/
© 2026 RiffOn. All rights reserved.
  1. We Study Billionaires - The Investor’s Podcast Network
  2. TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve
TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network · Feb 15, 2026

Learn vital investing lessons from history's wildest financial stories, from Isaac Newton's FOMO to Muhammad Ali's strategic patience.

Bernie Madoff’s Fraud Was Exposed by the Impossibility of His Consistent Returns

Analyst Harry Markopoulos identified Madoff's Ponzi scheme in five minutes, not with insider information, but by recognizing his promised 14% returns with no risk were mathematically impossible. Consistently perfect results are a major red flag, as even the best investors have down periods.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

Muhammad Ali’s “Rope-a-Dope” Tactic Is a Model for Patient, Inactive Investing

Ali defeated a stronger opponent by absorbing blows and waiting for the right moment. This "masterly inactivity" is a powerful investing strategy. Instead of constant trading, long-term investors should let high-quality businesses compound, understanding that the decision *not* to act is still an active, and often superior, choice.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

18th Century "Bubble Companies" Were Functionally Identical to Modern SPACs

During the 1720s South Sea Bubble, hundreds of speculative companies emerged with no revenue or clear business plans, mirroring the 2020-2021 SPAC boom. One notorious company was pitched for an "undertaking of great advantage, but nobody knows what it is." This highlights that financial vehicles designed to capitalize on market euphoria are not new.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

The Aeroflot 593 Crash Warns Investors Against Complacent "Autopilot" Thinking

An Aeroflot flight crashed after a pilot's son inadvertently disabled the autopilot without a clear alert. This is a metaphor for investing complacency. During bull markets, it's easy to rely on "autopilot" and ignore hidden risks. Investors must remain vigilant and actively monitor their thesis to avoid catastrophic, unforeseen losses.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

Bobby Bonilla's Deferred MLB Contract Shows Compounding Beats High-Risk Returns

Baseball player Bobby Bonilla receives $1.19M annually until 2035 from a 1999 contract, thanks to an 8% interest rate. This deal highlights the power of compounding and deferred gratification, contrasting with the Mets' owner who chased fraudulent high returns with Bernie Madoff, illustrating a disastrous alternative.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

The 1987 Market Crash Reversal Was Triggered by a Small Anomaly in Futures Pricing

On the Tuesday after Black Monday 1987, with the financial system near collapse, the market's rebound was sparked by a sudden buying wave in MMI futures. This flipped them from a discount to a premium, activating arbitrage traders who injected crucial liquidity. It shows market bottoms can be unpredictable and initiated by seemingly minor events.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

Sir Isaac Newton's South Sea Bubble Loss Shows Intelligence Can’t Beat FOMO

Even one of history's most brilliant minds, Isaac Newton, fell victim to financial mania. He invested in the South Sea Company, sold for a profit, but then FOMO drove him to reinvest at the peak, leading to massive losses. This demonstrates that emotional discipline, not just intelligence, is crucial for investing success.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

Buffett’s Amex Bet During the “Salad Oil Scandal” Proves Strong Brands Survive Crises

When an Amex subsidiary was embroiled in a massive fraud, its stock dropped 45%. Warren Buffett's research found customer trust in Amex's core products was unshaken. This reveals that markets can overreact; truly strong brands often have durable customer loyalty that withstands major scandals, creating opportunity.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

America Created Its First Inflation-Indexed Bond for Revolutionary War Soldiers

To combat desertion from soldiers whose pay was becoming worthless, the U.S. government created an inflation-indexed bond during the Revolutionary War. Its payments were tied to the price of four essential goods: corn, beef, wool, and leather. This historical precedent demonstrates that protecting against currency debasement is a long-standing governmental concern.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

18th Century French Tontines Created a Morbid Market for Young "Immortal" Girls

To maximize payouts from life annuities, 18th-century Swiss bankers nominated young girls from wealthy families who had survived smallpox as beneficiaries, creating a securitized investment based on their longevity. This historical example of actuarial arbitrage shows how financial engineering can push ethical boundaries by turning human lives into financial instruments.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago

Media Mistook Coca-Cola's Ex-Dividend Price Drop for a Cristiano Ronaldo Snub Effect

A viral story claimed Ronaldo's actions wiped $4B from Coca-Cola's value. The actual cause was a pre-scheduled ex-dividend date. This illustrates how media can create false narratives by confusing correlation with causation and why investors must perform their own due diligence, rather than reacting to headlines.

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve thumbnail

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network·4 days ago