Ask HTM - Best Grocery Cashback Credit Cards, Risking it with Ultra Cheap Car Rentals, & Giving Up on Home Ownership #1039
whatshot 11 snips
Sep 22, 2025
Listeners dive into intriguing personal finance questions! They explore strategies for managing a hefty cash windfall from a home sale. The discussion also covers the best grocery credit cards and the pros and cons of annual fees. High earners learn about the backdoor Roth process. Additionally, the risks of opting for ultra-cheap car rentals are analyzed, alongside tips for effectively paying off credit card debt. It's a treasure trove of financial insights and practical advice!
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question_answer ANECDOTE
Budget Rental Letdown
Matt booked at a Budget location with poor reviews and arrived to an hours-long problem when the reserved vehicle wasn't available.
The experience soured him on that location despite liking the brand elsewhere.
volunteer_activism ADVICE
How To Deploy Large Home Sale Proceeds
Put proceeds you won't need soon into a taxable brokerage so money can grow and remain liquid.
Keep a cash buffer for short-term needs or a mini-retirement and earmark estimated taxes from the duplex sale.
insights INSIGHT
Primary Home Sale Vs. Investment Property Taxes
Selling a primary residence often yields tax-free gains under the home sale exclusion.
Rental or duplex sales, however, typically trigger long-term capital gains and need tax planning.
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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 - Selling a home and renting instead: what do we do with cash from the closing table?
2 - Best credit card for groceries: but what about ethical fatigue from asking for annual fee waiver?
3 - High income Roth investors: how do we go about (legally) shoehorning some dollars in there?
4 - Car rental deals: is is worth it to go with the ultra cheap car rental that’s a fraction of the regular cost?
5 - Debt payoff: what’s the best method for knocking out 4 credit card balances?
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
Use Undebt.it to help you figure out a get-outta-debt plan
If you make too much to directly contribute to a Roth, the "backdoor Roth" might be just the thing to get you invested.
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.
Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
During this episode we enjoyed a Fat Pug by Maplewood Brewing! 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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