How to Money

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Latest Episodes:

The Money Convos You Need to Have With Your Parents w/ Beth Pinsker #1193 Sep 16, 2026

Show notes

Financial caregiving is coming for you, whether you like it or not. Rich or poor. Married or single. Famous or anonymous. At some point, someone we love is likely to need us to step in and help care for them. And taking them to a doctor’s appointment is just the tip of the iceberg. Because when someone you love starts to need care, their financial life can very quickly become your financial problem, too. Bills. Bank accounts. Insurance. Investments. Long-term care. Even the question of who gets to make decisions when they can’t make them for themselves. You can put your fingers in your ears and hope you never have to deal with it. Or you can do something that’s much less painful: start preparing before there’s a crisis. We’re joined by Beth Pinsker and her new book, My Mother’s Money, is part memoir and part practical guide to navigating the financial realities of caring for an aging parent. We discuss:

The impact of celebrity deaths on estate planning awareness
Beth's insights on fighting for proper healthcare and rehab stays
Using savings, insurance, and safety nets for long-term care
When and how to have tough conversations about aging and finances
The importance of community, connection, and proactive planning
Practical advice for digital legacy and online account access
Lessons learned from caring for her mother that changed her perspective
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.

Ask HTM - Affordable Bathroom Reno, Forging Family $ Values, and Trump Account Scam? #1192 Sep 14, 2026

Show notes

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 - Forging family values: what are some exercises my wife and I can practice to get on the same financial page? (Check out the HTM Money Mission Statement)

2 - Trump accounts: is this really free money and should my extended family contribute to this account?

3 - 401k rollover: should I keep ‘em separated, or combine my 401k accounts into a singular easy to manage login?

4 - Savings rate calculations: do I include my employer contribution or just keep to my own personal savings rate?

5 - Bathroom remodel: what are the best ways to pay for it to optimize rewards, cashback, and discounts?!

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.

Friday Flight - 529 Hacking, Hollowed-Out Home Ec, & Sucky Stock Pickers #1191 Sep 11, 2026

Show notes

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:

Foldable iPhone Duo
$5k dividend checks
529 hacking
Hollowed-out home ec
Post-penny economy
Gen Zers carrying balances
Are platinum cards worth it?
Bogus investment advisors
Sucky stock/poor pickers
Hot cars under $20k (hint: probably a Toyota or Honda)
New Rav4 turning heads
Gas prices
Hypermiling to 83 mpg

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.

Best friends out!

See omnystudio.com/listener for privacy information.

The Financial Case for Moving Abroad w/ Richelle Gamlam #1190 Sep 09, 2026

Show notes

Spain. Vietnam. Tanzania. Georgia… the one in Europe of course. Ever catch yourself daydreaming about building a life somewhere far beyond the borders of the US? There’s a lot to love about living here. But for many, the pull to see more of the world never really goes away. What’s fascinating is that moving abroad isn’t just a lifestyle decision, it can be a financial one too. Different countries come with different costs, and entirely different ways of thinking about work, money, community, and quality of life. Our guest today is Richelle, founder of Move Abroad Coach. She’s spent more than 12 years living across half a dozen countries and has helped over 3,000 people navigate the leap overseas. Through that work, she’s gained a unique perspective on how where you live can dramatically shape your life and finances… often in ways most people never stop to consider. Today, we’re talking about the real pros and cons of leaving your home country behind: the money, the mindset shifts, the tradeoffs, and the opportunities. Specific topics include:

Why Rochelle splurges on personal growth
Her first move abroad was a major learning experience
Moving abroad can be a financial strategy
It’s not a vacation… it’s real life in a new place
Remote work and self-employment make the move easier
Digital nomad visas open up more options
Healthcare can be far more affordable overseas
Families can absolutely move abroad too
Fit matters more than fantasy
And check out her Move Abroad Bootcamp!

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Ask HTM - Buying With Other People's Money, Vanguard Digital Advisors, & Money Gear 7 Celebrations #1189 Sep 07, 2026

Show notes

1 - Other people's money: Is financing more of our new home the best way to get the lowest rate?

2 - $300,000 windfall: Help me to efficiently drain an inherited 401k and invest for the long haul!

3 - Vanguard digital advisor: I’m 29, living in Brooklyn, and saving up for a house - is a robo advisor necessary?

4 - Money Gear 7: We’ve turned our 30 year mortgage into a 12 year - how should we celebrate?

5 - Backdoor Roth: I make too much to contribute to a Roth IRA so is a backdoor worth it?

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Car Insurance Competition, Early Retirement Increasing, & HOA Horrors #1188 Sep 04, 2026

Show notes

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Build a Retirement You'll Actually Enjoy w/ Wes Moss #1187 Sep 02, 2026

Show notes

Anyone else a little tired of hearing about ‘retirement?’ It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired—or about to retire—are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. They worked at the same radio station for well over a decade. He's still there because, believe it or not, terrestrial radio is still alive and well. His show, Money Matters, has helped countless listeners make smarter decisions about their money, their investments, and, yes, their retirement. Wes has a new book out that challenges a lot of conventional thinking about what makes retirement successful, and today we're diving into the financial and non-financial choices that can help you avoid the regrets so many retirees have. Today we discuss:

Why his new research updates his earlier work on happiest retirees rather than replacing it entirely.
Fear around retirement is often amplified by nonstop media coverage.
Wes says more money alone does not erase anxiety, even for people with $3 million or more.
Wes defines happiness in a more Aristotelian way, focusing on fulfillment and purpose rather than pure pleasure.
He introduces “money green zones” for investable assets, income, and years left on a mortgage, arguing that happiness rises when retirees land in those ranges.
A major theme is core pursuits, which Wes describes as hobbies on steroids. The happy retiree group tends to have 5 or more, and they spend about 20 hours a week on them versus about 13 for less happy retirees.
Wes warns that purpose does not just appear in retirement. It has to be built intentionally well before leaving work.
They talk about the “friendship recession” and how it gets harder to make close friends with every decade, making community a key retirement asset.
The conversation also covers the emotional power of being able to say you could retire now, even if you choose not to. Wes says that confidence correlates with a 21% jump in happiness.
On the financial side, Wes explains why a retirement plan, safe assets, and a flexible withdrawal strategy can reduce fear and improve spending confidence.
They discuss Social Security timing, with Wes leaning toward using it sooner if doing so helps someone retire a year or two earlier and live better.
How much of a remaining mortgage leads to higher levels of happiness
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.

Best friends out!

See omnystudio.com/listener for privacy information.

Ask HTM - 3% Mortgage Paydowns, Brokerage Account Tax Bills, & Am I “Extra” For Wanting AC?! #1186 Aug 31, 2026

Show notes

1 - Extra cash: Should we use our savings to pay down a mortgage that’s at 2.8% for 30 years?

2 - Brokerage taxes: How do I prepare for paying taxes on dividends and could you explain ‘tax drag’?

3 - Credit card apps: Am I crazy for feeling hesitant to enter my credit card information into card maxing apps?

4 - Hot and tired: Our window units aren’t keeping up with the heat so is it OK to finance central air?

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 Forgotten Lake 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 - America’s Debt Debacle, Perpetual Shopping, & Mystery Vacations #1185 Aug 28, 2026

Show notes

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.

Best friends out!

See omnystudio.com/listener for privacy information.

How Americans Got Rich: The History of Wealth in America w/ Joseph Moore #1184 Aug 26, 2026

Show notes

“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.

Best friends out!

See omnystudio.com/listener for privacy information.

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