The Stacking Benjamins Show

Tales of Financial Horror (and how we exorcised them) SB1755


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Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral.

Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking ghostly car-leasing nightmares, investment decisions that refuse to stay buried, and the kind of money mistakes that haunt you long after Halloween is over.

But here's the thing about financial horror stories: they're only scary if you don't learn from them. Every tale in this episode comes with the lesson that could've prevented it—the red flag that got ignored, the advice that should've been followed, the moment when "this seems like a bad idea" got drowned out by "but everyone else is doing it."

From impulse purchases that turned into long-term regrets to the financial advice that sounded great... until it didn't, this crew proves that the scariest monsters aren't in the movies. They're in our bank accounts, our retirement plans, and that subscription we forgot to cancel three years ago.

Plus: Doug delivers Halloween trivia with a full-moon twist, because even financial terror deserves a side of fun.

What You'll Walk Away With:

• Real financial horror stories from people who lived to tell the tale (and learn from it)

• The common thread in most money disasters—and how to spot it in your own life

• Why car leases, "great investment opportunities," and "everyone's doing it" should always make you pause

• How to turn your own financial frights into lessons instead of letting them haunt you forever

• The confidence to say "no" when something feels off, even if you can't explain why

This Episode Is For You If:

• You've ever made a money decision you immediately regretted (welcome to the club)

• You want to learn from other people's expensive mistakes instead of repeating them

• You've got a financial skeleton in your closet and need to know you're not the only one

• You appreciate brutal honesty wrapped in humor—because laughing at financial pain is cheaper than therapy

• You're ready to face your money fears instead of hiding from them until tax season

FULL SHOW NOTES: https://stackingbenjamins.com/money-nightmares-wallet-portfolio-credit-1755

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!


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