Here's the secret nobody tells you: your money problems probably aren't math problems.

Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it.

Your financial plan shouldn't feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you'll actually stick to. If you've ever felt like you're "doing it wrong" because your strategy doesn't involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief.

Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they're just expensive complexity, and how everyday investors should think about them (if at all).

Plus: travel stories, Neighbor Doug's trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap.

What You'll Walk Away With:

Carl Richards' framework for simplifying your financial life—and why "The Behavior Gap" matters more than your rate of return
Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them)
How to filter out financial noise and focus on the handful of things that actually move the needle
The truth about options trading: when it's a smart risk management tool and when it's just expensive gambling
Permission to keep your plan simple—even if it feels like everyone else is doing something fancier

This Episode Is For You If:

You feel like everyone else has figured out money except you
Financial jargon makes you want to hide under a blanket
You've got a solid income but still feel anxious about your money decisions
You'd rather learn through real stories than get lectured by a guy in a suit
You want to finally understand why you make the money choices you do (good and bad)

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-manage-your-money-goals-and-life-with-carl-richards-1751

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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The Weekend Edition | 29-30 Nov 2025

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