News and Updates

June 22, 2026

The S&P 500 Is Not as Diversified as You Think

When people tell me they’re diversified because they own an index fund, I understand the logic. You’re spreading money across hundreds of companies. That should smooth out the risk, right? […]

June 18, 2026

When One Spouse Runs Everything: Building a Plan Before You Need It

A listener wrote in recently with a question that is much more common than I expected. She has managed every dollar of her family’s $19 million balance sheet for 30 […]

June 16, 2026

The Vacation Home Just Changed: What to Do When the Rental Income Disappears

Zoning changes that restrict short-term rentals are showing up in more markets every year. For years, homeowners have built retirement plans around VRBO and Airbnb income, and in a growing […]

June 10, 2026

The Smartest Way for Grandparents to Pay Your Kids’ Tuition

A listener wrote in with a great problem to have. Their parents have offered to pay private school tuition for the grandkids and are planning to write a check each […]

June 9, 2026

Why Living Off Dividends Feels Safer Than It Is

A listener wrote in saying they retired last year and a friend suggested reconstructing the portfolio to live entirely on dividends so they would never have to touch the principal. […]

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