Explorez tous les épisodes du podcast How to Money
| Titre | Date | Durée | |
|---|---|---|---|
| Friday Flight - Pruning Property Taxes, Midterm Madness, & Passive Income Poppycock #1212 | 30 Oct 2026 | 00:44:35 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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. | |||
| Why Smart Investors Make Crazy Decisions w/ Alex Edmans #1211 | 28 Oct 2026 | 00:52:02 | |
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:
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Best friends out! See omnystudio.com/listener for privacy information. | |||
| Ask HTM - Job Offer Conundrum, $55,000 Landing in Checking Account, & Teen Trading Tightrope #1210 | 26 Oct 2026 | 00:53:28 | |
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?
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| Friday Flight – Souring Sentiment, Time Famines, & Rich Ol' Renters #1209 | 23 Oct 2026 | 00:48:02 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| Owning Unsexy Businesses to Build Wealth w/ Alex Smereczniak #1208 | 21 Oct 2026 | 00:55:06 | |
America has a long history of entrepreneurship. Some of the biggest, most recognizable companies in the world started with one person taking a risk and building something from scratch. And for good reason: owning a business can be an incredibly powerful path to building wealth. But there’s a problem. A lot of people want to be their own boss… they dream about leaving the 9-to-5, having more control over their time, and building something they actually own. But when it comes time to take the leap, the fear of the unknown can be pretty powerful. Here’s the good news: you don’t necessarily have to invent the next great thing in your garage at 2 a.m. There’s another path to business ownership that’s been around for decades: buying a franchise. Alex Smereczniak is an entrepreneur who started Franzy, a platform that connects aspiring business owners with franchise opportunities. Today we discuss the realities of owning a small business, who should consider it, how to evaluate an opportunity, whether buying a franchise is actually a good way to build wealth, and much more including:
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| Ask HTM - Selling an EV to Get Ahead, Juicing Your Down Payment Returns, and Hacking an HSA to the Max #1207 | 19 Oct 2026 | 00:54:33 | |
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 - Home reno: but should I goose my savings with special bank offers in the meantime? 2 - HSA overload: what are the tax DISadvantages if I set aside too much in my Health Savings Account? 3 - Baby car: does it make sense for me to sell the Tesla now that we’re expecting our second kid? 4 - Life insurance: what do I do about a previous benign cancer diagnosis now that I need life insurance? 5 - Avoiding medical debt: check out the AI clone advocating for you at the MarshallAllenProject.org!
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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 - Tempting TIPS, Sticky Shrugflation, & Subprime Struggles #1206 | 16 Oct 2026 | 00:48:32 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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. | |||
| Investing Will Never Be the Same w/ Robinhood’s Steph Guild #1205 | 14 Oct 2026 | 00:48:25 | |
Robinhood didn’t just join the investing revolution over the past decade… they reshaped it. Robinhood pushed investing toward zero commissions, brought millions of new investors into the market, and even introduced the first IRA match. They’ve been willing to innovate in ways that have sometimes been controversial. It’s a platform with enormous sway, especially among younger investors. But what does Robinhood think the future of investing looks like? What are they getting right, what might they be getting wrong, and what does the future look like for normie investors? Steph Guild is Robinhood’s Chief Investment Officer, and she’s here to help us answer those questions today. We get into:
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| Ask HTM - Is Robinhood Gold Worth It, Sandwich Generation Legal Maneuvers, & Nursing to Make Bank #1204 | 12 Oct 2026 | 01:01:05 | |
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! First we debate the merits of $2 decisions, then…
1 - Invest actually: how do I avoid the mistake of not actually investing within my Roth IRA? 2 - Aging parents: where’s the to-do list and how should I create a will and estate plan for my parents? 3 - Dropping stocks: as I get closer to retirement, should I more aggressively shift to cash by selling? 4 - Nursing school: good idea to use my Roth IRA to fund my nursing degree? 5 - Robinhood Gold: now that I finally got the invite is it worth the $60 annual fee?
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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 - Faltering Friendships, Super Intelligence for Savers, & Birthdayzillas #1203 | 09 Oct 2026 | 00:46:51 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| Scoring the Most Financial Aid for College w/ Phillip Levine #1202 | 07 Oct 2026 | 00:55:40 | |
The economics of higher education are pretty messed up and colleges know it. Sure, we're sometimes our own worst enemies when it comes to spending. But the pricing system itself seems almost designed to confuse: opaque, inconsistent, and nearly impossible to decode from the outside. Which means there's real money on the table for families who take the time to learn how admissions and financial aid actually work… and which hoops are worth jumping through and which aren't. Get fluent in this system, and you could save yourself tens of thousands of dollars. Stay in the dark, and you're leaving that money on the table. We're joined by Phillip Levine, an economist and professor who's spent his career studying education finance and his new book, Hidden Tuition, pulls back the curtain on how the system really works, and what families can do to navigate it on their own terms. Today we discuss:
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| Ask HTM - Getting Political, Paying for Hot Stock Tips, & Fixing an Old Toyota #1201 | 05 Oct 2026 | 00:52:52 | |
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 - Stock tips: why do so many people pay for stock tip subscriptions?! 2 - Toyota time: is it worth dropping a lot of money on our old Corolla? 3 - Income bump: how can I offset my taxes while still achieving some financial goals? 4 - Political: does iHeart prevent you guys from talking politics on the podcast more often? 5 - Medical debt: what’s the site that helps you to get out of medical debt?
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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 - Muse is Meh, Homebuying with Homies, & Commuting Costs Climb #1200 | 02 Oct 2026 | 00:48:21 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| You Saved It. Now Give Yourself Permission to Spend It w/ Jean Chatzky #1199 | 30 Sep 2026 | 00:46:09 | |
61% of Americans say they’re more afraid of running out of money than they are of dying… the idea of spending our later years stressed about money is so terrifying that some people would rather face the great unknown than deal with their own financial plan. And yet, far too many people are taking the “I’ll figure it out someday” approach when it comes to retirement. They’re hoping things work out instead of building a plan that gives them confidence and freedom. Our guest today believes retirement doesn’t have to be defined by fear and uncertainty. With the right decisions, we can worry less about money and spend more time enjoying the life we’ve worked so hard to build. Jean Chatzky has spent decades helping people make smarter decisions with their money through her work on the Today show, her AARP columns, her books (the latest of which is titled The Forever Paycheck), and her podcast. Today we discuss what retirement looks like in this modern era, how we can prepare for it without letting fear take over, and we dig into topics like:
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| Ask HTM - Early Retirement with a 457b, Surrendering Life Insurance, & Moving to a Bigger House #1198 | 28 Sep 2026 | 00:58:51 | |
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… will or won’t Joel run a 50k?! But then we get to:
1 - Cash surrender: or keep a life insurance policy around and how will it impact my student loan payment?! 2 - Early retirement: should I prioritize my 457 if I’m interested in retiring as a firefighter at age 53? 3 - Best yield: where should we keep the downpayment for a new home purchase? 4 - Buy my car: wise advice if you want to sell your car for the most money. 5 - 1% AUM: how do I keep my parents from getting ripped off?
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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!
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| Friday Flight - Illiterate Americans, Shrinking Shoulder Season, & Rate Hike Reactions #1197 | 25 Sep 2026 | 00:46:42 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| Fighting Back Against a Broken Healthcare System w/ Dr. Jordan Grumet | 23 Sep 2026 | 00:52:20 | |
Does anyone look at the U.S. healthcare system and think, "Yep, everything's working great"? Probably not. It's not because we don't have talented doctors or dedicated healthcare workers. It's because a growing web of corporate interests, distorted incentives, and financial middlemen has turned healthcare into one of the most expensive and frustrating systems in the developed world. In his new book, The Healthcare Heist, Dr. Jordan Grumet – who is also a personal finance podcaster, writer, & speaker – exposes how that happened. Medical bills remain a major source of debt and bankruptcy for American families, but Jordan argues that none of this is inevitable. More importantly, he lays out practical solutions to help individuals. Today we discuss:
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| Ask HTM - New(ish) Phones, New(ish) Cars, and New Big Financial Goals! #1195 | 21 Sep 2026 | 01:04:09 | |
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! A little Southwest companion pass and airline talk before we dive in:
1 - Big goals: what should I focus on next after I’ve paid off my house?! 2 - Parent help: should I get a power of attorney or keep it simple with a joint account to help my aging parents? 3 - Mach E: am I the only one using an electric vehicle as a way to save a ton? 4 - Newish iPhones: where’s the best place to look if I don’t want to buy brand new? 5 - Venmo vs Zelle: which are the best P2P payment apps for my daughter to use?
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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!
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| Friday Flight - Guilt-Ridden Spending, Sneaking Socialism & Home Buying Help #1194 | 18 Sep 2026 | 00:48:26 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| The Money Convos You Need to Have With Your Parents w/ Beth Pinsker #1193 | 16 Sep 2026 | 00:49:53 | |
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:
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| Ask HTM - Affordable Bathroom Reno, Forging Family $ Values, and Trump Account Scam? #1192 | 14 Sep 2026 | 00:54:29 | |
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?!
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| Friday Flight - 529 Hacking, Hollowed-Out Home Ec, & Sucky Stock Pickers #1191 | 11 Sep 2026 | 00:48:45 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| The Financial Case for Moving Abroad w/ Richelle Gamlam #1190 | 09 Sep 2026 | 01:00:03 | |
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:
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| Ask HTM - Buying With Other People's Money, Vanguard Digital Advisors, & Money Gear 7 Celebrations #1189 | 07 Sep 2026 | 00:55:49 | |
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 - 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?
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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!
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| Friday Flight - Car Insurance Competition, Early Retirement Increasing, & HOA Horrors #1188 | 04 Sep 2026 | 00:48:22 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| Build a Retirement You'll Actually Enjoy w/ Wes Moss #1187 | 02 Sep 2026 | 00:56:16 | |
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:
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| Ask HTM - 3% Mortgage Paydowns, Brokerage Account Tax Bills, & Am I “Extra” For Wanting AC?! #1186 | 31 Aug 2026 | 00:53:05 | |
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 - 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?
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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!
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| Friday Flight - America’s Debt Debacle, Perpetual Shopping, & Mystery Vacations #1185 | 28 Aug 2026 | 00:50:31 | |
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:
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| How Americans Got Rich: The History of Wealth in America w/ Joseph Moore #1184 | 26 Aug 2026 | 00:59:10 | |
“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:
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| Ask HTM - Overrated HSA, 13% Dividend Yields, & Getting Into Real Estate #1183 | 24 Aug 2026 | 00:57:46 | |
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?
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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!
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| Friday Flight - Friendly Financial Advice, Student Loan Shakeout, & Checks are for Chumps #1182 | 21 Aug 2026 | 00:47:37 | |
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:
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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!
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| Parenting Like A Millionaire w/ Millennial Revolution #1181 | 19 Aug 2026 | 00:59:06 | |
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:
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| Ask HTM - Escaping Dealership Ripoffs, Aldi’s Rising Prices, & The Misery of Being House Poor #1180 | 17 Aug 2026 | 00:55:20 | |
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 - House poor: What to do when all your money goes towards your mortgage? 2 - Aldi: Is it true that the best budget grocery store isn’t taking the AMEX Blue Cash Preferred anymore? 3 - Expensive babies: Should I plan to carry newborn delivery costs on a credit card? 4 - Car dealership: How can I avoid fees and cut other costs when I shop for a car at the dealership?
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During this episode we enjoyed a Juicy A by Flying Monkey 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!
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| Friday Flight - Cash Hoarding, Spendy Sports, & WFH Fees #1179 | 14 Aug 2026 | 00:47:50 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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!
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| Never Worry About Money Again w/ Jesse Mecham #1178 | 12 Aug 2026 | 00:56:24 | |
Frugality is a cornerstone of personal finance advice: cut back, spend less, reduce waste. And for the average American drowning in debt, that’s often solid advice. But money isn’t meant to just sit there untouched—it’s also meant to be spent, experienced, and enjoyed. In fact, even the money you save is really just deferred spending. And let’s face it: money isn’t easy to come by. We work hard for every dollar we earn. So maybe the answer isn’t simply spending less. Maybe it’s spending with more intention. Our guest today wants you to worry less about money, and he argues that the path there isn’t endless deprivation—it’s changing the way you think about spending altogether. Jesse Mecham is a best-selling author and founder of YNAB, the beloved budgeting app that’s helped millions take control of their finances. Today we discuss his brand new book, Never Worry About Money Again, and dive into concepts like:
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| Ask HTM – Investing or Parking Cash, Ignoring Family Money Advice, & When Rates are Low Enough for a Refi #1177 | 10 Aug 2026 | 01:06:10 | |
Big money mistakes usually come from doing the “smart” thing too soon. We break down listener decisions that look simple on the surface, but could cost you thousands if you get the timing wrong… from where to park a home-sale windfall, to whether a refi is actually worth it, to why stock-picking advice from family can be a trap, and more! 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! If you’re sitting on cash you’ll need soon, debating whether to become a landlord, or wondering if your mortgage rate is low enough to justify another refinance, we give you the clearest path forward. We also tackle the hidden risk in chasing returns with individual stocks and ETFs, and explain why boring, liquid, diversified choices usually win when the clock is ticking. You’ll discover: Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Bear Hug IPA by Market 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 - Frustrating Funflation, Money Morons, & Home Haters #1176 | 07 Aug 2026 | 00:53:32 | |
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:
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
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. | |||
| A Field Guide to Wealth & Purpose in Your 20s w/ Jack Raines #1175 | 05 Aug 2026 | 00:57:32 | |
There’s a lot packed into your 20s. You’re getting an education — formal or otherwise. You’re figuring out what you believe about work, money, relationships, success, and who you want to become. Sure, that process doesn’t stop at 30, but your 20s are especially formative. And there’s no shortage of advice aimed at young adults. Commencement speeches. Career gurus. Personal finance influencers. But a lot of it misses the deeper question of what actually matters. And in a world full of noise, it’s getting harder to separate wisdom from status signaling. Today we’re joined by Jack Raines. He’s a young guy who made some pretty countercultural choices — walking away from prestigious jobs, big paychecks, and conventional definitions of success to build a life on his own terms. His new book, Young Money, is part memoir, part guidebook for the generation coming behind him and today we discuss:
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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!
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| HTM is BACK! (Video Edition) #1174 | 03 Aug 2026 | 01:06:17 | |
Join our first ever video podcast as we explore the latest in personal finance, technology, and lifestyle, sharing insights and practical tips to improve your financial well-being and enjoy life to the max! Today we get into:
Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
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!
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| Popular Money Advice That Just Ain’t Right #1173 | 31 Jul 2026 | 00:48:12 | |
Searing your steak as a way to ‘lock in the juices’ is something we’ve heard folks recommend for years! Get that grill hot as blazes, toss on your steak, and reap the juicy medium-rare rewards. But even though there might be a kernel of truth here, culinary scientists tell us that it’s not actually the best method. It turns out that the reverse sear is the better way to do it! Similarly, there are phrases and ideas in the personal finance space that get preached as though they’re the gospel truth. And there are a number of reasons why certain bits of advice stick with us- maybe it intuitively makes sense or perhaps it’s packaged well and is just flat-out catchy. We’re all looking for guidance and shortcuts but that doesn’t necessarily mean that these sayings are sage advice. So today we call out some of the biggest culprits on the show and share how you should be thinking about your money.
Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed an Uplifted Scottish Ale by Talisman Brewing- thanks Andy for donating this one to the pod! 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. | |||
| Preparing for the Unthinkable w/ Chanel Reynolds #1172 (Bestie Ep) | 29 Jul 2026 | 00:57:14 | |
Dying without the proper documents in place can cost your loved ones a ton of money! The latest research shows that probate can easily take a 3% to 7% bite out of your estate. And this is a topic that’s been on our minds for months since episode 704, when we had our wives on the podcast. We realized that the ladies might have a general idea of what to do if one of us died, but for the most part they would be rudderless since both of us handle the bulk of our finances in both of our families. That’s why we’re pumped to talk with Chanel Reynolds who has been on a mission for the past decade, to help folks do what she wished she’d done, before life takes a detour. Chanel founded GetYourShitTogther.org and she authored the book “What Matters Most”, both dedicated to help folks to prepare to face the inevitable reality of death. We discuss digital hygiene and staying organized with your accounts and passwords, key estate planning documents, using online software vs hiring an attorney, beneficiaries and transfer on death deeds, how to effectively approach conversations with family, funeral preparations, and much more!
Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Megalodon American Imperial Red which was homebrewed by listener Greg- thanks for sharing! 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!
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| Ask HTM - Vital Insurance That’s Not On Your Radar, Budgeting w/ A Variable Income, & Taxes Owed When You Sell Your House #1171 (Bestie Ep) | 27 Jul 2026 | 00:51:46 | |
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 - How do I go about creating a budget with a highly variable income? 2 - As new parents we want to start saving money into a 529 plan but how much should we aim to invest? 3 - Avoiding capital gains when selling a primary residence? 4 - Should most folks have long term disability insurance? 5 - Taking advantage of “3 paycheck months”!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Malpais Stout by La Cumbre Brewing- a big thanks to Bob for donating this one to the pod! 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!
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| AMA: Better Know the Podcast Hosts! #1170 (Bestie Ep) | 24 Jul 2026 | 01:06:01 | |
Check out our first ever AMA: an ‘ask me anything’ where we focused on personal questions as opposed to personal finance related content! Typically we’re either interviewing someone in the personal finance space, answering listeners’ money questions, doing a deep dive on a particular topic, or covering the latest personal finance news- but we thought it’d be fun for y’all to get to know us more on a personal level. These are the kinds of topics you might hear us talking about if we were grabbing a bear at a local brewery! So have a listen as we answer questions having to do with how we met, how our faith impacts our finances, other careers we’ve considered, long-term fitness goals, the biggest decisions we’ve ever made, favorite bands or genres, finding work-life balance, where we want to travel, and more!
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During this episode we enjoyed a Double Top by Akademia Brewing! 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!
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| Mental Health is Financial Health w/ Aja Evans #1169 (Bestie Ep) | 22 Jul 2026 | 00:52:44 | |
The fundamentals of personal finance aren’t all that complicated- there’s a reason why we came up with the Money Gears: 7 straight forward steps to take with your money. We could probably boil it down even more: spend less than you make, and invest the rest! So while the core principles of growing wealth are fairly simple, then why aren’t more Americans handling their money better? One reason is because we, as individuals, are incredibly complex! And that complexity can lead to a disconnect between what we know we should be doing with our money, and what we actually end up doing. Sometimes we need someone to guide us, which is why we’re excited to talk with Aja Evans. Aja is a Licensed Mental Health Counselor with over 10 years of experience and she works to help people move toward financial wellness by understanding their relationship with money, their money mindset, and how their feelings impact what they do with their money. And today we discuss confronting our money beliefs, social media’s impact on our finances, financial trauma, setting boundaries, and more!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Quality Time by Inner Voice Brewing! 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 - Are FSAs Worth The Hassle, Making Too Much for a Roth, & Mentally Shifting from Saver to Spender #1168 (Bestie Ep) | 20 Jul 2026 | 00:53:40 | |
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 - What are the tax consequences of selling a single stock within my Roth IRA? 2 - How do I shift my mindset from saver to spender as I enter my retirement years? 3 - I’m getting close to making too much money to qualify for a Roth- how can I avoid that income threshold? 4 - Will closing a bank account that I’ve had since my teenage years hurt my credit score? 5 - Are Flexible Spending Accounts (FSA) worth the hassle?
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Blood Orange Double Wit by Ponderosa Brewing- a big thanks to Bob for donating this one to the pod! 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. | |||
| The Science of Smarter Spending #1167 (Bestie Ep) | 17 Jul 2026 | 00:51:19 | |
We love nerdy board games! And one of the things that makes them fun, besides getting to play them with friends and family, is the competition for scarce resources. For instance with the Settlers of Catan, it takes a few rounds of play to get the resources you need to build the settlements, cities, and development cards that help you rack up victory points in Catan. It’s a classic that still holds up, and like most games it's all about tradeoffs. Should you focus on building a road or upgrading to a city? You can’t do it all and you can’t get everything you want all at once. And it turns out that our financial lives are kind of like a game of Catan as we’re always making tradeoffs as well- in particular when it comes to our expenses. We’re torn between the decision of spending big money on an item that we know is going to last, versus an inferior item that will get the job done- at least for a little while, before inevitably breaking. Today we talk about the pros and cons of planned obsolescence, the culture of disposability, the buy it for life movement, as well as changing the way we think to ensure that we’re allocating our dollars to maximize satisfaction!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Song of Winter by Hill Farmstead- a big thanks to Michael and Emily 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!
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| Turning Thousands Into Millions w/ Paul Merriman #1166 (Bestie Ep) | 15 Jul 2026 | 00:58:05 | |
Sure you could simply invest in a target date fund, or even take the more aggressive path by going all-in on equities and investing solely in the S&P 500. But what if that means you’re potentially leaving millions on the table by the time you reach retirement? That’s the question at the center of our conversation today with our guest Paul Merriman. He is the author of eight books, has a regular column at MarketWatch, is a legend in the DIY investing arena, and is an advocate of the Two Funds for Life investing strategy. That strategy outperforms the S&P and we discuss how you’re able to do that with small-cap value stocks! After Paul retired from his wealth management firm he founded the Merriman Financial Education Foundation a little over a decade ago. Of course it’s a non-profit, and is “dedicated to providing comprehensive financial education to investors at all stages of life” which is a mission that really resonates with us- he wants individuals to be informed and to understand how much they might be missing out on. We look at the historical data and it’s convincing enough that we might be changing how it is that we invest for our future!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Discipline Dubbel by Bold Monk! 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 - Societal Impact of Credit Card Fees, Auto Transfer vs Auto Invest, & Shielding Your Credit Report from a Bill in Collections #1165 (Bestie Ep) | 13 Jul 2026 | 00:51:06 | |
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 - I have a recurring transfer to my Roth IRA but is that money actually invested? 2 - How do I keep a bill in collections from hitting my credit report? 3 - Should my life insurance death benefit be based on my outstanding debts or on a multiple of my annual income? 4 - If the societal impact of credit card fees are so negative, shouldn’t we avoid using them altogether?
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed a Walk on Water White by Bold Monk! 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. | |||
| Buffettisms: Lessons from the GOAT Investor #1164 (Bestie Ep) | 10 Jul 2026 | 00:46:10 | |
Who is the greatest actor of all time? You might have an opinion- maybe it’s Meryl Streep or Daniel Day-Lewis, but this would likely lead to a pretty fierce debate. And the same could be said about athletes- who is the greatest? Is it Michael Jordan or Michael Phelps? Well it depends on who you’re asking because it’s in the eye of the beholder to a certain extent. We all want to know what sets the greatest in their given field apart from the ones who were just really good. Luckily the greatest investor conversation isn’t nearly as fraught. Warren Buffett is the GOAT in our eyes and we’re certainly not alone in that assumption. And it’s not only due to the returns he’s garnered- his longevity, consistency, and humility are admirable as well. So today we’re going to talk about the GOAT investor and what financial, and life lessons we can learn from him. How you should approach your investments, how long you should be holding them, and what you should be investing in are just a few questions we’ll answer today.
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During this episode we enjoyed a Blender Black-Ras by New Park Brewing- thanks for donating this one to the pod Matthieu! 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!
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| The Myth of the Broke Millennial w/ Dr. Jean Twenge #1163 (Bestie Ep) | 08 Jul 2026 | 00:52:56 | |
There’s a massive difference between how something feels versus the actual reality. We’re talking about vibes as opposed to empirical evidence. And that’s why we’re happy to talk with Dr. Jean Twenge who is a professor of psychology over at San Diego State University. She has researched the personal finances of the different aged cohorts and few experts have addressed the topic of generational change as well as she has. Dr. Twenge has written multiple books on the defining characteristics of specific generations- she did that in her book iGen where she focused on Gen Z, and her latest book, Generations, covers the oldest Silent Generation to the youngest Polars. And an article that she wrote in the Atlantic really caught our eye, because not only did she write about our generation, but she spoke directly to the wealth accumulation of Millennials which of course we found particularly fascinating. Today we discuss generational stereotypes, the impact of individualism and technology on wealth, some of the bigger financial obstacles we face today that our parents didn’t have, the ‘slow life strategy’ and what that means for Gen Z, plus much more!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
During this episode we enjoyed an Icelandic Arctic Pale Ale by Einstok Olgerd! 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!
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