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How to Money
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  • How to Money

    Ask HTM - Side Hustles for Your Stocks, Capital Gains Harvesting, & Maxxing HSA Benefits #1213

    02/11/2026 | 57 mins.
    We’re kicking off the week by answering your 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! But first we debate if Joel is frugal or cheap for sending in his Darn Tough socks, but then we get into:

    1 - Fully Paid Lending: Vanguard is offering it so should I opt in to make extra on my portfolio?
    2 - Capital gains harvesting: my CPA says I can take $40,000 in capital gains and pay no tax… legit?
    3 - HSA benefits: I want to make the most of my wife’s health savings account, but is it worth dropping my state provided health coverage?
    4 - Debt payoff: what app or formula is best for me to eliminate my debts the most effectively?
    5 - Catch-up: should my catch-up contributions be made as pre-tax or post-tax dollars?

    Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
    YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
    Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
    Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
    Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
    Money Gears: knowing what to do with your money is crucial to your personal finance journey.
    MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.
    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.
  • How to Money

    Friday Flight - Pruning Property Taxes, Midterm Madness, & Passive Income Poppycock #1212

    30/10/2026 | 44 mins.
    Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like:
    New delayed flight compensation rules
    Expensive holiday flights
    Pruning property taxes
    Property tax work-off plans
    Vibes say “recession”, everything else says “normal”
    Midterm madness
    Passive income poppycock
    Grass is always greener… (in Europe)
    Rejected returns
    Charity at checkout

    Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
    YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
    Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
    Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
    Money Gears: knowing what to do with your money is crucial to your personal finance journey.
    MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.
    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.
  • How to Money

    Why Smart Investors Make Crazy Decisions w/ Alex Edmans #1211

    28/10/2026 | 52 mins.
    We investors like to think we’re rational. We carefully weigh the facts, analyze the fundamentals, and make smart decisions with our money. Except… we’re human. And when it comes to investing, humans can behave a lot more like a herd of wildebeest than a lion stalking its prey. We chase what’s hot, panic when things fall, and routinely get swept up in the mood of the market. Our guest today argues that markets can look like they’re being driven by cold, hard economic fundamentals, when underneath it all, investor sentiment can be pulling the strings. In his new book, The Madness of Markets, Alex Edmans discusses that AND what individual investors can do about it. Alex is a writer, speaker, and professor of finance at London Business School. We discuss:
    How sports outcomes can impact market sentiment and stock prices
    Investing should be based on personal circumstances and risk tolerance
    Corporate culture can be a predictor of company performance
    Speculation can be a part of investing, but should be limited
    Playing it too safe can lead to significant financial losses
    International diversification can protect against domestic downturns
    Understanding your own investment psychology is key to success
    Investing in the stock market generally yields good returns
    And much more!
    Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
    YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
    Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
    Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
    Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
    Money Gears: knowing what to do with your money is crucial to your personal finance journey.
    MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

    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.
  • How to Money

    Ask HTM - Job Offer Conundrum, $55,000 Landing in Checking Account, & Teen Trading Tightrope #1210

    26/10/2026 | 53 mins.
    We’re kicking off the week by answering your 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! But first we debate if Joel is frugal or cheap for sending in his Darn Tough socks, but then we get into:

    1 - Job offer: is it smart to take a job that has lower base pay if the upside potential is better?
    2 - Disability insurance: should we consider long-term disability with my wife’s mobility waning?
    3 - Child support: how should I allocate a lump-sum child support payment of $55,000?
    4 - Pre or post tax: now that I have a Roth 401k available, should I go all-in with pre-tax investments?
    5 - Teen trading: how can I teach my teenager about investing and should he use a platform like Bloom?

    Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
    YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
    Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
    Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
    Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
    Money Gears: knowing what to do with your money is crucial to your personal finance journey.
    MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.
    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.
  • How to Money

    Friday Flight – Souring Sentiment, Time Famines, & Rich Ol' Renters #1209

    23/10/2026 | 48 mins.
    Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like:
    Walmart and Sam’s joining forces
    Kids getting some SpaceX
    Souring sentiment
    Cell phone bills skyrocket
    Time famines
    Is cash really king?
    $5.3M American Dream
    Degrees that pay
    No more Airbnb chore list
    Airbnb rental backfire
    Rich Ol’ Renters

    Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
    YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
    Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
    Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
    Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
    Money Gears: knowing what to do with your money is crucial to your personal finance journey.
    MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.
    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.
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About How to Money
Best friends Joel and Matt are the co-hosts of How to Money which is all about providing the knowledge & tools that normal folks need to thrive in areas like debt payoff, DIY investing, and crucial money tricks that will provide continuous help along your journey. We believe that access to unbiased and jargon-free personal finance guidance is more necessary than ever before. When you handle your money in a purposeful, thoughtful way that works for your lifestyle, you can really start living a rich life.
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