Treasury Ladder vs. Money Market: Structuring Cash After a Business Sale
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...
When the AUM Math Stops Working for You
May 13, 2026
A listener wrote in recently with a story that comes up more than people realize. He has about $18 million...
A Framework for Evaluating Private Clubs, Jet Cards, and Family Offices After a Liquidity Event
May 7, 2026
When you sell a business, the offers start showing up. Within months of the close, your name is on lists...
Does 529 Superfunding Make Sense When Your Estate Is Already $40 Million?
May 6, 2026
Listeners who’ve built real wealth tend to come at 529 plans from a very specific angle. A grandparent recently asked...