EPS 47 - “The $500 Question: Pay Down Debt, Invest, or Buy a Second Home?”

In this episode of Pink Money, Jerry Williams tackles a deceptively simple financial question: What’s the smartest move for an extra $500 a month? Should you pay off your mortgage early, invest in the market, or buy a second home to generate income?

Jerry breaks down the pros and cons of each path—from the emotional security of being mortgage-free to the risks and rewards of the stock market, to the real-world headaches (and potential profits) of becoming a landlord. Along the way, he shares personal anecdotes about rental experiences, hard-earned lessons about risk tolerance, and a wild true story that underscores why it pays to know who you’re getting into business with.

This candid, conversational episode reminds listeners that money decisions aren’t one-size-fits-all—they depend on your goals, risk comfort, and what “security” really means to you. As Jerry says, “It all depends.”

👉 Visit PinkMoneyPodcast.com
to take the listener survey and share your vote:
A) Pay down the mortgage
B) Buy a second home
C) Invest in the market
or D) Something else entirely?

(Includes Jerry’s closing thoughts on Nancy Pelosi’s legacy and why true leadership leaves a lasting mark.)

💬 Have a question or comment? Contact Jerry here