My Company Stock Dropped 30%—Should I Cash Out Now?

Summary

Episode Summary: “My Company Stock Dropped 30%—Should I Cash Out Now?”

Podcast: Ramsey Everyday Millionaires
Hosts: Ken Coleman & Jade Warshaw, Ramsey Network
Date: November 28, 2025

---

Main Theme & Purpose

This episode centers on a listener call from Brittany, an employee whose company stock (a significant portion of her portfolio) has lost about 60% from its all-time high and sits at a 30% average loss. The episode’s focus: Should she hold her vested shares in the hopes of a turnaround, or cash out and reinvest in diversified index funds? Ken and Jade provide contrasting, practical, and candid advice to help Brittany—and listeners—navigate the emotional and practical sides of managing company stock.

---

Key Discussion Points & Insights

1. Brittany's Situation: The Dilemma

[00:18–01:34]

• Brittany has been with her company for five years, accumulating $150,000 in vested company stock through annual equity grants.
• The company’s stock is now down 60% from its 2021 peak, and 30% from Brittany's average purchase price.
• The stock represents about a third of her brokerage account.
• She is a “long-term investor” and does not urgently need the money, but finds it hard to make an unemotional decision.

2. Ken’s "Hold" Perspective

[01:34–03:30]

• Ken urges Brittany (and listeners) to set emotion aside and focus on facts.
• Recommends reviewing public information—what the CEO and board are saying about turnaround efforts—and understanding the reasons behind the stock’s decline.
• Points out, “There’s a reason why that stock has gone down. True or false?” ([02:14])
• On learning the company has shifted focus and experienced a CEO change—Ken believes this isn’t necessarily a red flag, especially given a stated turnaround plan and new products coming.
• Concludes: “This smells very good to me. I don’t have any suspicion about this at all. I think this is a hold position for you.” ([03:16])

3. Jade’s "Sell and Diversify" Perspective

[03:30–05:29]

• Jade stresses the risk of single-stock concentration, no matter how the shares were earned: “I just would never tell somebody to invest their money [in single stocks].” ([04:06])
• She recommends Brittany move vested assets into an index fund quickly upon vesting and not add to the risk: “...the moment it vests, I'd move it to an index fund...going forward, I would move.” ([04:06])
• For the $150,000 already vested, Jade concedes it’s reasonable to leave it for now if Brittany wants to see if the value recovers, due to the emotional weight.

4. Reconciling the Advice & Emotional Factors

[05:29–06:16]

• Ken agrees with Jade about not holding single stocks going forward but holds firm on the unique context: “...I'd give the CEO a chance. Let's see if a year from now they can get some of that back and then you can move it. That's all I'm saying.” ([04:50])
• Jade reiterates that her practical inclination would be to move to diversification—even with losses: “I would probably move it because I'd be like, I just don't want it in single stocks. And I've already taken a loss.” ([05:29])
• Both agree: there’s no 'wrong' answer here, as Brittany's financial foundation is solid and the money is “house money.”

5. Risk & Behavioral Finance: The Betting Analogy

[06:16–07:12]

• Jade: “I'm the exact opposite. I'm like, it's not your money. So there's really no reason to be emotional. I just move it and go, whatever. I have $150,000. How do I want to invest?” ([06:16])
• Ken: “You're playing with house money... So I'm a little bit more aggressive.” ([06:26])
• Jade: “We're betting.” ([06:30])
  Ken: “If she holds...she is betting that the CEO and the new leadership...could end up [fixing it].” ([06:31])
• Jade: “I wouldn't take that bet.” ([06:42])

6. Brittany’s Decision and Studio Audience Poll

[06:52–07:49]

• Brittany: “It doesn’t sound like there’s a wrong decision here...I think I'm going to try to be a little loyal...and hold.” ([06:52])
• Ken polls the lobby audience:
  • Almost all prefer to “hold a little bit and wait at least a year” over cashing out immediately. ([07:32])
• Jade playfully calls the holders “risky business.” ([07:42])

7. Wrap-Up: No Wrong Move & Takeaways

[07:49–08:53]

• Both hosts reinforce that Brittany (and listeners in similar situations) is not making a wrong move with either choice.
• Ken: “What a benefit to people who have that option. Stock options are very nice.”
• They close with an anecdote about the rewards and risks of stock compensation.

---

Notable Quotes & Memorable Moments

• Ken: “There’s a reason why that stock has gone down. True or false?” ([02:14])
• Brittany: “I have some suspicions...moved away from our core competency...CEO transition…” ([02:18])
• Ken: “This smells very good to me. I don’t have any suspicion about this at all. I think this is a hold position for you.” ([03:16])
• Jade: “...the moment it vests, I'd move it to an index fund...because I don't want money invested in single stocks, especially in a company that's very soft right now.” ([04:06])
• Ken: “I'd give the CEO a chance. Let's see if a year from now they can get some of that back and then you can move it.” ([04:50])
• Jade: “I have $150,000. How do I want to invest? That's the way I think of it.” ([06:16])
• Ken: “You're playing with house money.” ([06:26])
• Jade: “I wouldn't take that bet.” ([06:42])
• Brittany: “...going to try to be a little loyal...and hold. I do believe in the company.” ([06:52])
• Ken: “There’s one guy that’s giving me a polite golf no. But in all seriousness, I think, Brittany, you're very wise. You're not doing anything wrong.” ([07:50])

---

Important Segment Timestamps

• 00:18 – Brittany’s question and company background
• 01:34 – Ken analyzes Brittany’s situation
• 02:14 – Ken and Jade discuss reasons behind the stock drop
• 03:30 – Jade lays out her more conservative “sell & diversify” stance
• 04:06 – Brittany can move assets to an index fund any time
• 05:29 – Hosts reconcile perspectives and advise on emotion vs. logic
• 06:16 – “House money” versus betting and risk analysis
• 06:52 – Brittany’s final choice; crowd poll
• 07:49 – Hosts agree there’s no wrong answer, discuss pros and cons of company stock
• 08:53 – Final anecdotes and close

---

Key Takeaways

• Balance Facts & Emotions: Decisions on company stock should weigh both the business facts (leadership, future prospects, risks) and your own emotional comfort with risk.
• Diversification Reduces Risk: Even “house money” in single stocks carries unique risks; moving future vested shares to broad index funds is prudent.
• No Wrong Answer: In this context, with Brittany’s solid overall financial position, either holding to see if there’s a rebound or cashing out to diversify is valid.
• Keep Perspective: It’s important not to anchor your decisions purely on hope, fear, or loyalty—each financial move should fit your goals and risk tolerance.

---

This episode highlights the complexity—and emotional weight—of managing company stock, with hosts modeling both analytical and practical approaches to big-money decisions.

Transcript

[Host]

This episode is brought to you by SmartVestor. Connect with an investing pro near you at RamseySolutions.com SmartVestor Brittany is up next in Portland, Oregon.

[Ken]

Brittany, how can we help today? Hi there.

[Brittany]

So I have been working at a company for about five years now and as part of my compensation I receive equity grants every year with a four year vesting schedule. And I have basically just been letting those shares vest and then they move into my brokerage where I've just been holding onto them. Unfortunately, over the last few years the stock has essentially tanked. It's down 60% from its all time high which occurred in November of 2021. And as a long term investor, I don't need the money, but I've been slowly watching the value of that position decline and decline and I feel like I'm at a point now where I'm wondering should cut my losses and sell out of what's vested and move that money into, you know, either a broader index fund or should I try to see it through? Right now the total value of the position is around $150,000, which is about a third of my overall brokerage account. Yeah. And the total, the average loss on, on that is about 30%. So it's painful, it's emotional and I can't make an unemotional decision about it. You guys can give me unemotional advice.

[Ken]

Yeah. So first have is I thought I heard you say you're a long term investor and so this is all gravy for you, this company stock. You're doing your own investing and so you know you're going to be fine long term. Correct? Did I hear that?

[Brittany]

Yeah, that's my hope. That's the goal.

[Ken]

Yes. All right, then the next question that I would have, and I'm answering this as if I were you, so I have no emotion in this. So I'm going, okay, what would I do? All right, so what I would do is I would say, what? What do I know? And let's not look at opinion pieces in the media, but to the best of our ability, let's look at what the company's saying. Let's look at what we can learn from insiders in the building. There's a reason why that stock has gone down. True or false?

[Jade]

True.

[Ken]

Might be a few big reasons. Do you know what the reasons are?

[Brittany]

I have some suspicions. I have some solid leads and solid hunches which are, you know, we moved away from our core competency, started investing in things outside of our main space. We've had a CEO transition. New CEO has been in place for about a year.

[Ken]

And what? Pause, pause, pause, pause. So what his new CEO said about it, because the board brought him in to fix this problem primarily. I know that. Without knowing what this company is or what they do. I know that. So what is he saying publicly? What is the board saying? Because you can go look this stuff up. That's public information. So what are they saying?

[Brittany]

Yeah, you know, we have a turnaround plan in place. I think the expectation is we're going to continue to see softness both on top line and bottom line for at least another year. But the expectation is that by fall of 2020 new products should be in market and there's a lot of optimism around that new product. I think the biggest question continues to be around tariffs. We're incredibly susceptible to tariffs.

[Ken]

Exactly, exactly. All of this smells very good to me. I don't have any suspicion about this at all. I think this is a hold position for you.

[Jade]

I disagree. I think. I disagree.

[Ken]

Tell us why. I'm actually intrigued to hear why you would disagree with that Very sensible position.

[Jade]

I'm, I'm, I have two sides of it. So it's possible that. So this is, I mean this is not your money. It's not like you're investing in this stock. This is stock that they're giving to you. How quickly can you move it over to something else? How quickly could you move it to an index fund once you've received it, how long does it take for it to vest?

[Brittany]

So it's a four year vesting schedule, 25% per year. And then like I said, I have 150k that's fully vested just kind of sitting in the stock. I can move out of that as quickly, quickly as tomorrow.

[Jade]

I mean, if you wanted to sit on what's currently there, it wouldn't bother me. But up moving forward, what I would do is the moment it vests, I'd move it to an index fund because. Or I'd move it elsewhere because I don't want money invested in single stocks, especially in a company that's very soft right now. I, I just would never tell somebody to invest their money there. Therefore I also wouldn't advise somebody. I understand it, but it's the same principle. I wouldn't necessarily advise somebody to leave there now. That's why I said if you want to keep the 150 there for now and see if it regains, but going forward I would move.

[Ken]

Yeah, I don't have a problem with that.

[Jade]

Do you see what I'm saying? So, yeah, yeah.

[Ken]

I was just talking about the what.

[Jade]

What I was addressing increasing my losses going forward.

[Ken]

That's fair. And I don't disagree with Jade on that. What I was addressing is what you called about. I thought to say, what do I do with this current stock that has lost all its value? And if it were me in your situation, I agree with what Jade's saying in the future, but I'd say on this particular thing, I'd give the CEO a chance. Let's see if a year from now they can get some of that back and then you can move it. That's all I'm saying. And that's a unique situation. This is such a unique call in that situation. I'd probably wait and see if the company can turn things around for that reason. But I also wouldn't have the first problem if you said, I'm out.

[Jade]

I was going to say, if I were in your shoes, I don't think there's any problem with you doing what Ken said or doing what I suggested. If I were in your shoes, I would probably move it because I'd be like, I just don't want it in single stocks. And I've already taken a loss. I've already taken a hit. I'd rather this be diversified. That's just what I would do in order for you to stomach it, is why I said what I said, which is, hey, leave what's there, but going forward, make sure you quickly move, you know, as soon as it best.

[Brittany]

Yep.

[Jade]

I'm just trying to. This is an emotional thinking, you know it is.

[Brittany]

I was just trying to work through.

[Jade]

The emotional side of it. That's all.

[Ken]

And that's why, again, the only reason I said what I said is because her emotion is where it is. And so it's like, you're not relying on that money.

[Jade]

Yeah.

[Ken]

This is what I would call found money. And I'd go, if you're emotional about it, ride the roller coaster a little bit longer. See if they get it back.

[Jade]

And that's so funny, because I'm the exact opposite. I'm like, it's not your money. So there's really no reason to be emotional. I just move it and go, whatever. I have $150,000. How do I want to invest? That's the way I think of it.

[Ken]

You're playing with house money.

[Jade]

It's. How's money?

[Ken]

So I'm a little bit more aggressive.

[Jade]

So we're betting.

[Ken]

I'm not bet. Yes. She is. In this case. She is. She's going. If she holds.

[Jade]

Yeah.

[Ken]

And doesn't move it. She is betting that the CEO and the new leadership and the analysis could end up.

[Jade]

I wouldn't take that bet. I wouldn't take it.

[Ken]

And that's your prerogative.

[Jade]

It is.

[Ken]

She got two advice. I know you got two pieces of advice, Britney. What are you going to do?

[Jade]

Brittany, you tell us.

[Brittany]

Well, I think the good news is that it doesn't sound like there's a wrong decision here. You know, there's not clear something that I'm doing wrong. And so, you know, as an employee of the company, I think I'm going to try to be a little loyal, have faith, have optimism and hold. I do believe in the company. I do believe we're in a rebound. We always have in the past.

[Ken]

So I'm going to poll the audience in the lobby.

[Jade]

Don't forget going forward that it's a single stock. Just don't forget that going forward.

[Ken]

All right, now, just for fun, we got probably 30, 40 people in the lobby lobby. Raise your hands if you would go ahead and get out of the stock and cash out. Raise your hand.

[Jade]

My guy right there.

[Ken]

One guy.

[Jade]

One, one loyal.

[Ken]

One guy.

[Jade]

One loyal guy.

[Ken]

Now let's see how this one goes. If you would hold a little bit and wait at least a year. The Ken position, raise your hand. Oh, it's overwhelming.

[Jade]

Listen, I gotta tell you betters. I gotta tell their risky business.

[Ken]

It's rare that I'm right. And so I'm gonna soak in this one.

[Jade]

Lap it up, Ken.

[Ken]

I tell you what, I've been married 27 years. I have three teenagers. I'm never right. You know what I mean, people? Thank you very much. There's one guy that's giving me a polite golf no. But in all seriousness, I think, Brittany, you're very wise. You're not doing anything wrong. No, it's not her money, it's not your money. So you decide what you want to do with it. But I like that. It's a really interesting call. And in that situation with a public company, the proof is in the pudding. And here's what I know about public companies. If this guy doesn't get it right.

[Jade]

The next guy, then they're going to get somebody. There will be a next guy who gets it right.

[Ken]

And so that's where my mindset is. So I'm thinking long term play in this unique situation. But I loved your advice too. I, I, it's hard not to take advantage of that and by the way, to fully come back to your, your point of view going forward as she gets new stuff. I, I love that idea of going moving it over. Thank you. Thank you very much.

[Jade]

I'll take it from here.

[Ken]

And I'll take it. So I would do that as well. And I want to stipulate that.

[Jade]

Yeah.

[Ken]

I just was so stuck in my other position then. Now.

[Jade]

None of it was wrong.

[Ken]

No, no, no. So a very interesting stuff and what a benefit to people who, who have that option. I know stock options are very nice. Hello. I got a friend. I got a friend who shall remain nameless who just recently left a massive company.

[Jade]

Oh yeah.

[Ken]

And he cashed out and boy, oh boy.

[Jade]

Cha Ching.

[Ken]

Oh boy. He had a good day, folks. I had a good day just hearing about it and I didn't get anything from it.

[Jade]

That's a good friend right there.

[Ken]

The afterglow of his stock cash in was so nice that I even felt good.

[Host]

Thanks for tuning in to Ramsey. Everyday millionaires need help with your investments? Connect with a smartvestor [e-mail] smartvestor or click the link in the show notes. Ramsey Solutions is a paid non client promoter of participating pros. Learn [e-mail] SmartVestor.