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Perennial Pride

Sep 10, 2026

When someone tells Tom they want to pay less in taxes, he's learned that's rarely the real question. In this episode, he breaks down what's actually going on beneath that statement, and why the strategies that move the needle, like entity structuring, Roth conversion timing, and cash balance plans, take years of...


Sep 3, 2026

Charitable giving sounds simple until you get into the details, and most people never make it past the first question: where do I even start? In this episode, Tom walks through the giving landscape from cash donations and donor-advised funds to charitable trusts and leveraged giving, and why the reason behind your...