Your Company Stock Is Crashing. Here’s What Executives Actually Do About It.

In this 12‑minute conversational video, Brian Dress, CFA (Director of Research and advisor at Left Brain Wealth Management) and Nolan Langford, CFA (Chief Investment Officer) walk corporate executives through the emotional, analytical, and practical steps needed when a large, concentrated position in company stock is falling sharply. They begin by emphasizing that reacting without a plan—or doing nothing—is the worst response. The hosts then explore the psychological toll of seeing net‑worth erode, the common bias of anchoring to past stock prices, and the need to separate loyalty to the company from personal financial prudence. They outline a decision‑making framework that includes: (1) assessing the stock’s fundamentals and whether the decline is temporary or structural; (2) enumerating tactical options beyond “sell all” or “hold all,” such as partial sales, systematic sell‑downs, using employee stock purchase plans, buying more shares if the outlook is positive, hedging with options, or repurposing proceeds for diversification; (3) understanding tax consequences of restricted stock units, capital losses, and severance timing; (4) initiating a concrete first action—selling a modest block of shares to break inertia. The discussion then shifts to family dynamics, advising executives to involve spouses and discuss risk tolerance. Finally, they detail what a first meeting with a wealth advisor should look like: required documents (stock statements, 401(k), tax returns, estate plans), questions to assess advisor expertise with concentrated positions, compensation structure, fiduciary status, and tools provided. Throughout, they stress the importance of a tailored plan, early action, and seeking advisors who can give specific, stock‑focused advice rather than generic advice.
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If your company stock has dropped significantly and your net worth has dropped significantly along with it, the worst thing that you can do right now is to react without a plan in place. And the second worst thing you can do is nothing at all. Nolan and I are going to talk about a third option in today's video.
Sure. Every major downturn in a concentrated position sorts executives into two groups. The ones who had a plan, even a simple one, and the ones who didn't. The outcomes are consistently different. Today we're going to talk about what that plan looks like.
And by the end of this video today, you'll know what moves are actually available to you right now, what the one action is that you can take today to start turning this around, and what to avoid. Let's go. Before we get into it, I'm Brian Dress, Director of Research and also an advisor here at Left Brain Wealth Management. We're an independent advisory firm based in Naperville, Illinois. We work specifically with corporate executives in situations just like this one. And with me as always is Nolan Langford, our CFA and Chief Investment Officer. Nolan, quickly for anyone new here, introduce yourself.
Yeah, I spend most of my time doing deep fundamental research of individual companies, so I've watched a lot of these situations play lay out from the inside.
Perfect. So glad to have you here to talk about this. Today we're covering what to do when your concentrated position has declined significantly, your actual options, what the data tells us about how executives navigate this well versus poorly, and one concrete action you can take today, even if the full solution isn't clear yet. If this is useful, hit subscribe. Now let's get into it. So Nolan, before we get into tactics, we wanna acknowledge what this really feels like. This is really a feeling situation. Almost above all else, because that really does matter. We want to acknowledge the fact that there are executives out there sitting on big piles of shares which have gone down in price. And that really is painful when someone's watching that net worth decline in real time. What's going through their head?
You know, I feel for these people. You know, it's not just numbers on a piece of paper. You know, a lot of times that executive have tied in that net worth um, that financial statement into hopes, dreams, marriages, vacations, early retirements, standards of living. And when those numbers start to shrink, you know, those commas and zeros are removed, it can have a devastating impact. I imagine it could lead, um, you know, some of these executives to the psychologist chair, and in some cases depression. It is a really, really difficult situation. You know, think about these executives Sounds like we're talking about today, these software executives, but in future years it could be retail, it could be oil and gas or sort of any sector. Sure. But it is a really difficult situation, particularly if you're in one of these industries like software where a good chunk of your comp every year is in company stock.
Right.
Man, is that difficult.
Absolutely. So we want to acknowledge the fact that there are certainly emotions tied up into this and sometimes that makes it difficult to make the right decisions. And so Part of what we do here is help people push past some of those emotional barriers and biases and make the right decision. So that's what we're gonna discuss today. You're not gonna solve your problem all in one go, all in one decision. But it does require a plan and a framework to come up with something to put in place to help solve sort of the challenges that come along with this difficulty of a stock falling when it makes up a big portion of your net worth. Someone in this situation, sometimes doing nothing feels unbearable, but sometimes doing nothing is kind of the way that they respond to it because we have inertia, and sometimes it's very difficult to make a decision where you feel like you're going to have to take a loss. So let's talk a little bit about how do you channel this energy productively without making a reactive mistake? So as we said, we've got the people who want to make no changes, and there's probably people who want to make dramatic changes. How do you deal with that?
So I think in this case, we definitely— I opened up talking about how emotional and how emotionally painful I feel for these people. But in this case, when we talk about action, we really want to leave our emotions aside.
That's right.
And at this case, we want to make kind of well-reasoned, more calculated decisions. And so yes, I need to take stock of my individual situation, pardon the pun, but then I also need to independently evaluate objectively what's going on in this business that's causing this stock to fall. And is it permanent or is it temporary? And the, the results of that analysis is gonna help me make the, a, a proper decision.
Okay. So that's what we're gonna talk about today. What are some of the ways that we analyze, uh, a stock that of a company that people are in kind of in the caught in this situation where the net worth is falling precipitously? How do we analyze it and then how do we plan around it? And some of the ways that you can maybe take a couple of steps today to sort of take away a little bit of the pain, alleviate some of that pain. If this resonates with you, if you recognize any of these reactions in yourself right now, hit like. It helps us reach more executives who are sitting in your exact situation. And if you know someone who's going through this, please share it with them. Uh, we want to get this material out to as many people who are in this difficult situation as possible. That could be the most useful thing you do for yourself today and for, uh, your colleagues as well. So With that being said, let's talk about what's actually happening in this situation, what you can do about it. So let's talk about Nolan. I want to talk to you and lean on your expertise and experience here in this situation. You've spent your career not only doing fundamental research of individual businesses for investment decisions, but also doing the analysis for people who have come and worked with us here at Left Brain who might be in this situation where they have a lot of their net worth tied up in one stock. Happens to be falling in price. When you see executives in this situation, is there a pattern you've seen before?
I'm going to say it runs the gamut. I mean, I guess you can bucket them into a few different buckets. And like you were saying before, a lot of it has to do with the individual, him or herself, their personality, their timeline, and their outlook on the world. I will say universally, If it's a high-ranking executive, one of the things that complicates it that is a common denominator is this company loyalty.
Okay.
Even in today's environment where every company looks at every employee as a free agent, employees themselves haven't become that mercenary. There's still a high degree of company loyalty, drinking the Kool-Aid. Sure. Which probably got them to their position. And the higher, the more stock you have, it's likely the higher position that you've reached. Right. And so I kind of get it. You want to be a team player. But when you're looking at your net worth statement, you kind of have to be a mercenary. You want to be independent. And, um, and so I would think that would be the one common denominator is the overwhelming, not only belief in the company, but the desire for the company to do well.
So we're going to talk about what sort of some of your options are, but let's speak sort of to the urgency of the moment, Nolan, when you're in this situation, you mentioned you're a high-ranking executive in a company, you've got a ton of your money, your family's net worth and wealth tied up in one stock and it's going the wrong direction. Kind of how do you deal with that today? What are some things you can do today?
So I definitely think that, you know, it depends on the degree to which it's going the other way. If it just isn't moving, you know, there's a lot of stocks that we say are just kind of dead man walking. They're just kind of stuck in the mud. They haven't gone up a lot, hasn't gone down a lot. And so I'm not happy that my stock hasn't gone up, but it hasn't gone down either.
Right.
So I think there's still some action we can take, but the urgency isn't quite the same as when I got some company that has fallen 60%, 70% and it's in free fall. Yeah. There it looks a lot more existential and I really want to find out, hey, what the heck is going on? Is this rational? Is it irrational? Is there something I don't know? So there I think you're— more compelled to take swift action.
And I think there's a corollary too, to what you said. So you mentioned a stock that might be going down 60, 70%, but there's also the types of stocks where if the stock market overall might be doing well, but your stock's kind of sitting there doing nothing, that's a fairly similar situation, I would say. Would you agree to that?
In the real world it is, but I don't think in executive's mind it's not the same.
I see.
You know, if last year my shares were worth $2 million and this year they're worth $2 million, they just haven't gone anywhere. And even if the stock market's up 25% or 30%, and if I didn't have my basket of shares at $2 million, it could have been $3 million. It's just opportunity cost. And so you can't take that necessarily to the bank, or people don't take that to the bank. So it's just not moving very much. In a lot of cases, those people, Brian, those executives, they should be compelled to move. But human nature being what it is, they're not. You have to take people to the house of pain before they really want to do something. Okay.
So that's what we want to discuss this. And sometimes we want to help people. You don't want to get to that house of pain. Maybe you can make a move or change before you get there. And the fact of an underperforming stock, even if it's not falling, is an indicator that you may have trouble ahead. So that's something that we want you to consider, even if you're not in that house of pain quite yet. But let's talk about, Nolan, what the options are right now. So as we say in pretty much all these situations, it's never an all or nothing. You're— it's never a matter of sell all your shares tomorrow or just do nothing. What are the menu of options that are available to someone in a concentrated position that's down right now? Other than just sell or hold?
As you're talking, you know, what comes to mind, Brian, is, um, Meta, a real-life example. Meta is a business that we like. For those listeners who aren't familiar with Meta, it's Facebook, it's WhatsApp, it's Instagram. It's a business that we like a lot. But if you go back just a couple of weeks— we're taping this in very late in April of 2026— so prior to a couple weeks ago, Meta shares just really hadn't done much, and they kind of underperformed the market, right? They're kind of going through this AI build out and spend. And as part of that, they're actually laying off a good chunk of their staff so they can spend more on AI. And I don't think the stock market and investors are loving the hundreds of billions they're spending on AI, but it's a business we like. We still think it has a very optimistic future and we think the outlook is great. We like the moves that they're making. Now, if you're an executive working there and you just found out, you know, your position's gonna be eliminated. And you've got these company shares, right? And they haven't worked. You know, that's a heck of a conversation. If I'm an executive that was doing part of the restructuring, I'm on the other side, so I'm going to make it fine. But I kind of see the strategy that the company is using. Even though my shares haven't performed, my strategies as an executive one is going to be very different than the executive two that was just given his pink slip, right? So I think if I'm executive one and I see what's happening and the stock hasn't worked, maybe I think that's an opportunity to add shares. Okay, so now I just need to talk to my advisor and think about what's the best way to do that. Do I buy them outright in my brokerage? Is there some move I can make with my stock options? Do I want to double up on my employee stock purchase plan? Should I add them in my 401? Like, what's my best way because I like this opportunity if I'm not overexposed.
Okay.
Very different conversation than the executive that's just been terminated because you got some feelings involved. There's also some economic impact. You know, what does my severance package look like? What are my employment opportunities look like on the other side? And what does that timeline look like? How many shares do I currently own? So it could be an opportunity. But the question is whether I'm in a position to take advantage of that opportunity. So it depends on the business, whether this is a temporary thing, a pause that refreshes, rather it's more existential. And then where I fit in the whole scope of that.
So as again, as we said, you could sell everything, you could hold everything, but there's obviously a middle ground in there, which is you can sell some. So, and then there's also some tax implications. So Nolan, if I have some shares that I own, say at $100 a share and that's trading $70 a share, Talk about, you know, in terms of we're trying to help people get off of that inertia of just doing nothing. What are some of the tax benefits of maybe making that move today?
So I don't know if there are benefits, but there are certainly tax consequences. So let's use your example. I have $100,000 in these shares. I'm just going to keep using Meta. Maybe I shouldn't, but we just did. Nvidia. You just pick the company. But let's say I have $100,000 in shares. We're going to assume in my case, in this case, that these are restricted stock units that were granted to me. And just to make it easy, let's just say all of my vesting happened for the $100,000 shares this year.
Okay.
Let's say it was in April. So I know at the end of the year I have $100,000 that's going to hit my 1040 in ordinary income. Yeah, that's the first thing I know. So now if I'm sitting there and it's the end of the year and let's say we go to your analysis and the stock is down and let's say they're not worth $100,000 anymore, they're worth $70,000.
Right.
So you're right, I have to take a look at this. So they hit me on the top with ordinary income, right? But now that I own the shares, if I sold them, it would be a capital loss. It's not an ordinary loss, and I cannot write off a capital loss against ordinary income.
Exactly.
So that's quite the sticky wicket.
It is.
And if I need the cash because I'm not going to be working and my severance didn't hit That would be something different. But in this case, let's say I did get severance and the severance was a lump sum. So they gave me 12 months of pay, but they gave it to me all in a lump sum. Now this year's a really bad tax year. I had $100,000 hit my ordinary income. I got the grossed up severance all in this year. That may make me think about things differently in how I handle the rest of my shares.
Okay, so you, you're definitely giving voice to the difficulty of the situation here. What are some— we want to talk about what you can do today though. And not necessarily in that example of being terminated, but just maybe someone that's just holding a bunch of shares, you know, their position in the company continues to be secure. What I hear a lot of times with executives, and I've spoken to a couple people in the last year, they don't know where to start because as you said, any decision they make comes with some sort of negative consequence. So it feels sometimes it feels better to just kind of do nothing and avoid those consequences. And a big solution feels overwhelming. What do you tell somebody like that?
Just get started.
Okay.
You know, body in motion tends to stay in motion, to act it on by an outside force. And it's kind of the same thing with inaction. You have to actually get the ball rolling before it can start rolling.
Okay.
And so you're right, we've seen this a lot in the case of, um, You know, we've got people we've talked to here from Accenture. You know, Accenture for a very long time was a blue chip stock. You could kind of set your watch to it, but it kind of fell out of bed here in the last year, year and a half with everything that's going on in AI. And so there's a lot of consultants and executives there that are high ranking that have a lot of shares that make up their net worth, and they're just kind of paralyzed, right? Is it going to come back? Is it not going to back? I still want to do anything. Where do I even start with my shares and what should I do? And just, they just hands over face. And yeah, that's certainly the wrong answer. But I think to get started with something, take the statements into the advisor's office and have a conversation. That's a good way to start. If I'm thinking of doing something with my shares and I got 100,000 shares, you know, maybe I start with 100 shares, trimming out 100 shares.
Maybe we do that.
At 100 a week at a time. But almost inevitably, the worst thing to do is nothing. No plan. And I ain't even going to think about a plan. I'm just— I mean, what are they waiting for? Godot? I mean, what?
I think a lot of times what is happening is what's called anchoring. So my stock traded at X price 2 years ago, and now it trades at 50% less than that and it feels, you know, I just want to wait for it to come back to that other price. I know from a logical perspective that doesn't make sense, but talk to— speak to us from an emotional perspective of how to kind of move past that.
You know, this is one where, you know, they might want to sit on the psychiatrist's table, put their feet up for a few hours and pay the fee. I think you have to really, you know, the anchoring thing is tough. The way I like to think about the argument is, you know, I had $1 million and now it's, in your example, I have $500,000.
Right.
So I can anchor to the million, but it doesn't have to be that vessel that gets me back to the million.
Sure.
I just need to get back to a million. So I just need to think about, I'm at $500,000 now. Mm-hmm. What's the best way to get my $500,000 to double?
Okay.
Now I just been in a shipwreck. Right. So if I'm going to get back to a million, do I want to climb back in that broken ship and count on that one to get me back to a million?
Okay.
Could be if we patched it up good, but it's likely— let me just switch boats. And so let me take my half million and let me look at some things that are doing well. Well, the outlook is brighter where my probabilities getting back to a million are much brighter. And so there certainly needs to be some thought exploration around that. And again, the head in the sand thing probably is not the best way to go.
That's a great analogy. And I think it makes a lot of sense what you're saying. It's hard, especially when you're in the company, if you believe in what they're doing. And it's hard to think, well, maybe there's a different ship that is going to sail a little bit more smoothly.
Think about the opposite, though, Brian. Let's imagine you're the person in the executive suite and I had a million and I'm at this company, I've given my heart and soul to it. I'm in every meeting, I'm showing up at the company picnic, you know, I'm wearing the t-shirts, I'm doing the 5K run.
Okay.
My million just went to half million. So clearly there's something happening in the business. It's probably not positive right now. They come and get rid of me. My half million just was cut in half. I just lost a half million. Now they get rid of me and I lost my job to boot. Yeah.
Yeah.
Like, my goodness. So, you know, yeah.
So you got to do what you can to make sure you don't lose in a couple of different ways. And then what do you do after that first move? So if we say the first move is sell a few shares, some people might worry, okay, well, I've sold a small piece of it. It feels like I've done something, but now this whole position sitting there, uh, continuing to deteriorate. What goes on? What's the next step or next stage from there?
You know, I think that's probably a good thing. Yeah, I think if you're in a sink, you know, if you have a stock that's just not working and likely if we're having a conversation, it probably hasn't worked for a while because it's generally not, you know, we had a bad month. Generally people aren't going to take action. You know, our position is anytime an individual stock gets to be 10% or more of your net worth, you should have a conversation independent of whether the stock's doing really well or doing bad. You should always have a plan and always be thinking about it. But for the average executive, I know how human nature works and that's not it. And so if it's working, they're not going to do anything. And if it's sitting there stagnant, they're probably not going to do anything. It's if it's not doing well and it's probably not the first month. So if this is an executive thinking about this, your stock hasn't worked for an extended period of time. Yeah. And so I do think you're right. I think selling some to get started, I think kind of makes sense. And, you know, the question we need to have is how much do we need to sell? Should it just be more than this little bit? The first $100 we sell, first 100 shares, are just to get the ball moving, just to get the wheels in motion. Yeah, yeah. And then we need to think about, you're right, how quickly and how much and over what time period and what we can do next. We certainly want to take some action with this stock and Uh, you don't generally want to wait until it's too late. The worse it gets, the more difficult it's going to be to make that decision. We've seen that all too well after the Y2K blowup. There's way too many executives I've met with where I've seen fortunes just ruined. And the more I tried to pull on that string to take action, the more violent the fall of the stock, the less likely they were to do anything. Parachute won't open.
No. And healthy businesses, generally the stock doesn't fall like that.
Correct.
Let's talk about executives. You are yourself, you're there doing your own thing, but you've got a family, a partner, children. A lot of times this is happening, but you don't have any conversation with your family, discuss it. Does that match kind of what you've seen over the years? And how does someone in this situation approach that?
I have seen that a lot, particularly in this case, Brian, with stocks that have done well.
Okay.
So what I found, and I'm kind of stereotyping here, but what I found a lot is, you know, somebody works for one of these AI companies. Mm-hmm. And maybe they joined as a startup or after they got going, they got a lot of stock. Stock does well.
Okay.
So there's a lot of planning, obviously, uh, actually that a lot of times doesn't happen because you have so much money. You know, if they've done really, really well and we're talking you know, not just 6 figures, we're talking 7, 8, sometimes 9 figures. You know, why do I need to apportion money to the side for my kids to go to college? You know, that's only $250,000, $350,000, right? My stocks are worth several million. Clearly, when they get to college, I can just peel some off and pay for it. Yeah. So actually, you would think those people do a lot less planning because they're so rich, they know the money is just going to be there. We like segregating and putting things to the side, right, in a separate account, a separate college account away from your stock account. And so we can kind of breathe deeper and, um, not worry so much about it, right? Your premise was correct though. Typically it's not a lot of discussion with the spouse or the kids. It's just the executive kind of knowing in the back of their mind, I have enough money to pay for everything. So why do I need to worry about modeling or planning, right? Or, you know, thinking about a plan B?
Yes, things can change quickly and it's important to plan in a way that's prudent just in case things do go badly. Your obligations are covered.
In a lot of cases, you can be more aggressive. So some of these hard-charging investors have a high risk tolerance and maybe they're just aggressive investors. It's like, well, I'll deal with it. And in that case, I think the planning in that case doesn't slow you down. It can help speed you up.
Sure.
I know college is taken care of. I know my retirement is taken care of. I know the weddings for my daughters, all of those are taken care of. Any bequest that I want to have, my financial legacy, all that's sewn up. Now it's go time. So if I want to have 100% of my money in my company stock, everything else is taken care of. There's really no downside for me. Now I can really push the pedal to the metal. Okay.
I like that. That makes sense. And that's a good way to sort of incentivize people to plan that they do think they're secure already. Let's get back into this household conversation. What do you say to the executive whose spouse is more worried than they are? So a lot of times, like you said, you know, the executive's got visibility into the company. They think, oh, it's going really well. And maybe the spouse wants to do what we just mentioned, be prudent, put things away in different buckets to where, you know, obligations are covered no matter what happens. How do we manage that dynamic?
You know, I'm going to throw this back to you. I'm going to give my answer, then I'm going to throw it back to you to see what, what you think about this. I actually think that's a healthy marriage. Yeah, I think that's a healthy partnership because you got one person that sees it one way, another person that sees it another, you know. And typically you're always compromising in good relationships, so they're going to sort of meet in the middle. And as an advisor, that's great pre-work for me. I don't have to bring this, bring this man or woman to the middle. Their spouse has already gotten them there. So let's come up with a plan that makes both sides happy.
Right.
So I think that's healthy. So in your case, what has been your experience?
Well, my thoughts about it is I think that the executive needs to have the humility to listen to their partner and understand their concerns. And like you said, you might come to a better decision-making process bringing both people's concerns to the table. Right. And considering that, in my experience, I think, yes, I think you're going to make better decisions if you, you know, if one person's definitely more aggressive, one person's more conservative, you come to the middle, compromise in some way, shape or form, you're going to make better decisions because there's blind spots to both approaches.
Yeah, I agree. And oftentimes your other half, they call them the better half for a reason. Yeah, they see things you don't. You know, think about you and your wife. How many times have you introduced her to a friend? It's somebody you, you love. I mean, you'd go to the end of the earth with, and then your spouse needs to be like, I don't really like that energy. It's just really, you know, something right ain't right with this guy, this woman. Yeah, I mean, it happens often. So you have to kind of listen, uh, yeah, you know, that person is an intelligent being and you have to take what they say into consideration.
Yeah. You know, the judgment of two people is better than the judgment of one person more often than not.
Okay.
And so let's bring it to the practical. We're going to kind of bring things around to a conclusion here. What to expect when you talk to an advisor, Nolan. So let's be practical. A lot of people don't pick up the phone who are in this situation just because it's the fear of the unknown. They don't know what's going to happen on the other side of that phone call. What should an executive in this situation with the stock kind of falling or cratering with a net worth kind of falling, uh, apart a little bit. Expect from a first conversation with a wealth manager like us about a situation like this?
Well, there's a few, but the first thing is if I'm calling an advisor, I want somebody who can give me advice. Mm-hmm. And not generic advice about planning and about tax rates and what the college rules are. Specific advice on my company stock? If I'm a— so we're speaking to company executives that gets compensated by owning shares of company stock. So if you own company stock, we're talking to you. And if you're calling an advisor, the first thing I'm going to ask, not about advice, I'm going to ask specific advice. What do you know about my company stock? How many executives do you work with that have company-owned stock? And tell me your thoughts on my company stock. Now, after that, we're going to all, you know, we want to do a financial model, we want to do financial planning, we want to take taxes into consideration, estate planning consideration. You know, how much income I'm going to need for retirement. I want you to build my financial model, give me digital tools. I want all of that. But if I'm talking to some person who's only done mutual funds and I'm talking to him, it's just not a match.
Yeah. You need someone who's willing to take an— willing and able to take an opinion, intelligent opinion on the situation you're in. That means having some ability and some framework and some infrastructure in place in order to make that analysis and give you some thoughts. How do you think a first meeting would go? Just to kind of give people a picture of what it would look like. What would a first meeting look like? What should they bring to that first meeting? And what would a good first meeting look like in this situation for them?
Yeah, I'm glad you asked that because a lot of times we get into a meeting and people are not prepared. I think that's a bad first meeting. So the first thing we'd like is for people to know where they are. There's not a lot that we can do to help if we kind of don't know the current situation. It's like calling the doctor's office and saying, you know, can I come see you? I don't feel well. Next question is going to be, okay, well, what's wrong? And if the person says, well, I don't know, that's not a very helpful answer. So the first thing we'd like is for them to grab specific documents. You know, we're going to want to know how many shares you own. You know, do you get matches? And we want to see a 401 statement. We want to see your stock plan statement, your 401. Do you have a pension? And we want to see your tax return. If you've done an estate plan, show us your trust. So those documents, please grab those and have those handy for the first meeting. In our case, we like them to upload it to the digital vault so they can securely send them to us, preferably in advance, to give us some time to do an analysis so we can make our first meeting together a productive use of both of our time. Okay, let us evaluate it, and then let's sit down, and then let's talk about what's important to you, Mr. and Mrs. Client. Where you at right now? Where you're at in your career? How you feeling about, uh, life? How long do you want to work? Are you going to stay at this job for a long time? And so We can have that discussion and then we can show you what we found. And together, that's the first step in kind of building a strategy to move forward.
Okay. And then let's, a little advice to the people who are trying to get advice. What kind of questions should an executive be asking an advisor in a first meeting like this?
So I like to start with capabilities and experience.
Okay.
You know, have you worked with other executives before? With concentrated stock positions? Do you analyze individual company stocks yourself and give opinions? Right. Those are things I'd like to know. And, you know, hey, how do you work with clients? How do you charge? You know, is it commissions? In what way does our relationship work? You know, if it's at a big firm like a Merrill Lynch or Morgan Stanley, the companies that most people know and have heard of and that manage these stock plans, Those are commission-based advisors.
Right.
So that might not be the best fit for every executive. A lot of people go in expecting a fiduciary and getting something less than. So in which way, what's your relationship with clients? Are you a fiduciary or are you a salesperson? Are you paid commissions or are you just paid a fee, you know, over time? So those are things. Those are things I definitely, I definitely want to know. And how many clients like me, you know, do you currently work with? How often can I expect to hear from you?
Okay.
Tell me about, you know, after we're working together, tell me what tools you have. You know, do I get a digital locker? Do I get a dashboard where I can see my holdings? Right. Things like that are important.
And what would be kind of some red flags?
You know, I think unfortunately in our industry, Um, because of the way that people are comped and people can do well working in financial services, a lot of people have these titles and it sounds like they're kind of advisors working in your best interest, but they're not. Things like financial consultants or, um, these other nebulous titles. Like there's a lot of people that just sell annuities or insurance products, right? They may be financial analysts, financial consultants, and they're really just an insurance person in drag. Some people are not that experienced. You know, if you work for a big Wall Street Wall Street firm, a lot of people will go in assuming because the person works there that that person themselves is experienced just because the firm itself has been around a long time. So I certainly want to know the person that I'm working with. I certainly want to know about them and how successful they've been and how long they've been working with people. We talked about method or means of compensation. How are you compensated? You know, how will we judge If we're working together, Mr. and Mrs. Client, Mr. and Mr. Advisor, how will I know if you've done a good job for me?
Okay.
You know, hey, will you create, monitor my financial plan? Is that you or is that somebody else? And as an advisor, how active are you in my financial affairs? So things like that, I think, are reasonable ways to start the conversation. Okay.
So just to recap, Nolan, we've talked a lot about the emotions around kind of being in this situation of having a lot of concentrated company stock. That's not doing so well, what are some of the kind of the first steps that you might take and what an advisory relationship might bring to the table for you and what you can expect when you do get started. So just to kind of demystify things, any final thoughts before we close the video?
My heart goes out to these companies, executives working for these publicly traded companies. You know, it's hard work. It's hard work. They're often stressed. I know they're not appreciated. And oftentimes they don't have the longevity of career that we would like. You know, how many times have we seen a client that's been working for XYZ publicly traded company? We started working with them when they're in the building wealth stage. And when we're doing our modeling, they're like, yeah, I don't mind working to 65, maybe 62. If things work out well for me and I can retire early, maybe it's 60. As long as I'm healthy, I don't mind doing it. And lo and behold, it seems like more often than not, Something happens around that early to mid-50s area where the company cuts the position, or they come around with early retirement packages, or the person's forced out. So they don't get to work. You know, they probably have— a lot of these executives have 5 to 10 more good productive years where they're valuable. They have all this knowledge, they're team players, they're valuable to the organization. And for whatever reason or not, the organization themselves don't see it that way.
Yeah.
So you really have to be prepared if you're, um, an executive, um, that in the back of your mind you always have to factor in maybe I won't make it to 60. My plan is to work to 60, 62, 65, but what happens if this company asks me to leave at 53? What does life look like afterward? Which means my money has to do very, very well in my early years because it may have to carry me for a while.
Absolutely. Good point. If you're watching this and you haven't had this conversation yet with your partner, with your advisor, even with yourself about the real numbers, about your concentrated position in company equity, that is where you need to start. I'm Brian Dress, Director of Research here at Left Brain, also an advisor. Book 20 minutes with me. No pitch, no pressure. We'll put the picture together, learn about what you've got going on, see if we could help you put together a plan to optimize and kind of maybe dig out of this hole that you're, you're currently in with this company stock and this company concentration going against you. Bring your partner and there's a link in the description. We'll also let you know we're going to put the e-book here on the screen that we put together. It's the Executive Guide to Managing Company Stock. It's a great read for you to understand some of the details around company equity, some of the different types of equity and some of the different kind of general strategies around that. Uh, so we definitely, uh, encourage you to download that ebook. The link will be down in the description. Nolan, thank you for being with us. We wanna thank all of our, uh, executives and other viewers for being with us, and we'll be back with you again with the next Fundamentals of Investing. Thank you so much.
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