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...
The Smartest Way for Grandparents to Pay Your Kids’ Tuition
Jun 11, 2026
A listener wrote in with a great problem to have. Their parents have offered to pay private school tuition for...
Why Living Off Dividends Feels Safer Than It Is
Jun 11, 2026
A listener wrote in saying they retired last year and a friend suggested reconstructing the portfolio to live entirely on...
Treasury Ladder vs. Money Market: Structuring Cash After a Business Sale
Jun 4, 2026
A listener wrote in: They sold their business 18 months ago and are sitting on roughly $12 million in cash,...
Do You Have to Charge Your Kids Rent to Use the Family Lake House?
Jun 3, 2026
A question came in recently from a couple who own three properties across two states. Their kids and grandkids use...
Pre-IPO Planning: What to Do Before the Lockup Lifts
May 28, 2026
A software engineer at one of the major AI companies wrote in this week. He joined three years ago, the...
Why Hitting $10 Million Didn’t Feel Different
May 28, 2026
A listener wrote in this week with a problem I hear constantly from successful business owners. He is in his...
Charitable Remainder Trust vs Donor Advised Fund: Which One Fits Your Situation
May 21, 2026
At some point in the planning conversation, families with charitable intent will ask whether a donor advised fund or a...
What SECURE 2.0 Actually Lets You Do With a Leftover 529
May 21, 2026
A listener wrote in saying their family funded a 529 for their daughter starting when she was born, and that...
The Right Way to Buy a Car for the Family Nanny
May 14, 2026
A listener wrote in with what felt like a simple question. They have a full-time nanny who has been with...