Jesse Cramer Fee-only fiduciary financial planner who left aerospace engineering, where he worked on space telescopes, to advise clients on retirement planning.

“A very common mistake that investors make is they conflate the future prospects of a company, which might be good, with the idea that the company is a good stock to own at the current price. The optimism the CEO is telling you as an employee ought to already be reflected in the price. Just because the CEO thinks your company has good prospects doesn't mean you ought to own a large amount of that company stock.”

The Stacking Benjamins Show · Money & Markets · October 2026

Context

The panel was debating what to do when employer stock, here an AI company, has grown to a large share of a portfolio. Cramer argues against holding a big position just because the outlook sounds bright.

Listen to the episode → More from Jesse Cramer → More Money & Markets quotes →

Transcript

The Stacking Benjamins Show Around 12:16 into the episode

Paula Pant

…about the overall industry higher than I would rank optimism about the company specifically. So industry optimism might change my answer or might make me a little bit more prone to holding. But overall, I think the biggest factor is what role does this amount of money play in your own life.

Speaker 2

Jesse, let's say it's an AI company right now. Paula talking about the industry. Does that make you more nervous or less nervous?

Jesse Cramer

Probably makes me more nervous if it's an AI company. But on the whole, again, it's this is a publicly traded company. There's an argument to be made that the optimism within the company, the optimism that the CEO is telling to you as an employee, that that optimism ought to be already reflected in the price of the company itself. And I think a very common mistake that investors make is they conflate the future prospects of a company, which might be good, with the idea that the company is a good stock to own at the current price. And those two things aren't always the same. Because really the argument ought to be if the CEO says, hey, things are really, really good. And if you as the employee think, oh, things are really, really good. And also the stock price happens to be vastly undervalued. That's harder to justify the undervalued part. But make a long story short, just because the CEO thinks that your company has good prospects doesn't mean that you ought to own a large amount of that company stock.

Joe Saul-Sehy

Oh, G, I want to finish this discussion with you on scenario number one, this very scary scenario. We have to. Probably not funny when you laugh at your own sound effect, is it? You mentioned selling options. Do you sell options to protect your downside? Do you sell options to maybe squeeze more…

Speaker 2

or to bring out some more cash?

Joe Saul-Sehy

Based on the question that you asked earlier about just kind of starting from that thesis of it's 38% and what do we want to do with it? The only risk that you have isn't that it goes up because that would be a good outcome. It's, I guess, by definition volatility, but it's a good volatility. It's…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

More from The Stacking Benjamins Show

“What you need if you're going to do this is really good insurance that you are going to be okay if this marriage doesn't last. And so the paper shows that buying a home serves as that insurance because the home is going to be divided in the case of divorce. And so we see that couples who own homes are more likely to specialize.” — Corinne Low, The Stacking Benjamins Show

“And your job does not love you back. If your job goes through downsizing or has a financial crunch, they will lay you off. Love will not keep you there. Okay. You are not actually a family. So I think it's important to be a little bit less romantic about these relationships with our jobs and a little bit more transactional.” — Corinne Low, The Stacking Benjamins Show