We Answer Your Awesome Questions: HSAs, Roth Conversions, Trusts, and More (SB1730)

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Sep 3, 2025

Join Anna Allum, a CFP with a unique journey into finance, as she shares her insights on pressing money questions. Discover how to turn your HSA into a retirement tool, the right timing for Roth conversions, and essential details about trusts that could save you money. The conversation dives into the mental side of finances, highlighting the power of a positive mindset. Plus, enjoy some light-hearted humor about AI at fast food joints, proving that financial discussions can be both informative and entertaining!

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ADVICE

Convert To Roth Strategically

Convert traditional IRA money into a Roth while you can stay in lower brackets to control taxes and future RMD/Medicare effects.
Pay conversion taxes from cash (not withheld) and plan year-by-year for market and cash-flow changes.

INSIGHT

Unknown Taxes Favor Early Action

Future Medicare premium changes and unknown future tax rates make Roth timing uncertain and personal.
Favor conversions now for simplicity if you can afford the tax and avoid future unknowns affecting Medicare.

ADVICE

Self-Insure Roadside Assistance When Sensible

Drop roadside assistance if you can self-insure by carrying a spare tire and jumper cables and accepting occasional tow costs.
Compare occasional out-of-pocket costs to annual premiums before keeping add-on coverage.

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What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy, OG, special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-style tangents.

This week’s listener lineup serves up a buffet of topics: how to turn an HSA into a stealth retirement account, whether a Roth conversion is the right move (and when), the tricky little details that make or break a trust, and what’s happening in the ever-shifting world of auto insurance. Along the way, we get into the mental game of money—why positive thinking might be more than motivational fluff—and how planning isn’t just about the plan on paper.

From Anna’s seasoned perspective to OG’s no-nonsense approach and Joe’s knack for cutting through the noise, you’ll walk away with strategies you can actually use. Plus, we can’t resist a detour into AI at the Wendy’s drive-thru (yes, it’s a thing), proving once again that money talk is always better when you leave room for curiosity.

What You'll Learn This Episode:

How to decide if a Roth conversion makes sense for your tax picture
Ways to supercharge an HSA for long-term wealth (and not just medical expenses)
Trust basics you might be overlooking—and why that could cost you.

The latest trends in auto insurance and how they might affect your rates

Why mindset matters just as much as math in building financial confidence

Questions to Ponder (or Argue Over in the Basement)

If you were starting an HSA today, how would you use it—medical safety net or stealth retirement account?
Have you considered a Roth conversion? What’s the one factor holding you back?
When it comes to trusts, do you prefer to keep heirs in the loop or keep plans private until needed?
How do you decide when to update your insurance coverage versus just shopping for a better rate?

FULL SHOW NOTES: https://stackingbenjamins.com/questions-from-the-stacker-community-1730

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

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