Inside Out Money

Latest Episodes:

161. Our 91% vs. 9% of Life: 4 Lessons from 4 Years of Early Retirement May 03, 2026

Show notes

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/

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

Show notes

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/

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

Show notes

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/

158. The Science of Less - Why Subtraction Is the Ultimate "Less Is More" Strategy Apr 12, 2026

Show notes

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/

157. Audit Your Influences - Why Your Financial Role Models Matter Apr 05, 2026

Show notes

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/

156. Treat Your Morning Like Your Money - The Power of Compounding Habits Mar 30, 2026

Show notes

I used to consider sleeping in to be the ultimate flex, but I’ve learned the flex might actually be waking up. Creating a personal structure is a powerful gift you can give your future self. Greg and I discuss the surprising connection between your alarm clock and your bank account, exploring how getting your own routines in order naturally inspires your partner to do the same without sparking a defensive fight. By reframing waking up as a proactive commitment to yourself rather than a reactive, people-pleasing chore, you can reclaim your energy, overcome early retirement ennui, and build the daily scaffolding necessary for a truly wealthy life.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/156-treat-your-morning-like-your-money-the-power-of-compounding-habits/

155. Willpower and Discipline Aren't the Answer, but This Is Mar 22, 2026

Show notes

We’ve been told all of our lives that willpower, discipline, and more inner fortitude are what we need to accomplish just about any goal, but what if it’s not? True financial freedom doesn't actually come from trying harder; it comes from situational agency and designing an environment where your money takes care of itself while you are busy living. We explore why willpower is the least effective tool in your kit and how high achievers simply experience fewer temptations because they have pushed away the distractions. By automating the path of least resistance and creating friction for your impulses, you can stop fighting your environment and start fixing your systems to fund the things you actually love.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/155-willpower-and-discipline-arent-the-answer-but-this-is/

154. Buying Back Your Brain - Tactics to Exit the Overwhelm Loop Mar 16, 2026

Show notes

Overwhelm is more than a feeling; it is a hidden financial variable that makes sound long-term decision-making biologically impossible. We explore the reality of overwhelm and how reactive spending and convenience taxes can cost us. We discuss tactical ways to downshift your nervous system, fight overwhelm, and regain control of your money and financial decisions.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/154-buying-back-your-brain-tactics-to-exit-the-overwhelm-loop/

153. Return on Hassle - Escaping the Complexity Trap Mar 09, 2026

Show notes

People profit from complexity, but some of the most successful investors prioritize their return on hassle (ROH), even over their ROI. We dig into the age-old debate of trading our time for our money and explore how complexity can make us become an employee of our own wealth. By shifting our focus from complex optimization to intentional simplicity, we can stop paying a "hassle tax" with our lives. Let’s look at why the best-performing portfolios are often the most invisible ones and how you can audit your own financial and personal decisions to reclaim your mental bandwidth.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/153-return-on-hassle-escaping-the-complexity-trap/

152. Be Rich, Don’t Look Rich - The importance of Stealth Wealth Mar 02, 2026

Show notes

We explore the art of stealth wealth, avoiding lifestyle inflation and living below your means. Stealth wealth is the practice of maintaining a modest lifestyle despite significant financial assets; it’s the original millionaire-next-door concept. Before we dive into the stealthy stuff, we riff on everything on our minds lately, from financial to general life updates.

Get the full show notes, show references, and more information here: https://www.insideoutmoney.org/152-be-rich-dont-look-rich-the-importance-of-stealth-wealth/

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