How to Money

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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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10 snips
Nov 17, 2025 • 49min

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

This week, the hosts tackle listener questions about the pros and cons of home renovation versus moving. They discuss strategic decisions like budget and hiring professionals for a home addition. The conversation shifts to the impact of canceling an old credit card and ways to mitigate credit score damage. There's also insightful advice on whether to pay off student loans now for peace of mind or hold out for potential forgiveness. Finally, they explore the advantages of investing in Health Savings Accounts for future medical costs.
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9 snips
Nov 14, 2025 • 36min

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

Discover the latest financial news impacting your wallet! Learn about the proposal for 50-year mortgages and the risks they entail. Robinhood's entry into the mortgage market raises questions about quick applications and comparison shopping. As the holiday season approaches, find budgeting tips to avoid overspending on gifts. Explore local assistance resources for those in need. Plus, understand the consequences of investment fee transparency changes and why using family code words can protect against scams.
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24 snips
Nov 12, 2025 • 53min

How AI Will Impact Your Investments w/ Vanguard's Joe Davis #1061

Joseph Davis, Vanguard's Global Chief Economist and author of *Coming Into View*, shares insights on the profound impact of AI on investing. He discusses how AI's productivity enhancements will stretch beyond the tech sector and reshapes financial forecasts, emphasizing the need for diversification and low-cost investments. Davis challenges common assumptions about demographics and underscores the importance of stress-testing financial goals against potential market fluctuations. He also highlights the evolving tech cycle and its implications for portfolio management.
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11 snips
Nov 10, 2025 • 51min

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

Listeners dive into personal finance dilemmas, starting with tips on switching health insurance providers for affordability. The conversation shifts to Buy Now, Pay Later scenarios, exploring if discounts make this option worthwhile. The hosts discuss the balance between investing and paying off high-interest debt, stressing the importance of maintaining emergency savings. They also tackle concerns about early mortgage payoff impacting credit scores and clarify how 401(k) contributions should factor into one's savings rate.
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10 snips
Nov 7, 2025 • 36min

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

This week dives into pressing financial issues, like the staggering $50k average for new cars and the rising trend of long car loans. Find out why the misleading $10,000 new car tax break may not benefit most. Explore the implications of AI on job stability and career shifts after the pandemic. Additionally, discover how extreme frugality and side hustles can manage financial uncertainty. Don't miss discussions on the creepy rise of household robots and the ad saturation we face in daily life.
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15 snips
Nov 5, 2025 • 56min

Work Less, Live More w/ Juliet Schor #1058

Juliet Schor, an economist and sociology professor at Boston College, explores the power of four-day workweeks in transforming our lives and work culture. She discusses how societal pressures prioritize work over personal time, yet many prefer time off when given the choice. Juliet shares insights on the psychological benefits of an extra day, the growing adoption of shorter workweeks by companies, and how this shift can enhance productivity and well-being. She also emphasizes the need for efficiency gains and cultural change in the workplace.
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9 snips
Nov 3, 2025 • 46min

Ask HTM - Spending on a Tax Pro, Frugal Practices for Millionaires, & Ending a Termite Bond #1057

Listener questions take center stage as the hosts dive into selecting the right tax professional and the costs involved. They tackle the frugal versus cheap debate over reusing Ziploc bags, and discuss updating a 30-year-old trust. Market dynamics affecting high-yield savings account rates are explained, along with tips on whether to renew a termite warranty or take DIY action. Plus, there's a fun beer review that adds a refreshing twist to the conversation!
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11 snips
Oct 31, 2025 • 35min

Friday Flight - Discount Burnout, Bubble Trouble, & Rejoicing Renters (plus roadkill, gold bars, more...) #1056

This week’s financial insights are both quirky and essential! Discover the legality and attitudes around eating roadkill while you ponder affordable Thanksgiving meals at Aldi. The hosts tackle discount burnout with smart shopping tips and question if high-flying AI stocks are a bubble. Gold’s recent surge gets dissected, alongside risks of leveraged ETFs. Plus, learn about the fallout of winning bidding wars and the changing rental market, all while Gen Z grapples with credit challenges. Tune in for a mix of humor and practical advice!
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13 snips
Oct 29, 2025 • 1h 2min

DIY or Delegate: the Financial Advisor Conundrum w/ Pam Krueger #1055

Pam Krueger, an award-winning investor advocate and the CEO of WealthRamp, discusses the crucial decision of whether to DIY your finances or hire a professional. She emphasizes that individuals drive their financial outcomes, debunking the myth that simply hiring an advisor guarantees success. Pam highlights the importance of transparency in advisor fees and the value of vetting fiduciary advisors. She also shares tips on finding quality advice, navigating industry pitfalls, and knowing when it's time to part ways with an unsatisfactory advisor.

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