135: Garrett Gunderson - Comedy, Rockefellers, and Tax Secrets Used by the Ultra-Wealthy

Garrett Gunderson has worn a lot of hats—New York Times bestselling author, financial educator, entrepreneur, and even stand-up comedian. And in this episode, he connects the dots between all of them to give advisors fresh tools for both business and life.

We explore what advisors can borrow from stand-up comedy to level up their presentations, how the Rockefellers built a system to preserve wealth while the Vanderbilts lost theirs, and the advanced tax strategies that capture the attention of entrepreneurs and high-net-worth clients.

3 of the biggest insights from Garrett …

#1.) How Comedy Translates Into More Engaging Presentations

Advisors face the same challenge as comedians: keeping an audience engaged. Garrett explains why presence matters more than polish, how to handle disruptions with confidence, and why the best connection often comes from the unplanned moments.

#2.) The Rockefeller Method in Action

Two wealthy families took very different paths: the Rockefellers built a system that preserved wealth for seven generations, while the Vanderbilts lost theirs in just three. Garrett unpacks the specific tools—like trusts, family constitutions, and insurance—that made the difference.

#3.) The Tax Plays That Make Affluent Clients Lean In

Entrepreneurs and high-net-worth families don’t want surface-level advice—they want strategies they’ve never heard before. Garrett shares advanced ideas like reclassification of income, overlooked deductions, and even how donating art can unlock surprising tax advantages.

SHOW NOTES

https://bradleyjohnson.com/135

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DISCLOSURE

DBDL podcast episode conversations are intended to provide financial advisors with ideas, strategies, concepts and tools that could be incorporated into their business and their life. No statements made in the episode are offered as, and shall not constitute financial, investment, tax or legal advice. Financial professionals are responsible for ensuring implementation of anything discussed related to business is done so in accordance with any and all regulatory, compliance responsibilities and obligations.

The Triad member statements reflect their own experience which may not be representative of all Triad Member experiences, and their appearances were not paid for.

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