Family Offices, Tax Strategy & Asset Protection: A Masterclass with Thomas J. Handler

November 12, 2025·29 min·2 clips

Tom Handler explains why billionaire taxes backfire as wealthy families flee states like Illinois and Massachusetts.

Episode 846 starts with an easy return. The host brings back Tom Handler, calls him an old friend and repeat guest, and sets him up as a wealth protection voice. The mood is loose, with the usual business-radio housekeeping first: live stream platforms, a sponsor note, and South Florida credentials. Then the conversation turns. A political aside about law enforcement and deportation opens into a broader complaint about unpopular taxes and the local officials stuck collecting them. Property tax takes over from there. Handler says getting away from real estate tax would make him happier, because paying over and over on property someone already owns just feels wrong. He gets specific with Illinois, where he says taxes run around $22,000 per million and a couple million dollars barely buys a livable place. Then he compares that with moving outside Denver, buying more house and land, and paying far less in real estate tax. The catch is the part nobody gets to wave away. Local governments still need money for schools, park districts, police, and basic services. So the complaint may be easy to understand, but the replacement has to work for counties and local jurisdictions that already rely on that revenue. The close comes back to familiar ground: sponsors, the University of Florida Bergstrom Center for Real Estate Studies, and a Chicago work memory. It ends with a plain shove from the host: find a way, stop making excuses, and go make something happen.

As heard by us

A practical wealth-protection conversation centered on property taxes and deduction limits.

Tom Handler and Jim Freed frame wealth protection through property taxes, deduction limits, and the steady cost of owning where the bill never really stops.

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Why you'd press play

You want a blunt read on wealth protection from a repeat guest the host keeps bringing back.

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