How to Money

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Dec 10, 2025 • 50min

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 loans feels like an eternal struggle… the new normal with no end in sight. But like our guest today, you can reject that fate and rewrite your story. Jade Warshaw paid off almost half a million dollars in consumer debt over the better half of a decade. Now she uses her hard-earned knowledge to teach others how to do the same. She’s a Ramsey personality and is the author of the new book ‘What No One Tells You About Money’ which explores the emotional side of personal finances. We dive into that and also cover: Facing deep emotional struggles when dealing with debt Financial discussions should include emotional health Debt can strain personal relationships significantly Understanding money involves more than just numbers Feeling isolated in financial struggles Role of debt in growing a family Good debt vs bad debt Jade’s final piece of advice And much more!   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: Jade’s new book, out January 6th: What No One Tells You About Money Instagram, TikTok, Facebook, and X. 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.
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Dec 8, 2025 • 50min

Ask HTM – Newlywed Downpayment Debate, Good Car Loans, and Failing to Max Retirement Account #1072

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 - Downpayment debate: should we put down more than 20% if we have extra money in our investment accounts? 2 - Car loan: is it worth signing up for a car loan with the dealership if it means I snag a four-figure discount? 3 - Special needs: how do I support my son with Down Syndrome while also preparing for retirement some day? 4 - Annuities: are annuities the ticket as a safe alternative investment? 5 - Maxing accounts: how discouraged should I be that I’m no longer able to max my HSA and Roth IRA?   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: Our episode with the Shefska’s on how to pay as little as possible for your new car! 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 Measured Procession of Veracity by Burial! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.
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9 snips
Dec 5, 2025 • 38min

Friday Flight - AI Toys, Homeowners Held Hostage, & Impoverished Americans

Dive into this week's financial insights! Discover how Gen Z is pulling back on spending, particularly on trendy AI toys, while holiday shopping shows signs of slowdown. Learn about the growing problem of unused gift cards and the unfortunate reality for homeowners feeling trapped by low mortgage rates. Explore the debate on poverty in America and the potential benefits of geographic arbitrage for retirees. Plus, stay informed about upcoming Real ID requirements that could affect your travel plans!
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Dec 3, 2025 • 54min

Gen Z vs. The Old Money Rules w/ Lillian Zhang #1070

In this chat with Lillian Zhang, a first-generation immigrant and author of The New Money Rules, we dive into the financial psyche of Gen Z. Lillian shares how COVID and job market shifts shape their money views. She critiques traditional strategies in favor of riskier investments that resonate more with younger folks. Lillian also touches on the importance of financial literacy and the evolving definition of financial freedom—moving from scarcity to valuing experiences. Plus, she champions the idea of 'loud budgeting' for social accountability!
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11 snips
Dec 1, 2025 • 52min

Ask HTM – Mortgage Payoff Loophole, DAFs to Maximize Tax Deductions, and Legally Evading a Medical Bill #1069

This episode dives into listener questions on various financial hacks. Discover the pros and cons of velocity banking for mortgage payoffs. Unpack the benefits of Donor-Advised Funds and how to maximize tax deductions. Learn whether to prioritize Roth IRA contributions or an employer-sponsored 457b for retirement. Evaluate strategies for negotiating medical bills and when to accept discounts. Finally, get insights on life insurance needs for single parents with investments. A treasure trove of financial advice awaits!
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15 snips
Nov 28, 2025 • 51min

Friday Flight: Leftover Turkey Edition! #1068

This discussion emphasizes gratitude during the busy holiday season, focusing on how financial decisions enhance life quality. Listeners share inspiring stories of achieving emergency savings, making prudent moves, and embracing debt freedom. They celebrate simplifying life through smart budgeting, strategic living, and prioritizing family time. From saving for tuition to transitioning into retirement gradually, the conversation reflects on the impact of intentional money choices beyond just numbers.
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14 snips
Nov 26, 2025 • 53min

The World Is Getting Better w/ Marian Tupy #1067

Marian Tupy, a senior fellow at the Cato Institute and founder of HumanProgress.org, dives into the surprising ways humanity has advanced despite perceived setbacks. He discusses how openness to ideas has driven innovation since the 18th century, challenges the negative media bias shaping our views, and emphasizes the fragility of progress. Tupy highlights the importance of gratitude, the rise in life expectancy, and the connection between economic freedom and prosperity, all while presenting a hopeful perspective on the future.
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15 snips
Nov 24, 2025 • 53min

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

Tune in for engaging listener questions that cover a range of financial topics! Discover whether to file an insurance claim for a new roof or how to approach a Roth conversion for your 401(k). Get insights on rebalancing your tech-heavy portfolio amid potential bubbles and explore whether switching savings accounts is worth it. Finally, learn the differences between Health Reimbursement Arrangements and HSAs during open enrollment. Plus, there's a beer review to wrap things up!
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14 snips
Nov 21, 2025 • 40min

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

This week, the hosts dive into soft switching at banks, making account transitions smoother without full moves. They critique a controversial buy-now-pay-later credit card and explore the complexities of rising credit card fees. Tariffs are driving grocery prices up, while meat trends show a shift from beef to chicken. They call out ludicrous prices on items like an iPhone pocket sock and a $300 water bottle. Plus, they discuss the lower price of GLP-1 drugs and the implications of poor credit on car insurance rates.
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14 snips
Nov 19, 2025 • 57min

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

Hannah Cole, a tax educator and founder of Sunlight Tax, aims to demystify taxes for the self-employed. She shares her mission to empower creatives to embrace deductions, bookkeeping, and filing without fear. Hannah discusses the forgiveness of the IRS, the importance of organizing receipts, and understanding when a hobby becomes a business. She also highlights the advantages of starting a business in the U.S. and why DIY taxes can be a smart choice for many. Tune in for practical tips and a refreshing take on tax worries!

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