The Stacking Benjamins Show

Most of us were never taught this stuff. So, where do you actually start? Thirty-nine states now require a personal finance course to graduate from high school. That's real progress — and it still might not be enough. Because financial education isn't a one-time event. It's a living curriculum that has to grow with you, stay connected to your actual life, and — crucially — help you get out of your own way when things get emotionally charged. This week, Joe and the crew build that curriculum from the ground up. Whether you're 22 or 52, there's a starting point here for you. Rubin Miller — Financial advisor, founder of Peltoma Capital, and author of the Fortunes and Frictions blog. Came from the investment world before financial planning, which means he sees the whole game differently and isn't afraid to say so on LinkedIn. Paula Pant — Afford Anything host, behavioral finance truth-teller, and the person who goes on record this week with a very confident guess about the trivia answer. OG — The basement's own financial planner, father of a teenager who wants to day trade, and enthusiastic opponent of giving the government any money he doesn't absolutely have to. On building the foundation: Why the first step in any financial plan is an honest accounting of where everything actually stands: income, spending, assets, debt, all of it What's coming up in the next three to five years and why that question matters more than any abstract retirement calculation Why teaching a 17-year-old about mortgages probably doesn't stick and what actually does The one thing traditional savings accounts do really well (hint: it's great for banks, not for you) Why your behavior matters more than your math and what to do about it On protecting what you're building: The insurance mistake most people make: spending too much protecting low-probability events and too little protecting high-probability ones Why disability insurance is more expensive than life insurance and what that price difference is actually telling you When improving your credit score should not be your priority (this one surprises people) Why debt is never really "good," just occasionally less bad On growing your money: What an investment philosophy actually is and why you need one before you pick a single fund The behavioral biases — recency bias, loss aversion, the availability heuristic — that make smart people do dumb things with their portfolios Why nobody ever thinks they're panicking. They just think the circumstances changed. Why taxes are a year-round event, not a February problem The financial media teaches you to chase. New strategy, hot sector, better fund. But the research keeps landing in the same place: most investors' biggest obstacle isn't information. It's themselves. The curriculum that actually helps isn't the one that covers the most ground. It's the one that connects to your real life, your real timeline, and the emotional triggers that quietly blow up even the best-laid plans. Start there. Everything else builds on top. Rubin joins the crew for the first time and immediately plays trivia on Jesse Cramer's behalf — which feels both generous and karmic, given that Jesse and his wife Kelly just welcomed a new baby into the world (on Jesse's birthday, no less). Doug brings the Eddie Murphy birthday trivia energy. Paula goes on record with a very confident guess. OG applies his usual ironclad logic to arrive at his number. Someone wins. Someone absolutely should not have said what they said out loud before the answer was revealed. MENTIONED / RESOURCES Rubin Miller's blog: fortunesandfrictions.com Peltoma Capital: palomacapital.com Rubin on LinkedIn: search Rubin Miller Paula Pant: Afford Anything podcast, wherever you listen OG's calendar: stackingbenjamins.com/OG Wall Street Journal piece on personal finance requirements by state New to the basement? Subscribe so you never miss an episode — and if this one made you want to finally build your own financial curriculum, that's the whole point. FULL SHOW NOTES: https://stackingbenjamins.com/looking-at-your-money-report-card-1824 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices