Ask HTM – Mortgage Payoff Loophole, DAFs to Maximize Tax Deductions, and Legally Evading a Medical Bill #1069

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Dec 1, 2025

This episode dives into listener questions on various financial hacks. Discover the pros and cons of velocity banking for mortgage payoffs. Unpack the benefits of Donor-Advised Funds and how to maximize tax deductions. Learn whether to prioritize Roth IRA contributions or an employer-sponsored 457b for retirement. Evaluate strategies for negotiating medical bills and when to accept discounts. Finally, get insights on life insurance needs for single parents with investments. A treasure trove of financial advice awaits!

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ANECDOTE

When Manufacturers May Disappear

Joel recounts concern over Rad Power Bikes possibly going out of business and how that affects warranty and parts availability.
He recommends caution buying products from companies that might not support them long-term.

ADVICE

Skip Velocity Banking Complexity

Avoid complex 'velocity banking' schemes and prefer straightforward extra mortgage payments or refinancing when rates fall.
Prioritize higher-impact goals (retirement, high-rate debt) before aggressively paying a low-rate mortgage.

INSIGHT

Mortgage As A Flexibility Tool

A reasonable mortgage rate lets you pursue multiple goals simultaneously instead of rushing to pay it off.
Keeping liquidity and investing (Roth, 401k match) often beats accelerating mortgage principal.

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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 - Accelerated Mortgage Payoff - is velocity banking a smart way to quickly pay off my mortgage?

2 - Donor Advised Funds - do I get to deduct more from my taxes if my donor advised contribution grows after investing?

3 - Retirement Investing - am I better off contributing to my Roth IRA or my employee sponsored 457b?

4 - Medical Bills - should I take an offer for a medical bill discount by paying before the end of the year, or is there a better option?

5 - Life Insurance - I already have rental properties and a 401k that my baby could inherit so do I also need life insurance?

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

We talked about Donor Advised Funds in depth with Adam Nash.

If you’re looking for the best place to open a donor advised fund then look no further than Joel’s review of Daffy.

A great physical fitness newsletter by friend of the pod, Drew: Move To Improve
Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
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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 an Automatic IPA by Creature Comforts! 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!

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