They Left NYC for a $13,000 House in Italy

7/14/26: Cassandra and her husband made headlines after leaving New York City to buy a home in rural Italy for just $13,000. She breaks down what motivated the move, how she’s adjusted to life in a tiny mountain town, embraced a lower-cost lifestyle, and whether trading the conventional American dream for a simpler life abroad was worth it.

Plus: Jill and Mark explain what SpaceX’s inclusion in Nasdaq index funds actually means for investors, and why one TikToker’s recommended tax loophole is complete nonsense.

How to Get the Shopping High Without Spending a Dollar

7/9/26: “Dopamine sites” are on the rise in South Korea, allowing people to simulate the thrill of online shopping or food delivery without spending any actual money. Could this be the fix for compulsive spenders? 

Plus: Jill helps caller Danielle navigate a financial crossroads: after taking a pay cut to make work and life more manageable, she’s now facing higher-than-expected college costs for her child while trying to stay on track for retirement.

Starter Homes Are a Million Bucks Now

7/7/26: Starter homes now cost a million dollars in many parts of the country, leaving younger generations wondering whether homeownership is still a realistic goal. Jill asks whether buying a house should remain a cornerstone of the American dream, or if the idea itself has become outdated. 

Plus, caller questions: Dorian is feeling the financial strain of wedding season as travel costs, gifts, and pricey trips pile up. And Andrew, a brand-new dad, wants to know whether now is the right time to buy term life insurance.

Don’t Buy a House Together Until You Hear This

7/2/26: Caller Aaron has a family mess on his hands: his cousin bought a house with a girlfriend, they broke up, and now his cousin's credit is still tied to the property while the ex continues living there and refuses to refinance. Jill explains exactly what to do before buying a major asset with someone you're not married to.

Plus: Jill breaks down the new student loan landscape effective July 1, 2026, how parents and prospective students should navigate the new rules, and why taking on debt for college may not be worth it anymore.

Boomer Parents: It’s Time to Cough It Up

6/30/26: Bad news for the people hoping their parents die soon. 

Americans have been anxiously awaiting the so-called "great wealth transfer," where trillions of dollars are expected to pass down from Baby Boomers to their kids, but people are living longer and holding onto their assets.

Plus, caller questions: Toby asks whether sterling silver jewelry is actually a worthwhile investment, and Dave wants to know whether taking a pay cut to improve his quality of life is financially realistic.