Ask HTM - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066

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Nov 24, 2025

Tune in for engaging listener questions that cover a range of financial topics! Discover whether to file an insurance claim for a new roof or how to approach a Roth conversion for your 401(k). Get insights on rebalancing your tech-heavy portfolio amid potential bubbles and explore whether switching savings accounts is worth it. Finally, learn the differences between Health Reimbursement Arrangements and HSAs during open enrollment. Plus, there's a beer review to wrap things up!

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ADVICE

Say No To Sketchy 'Free Roof' Claims

Avoid hiring fly-by-night roofers who push insurance claims for a "free roof."
Pay for needed roof work yourself rather than filing dubious claims that raise premiums and hurt future insurability.

ANECDOTE

Contractors Chasing Storm Payouts

Joel recalls roofers who head to storm-hit areas to solicit big payouts from insurers.
He warns those companies often prioritize quick insurance checks over quality work.

INSIGHT

Claims Have Hidden Collective Costs

Bogus insurance claims create collective-action costs that raise premiums for everyone.
Even a legitimate insurance payout still costs you via deductibles, higher future premiums, and CLUE reports.

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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!

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