Financial Horror Stories, Vol. 5: The All-Monster Edition
Rule Breaker Investing
October 21, 2026
The witching hour approaches! For the fifth consecutive Halloween, Motley Fool retirement expert Robert Brokamp returns to haunt Rule Breaker Investing with tales of financial terror.
Speakers David Gardner, Robert Brokamp
David Gardner (0:01)
Remember that opening scene from Twilight Zone the movie? Two guys driving down a rainy highway at night, telling each other scary stories.
Dan Aykroyd and Albert Brooks. One finally turns to the other as he pulls the car over. Hey, you wanna see something really scary? Well, I won't spoil what happens next. I saw it in the theater in 1983 when I was 17, and I can tell you, it scared me. Well, I'm not Albert Brooks, and I don't have Dan Aykroyd this week, but I've got the next best thing, The Motley Fool's longtime retirement expert, Robert Brokamp, returning for our fifth annual Halloween Fright Fest. And this year, we're changing things up. The ghosts of Financial Mistakes Past have given way to seven monsters that may be lurking in, dear listener, in your own financial life. Some you know, some you may never have suspected, and all of them are worth confronting before they come for you.
Financial Horror Stories, Volume 5, the all monster edition, only on this week's Rule Breaker Investing.
SPEAKER_2 (1:15)
It's the Rule Breaker Investing podcast with Motley Fool co-founder, David Gardner.
David Gardner (1:24)
Welcome back to Rule Breaker Investing. It's getting scary out there. Halloween is approaching, although I do wonder whether Halloween starts a little earlier every year. I think I say this every year. I feel like I started seeing those enormous skeletons and animated zombies on people's front lawns. I'm going to say now back in late August.
At this rate, give it another decade and it'll be Halloween year-round in America.
To the roughly one-fifth of our listeners joining us from outside the United States, welcome to our peculiar American tradition. This is Financial Horror Stories, Volume 5 It's the all monster edition. For the past four years, my good friend and longtime fellow fool, Robert Brokamp has joined me around Halloween to share true financial horror stories, often involving famous people whose financial decisions came back to haunt them.
This year, we're changing up the formula. Robert has dreamed up seven financial monsters, each representing a danger that could be lurking in our own financial lives. Now, the monsters may be imaginary. The financial dangers, though, are very real, and as always, we're here to do more than frighten you. Each monster, I think, will come with a lesson and we hope a way to defeat it, and that's how we make the world smarter, happier, and richer even at Halloween. A quick reminder, the next week is our October Mailbag. We'd love to hear from you. Send your stories, questions, your thoughts, your scary stories too, to rbi at fool.com. You can also find us on TwitterX at RBI Podcast. A quick reminder, we're also accepting audio submissions now. If you want to bring your own scary voice and share a scary thought or scary story on next week's Mailbag, your audio submission is also welcome at rbi at fool.com. All right, so let's open the crypt, summon our first monster, and welcome back the man who has made frightening our listeners an annual tradition, Robert Brokamp. Welcome back to Rule Breaker Investing.
Robert Brokamp (3:29)
Sweet cheeses, David. It's great to be back. I love this tradition. I know we're entering the best time of the year when I get that slack from you saying, are you ready? And I'm always ready.
David Gardner (3:40)
And you are always ready. And for four years, as I mentioned at the top, Robert, you've brought us true stories of financial misfortune. Some of the world's most famous people. Turns out we can all make mistakes. This year, though, I asked you to create the monsters yourself. I understand you have brought seven. Is that right?
Robert Brokamp (3:58)
This is true. I have seven.
David Gardner (4:00)
Seven financial monsters. And I'm trusting, Robert, that each one has something useful to teach us about our own money. But before we unleash them, I have one question for you. Should our listeners be more afraid of the monsters they already know about, or the ones they don't even realize are lurking?
Robert Brokamp (4:21)
I would say probably more of the latter, because anyone who's listening to this podcast is probably a relatively sophisticated person when it comes to money and investing. So they probably already prepared for some of these, but there are going to be a few that while they know are out there, they may not be doing enough to prepare.
David Gardner (4:41)
That is a sufficiently unsettling thought. I think we're going to keep the identities then of these seven creatures under wraps until each makes its appearance. So Robert Brokamp, let's meet monster number one. What is the title of the tale about this monster?
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