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Friday Flight - AI Money Impacts, Side Hustle Salad Days, & Sullen Savers #1113
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Are Teachers Doomed to a Broke Retirement? w/ Shaun Morgan #1112
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Ask HTM - Debating a Raise vs WFH Flexibility, Investing in Nvidia, & Digital Hygiene Frugal or Cheap #1111
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Friday Flight - Jump at the Pump, Lessening Leverage, & Tapping Too Soon #1110
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Bouncing Back from Bankruptcy & Business Failure w/ Phil Sanders #1109
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Ask HTM - Housing Rule of Thumb, Axing a Boat Payments, & Making Bank on the World Cup #1108
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Friday Flight - Tariff Turmoil, Winning So Much, & Border-Hopping for Bargains #1107
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Die with Zero w/ Bill Perkins #1106
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Ask HTM - High Net Worth but still Paycheck to Paycheck, Better Investing for Freelancers, & the Necessity of Amazon Prime #1105
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Friday Flight - 401k Mullets, Crappy Coffee, & Bitcoin Bashing #1104
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Why Being “Good With Money” Still Feels So Hard w/ Shannah Game #1103
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Ask HTM - Student Loans in Administrative Forbearance, Intentionally Entering into Collections, and Financial Infidelity #1102
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Friday Flight - Stealthy Skimpflation, Janky Job Markets, & Day-Trading Doris #1101
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Talk About Money Without Fighting w/ Dr. Sonya Lutter #1100
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Ask HTM – ADU vs iBonds, Timing a Silver Sale, and HELOC Unlocking Landlord Status #1099
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Friday Flight - ‘The Lipstick Effect’, Cheap Chinese EVs, & DIY Solar #1098
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The Case for Frugal Hedonism w/ Annie Raser-Rowland #1097
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Ask HTM – Money Gears Mixup, Stewarding an Inheritance, & Turning to Gold! #1096
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Friday Flight - Richer Refunds, Best Costco Buys, & $3 Dinners (don’t have to be this sad!) #1095
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Student Loan Chaos Explained w/ Stanley Tate #1094
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Ask HTM – Assets to Boost My Credit Score, Lifestyle Geographic Arbitrage, and Car Loans to get Wealthier #1093
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Friday Flight - Points for Paying your Mortgage, Credit Card Consultants, & AI UBI (to each according to his need!) #1092
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The Art of Spending w/ Morgan Housel #1091
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Ask HTM - Combatting Healthcare Premium Hikes, Purchasing Long Term Disability, and WTD with Nine-Figure Wealth #1090
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Friday Flight - Credit Card Caps, Free Rent, & Pokemon Investing #1089
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Own Your Time: Build a Life You Control w/ Andy Hill #1088
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Ask HTM - Gym Edition Frugal or Cheap, Blaming the Baby for Lifestyle Upgrades, and Dipping into Savings for a Camper #1087
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Friday Flight - Return Rabbits, Double Majoring, and Nihilistic Renters #1086
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Spending Life Wisely: Vicki Robin on Money, Meaning, and Time #1085
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Your Smart Money Guide for 2026 #1084
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The High Cost of Crappy Credit (Bestie Ep) #1083
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Time > Money w/ Ben Miller (Bestie Ep) #1082
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Ask HTM - Work Provided Life Insurance, Compounding Returns with a 401k True-Up, & Selling a Home to an iBuyer (Bestie Ep) #1081
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Holiday Special: 2025 Lessons, Risky Bets, and an Alaska Surprise (BONUS EP)
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Who Wants to *Literally* Be a Millionaire? (Bestie Ep) #1080
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Families Fly Free w/ Lyn Mettler (Bestie Ep) #1079
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Ask HTM - Caring for Parents, Dreaming of Partial Retirement, and Paying Extra on the Mortgage #1078
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Friday Flight - Deceptive Dollar Stores, Frustrated Flippers, & Betting Your Credit Card Balance #1077
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Becoming a Rational Investor w/ Ben Felix #1076
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Ask HTM – Double Dipping Expense Ratios, Wealth Building with High Deductibles, and when 50 Year Mortgages Make Sense #1075
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Friday Flight - Political $ Planning, Free Electricity, & Cash is Cringe (plus Instacart Iniquity, Advent Calendars, more...) #1074
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Jade Warshaw on Escaping the Debt Trap and Rewriting Your Story #1073
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Ask HTM – Newlywed Downpayment Debate, Good Car Loans, and Failing to Max Retirement Account #1072
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Friday Flight - AI Toys, Homeowners Held Hostage, & Impoverished Americans
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Gen Z vs. The Old Money Rules w/ Lillian Zhang #1070
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Ask HTM – Mortgage Payoff Loophole, DAFs to Maximize Tax Deductions, and Legally Evading a Medical Bill #1069
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Friday Flight: Leftover Turkey Edition! #1068
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The World Is Getting Better w/ Marian Tupy #1067
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Ask HTM - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066
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Friday Flight - Soft Switching, Tariff Turnaround, & Ozempic Face #1065
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Don’t Let Taxes Terrify You w/ Hannah Cole #1064
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Ask HTM - Vital Home Reno or Moving Factors, Dropping Credit Without Dinging Your Score, & Student Loan Forgiveness or Payoff #1063
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Friday Flight - Forever Mortgages, Ruining Reward Cards & Free Tax Filing Fail #1062
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How AI Will Impact Your Investments w/ Vanguard's Joe Davis #1061
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Ask HTM - Open Enrollment Entanglements, Worthwhile BNPL Scenarios, & Continuing to Investing with Outstanding Debt #1060
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Friday Flight - Ridiculous Car Refinancing, Occupation Consternation, & Ads Everywhere #1059
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Work Less, Live More w/ Juliet Schor #1058
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Ask HTM - Spending on a Tax Pro, Frugal Practices for Millionaires, & Ending a Termite Bond #1057
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Friday Flight - Discount Burnout, Bubble Trouble, & Rejoicing Renters (plus roadkill, gold bars, more...) #1056
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DIY or Delegate: the Financial Advisor Conundrum w/ Pam Krueger #1055
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Ask HTM – Sinking Funds for BIG Purchases, PTO Advances, & Investing for Early Retirement #1054
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Friday Flight - Moneyless Millionaires, Credit Card Churning & AI Goes E-Commerce #1053
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Can Love Survive a Budget!? w/ Doug & Heather Boneparth #1052
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Ask HTM - Medium-Term Investing Conundrums, Naughty Credit Card Behavior, & Vapid Vesting Periods #1051
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Friday Flight - Accidental Landlords, Debilitating Debt & The WFH Premium #1050
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Money Truths You Won’t Hear Anywhere Else w/ Len Penzo #1049
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Ask HTM – Quick Cash with eBay, Making Quarterly Estimates, & a Home Appraisal Goes Awry #1048
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Friday Flight - Refi Revival, Delay Pay Disaster, & Landline Love! #1047
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The Demographic Dilemma and Your Dollars w/ Melissa Kearney #1046
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Ask HTM - Avoiding the Credit Card Burn, Timing a HELOC, & Solar to Retire Sooner #1045
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Friday Flight - Underwater Autos, Freelancing FTW, & E-Fund Idiocy #1044
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Pulling the Most Powerful Money Levers w/ Professor Kristen Carioti #1043
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Ask HTM - Break-Even Bank Switch, Doubling Down on a 457b, & Financing an ADU for Extra Cash #1042
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Friday Flight - 'Just In Case' Planning, Consumer Caste System, & Credit Scores Crashing #1041
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Eat the Avocado Toast w/ Justin & Haley Brown-Woods #1040
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Ask HTM - Best Grocery Cashback Credit Cards, Risking it with Ultra Cheap Car Rentals, & Giving Up on Home Ownership #1039
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Friday Flight - Pricey Porch Pumpkins, Twitter for Trading, & Saving for a Spouse #1038
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Cutting Taxes & Retiring Sooner w/ Cody Garrett #1037
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Ask HTM - Gifting $ to Other’s Kids, Most Affordable Protein, & Snagging the 529 State Deduction #1036
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Friday Flight - Flipping For Cash, Health Insurance Hikes, & Grim Googling #1035
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Financial Freedom on Less than $40k w/ Hope Ware #1034
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Ask HTM - Condo Cold Feet, Investing in ABLE Accounts, and the Best Interest Rate Ever #1033
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Friday Flight - Forgotten 401k, Peaking Pessimism, & Loyalty is for Losers #1032
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Built to Borrow: The Hidden Forces Behind Debt w/ John Dinsmore #1031
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Ask HTM - Is a 25% Savings Rate Overkill, Avoiding State Minimum Insurance Requirements, & Eliminating 401k Loans #1030
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Friday Flight - Pre-K For Pay, Helicopter Savers, & Politics Shmoliticks #1029
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Move to Puerto Rico to Axe Taxes w/ Rachel Farris #1028
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Ask HTM - Acorns to Jumpstart Investing, Seasoning a Cash Gift, & Social Security Running Out #1027
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Friday Flight - Digital Nomad Fatigue, Treat Culture, & Retired Renters #1026
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Defend Your Digital Life w/ Nathan Bartram #1025
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Ask HTM - Spending Cash Windfalls, Retirement Investing vs College Savings, & So You Think You Can Landlord?! #1024
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Friday Flight - Housing Boom Busts, AI-Induced Outrage, & Infinite Workdays #1023
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Moving Up The Wealth Ladder w/ Nick Maggiulli #1022
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Ask HTM - Jumping Back Into the Workforce, HELOC Cash Grab, and Free Life Insurance Gotchas #1021
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Friday Flight - Bad RAPs, Price Match Murder, & Premium Points Credit Cards #1020
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WE BACK - Frugal Fun, Travel Tips, & Sabbatical Takeaways #1019
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Jesus Christ Super-Saver: Ancient Wisdom & Your Money (Bestie Ep) #1018
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How Complicated Should Investing Be? (Bestie Ep) #1017
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Small But Mighty Real Estate Investing w/ Chad Carson (Bestie Ep) #1016
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Is Early Retirement A Smart Goal? (Bestie Ep) #1015
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