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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.

How to Money

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 - Home repair: should I get a new roof based on a roof inspector who says my insurance will cover it for free?
 
2 - Roth conversion: as an average wage earner who is maxing out my Roth IRA, should I convert my 401k as well?
 
3 - Tech heavy portfolio: should I rebalance my retirement portfolio away from AI if I think it’s a bubble?
 
4 - Savings rates: should I ditch Ally for another bank that’s paying a higher rate on their savings account?
 
5 - Open enrollment: I’ve always gone with my employer provided Health Reimbursement Arrangement, but is the HSA better?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • We referenced a bunch of previous episodes:
 • Finding 
financial freedom making less than $40,000 • a year with Hope Ware.
 Timing a Roth conversion • with CFP Cody Garrett.
 AI and your investments with Vanguard’s Joe Davis • .
 • I’m not sure who needs to hear this but 
Health Savings Accounts, or HSAs, are the ultimate retirement accounts. • 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.
 • 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 a Kirkland Signature Vintage Ale 2025 by Deschutes! 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.

Ask HTM - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066

We’re sharing another podcast we think you’ll enjoy, The Big Short Companion from Against the Rules, hosted by bestselling author Michael Lewis. The Big Short is now 15 years old and to mark the occasion, Lewis narrated a new audiobook version of The Big Short and is looking back on how the 2008 financial crisis still affects the world today. To make sense of Wall Street’s hangover from the crash described in The Big Short, Lewis calls up Matt Levine, author of the Money Stuff newsletter for Bloomberg Opinion. He’s also a former investment banker who was working at Goldman Sachs during the market crisis of 2008. He and Lewis talk about Bitcoin, bank regulation, and new forms of risk-taking—all ways Wall Street has changed since the crisis. Find The Big Short Companion from Against the Rules wherever you get podcasts and The Big Short audiobook wherever you get audiobooks.

See omnystudio.com/listener for privacy information.

Introducing: The Big Short Companion from Against the Rules: How the Financial Crisis Broke Wall Street

Time for a Friday Flight- our little sampling of the week’s 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:
 
 • Help us dominate the 
Daffy Voices for Good Campaign • !
 Burdensome credit card benefits Frankenstein BNPL cards Robinhood Gold 3% cashback credit card Cash delivered to your doorstep Soft switching Tariff turnaround Eat more chicken Delayed flight compensation iPhone pocket sock $300 water bottle Discounted drugs GLP-1 in the C-suite End of electric (cars) Credit history vs car insurers Car-play diem 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • 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.
 • 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.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Soft Switching, Tariff Turnaround, & Ozempic Face #1065

“Taxes for creatives” could have also been the title of this episode, giving the more entrepreneurially minded the boost they need to officially launch a little business they’ve been considering. But for most folks the topic of taxes isn’t comforting, it’s straight up terrifying… even though it shouldn’t be. Today’s guest, Hannah Cole, is on a mission to create fearless folks who launch into the world of deductions, bookkeeping, tracking, tax filing, and all the other terms that strike a little fear in your heart, with full confidence. Her new book, Taxes For Humans, acts as a field manual for self-employed folks to simplify their taxes and take the bull by the horns. Topics covered today:
 
 • Taxes can be intimidating, but understanding them is empowering
 • Creatives often struggle with the business side of their work, including taxes
 • The IRS is more forgiving than many people think
 • Receipts, tax forms, and bookkeeping are the key three systems
 • Deductions are available for ordinary and necessary business expenses
 • When and how much in quarterly estimates, in order to avoid penalties
 • A visual guide to tax deductions
 • And much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Be sure and check out Hannah’s new book, 
Taxes For Humans • , or just get it 
on Amazon • . And her 
visual guide to tax deductions • is especially cool for folks looking to organize their business expenses, who also hate IRS forms ;)
 • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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.

Don’t Let Taxes Terrify You w/ Hannah Cole #1064

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 - Home renovation: what factors did Matt consider when deciding to add on to his existing house?
 
2 - Credit cards: I want to cancel my oldest credit card, but how concerned should I be about dinging my credit score?
 
3 - Student loans: should I pay off my student loans or wait for forgiveness if I have the cash on hand to eliminate them?
 
4 - Medical expenses: could I fully subsidize my healthcare costs were I to aggressively invest my HSA dollars?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Converting your primary into an investment property is one of the easiest ways to create some 
semi-passive income • . 
 • I’m not sure who needs to hear this but 
Health Savings Accounts, or HSAs, are the ultimate retirement accounts. • 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.
 • 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 a Jeremy’s Changed by Fonta Flora! 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.

Ask HTM - Vital Home Reno or Moving Factors, Dropping Credit Without Dinging Your Score, & Student Loan Forgiveness or Payoff #1063

Time for a Friday Flight- our little sampling of the week’s 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:
 
 • Help us dominate the 
Daffy Voices for Good Campaign • !
 50 year mortgages Robinhood getting into the mortgage game Cash for Christmas FindHelp.org • is a great resource for those in need of food, shelter, transportation and more
 Flights not quite as delayed Expense ratio transparency Investment nudges by Vanguard $2,000 tariff rebate checks Fancy credit cards potentially no longer accepted RIP Direct File Avoiding all the scams Voice authentication via code words 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • 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.
 • 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.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Forever Mortgages, Ruining Reward Cards & Free Tax Filing Fail #1062

Everywhere you look, people are talking about AI. Some say it’s going to save the world; others think it might break it. But while the headlines focus on sci-fi futures and big-tech battles, we’re interested in something a little closer to home: what does all of this actually mean for us as everyday, DIY investors – today, and over the next decade? Fortunately, we don’t have to wing it. Vanguard’s global chief economist, Joseph Davis, has been studying the forces shaping our financial future – AI included. And in his new book, Coming Into View, he breaks down the megatrends that are poised to reshape the investing landscape. Today we discuss:
 
 • How Vanguard's mission focuses on aligning investor interests with their work
 • Predictions about lower future returns are based on economic fundamentals
 • AI's impact on productivity will extend beyond the tech sector
 • Cost management in investments is crucial for long-term success
 • Demographics alone do not determine economic growth outcomes
 • The importance of diversification in investment portfolios remains unchanged
 • Investors should stress-test their financial goals against potential market scenarios
 • And much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • To dig into more of how AI will impact your portfolio, check out 
Joe’s book: Coming Into View • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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 AI Will Impact Your Investments w/ Vanguard's Joe Davis #1061

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 - Open enrollment: what factors should I consider when hopping to a more affordable health insurance provider?
 
2 - Buy now pay later: how much of a discount would have to be offered to make a “pay in 4” worth considering?
 
3 - Money gears: should I hit pause on investing in order to finally get rid of my credit card debt?
 
4 - Credit score: would paying down my mortgage early hurt my credit score and my ability to invest in real estate later?
 
5 - Savings rate: should I include dollars automatically invested into my 401k when calculating my savings rate?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • 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.
 • 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 Upside Dawn by Athletic! 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.

Ask HTM - Open Enrollment Entanglements, Worthwhile BNPL Scenarios, & Continuing to Investing with Outstanding Debt #1060

Time for a Friday Flight- our little sampling of the week’s 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:
 
 Timeshare rescission periods $50k average for new cars Shorter car loans please Repos on the rise $10k new car tax break Occupation consternation AI labor market anxiety Career plan Bs $100 work lunch budgets Frugal habits going mainstream Creepy dumb chore robots Ads everywhere Avoiding the marketing 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • 11 questions to ask yourself, 
before quitting your job. • 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.
 • 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.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Ridiculous Car Refinancing, Occupation Consternation, & Ads Everywhere #1059

Nearly 100 years ago, economist John Maynard Keynes predicted that we’d be working 15-hour weeks by now due to gains in productivity and technology. Tim Ferriss claims that you can pretty much do it all in a 4-hour workweek! Neither of those seem plausible but our guest today takes a much more reasonable approach and says that 4-day work weeks are not only feasible but can lighten the load, allowing us to live more life – all while being more productive! Juliet Schor is an economist and professor of sociology at Boston College and is best known for her research on work, consumption, and economic inequality. Some of the topics discussed today include:
 
 • How cultural attitudes towards work can hinder progress
 • Four-day work week can improve productivity and employee satisfaction
 • Companies are beginning to recognize the benefits of shorter work weeks
 • People often prioritize work over personal life due to societal pressures
 • Ways to advocate and push for a more reasonable work week
 • Navigating a post-growth world requires reevaluating consumption habits
 • No amount of money can compensate for more work among certain workers
 • And plenty more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Be sure and check out 
Juliet’s book, Four Days A Week: The Life-Changing Solution for Reducing Employee Stress, Improving Well-Being, and Working Smarter • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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.

Work Less, Live More w/ Juliet Schor #1058

We’re kicking off the week by answering your questions! And if you have a question for us, we’d love for you to submit your own via HowToMoney.com/ask/

1 - If I try to purchase a home with cash, can I expect to get a better deal? How does this work?

2 - My employer is changing health coverage options, so what should I do with money that is in my HSA?

3 - What are CDs and are they a good idea these days?

4 - How should I go about shopping for the lowest mortgage rate?

5 - Should I be contributing to my 403b at work, or should I focus on my Roth IRA instead?

During this episode we enjoyed a Pseudo Sue by Toppling Goliath- thanks to Kelsey for donating this one to the show! And as we’ve ramped up the podcast with an additional Friday episode every week, we could really use your help to spread the word- let friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to spread the word to get more people doing smart things with their money in these difficult times!

Best friends out!

 
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See omnystudio.com/listener for privacy information.

Ask HTM - CDs are a Smart Move, Shopping for the Best Mortgage Rates, and What to do with an old HSA #214

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