30 or 40%. Let’s 

go back to my million dollars. If I got a million dollars and I’m working and I don’t need the 

money for another 15 years. Right. And it drops. 40%. And I know long-term, 

I believe in the company. I believe in this concept. It should not bother me. I know that long 

-term, this company is going to come back and it’s going to grow. And I don’t need access to money. 

The difference is that when I’m retired or close to retirement, I need access to money. 

So, if I had a million dollars that now went down to say 600,000, I’ve lost access to 400,000. 

And I now say I can’t. live on that money. I have to let it come back. Because if I start 

withdrawing now from 600,000, the compound effect of that is huge. And I think people, they 

start to get that in their head. If I say I got these million dollars and I don’t need to touch it, 

period, for the next 10, 15 years, stay in the company if you want to. But most people that are in 

retirement are saying, I got this asset that needs to be able to provide. So, I just wanted to add 

that. Access to money is really important when we’re… about retirement. So go ahead, Murs. I’m 

sorry if I cut you off there. What I was going to say in relation to what Nick just brought up is 

you’ve got this stock that grows. What we’ve all talked about with people, 

I think an easy way to envision it is this idea of taking chips off the table. 

It’s a common phrase that I think all of us use. What does that really mean? If you think about 

chips on the table, that’s really a poker type of or a gambling type of concept. 

but when you’re when you’re up a lot of times it makes sense to start taking some of those profits 

and putting them in your pocket or redeploying them into something else. That’s kind of the concept 

so that if there was an issue, if you got a few bad hands, you’ve got money in your pocket and 

you’re not going all in on some bad hands that you just don’t know what’s going to happen. So, I 

think with the stock market itself, if you look at this year in 2026, midway that we are, 

the stock market is up and somehow, it’s up. I think a lot of people would say that It doesn’t make 

sense that it’s up because of what we’re dealing with inflation and the Fed and things going 

on in the U.S. and things going on outside of the U.S. geopolitically and oil and all this stuff. 

And it doesn’t make sense that the market is up, but the market is up. Now, the market is up 

because of a handful of different stocks. And if you were to look and kind of, choose and see… 

There are plenty of stocks that are down in this realm of, say, 30 to 50 percent for the year. 

Right. And so that, I think, is what the sometimes the investor can ignore, 

which is the individual risk when you hold individual stock. Right. If you’re holding the index, 

I mean, how often do indexes go down 50 percent? It’s not all that common. The last one we would 

look back to is like a 2008 where the indexes were down that much. So it happens, but not all that 

often. But how often does an individual stock go down 30 to 50 percent? I mean, 

it happens every single year. Right. So, when you kind of frame it that way, the idea of taking 

chips off the table starts to make a lot more sense, especially like you said, Nick, is as we get 

closer to retirement and we start to need that money. Now, the question becomes is, 

how do we do this? So, Nick, in your financial planning and tax strategy types of meetings, 

you know, what are the things that you’re saying? client and I say, yep, I totally agree. 

My million in IBM, we need to do something. How do you approach that conversation? 

Yeah. So, our biggest approach is really at a tax standpoint. 

So how do we strategically sell out of that IBM stock or whatever it is, 

Cisco, Intel, and make sure that we’re not running into a huge tax bill? And so, a few ways that we 

do that, we’re strategically looking at other income sources year by year so we can kind of take 

advantage of where someone is from a tax bracket standpoint in a given year. 

And that’s different for everyone. So that’s a very individualized practice into what is going on 

this year in particular and how much can we potentially sell out of stock at a low tax rate. 

So, we can do that in any given year. And then we also have strategies to help with selling out of 

these highly appreciated positions. So, things like tax loss harvesting that we’ve talked to many of 

our clients about. And so that not and what that is just in a nutshell is in very high level is 

essentially using other funds that are non IRA money to. invest in the stock market and over time 

accumulate losses that are going to help offset gains from somewhere else. And so we have many 

clients who are accumulating losses in their accounts that is going to help and works perfectly for 

a scenario of selling out of a highly appreciated stock in any given year. So that’s a big strategy 

that we’re using too. Hey, by the way, on that one, because somebody here is generating losses. are 

we doing that generation of losses at the detriment to the return of the portfolio? No, 

that’s a good point. So the way that is essentially working is we are trying to, 

or essentially mimicking index. So we use the S&P 500 just as an example a lot. 

So if we broke open the S&P 500 and said, out of these 500 stocks, 

how are they doing? Are they all positive at any given point? And so the answer is no. In all of 

those 500 stocks, there are some that are at a gain. There are also some that are at a loss. And so 

if we’re going to be able to mimic the S&P 500, that’s any given year. 

there are going to be stocks at a loss. That’s just how it works in any sort of index. And 

so that’s not just out of purpose. That’s just going to happen. And so, we take advantage of those 

losses because we just can’t get away from them. They’re going to happen if we’re tracking an 

index. So that’s how we essentially accumulate the losses as they come up. 

And they can come up throughout any time during the year, potentially downturns. But even in a 

normal environment, like Murs said, the stock markets up this year, but there are many stocks 

that are at a loss. And so those losses help to offset the gains on the stocks that are doing 

really well. And it helps us to diversify. So, we’ve been able to accumulate losses of 10, 

20, 30,000, even while accounts are tracking the S&P 500. And so, with that, 

we can sell out of an… IBM stock, for example, that has 30,000 of gains with no tax consequences 

to the client. These are huge tax savings just from a strategy that we’re doing outside of that 

stock, which helps the client every single year going forward. Yeah, it is pretty cool. 

That strategy of direct indexing with tax loss harvesting, it’s pretty cool to be able to say, hey, 

the S&P was up 10 and I was up around 9 to 11. I did pretty much what the S&P did, 

but also, I was able to trim my IBM position next to no tax ramification. I mean, 

that is pretty special. There are not many other ways to do that. Although I know, Nick, when we talk 

about… You’ve got other strategies, too, that come up pretty common for some that are charitably 

inclined. In a nutshell, how do those work? Yeah. So, for someone who is charitably inclined, 

the way we’re looking at that is essentially, something called a donor advised fund. 

And so, for what’s called a donor advised fund, and this is typically someone who could create their 

own account at a broker. Charles Schwab or Fidelity and it’s their own charitable fund and so 

instead of what typically or what people typically do which is um pay taxes on money that they 

receive from a salary or from a distribution and then donate to it what we do with a donor advised 

fund is we are donating the highly appreciated stock at a 0% tax rate. 

So, with that fund, we can put the stock right into, and typically we’re using the most highly 

appreciated position. purchase of that stock and we put it right into a separate account without 

any tax consequences. And then so our clients are able to donate that stock without paying any 

taxes on the gains and they can donate that full amount of the stock. So that’s also for someone 

who is charitably inclined, a very, very important strategy to take advantage of highly appreciated 

stock and not pay any taxes on the gains. Yeah. So I think What we try to make sure that clients 

know is that if you just stay in this place of doing nothing, you only are compounding the problem. 

It’s not getting better. You know, you could you could you could just continue and say, 

I just don’t want to deal with it. But that doesn’t solve it. Just because I don’t want to deal 

with it doesn’t mean it’s going to get better. And so what we’re trying to, I think, throughout 

this conversation, as well as when we’re talking to clients is to say. hey, let’s come up with a 

plan to try to say, how do we diversify? How do we reduce the risk? How do we deal with the taxes? 

We’ve got strategies. We actually have more tax strategies that we can’t even go into right now, 

just based on time, that we can talk clients through that says, hey, we can do this and keep you in 

a low tax bracket, get you diversified and be able to help you in this situation. 

But I think ultimately what I think we can close out with is that if you’re listening to this and 

you’ve got You know you are in that kind of situation. 

Schedule a call with us. And so it’s pretty easy. All you have to do is go to our website, 

POMwealth.net, and you can just click anywhere in there and you can schedule a call. Our calendar 

will come right up and you will be able to schedule that conversation. And then we can look at your 

very specific situation. We’re talking very generalized today. But if you’re in that scenario and 

you go, I want to see what my situation looks like with our software, we’re able to show you a very 

specific plan for your situation. But I enjoyed the conversation, 

guys, and I hope maybe that this has helped people. So thanks for hopping on. Yeah, absolutely.