Ask HTM - Work Provided Life Insurance, Compounding Returns with a 401k True-Up, & Selling a Home to an iBuyer (Bestie Ep) #1081

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…

Holiday Special: 2025 Lessons, Risky Bets, and an Alaska Surprise (BONUS EP)

A big thanks to our friend Joe Saul-Sehy for inviting us to join an episode of Stacking Benjamins – we had a blast, and we think you'll enjoy this convo as well!   –   It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packe…

Who Wants to *Literally* Be a Millionaire? (Bestie Ep) #1080

Sherlock Holmes is a literary character we’re all familiar with who has the uncanny ability to solve any mystery he comes across. And one of the things that sets the British detective apart from others is his use of inductive reasoning to solve his cases. He begins with observations which then prop…

Families Fly Free w/ Lyn Mettler (Bestie Ep) #1079

Traveling for free sounds like a lofty goal for most folks. Sure if you’re single or if you’re a DINK couple- but there’s no way you can pull that off with an entire family in tow! Well, it’s actually easier than you think and our guest, Lyn Mettler, is here to explain how. Lyn is a long-time trave…

Ask HTM - Caring for Parents, Dreaming of Partial Retirement, and Paying Extra on the Mortgage #1078

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…

Friday Flight - Deceptive Dollar Stores, Frustrated Flippers, & Betting Your Credit Card Balance #1077

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 …

Becoming a Rational Investor w/ Ben Felix #1076

Tall fellas UNITE! Joel has to contend with talking with someone who is taller than him for a change, but that’s mostly besides the point (unless tall guys actually invest differently than the rest of the population!?). We’re joined by Ben Felix – one of the clearest voices in finance and investing…

Ask HTM – Double Dipping Expense Ratios, Wealth Building with High Deductibles, and when 50 Year Mortgages Make Sense #1075

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…

Friday Flight - Political $ Planning, Free Electricity, & Cash is Cringe (plus Instacart Iniquity, Advent Calendars, more...) #1074

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 …

Jade Warshaw on Escaping the Debt Trap and Rewriting Your Story #1073

In Greek mythology, Atlas holds the heavens on his shoulders as a punishment from Zeus. And every time you see an image of Atlas, remember the hundreds of millions of Americans who are perpetually burdened by debt. To many of those consumers, the weight of credit cards, personal loans, and car loan…