The Stacking Benjamins Show · Apr 3, 2026 · 1:05:10
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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:
On protecting what you're building:
On growing your money:
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
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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
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Episodes: The Stacking Benjamins Show