Episodes

  • 164. The Math of "Worth It" - Is Comparison Shopping Worth the Time and Money?
    May 24 2026

    We break down the mechanics of comparison shopping to determine if it’s a high-value move or if you’re instead trading your limited life energy for pennies. We explore how to consider convenience and value without falling into the trap of decision fatigue. We share the tactical math behind the “worth it” threshold, along with specific tips and tricks to leverage comparison shopping efficiently and fruitfully.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/164-the-math-of-worth-it-is-comparison-shopping-worth-the-time-and-money/

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    38 mins
  • 163. Billionaires Aren’t Better Than Us - The Wealth Ceiling
    May 17 2026

    This episode promises to remind you what really matters in life. Billionaires might fly private, but they’re drinking the same Coke and scrolling the same iPhone as the rest of us. We explore the "wealth equalizers" that hit a quality ceiling regardless of your net worth, from the crunch of a Honeycrisp apple to the stream of a bidet. And while billions certainly come with some luxuries and advantages, they also carry heavy baggage and isolation.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/163-billionaires-arent-better-than-us-the-wealth-ceiling/

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    1 hr and 2 mins
  • 162. Time Traveling to Improve Our Lives With Ginger From ChooseFI
    May 11 2026

    Time travel may just be the ultimate behavioral finance hack. We explore the neuroscience of how our brains perceive our future selves and how we can leverage this understanding to our advantage. By utilizing psychology, we share actionable strategies to bridge the empathy gap, helping us make financial and lifestyle choices today that our future selves will genuinely appreciate.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/162-time-traveling-to-improve-our-lives-with-ginger-from-choosefi/

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    1 hr and 20 mins
  • 161. Our 91% vs. 9% of Life: 4 Lessons from 4 Years of Early Retirement
    May 3 2026

    161. Our 91% vs. 9% of Life: 4 Lessons from 4 Years of Early Retirement

    These are the four big lessons we’ve learned from four years of early retirement, and they are perhaps even more applicable to people still working. After spending 91% of our lives following the schedules of teachers, bosses, and corporate deadlines, we’ve finally completed four years of total autonomy—the exact duration of a high school or college experience. We break down the profound shifts that occur when you transition from 41 years of conditioning into a life of complete agency, revealing why it takes time to deprogram your brain.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/161-our-91-vs-9-of-life-4-lessons-from-4-years-of-early-retirement/


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    59 mins
  • 160. Time Wealth and Second Chapters – The Ripple Effects of Leaving Corporate America
    Apr 26 2026

    It’s hard to believe that a year has passed since Andrew walked away from his high-stress corporate job. He’s now living a life filled with purpose, time, and a passion for custom bike fitting. Andrew opens up about how his life has transformed. You’ll hear about his massive drop in anxiety, the joy of having full control over his schedule, and how having a financial buffer helps him sleep soundly at night. Listen for insights, inspiration, and practical advice for anyone looking to redefine success and prioritize a fulfilling life. It might just help you take the first steps toward your own transformative journey.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/160-time-wealth-and-second-chapters-the-ripple-effects-of-leaving-corporate-america/

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    50 mins
  • 159. Waffle Week - On Friendship, Money Dates, ChooseFI, Taxes, Rental Income, Expense Tracking, Reclaiming Your Mornings, and More
    Apr 19 2026

    We talk about friendship, money dates, pelotons, open tabs, expense tracking, and so much more in the first and highly requested no-agenda episode. We also answer some listener questions and discuss standard vs. itemized deductions on your taxes, rental income as an early-retirement strategy, spending levels in early retirement, when Liz is going to retire, how we track our expenses, and more. And we might just explain to you what waffling means.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/159-waffle-week-on-friendship-money-dates-choosefi-taxes-rental-income-expense-tracking-reclaiming-your-mornings-and-more/

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    1 hr and 30 mins
  • 158. The Science of Less - Why Subtraction Is the Ultimate "Less Is More" Strategy
    Apr 12 2026

    We truly believe less is more, and so we’re challenging ourselves to focus more on subtraction and less on addition. The financial industry and broader world want us to believe that complexity is a necessary evil and will even improve our financial situation, but it’s just not true. We often say comparison is the thief of joy, but so is complexity! One of the most powerful financial moves we can make is focusing on subtracting, reducing our wants, and truly buying into the idea that less is more. By treating complexity as the thief of joy, you can stop running on the hedonic treadmill and start designing a simpler, higher-impact financial life.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/158-the-science-of-less-why-subtraction-is-the-ultimate-less-is-more-strategy/

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    54 mins
  • 157. Audit Your Influences - Why Your Financial Role Models Matter
    Apr 5 2026

    Who are your financial role models? Who we choose to emulate matters, and it’s important to avoid falling into a prestige trap. We are biologically hardwired to want to copy high-status individuals, even when these people often make poor choices and don’t emulate how we want to be in the world. We’re discussing our financial role models and why we want to be more like them. We also share some cautions to keep in mind when choosing your own financial role models.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/157-audit-your-influences-why-your-financial-role-models-matter/

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    55 mins