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.