Earn Your Leisure Podcast

Episode: Nancy Pelosi’s Stock Option Strategy Explained (And Why It’s So Effective)
Date: January 31, 2026
Hosts: Rashad Bilal & Troy Millings

Episode Overview

This episode dives into Nancy Pelosi’s highly scrutinized and legendary investing approach, specifically her stock option strategies. The hosts dissect her recent trades, the rationale behind her deep-in-the-money call options, and what retail investors can learn from the moves of political figures like Pelosi. The episode analyzes the companies she's picking, the technical underpinnings of her approach, and debates ethical implications and lessons for listeners.

Key Discussion Points and Insights

Politicians as Power Investors

• Hosts highlight how politicians, especially Nancy Pelosi, are among the most successful investors due to their portfolios' consistent outperformance.
• Pelosi’s investment decisions are widely tracked due to required reporting and the impressive scale of her moves.

Notable Quote

“The greatest investors you can argue are not on Wall Street, they're in Washington. When you see some of these politicians' portfolios… it's historic. And she's probably the top dog.”
— Financial Analyst 1 [02:09]

Breaking Down Pelosi’s Latest Trades [02:01–03:13]

Massive Trading Volume

• Pelosi reported $69 million in stock and options activity from late December 2025 to mid-January 2026.
• $26 million of this volume occurred in a single month.

Notable Quote

“So they released the information: $69 million in stock and options activity between late December '25 and mid-January '26. So in one month she did $26 million in stock trades.”
— Financial Analyst 1 [02:45]

Pelosi’s Deep-in-the-Money Call Options Explained [03:13–06:22]

Explanation of Strategy

• Pelosi bought 20 call options each for Google ($150 strike), Amazon ($150 strike), and Nvidia ($100 strike), all expiring January 2027.
• All strike prices are significantly below their current stock prices (Google at $331, Amazon at $240, Nvidia at $185).

Benefits of Deep-in-the-Money Calls

• Less speculative: High intrinsic value since the stock price is already above strike.
• Lower sensitivity to time decay (theta). Price swings affect the option value less drastically.
• Offers both upside leverage and partial downside protection compared to owning outright shares.
• It's more expensive but "the win is kind of built in."

Notable Quotes

“Her trading strategy is very unique... What she does is... buys deep-in-the-money calls. Why? Couple of reasons. The equity has far surpassed the strike, which means the intrinsic value is not speculative. There's already value built into it.”
— Financial Analyst 2 [03:27]

“So less decay, more upside. Intrinsic value is already built in. She's been doing this year over year, leap after leap.”
— Financial Analyst 2 [05:38]

Companies Pelosi Targets

• Google (GOOG)
• Amazon (AMZN)
• Nvidia (NVDA)

“The companies that she's choosing make a lot of sense... If we start seeing those companies over and over, oh, they know something. We just gotta follow the money.”
— Financial Analyst 2 [06:24]

Investment Insights for Listeners [06:45–07:17]

Practical Equity Entry Points

• Recommended buy entries (based on recent trades):
  • Google: $285.46
  • Amazon: $223.17
  • Nvidia: $173.65

Notable Quote

“For those who are not invested in the options, can I give prices away on the equity side?... Google: 285.46, Amazon: 223.17, Nvidia: 173.65.”
— Financial Analyst 3 [06:45]

Pelosi’s Profit-Taking Moves [07:17–07:56]

• Sold:
  • 45,000 shares of Apple
  • 20,000 shares of Nvidia
  • 10,000 shares of Amazon
  • 10,000 shares of Disney
  • 5,000 shares of PayPal
• Bought:
  • 25,000 shares of Alliance Bernstein
• Discussion on the wisdom of profit-taking at all-time highs.

Notable Quotes

“I'm not mad at some profit taking. You never lose by taking profit.”
— Financial Analyst 3 & 2 [07:36–07:39]

“Apple, Nvidia, Amazon hit all-time highs when she sold... That's a great profit-taking on those.”
— Financial Analyst 2 & 3 [07:56–08:10]

The Pelosi Family: Double the Investing Prowess [08:15–08:23]

• A brief aside notes that Nancy’s husband trades his own, separate portfolio — further doubling down on the family’s investing success.

“And that's just her. Her husband has his own portfolio. He the one… What different game they playing?”
— Financial Analyst 2 & 3 [08:15–08:23]

Memorable Moments & Quotes

• Power in Washington:
  “The greatest investors you can argue are not on Wall Street, they're in Washington.” [02:09]
• Intrinsic Value Focus:
  “There's already value built into it. Nvidia has already passed $100.” [03:27]
• Confirmation Bias:
  “What are the people in Washington investing in? Let's see... if we start seeing those companies over and over, oh, they know something.” [06:24]
• On Taking Profits:
  “You never lose by taking profit.” [07:39]

Timestamps for Important Segments

• 02:01 — Intro to Pelosi as an investor; scale of her trades.
• 03:13 — Detailed breakdown of her options strategy.
• 06:22 — Importance of company quality in her picks.
• 06:45 — Equity entry points for each company.
• 07:17 — List of recent sales and purchases, discussion on profit-taking.
• 08:15 — Acknowledgement of the Pelosi family's investing track record.

Conclusion

The discussion demystifies Nancy Pelosi’s deep-in-the-money call option tactic, underscoring why it’s effective and less risky with solid, blue-chip companies. The hosts encourage listeners to keep an eye on what influential figures on Capitol Hill are trading and to use those insights — not as a crystal ball, but as strong signals when making their own investment decisions. As always, “follow the money.”