Episodes

  • 168. The Weird, Irrational Psychology of How We Spend - From $25 Airport Muffins to $12 Underwear
    Jun 21 2026

    We like to think we make rational financial decisions, but the reality is our spending habits are heavily driven by weird, internal cognitive biases. Today, we unpack the completely subjective psychology of how we value money, from price anchoring to mental accounting. By exploring our own financial quirks—like happily splurging on vacation while refusing to buy a $25 airport muffin—we uncover how to align our habits with our true values. Developing a personal spending philosophy empowers you to stop sweating the small stuff and confidently put your dollars where they bring the most joy.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/168-from-25-airport-muffins-to-12-underwear-the-weird-irrational-psychology-of-how-we-spend/


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    1 hr and 12 mins
  • 167. How We Automate and Track Our Expenses - Our Favorite Monarch Tips & Tricks
    Jun 14 2026

    We share our best tips for using Monarch Money to track expenses, manage separate accounts, and keep our financial lives completely organized. We discuss how to remove the friction from budgeting and expense tracking and why a consistent approach beats perfection every time. Whether you are already a Monarch power user or just looking for a better system, we are breaking down the exact strategies that work for us.


    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/167-how-we-automate-and-track-our-expenses-our-favorite-monarch-tips-tricks/

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    1 hr and 3 mins
  • 166. The Complicated Path to Wealth - Why the "Simple Path" Isn't Easy
    Jun 7 2026

    In today’s complex world, society often complicates matters and exploits our desire for quick fixes. We must confront the truth: while the "simple path" to wealth may seem straightforward, it is anything but easy. Understanding the mathematics of wealth-building is simple, but mastering the necessary psychology and mindset can take years. The encouraging news is that by identifying these behavioral pitfalls and economic challenges, we can stay disciplined and focused on the boring yet proven path to building wealth. Embracing this journey is the key to achieving your financial goals.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/166-the-complicated-path-to-wealth-why-the-simple-path-isnt-easy/

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    1 hr and 17 mins
  • 165. The 529 Dilemma: How Much Do You Actually Need to Save for College?
    May 31 2026

    College is expensive, and I think we’re all wondering if we’re saving enough and what’s the “right” amount to save? We are influenced by what our parents did, what we feel we can afford, and a slew of other factors. Ultimately, we need to make a decision, have a plan, and start saving. We break down the actual costs of higher education and our individual perspectives on what is enough and how much we’ve each saved for our kids. And we remind you all that you have more flexibility than you think, especially with the recent SECURE 2.0 Act.

    Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/165-the-529-dilemma-how-much-do-you-actually-need-to-save-for-college/


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    1 hr and 18 mins
  • 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