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Friday Flight - America’s Debt Debacle, Perpetual Shopping, & Mystery Vacations #1185
08/28/2026 | 50 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:
Matt’s big reveal
Slick deals lingerie
America’s debt debacle
Job hopping superpower
Quick responses
“Leave the workforce” clause in prenups
Joint back accounts and happy couples
Is buy now pay later all that bad?
Perpetual shopping
Mystery vacations to save
Travel e-sim boom
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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.- “There’s nothing new under the sun.” That comes from Ecclesiastes. But it’s a piece of wisdom we tend to neglect. It's often said that those who forget history are doomed to repeat it. But what if a poor understanding of history does something else too: leaving us less grounded and giving us unrealistic expectations about how life used to be? It’s time for a history lesson today, but not just for the sake of memorizing names, dates, and events. Drawing on countless examples from history, national bestseller Joseph Moore argues that while we're constantly looking back with nostalgia at the "good old days," we may actually be living through the greatest era of prosperity. The books is How To Get Rich In American History, and today we unpack:
Why Americans misunderstand the past and over-romanticize earlier eras
The American Dream has been declared dead for centuries
Optimism and an internal locus of control matter financially
Why “stocks for the long run” is a modern idea
Early Americans were often told not to save money
Real estate myths: it does not always go up and it is not passive
FIRE as the CrossFit of personal finance
Women’s income has long been central to family wealth
Five takeaways from history: solve problems, take risks, move, marry well, believe you can do it
And much more!
Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
Cashback credit cards: 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. - 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!
1 - HSA: I don’t see how investing money in a Health Savings Account is going to move the needle for me?
2 - Dividend stocks: I keep buying individual stocks, but maybe it’s time to cut bait?
3 - Renovate/rent: We’re interested in getting into single family housing but how do we go about it?
4 - Cash reserves: What steps do I take to have 1-3 years of cash on hand for retirement?
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.
During this episode we enjoyed a Lakeside Kolsch by Lake of the Woods Brewing… thank you David S for sending this one our way! 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. Friday Flight - Friendly Financial Advice, Student Loan Shakeout, & Checks are for Chumps #1182
08/21/2026 | 47 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:
Friends and money in The Guardian
Ubiquitious sports-betting
Friendly financial advice
Whole Foods on the cheap
Suveillance grocery pricing
Student loan pause = mostly bad outcomes
Goodbye Grad and Parent Plus
Home equity piggy banks
Monitoring for fraudulent credit card charges
Checks are for chumps (Jay Z on the power of cash)
Vans are back baby!
“Dumb” cars
Flock cameras… good or bad?
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.- What’s harder: parenting… or the cost of it? We’re huge fans of having kids. They teach you so much, force you to become less self-absorbed, and – let's be real – it’s incredible to watch little mini versions of yourself running around bringing so much joy, purpose, and chaos to your daily life. But financially? Raising a family can feel more daunting than ever. Between housing, childcare, activities, and expenses that seem to multiply overnight, many parents are left asking: How do we make this work? That’s why we’re joined today by Kristy and Bryce of Millennial Revolution. They’ve written a practical new book, Parent Like a Millionaire (Without Being One), on raising kids thoughtfully and confidently without needing a seven-figure bank account. Today we discuss:
The impact of money on birth rates
Myths and facts of the cost or raising a child
“Big Baby”
Living smaller and avoiding unnecessary life upgrades
Nanny sharing and childcare alternatives
Teaching kids financial autonomy and independence
Joys of parenthood
Gift of financial independence while parenting
And much more!
Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
Cashback credit cards: 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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