by inside out money | Apr 5, 2026 | Andrew, Early Retirement, Investing, Lifestyle, Money, Psychology
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...
by inside out money | Mar 8, 2026 | Andrew, Early Retirement, Investing, Lifestyle, Money, Psychology
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...
by inside out money | Feb 22, 2026 | Andrew, Early Retirement, Investing, Lifestyle, Money, Psychology
This week, Andrew and I answer your money questions, starting with Andrew’s own real-time question: should he invest a lump sum all at once, dollar-cost average, or hold onto it in an attempt to time the market? We also answer other listener questions, including...
by inside out money | Feb 1, 2026 | Andrew, Early Retirement, Erica, Greg, Investing, Lifestyle, Lizgetsloaded, Money, Psychology
We are continuing our annual expense review tradition by digging even deeper into our 2025 spending. In part two, we move beyond the totals to examine the specific categories that often make or break a budget—from rising insurance premiums to the actual cost of our...
by inside out money | Jan 25, 2026 | Andrew, Early Retirement, Erica, Greg, Investing, Lifestyle, Lizgetsloaded, Money, Psychology
Analyzing where every dollar goes provides the ultimate leverage for financial independence, and in this annual tradition, we’re pulling back the curtain on our 2025 household spending. From finished decks and water filters to personal trainers and pilates, we break...
by inside out money | Jan 18, 2026 | Andrew, Early Retirement, Investing, Lifestyle, Money, Psychology
The initial thrill of optimizing your budget and automating your investments eventually fades into a long, quiet stretch known as the “Boring Middle.” We dive into why this phase is actually the ultimate sign that you are doing everything right, even when...
