A woman from Portland recently called into “The Ramsey Show” with a question that sparked an unusually sharp split between co-hosts Ken Coleman and Jade Warshaw. The caller, Brittany, has worked at the same company for five years and receives annual equity grants as part of her compensation. But the company's stock is down 60% from its November 2021 peak, and she wasn't sure what to do with the $150,000 in vested shares she's been holding.
Should You Hold Or Move On?
“It’s painful. It’s emotional. And I can’t make an unemotional decision about it,” Brittany admitted. She added that although she doesn’t need the money now, the consistent decline has her second-guessing whether to continue holding or cash out and diversify.
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Coleman urged Brittany to step back from emotion and assess what she knows. “Let's not look at opinion pieces in the media,” he said. “Let's look at what the company's saying. There's a reason why that stock has gone down. True or false?”
“True,” Brittany replied, citing reasons like straying from core competencies, a recent CEO transition, and vulnerability to tariffs.
She explained that the new CEO—who has been in place for about a year—acknowledged ongoing softness in both revenue and profit. “The expectation is that by fall of 2026, our new product should be in market and there’s a lot of optimism around that.”
Coleman found the turnaround strategy convincing and leaned toward holding. “All of this smells very good to me,” he said. “I think this is a hold position for you.”
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Warshaw disagreed. “I don’t want money invested in single stocks, especially in a company that’s very soft right now,” she said. Her advice was to sell future vested shares the moment they become available and consider moving the current position into an index fund.
“It’s not your money,” Warshaw said, referring to the stock-based compensation. “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 this?”
While Coleman preferred giving the leadership team more time, Warshaw took the more cautious, diversified route. “I wouldn’t take that bet,” she said flatly.
“And that’s your prerogative,” Coleman replied. “She got two pieces of advice.”
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Brittany ultimately decided to hold the shares, at least for now. “I do believe in the company. I do believe we’re in a rebound,” she said. “We always have in the past.”
The debate didn't stop there. Ramsey turned to the studio audience, asking them to raise hands if they would cash out. Only one hand went up. When he asked who would hold and wait, nearly everyone raised a hand.
“I’m going to soak in this one,” Coleman joked. “It’s rare that I’m right. I’ve been married for 27 years. I have three teenagers.”
In the end, both hosts agreed that Brittany wasn't making a mistake either way. But her call highlighted a rare moment where even the show's veteran voices clashed, and the crowd had an opinion of their own.
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