Behavior Gap Radio: Exploring Human Behavior...with A Sharpie

I’ve been wrestling with a question for years: Why do I always call Jason? Jason is a friend of mine who always affirms my ideas.This essay and sketch was my attempt to confront confirmation bias head-on. We’re wired to seek agreement. But that’s how bad decisions happen.In this episode of Behavior Gap Radio, I share the story behind it, and how I try to push myself to invite dissonance instead of comfort.This sketch is #92 in the new book. It’s called Stop Calling Jason. You’ll find it in ​Your Money: Reimagining Wealth in 101 Simple Sketches​, coming October 21, 2025.If you want a preview, I’ve put together a beautifully designed excerpt with seven of my favorite essays and sketches.

I’ve always been fascinated by this idea: We feel about as much emotional connection to our future selves as we do to a stranger. That explains a lot, doesn’t it? It makes saving hard. It makes planning even harder. This is one of the ideas I explore in Your Money: Reimagining Wealth in 101 Simple Sketches, coming October 21, 2025. It’s sketch #82. Want to see more from the book?

There’s this old mountaineering strategy called siege style.You drag everything up the mountain: extra oxygen, fixed ropes, backup boots, food for weeks, a team of porters.It works. But it’s heavy. Slow. Complicated. Sometimes, it leaves a mess.Then came a new idea: alpine style.What’s the minimum amount of gear we can bring and still make it to the top?It’s lighter. Faster. Riskier, maybe.But the quality of the experience? Higher. Way higher.So here’s my question:Are we climbing our financial mountains using siege style or alpine style?Because all that extra stuff—bank accounts you forgot about, old investment logins, tools you don’t use, subscriptions you meant to cancel—can start to get in the way.It feels productive until it doesn’t.At some point, the stuff stops adding value and starts subtracting from the experience.This sketch is just a simple downward sloping line: More stuff = Lower quality of experience.And if I’m honest?Sometimes I look at my own financial setup and think…“I might be dragging too m

When markets get scary, most people yell: DO SOMETHING.And most advisors respond with stats, charts, and long-term return arguments.But that’s not what people actually need.At least, not first.This is a behind-the-scenes look at one of my favorite essays in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.It’s called “Scary Markets Hugs.” Because before we talk about data and discipline, we need to talk about being human.

Every investor has felt it.The panic.The urge to act.The voice in your head saying: “Just get me out.”This is the big mistake.And if you’re not careful, it can undo years of thoughtful planning.In this video, I share the story behind one of my favorite sketches: The Big Mistake.This sketch and essay is 54 of 101 in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.

This might be the simplest sketch I’ve ever made.It’s just four shapes and one word: Diversification.But if you’ve ever built a REAL portfolio, you know exactly what it means.Here’s the uncomfortable truth most people miss: If you’re diversified the right way, you’ll always own something you don’t like.In this behind-the-scenes video, I unpack why that’s true... and why it’s actually a good thing.This sketch is part of my new book, Your Money: Reimagining Wealth in Simple Sketches, out October 2025.