Jesse Cramer

Things Jesse Says on Podcasts

Fee-only fiduciary financial planner who left aerospace engineering, where he worked on space telescopes, to advise clients on retirement planning. Founded The Best Interest in 2018, a free personal finance education blog and podcast for long-term investors. Hosts Personal Finance for Long-Term Investors and writes the Best Interest blog. Appears as a panelist on The Stacking Benjamins Show and has been a guest on The Boldin Your Money Podcast, ChooseFI and Earn & Invest.

Where to Find Them

Jesse Cramer hosts Personal Finance for Long-Term Investors , hosts The Stacking Benjamins Show , writes ChooseFI | Financial Independence Podcast and writes Retire With Purpose - The Retirement Podcast . They have also been a guest on Earn & Invest (2 times) , The Boldin Your Money Podcast and Mile High FI Podcast .

Recently: “8 Tricky Money Decisions: When to Cosign, Stretch, Take the Job, or Walk Away SB1917” on The Stacking Benjamins Show (October 2026); “13 Munger-isms for a Smarter Life - E155” on Personal Finance for Long-Term Investors (October 2026); “The "Billionaire Moves" People Want to Copy (But Can They?) - (AMA, E154)” on Personal Finance for Long-Term Investors (October 2026); “The Three Demons of Overconfidence - E153” on Personal Finance for Long-Term Investors (October 2026); “Money Ideas That Sound Great Until You Read the Fine Print (SB1905)” on The Stacking Benjamins Show (October 2026); “Retirement Planning's Hidden Tradeoffs | With Jesse Cramer (Ep. 114)” on The Boldin Your Money Podcast (October 2026).

What They Said

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.

The Stacking Benjamins Show · 2026-10-30 Permalink → Listen →
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.

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