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14 snips
Aug 29, 2025 • 36min

Friday Flight - Pre-K For Pay, Helicopter Savers, & Politics Shmoliticks #1029

Explore the debate over pre-K for pay and its impact on parental finances. Learn how job skill certificates may not guarantee job opportunities. Discover the pitfalls of helicopter saving and buying now, paying later. The hosts discuss how politics could affect your wallet and encourage teaching financial literacy to empower future generations. Get insights into evolving job application processes and the necessity for personalized financial advice. Wrap up with a cheerful reflection on the week's financial news!
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Aug 27, 2025 • 52min

Move to Puerto Rico to Axe Taxes w/ Rachel Farris #1028

Join Rachel Farris, a CPA and tax strategist, as she reveals the perks of moving to Puerto Rico under Act 60, including a 0% capital gains tax. She shares insights on the lifestyle changes expats face, from the cultural adjustments to the vibrant expat community. Rachel also discusses the financial implications for W2 workers and entrepreneurs, offering a balanced view of tax incentives and local engagement. Discover how this Caribbean paradise combines significant savings with a unique living experience!
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11 snips
Aug 25, 2025 • 53min

Ask HTM - Acorns to Jumpstart Investing, Seasoning a Cash Gift, & Social Security Running Out #1027

Listener questions kick off a lively discussion on investing, specifically whether to use the Acorns app and the nuances of real estate investments. The looming issue of the Social Security Trust Fund depleting by 2033 is tackled, sparking insights on proactive savings. Also covered are the timing for cash gifts to improve credit scores and considerations around choosing financial advisors. With a sprinkle of humor, the hosts delve into smart shopping habits and the complexities of car and home purchases.
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9 snips
Aug 22, 2025 • 38min

Friday Flight - Digital Nomad Fatigue, Treat Culture, & Retired Renters #1026

Discover the phenomenon of digital nomad fatigue and how treat culture plays into work-life balance. Delve into practical shopping tips for school supplies amidst rising costs and the importance of mindful purchasing. Explore the challenges of crowdfunded real estate and the appeal of traditional investment strategies. Uncover why more retirees are choosing to rent over buy, and navigate the complexities of lease purchase agreements. Packed with actionable tips, this discussion is a treasure trove for anyone looking to enhance their personal finance savvy!
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20 snips
Aug 20, 2025 • 57min

Defend Your Digital Life w/ Nathan Bartram #1025

Nathan Bartram, founder of TheNewOil.org, dives into the intricate world of digital privacy and security. He shares essential practices for safeguarding your online life, like leveraging password managers and enhancing privacy with advanced routers. Nathan discusses the pitfalls of e-commerce platforms and why he has a particular disdain for Amazon. The conversation also touches on the reality of VPNs, the importance of digital minimalism, and proactive strategies to protect your personal data amidst today's tech-driven landscape.
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8 snips
Aug 18, 2025 • 58min

Ask HTM - Spending Cash Windfalls, Retirement Investing vs College Savings, & So You Think You Can Landlord?! #1024

Listeners dive into various money topics, like whether to become a landlord with an extra property or invest for college amidst market ups and downs. A discussion unfolds on how to wisely use a six-figure inheritance, while practical travel tips emerge for a high school trip in Europe. The conversation also covers navigating kids' mobile tech use affordably and safely, plus insights on early financial education for children. This episode mixes humor with serious advice, creating an engaging financial journey.
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14 snips
Aug 15, 2025 • 37min

Friday Flight - Housing Boom Busts, AI-Induced Outrage, & Infinite Workdays #1023

Delve into the latest financial news with insights on the housing market's ups and downs. Discover the surprising rise of medical debt and contagious financial habits shaping decisions. The buzz around AI and its impact on customer service raises eyebrows, while hybrid workdays face an uncertain future as infinite workdays become the norm. Don't miss the intriguing discussion of crypto's place in 401ks and mortgage applications. Get ready to navigate the ever-changing world of personal finance!
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9 snips
Aug 13, 2025 • 50min

Moving Up The Wealth Ladder w/ Nick Maggiulli #1022

Nick Maggiulli, the author behind "Just Keep Buying" and writer of the insightful blog Of Dollars & Data, returns to tackle the intricacies of climbing the wealth ladder. He discusses how couples can invest together while navigating prenups and financial transparency. Discover the balance between net worth and liquidity, plus the impact of societal expectations on personal finance. Nick also shares how meaningful experiences can redefine financial freedom, encouraging listeners to focus on genuine happiness over mere frugality.
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25 snips
Aug 11, 2025 • 51min

Ask HTM - Jumping Back Into the Workforce, HELOC Cash Grab, and Free Life Insurance Gotchas #1021

Listeners dive into intriguing money questions, like weighing the pros and cons of re-entering the workforce and navigating the complexities of HELOCs. The discussion also tackles the nuances of early Social Security claims and the legitimacy of free life insurance through credit unions. Practical tips for managing student loans and the quirks of credit unions add flavor to the mix. Light-hearted moments about childhood movies and local beers balance the financial wisdom, making it an engaging and entertaining listen!
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15 snips
Aug 8, 2025 • 38min

Friday Flight - Bad RAPs, Price Match Murder, & Premium Points Credit Cards #1020

This week’s financial roundup dives into fascinating topics like the surprising longevity of purchasing power and the effects of new tax laws like the One Big Beautiful Bill Act. The discussion touches on the impact of soaring prices at the movies, from $80 popcorn buckets to Target's price match changes. Listeners are cautioned against following questionable student loan advice on TikTok and are urged to reassess their strategies for premium credit cards. It’s a mix of nostalgia, humor, and essential financial wisdom to kick off your weekend!

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