We’re kicking off the week by answering listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!

  1. Considering that my mom is a multimillionaire, should I listen to her personal finance and real estate advice even if I disagree?
  2. Do you have any books or recommendations for a teenager who is moving out on her own?
  3. What is the best platform to easily collect rent payments?
  4. Can I carry over any out-of-pocket medical expenses to a new health insurance plan?
  5. Are there any downsides to the Upside App- is it legit or too good to be true?

Additional links:

  • Real estate – While buying a bigger home isn’t a great move from a wealth building standpoint, buying another home might be the perfect way for you to get started in real estate. But it’s not as easy as it was 10 year ago.
  • Stock market – And of course we touched on investing during this episode- listen back to how we invest our money with brokerage houses like Fidelity, M1 Finance, and Vanguard.
    • Roth – If you’re not already investing in tax advantaged accounts, listen to why we think you should start with the beautiful Roth IRA.
  • Landlording – Some of the best platforms to manage your rentals and collect rent are: avail, innago, & RentRedi.
  • Upside app – It’s legit! Use the Upside app to find the best deals on gas, restaurants, and grocery stores.
  • Credit Card Tool – Looking for the right credit card for you? Then check out our new credit card tool that’ll help you to easily filter through all the cards based on your preferred airline, whether or not they have an annual fee, or simply by the cash back offer! Just toggle the sliders and you’ll know which card to consider.
  • Newsletter – Don’t forget to sign up for the best personal finance newsletter in all the land! It’s completely free and something we create to help you along your journey to financial freedom. It drops every Tuesday morning and you can always unsubscribe if you don’t dig it!

During this episode we enjoyed a So Happens It’s Tuesday by The Bruery! 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!

* Advertiser Disclosure: How to Money has partnered with CardRatings for our coverage of credit card products. How to Money and CardRatings may receive a commission from card issuers.
* User Generated Content Disclosure: Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

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3 comments on “Ask HTM: Downsides to the Upside App, Carrying Over Out-Of-Pocket Medical Expenses, & Ignoring Mom’s Financial Advice – Episode 652

  1. Cyrus Apr 3, 2023

    You forgot to mention the home sale tax exclusion benefit for selling current primary home which more than offsets sales commission and closing costs

  2. Clint Apr 13, 2023

    Hi Guys, after listening to this episode, I tried the upside app. Here’s the catch: your initital gas purchase savings is incredible, like 40 or 50 cents off per gallon. But that’s just to lure you in. The savings after that are more like 4 or 5 cents, and these are not the cheapest gas stations. Soooo it will take quite awhile to recoup your savings unless you eat out at the few restaurants listed. Not really worth the time in my opinion. And yes, too good to be true.

    • Thanks for that insight, Clint! We don’t use many of these apps ourselves. We get the desire to use them to save, but so often they save you so little that they’re just not quite worth the time it takes.