September 27, 2025: (Repeat) Loyalty Costs, Triple Tax Benefits, and the Power of Strategy

While we’re out of the studio this week, we’ve collected a selection of great discussions from the past few months. First, we look at a situation where a listener has been with his car insurance company for 25 years, but switching providers offers better coverage, lower deductibles, and hundreds in savings—what should he do? For many, the emotional weight of loyalty outweighs the financial upside of making a change. 

Next, D.J. breaks down Health Savings Accounts (HSAs) and explains why they’re one of the most powerful tools for saving money—thanks to their unique triple tax benefit. While many people use HSAs to pay for health-care expenses as they arise, there are compelling advantages to covering those costs from other funds and allowing the HSA to accumulate, benefiting from tax-deferred growth over time. 

If you’re rolling over your 401(k), should you reinvest all at once or ease in with dollar-cost averaging? Nick and K.C. break down the pros, cons, and emotions behind each strategy. 

After the break, we unpack the jaw-dropping strategy known as “Buy, Borrow, Die”—a legal tax loophole the ultra-wealthy use to build massive fortunes, fund lavish lifestyles, and pass on wealth to heirs nearly tax-free. It’s a masterclass in how America’s richest sidestep income and estate taxes, exposing the widening gap between the tax code for the few—and the one for everyone else. 

Join hosts Nick Antonucci, CVA, CEPA, Director of Research, and Managing Associates K.C. Smith, CFP®, CEPA, and D.J. Barker, CWS®, and Kelly-Lynne Scalice, a seasoned communicator and host, on Henssler Money Talks as they explore key financial strategies to help investors navigate market uncertainty. 

Henssler Money Talks — September 27, 2025  |  Season 39, Episode 39 

Timestamps and Chapters 

• 2:50: Loyalty vs. Logic: When Staying Costs More 
• 10:47: HSAs: Triple Tax Benefit 
• 21:21: All in at once or dollar-cost average? 
•  30:59: Buy, Borrow, and Die 

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Chapters

• 2:50 Loyalty vs. Logic: When Staying Costs More
• 10:47 HSAs: Triple Tax Benefit
• 21:21 All in at once or dollar-cost average?
• 30:59 Buy, Borrow, and Die