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

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Education, Business, Money, Investing, Financial Planning, Cfp, Personal Finance, Retirement

4.4 • 2K Ratings

🗓️ 3 September 2025

⏱️ 73 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Enjoy!

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Transcript

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0:00.0	My plan is sound, mathematically sound, it cannot fail, it's perfect.
0:07.9	Three months from now, I will be worth $50,000, independent for life.
0:28.4	Live from Joe's Mom's Basement, it's the Stacking Benjamin Show.
0:42.1	I'm Joe's Mom's Neighbor, Doug, and today the star of the show is you.
0:49.1	We're sharing your calls, emails, notes in our Facebook group, and more as we dive into HSAs,
0:56.0	trusts, auto insurance, the efficient frontier, health and retirement, and all bunch of stuff I can't think of.
1:01.6	And now, here are three people who are buckled in and ready to answer your questions.
1:07.2	It's Joe, OG, and CFP Anna Allen.
2:18.5	Can't figure out. I was going to give her the whole OJJG treatment, and I couldn't figure out how to do that. Ends in a syllable. It's a lot harder. Alam, mum, mum, mum, mum. Maybe next time we got to put Anna at the top. I think it would have just sounded like Anna aluminum if I did that. Hey, everybody, welcome back to the Stacky Benjamin show. I'm Joe Saul C. Hi, average Joe Money on X, Twitter, whatever you might call it these days. And the guy who these days and every day we call OG on the show is sitting across for me. Mr. O.G's here. How are you, brother? Oh, I'm just happy to be here. It's the middle of the week. It's a middle of a short week. So it's even better. You know what I dislike about Labor Day week is you get to Friday and you're like, wow, that was great. But then the following Wednesday, like, are you kidding me? I still have two days left of this. Like, I have to work all five days. How tough is that? Yeah. Tough for a guy like you. we'll find a way to get through. Of course, next week I had to Portland. So I get to work exactly one day next week, which is not too tough. How are you going to handle it? The person who's going to hopefully do all the work, OG, on this show is a woman who you have the pleasure of working with Anna Alam joins us.
2:19.1	How are you?
2:20.7	Hey, everyone.
2:21.7	I'm good.
2:22.2	Thanks.
2:23.8	Welcome to the party, Anna.
2:29.1	Your life must be a party because you get to work with OG every freaking day.
2:29.8	Yeah.
2:31.3	I talk to him Monday through Friday.
2:32.9	It's a blessing.
2:34.0	Pinch me.
2:36.2	Look how forced that smile looks.
2:42.5	It sounds like you're saying that's a paycheck depends on it.
2:44.3	Say nice things or else.
	...

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