Blind Ranking the Internet’s WILDEST Investment Stories
July 23, 2026
AI Summary
5 min read“I once saw someone tell Reddit their investing strategy was based on the phases of the moon,” George Kamel recalls, and that line sets the tone for this episode of Smart Money Happy Hour. Rachel Cruze and George Kamel blind-rank five real-world investing stories from the internet—some catastrophic, some surprisingly successful—and use them as a launchpad to explain what actually works for ordinary people. The throughline is simple: the most dramatic investing stories are almost always cautionary tales, while the boring, consistent approach is what quietly builds wealth over decades.
The Rankings: From Dumpster Fire to Quiet Success
The episode’s centerpiece is a blind ranking from worst (5) to best (1). The stories, in order of severity:
5. Woman loses life savings in crypto scam. An elderly woman answered a call from an unknown number in November 2023, shared her personal information, opened an account at crypto.com, and lost more than $663,000—her entire life savings. The FBI identified 33 total victims of the same fraud scheme, with combined losses of nearly $4.9 million. “When you're an elderly person, that is your life savings—that's worse,” Rachel says. The episode treats this as the most tragic entry, not just because of the dollar amount but because of the vulnerability exploited.
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What you'll learn
- 1 (00:05) **Blind Ranking Introduction** - Rachel and George introduce the concept of blind ranking the best and worst real-life investing stories on a scale from 1 (best) to 5 (worst).
- 2 (04:22) **Martha Stewart Insider Trading Scandal** - The hosts recap Martha Stewart's 2001 insider trading case involving ImClone Systems, which led to a five-month prison sentence.
- 3 (07:41) **Story #1: Bitcoin Mining Debt Disaster (Ranked #4)** - A Ramsey Show caller reveals her husband racked up $624,000 in debt (business loans, credit cards, 401k) trying to start a crypto mining business.
- 4 (10:06) **Story #2: Elderly Woman Loses Life Savings to Crypto Scam (Ranked #5)** - An FBI case details 33 victims losing a combined $4.9 million, with one elderly woman losing over $663,000 after answering an unknown call.
- 5 (13:27) **Story #3: Lottery Winner Success Story (Ranked #1)** - Tim Schultz won a $28 million Powerball jackpot at age 21 in 1999 and immediately hired a financial advisor, bucking the typical "lottery curse."
- 6 (18:08) **Story #4: Short-Term Rental Property Fail (Ranked #3)** - A Ramsey Show caller bought a short-term rental in 2024 to "build generational wealth" and get tax write-offs, but is now bleeding $3,000/month due to a DSCR loan with a five-year prepayment penalty.
- 7 (22:18) **Story #5: Boring 401k Success Story (Ranked #2)** - A Reddit user with a modest income and a family shares how consistent 401k contributions grew to $50,000, celebrating the power of compound growth and delayed gratification.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
🎟️ Get your ticket for Investing Essentials today!
When it comes to money, is boring always best? From everyday internet scams to rare lottery success stories, today we’re blind ranking the good, the bad and the just plain dumb of investing.
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Today’s Happy Hour Special: 🍾 French Blonde
Recipe By: Join Jules
2 ounces fresh grapefruit juice
2 ounces Lillet Blanc
1 ounce gin
1/2 ounce elderflower liqueur
3 dashes lemon bitters
Instructions: In a cocktail shaker, add all ingredients. Add ice and shake. Double strain into a chilled coupe or Nick and Nora. Garnish with a grapefruit slice!
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