Ask HTM - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066
How to Money
iHeartPodcasts
4.6 • 3.2K Ratings
🗓️ 24 November 2025
⏱️ 53 minutes
🧾️ Download transcript
Summary
Let’s kick off the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you might think it is, we want to hear it!
1 - Home repair: should I get a new roof based on a roof inspector who says my insurance will cover it for free?
2 - Roth conversion: as an average wage earner who is maxing out my Roth IRA, should I convert my 401k as well?
3 - Tech heavy portfolio: should I rebalance my retirement portfolio away from AI if I think it’s a bubble?
4 - Savings rates: should I ditch Ally for another bank that’s paying a higher rate on their savings account?
5 - Open enrollment: I’ve always gone with my employer provided Health Reimbursement Arrangement, but is the HSA better?
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
- We referenced a bunch of previous episodes:
- Finding financial freedom making less than $40,000 a year with Hope Ware.
- Timing a Roth conversion with CFP Cody Garrett.
- AI and your investments with Vanguard’s Joe Davis.
- I’m not sure who needs to hear this but Health Savings Accounts, or HSAs, are the ultimate retirement accounts.
- Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
- Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
- Join a thriving community of fellow money in the HTM Facebook group.
- Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
During this episode we enjoyed a Kirkland Signature Vintage Ale 2025 by Deschutes! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
Best friends out!
See omnystudio.com/listener for privacy information.
Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:02.6 | Guaranteed Human. |
| 0:04.1 | Welcome to How to Money. |
| 0:05.7 | I'm Joel. |
| 0:06.3 | I'm Matt. |
| 0:07.3 | And today, we're answering your listener questions. |
| 0:30.9 | Thank you. Your mustache, by the way, buddy, is looking quite fine. |
| 0:31.4 | Well, I think. |
| 0:32.2 | We've not talked. |
| 0:33.6 | Have we not talked about it on the show? |
| 0:34.3 | I don't think we have. |
| 0:34.9 | Might have mentioned it. Maybe early on we joked about it, but it's like |
| 0:37.5 | full on legit. Oh, we did joke about it early on because you're talking about it. It wasn't a joke in the beginning. It looked like a joke. No, it's like, it's just, it's like as thick as your hair up top. And I'm not disparaging either. But with the good, my thinning hair looks great with my, not so great mustache. |
| 0:53.3 | With the thin mustache as well. |
| 0:54.6 | No. |
| 0:55.1 | How long are you planning to keep it, by the way? |
| 0:56.8 | I don't know. |
| 0:57.3 | I'm kind of, |
| 0:57.9 | I feel like, My thinning hair looks great with mine, not so great mustache. With the thin mustache as well. |
| 0:54.6 | No, how long are you planning to keep it, by the way? I don't know. I'm kind of, I feel like it's one of our friends recently, one of our mutual friends recently said, you look more like yourself now with that mustache. And I thought that was the highest compliment. Honestly, that means they've gotten used to it. That's what that means. And I was like, but I think it was the first time he'd seen me with it. |
| 1:11.4 | Oh, really? |
| 1:11.8 | Yeah. |
... |
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