Behavior Gap Radio

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, o...

Most budgeting advice feels like punishment.

That’s how it felt to me, too... until I realized something simple but powerful:

💡 Money’s natural state is motion. That’s why we call it currency!
💡 And what really matters? Paying attention to where it’s going.

In this behind-the-scenes video, I talk about one of my favorite essays and sketches from my new book, Your Money: Reimagining Wealth in Simple Sketches.

This one is called Cash Flow Love, and it completely changed the way I think about budgeting.

If you’ve ever fe...

We’ve been told to spend less. Cut back. Control ourselves.

But what if we practiced spending better instead?

This is my behind-the-scenes thinking that shaped essay #30 in my new book, Your Money, coming out in October 2025. The essay is called “The Spending Practice."

This essay talks about guilt, values, and why learning to spend with intention might just be the most radical financial move you can make.

🎁 Want a preview of the book?
Email hello@behaviorgap.com with the subject line "Friend of Carl" and we’ll send you seven of...

This essay is from my new book, "Your Money: Reimagining Wealth in Simple Sketches."

It’s called “Enough Is Enough,” and in this episode, I unpack how we confuse more with better—and what it really means to have enough.

It’s a story about investing, dessert, and clarity.

Because enough can't be a number. If enough is a number, you'll never have enough. Enough is actually a state of being that we have to practice.

This is my behind-the-scenes thinking that shaped essay #20 in the new book coming out in October 20...

This essay might be one of the most important from my new book, "Your Money: Reimagining Wealth in Simple Sketches."

It’s called "Life Meets Money" and it’s about what really drives good financial decisions. Not markets. Not headlines. But the messy, human stuff underneath: goals, timing, fear, meaning.

This is my behind-the-scenes thinking that shaped essay #10 in the new book coming out in October 2025.

This is the essay:

Good financial decisions happen at the intersection of what’s going on in your life and what’s going on in the mark...

In this episode, Carl asks a provocative question: What’s the minimum effective dose of money? Just like medicine or exercise, more isn’t always better, and sometimes it’s harmful. Instead of chasing endless income, Carl invites us to define the results we actually want—freedom, security, joy—and then ask: What’s the least amount of money needed to get there? Because maybe the most radical act in a world obsessed with more is to say, “That’s enough”… and mean it.

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In this episode, Carl shares three quick stories—a successful entrepreneur feeling like a failure, a heartfelt compliment from his daughter, and a wildly accomplished friend still stuck in comparison. The punchline? Comparison is the thief of joy. But unlike most thieves, this one can be stopped. Carl invites you to join him in a “comparison audit” by asking: Who are you letting on your mental scoreboard—and why?

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In this episode, Carl explores the quiet panic so many of us are feeling about the future, especially young adults and the parents who love them. From canceled programs to crumbling plans, what do you do when the ground keeps shifting? Carl makes the case for a new kind of planning, one rooted not in certainty but in resilience. Not prepping for one disaster but building a foundation that helps you ride whatever wave comes next.

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In a world of AI-generated books, endless content, and virtual everything… maybe the rarest thing isn’t more information—it’s real human connection. In this episode, Carl asks a provocative question: What if the answer isn’t to become more like a machine, but more like a human?

Because connection—the kind that happens face-to-face, heart-to-heart—is becoming increasingly rare… and increasingly valuable.

Connection is the new luxury.

What does independence really mean? In this special Independence Day episode of Behavior Gap Radio, Carl unpacks the myth of the self-made person and explores the deeper truth: Real freedom isn’t about doing it all alone. It’s about knowing when to stand on your own—and when to lean on others.

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What if money is just a cheap shortcut? In this episode of Behavior Gap Radio, Carl shares a story about grandma’s dinner and explores the deeper forms of value we often overlook—like friendship, generosity, and shared purpose. Sometimes writing a check is the easy way out. But what if there’s something more valuable than money?

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What’s at the center of your life? In this episode of Behavior Gap Radio, Carl explores the idea that, for many of us, money has quietly become the organizing principle around which everything else revolves. But what if we chose something else? Family? Time? Meaning? It's worth asking.

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What if the problem isn’t you—it’s what we’ve been told is normal? In this episode of Behavior Gap Radio, Carl challenges our deeply held assumptions about money, enoughness, and the quiet madness of chasing what everyone else is chasing. Maybe the real goal is to be a little less normal… and a little more weird.

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In this episode, Carl revisits his favorite money metaphor—gathering wood for a fire—and adds a new layer: What kind of fire are you building? A small cabin fire or a 10,000-square-foot mountain lodge bonfire? The size of the fire changes everything. From burn rate to outflow, Carl explores how the metaphors we use shape the way we think about money and invites you to send him your own.

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In this episode, Carl explores the subtle but dangerous shift from treating money as a scoreboard to letting it become a mirror. When net worth stops being just a business metric and starts reflecting our fears, stories, and sense of self-worth, things get messy. What if the number isn’t telling you how you’re doing—but who you think you are?

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In this episode, Carl flips the script on everything we think we want from money. We don’t actually want money—we want what we think it will give us: safety, love, approval, and enoughness. And here’s the twist: you can feel those things before the numbers change. What if money isn’t the enemy or the goal… but the trick that wakes us up from the collective delusion we’ve been living in?

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In this episode, Carl challenges one of the deepest money myths out there: Money will finally make us feel safe, happy, or whole. He shares a core idea from his new book: You’re not bad with money, you’re just asking it to do the wrong job. From personal stories to a powerful quote by Austin Kleon, Carl unpacks how our suffering around money often stems from mistaken beliefs, not money itself. What if changing those beliefs could change everything?

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In this adventure journal episode, Carl shares a thought experiment that starts in a quiet cabin and ends with a radical reframing of how we think about money. What if money were like firewood—just fuel to keep things going? Not something to hoard, fear, or worship, but something to gather when needed, use wisely, and share freely. This isn't just a mindset shift—it's a new way of being. One rooted in trust, not scarcity.

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In this episode, Carl shares a raw segment from his new one-man show, built around two painfully honest sketches about envy and comparison. He reflects on the unspoken rules of the money game we all play—and what happens when someone dares to break them. From beaten-up minivans to Instagram-fueled status anxiety, this one’s about the stories we tell, the ones we’re afraid to admit, and the quiet power of saying four simple words: We can’t afford it.

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In this episode, Carl shares a raw, in-progress segment from his upcoming keynote. What if money is just a story we’ve all agreed to believe? A religion we all follow but no one admits to praying to? From Martians to mortgages, Carl invites us to step back and ask: When did we give money so much power?

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In this episode of Behavior Gap Radio, Carl returns from an accidental hiatus with a vulnerable reflection on why he keeps making the show—and why it matters that you share it. He relays a powerful idea from his recent conversation with author Austin Kleon: Money, up to a certain point, acts as a stabilizing force, but beyond that, it becomes an agent of chaos. If money walked into the room, what would you ask it?

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In this episode of the Deep Shift series, Carl explores how tactical curiosity—like obsessing over budgeting apps or fueling strategies—often hides something deeper. What starts as a surface-level decision can lead to a powerful emotional insight. Maybe it's not about interest rates… maybe it's about fear, identity, or old family patterns. Carl walks us through why it’s easier to talk spreadsheets than shame—and how simply asking, “Why are you asking?” can crack open the truth.

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In episode two of the Deep Shift series, Carl names the chase we all know too well: tactical curiosity. The frantic hunt for the perfect app, book, or tool isn’t really about solutions—it’s often a way to avoid the deeper, scarier questions. This episode invites you to pause the chase and ask, “What am I really trying to solve for?” Because awareness—not another download—is where real change begins.

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In this first episode of a new series, Carl introduces the Deep Shift framework—his attempt to map the real journey of change. It’s not about picking the right tactic or finding more information, it’s about uncovering what’s blocking the doing. From tactical curiosity to deep ritual, Carl explores why lasting change starts below the surface… and invites you to walk through it with him.

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In this wrap-up to the Your Wise Money Friend series, Carl shares where the idea came from and why it matters. People don’t want another financial plan—they want to feel okay. They want someone to walk with, someone who listens with golden-retriever-level curiosity. In this episode, Carl challenges us to become that kind of friend: no agenda, no judgment, just love, presence, and deep curiosity. Turns out you don’t need to know anything about money to be a wise money friend. You just have to care.

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In the final episode of the Your Wise Money Friend series, Carl reflects on what it means to hold the mirror gently. A wise money friend helps you see what’s really there—not with blame, but with compassion. It’s that rare mix of an empathetic hug and a well-timed kick in the butt. Because real clarity doesn’t come from shame—it comes from being seen, kindly.

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In episode nine of the Your Wise Money Friend series, Carl highlights a defining trait of true support: Instead of rushing to give answers, instead asking better questions. The kinds of questions that invite reflection, spark clarity, and open doors. Because real change doesn’t come from advice, it starts with curiosity.

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In this episode of the Your Wise Money Friend series, Carl shares a simple but rare truth: A wise money friend doesn’t have an agenda. They’re not selling, fixing, or convincing. They’re just fully present—genuinely invested in your clarity. Once you’ve felt that kind of presence, you don’t forget it… and you stop settling for anything less.

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In this episode, Carl continues the Your Wise Money Friend series with a powerful reminder: A wise money friend believes you are enough—even when you feel like you’ve screwed everything up. They don’t excuse your mistakes, they restore your dignity. Because real change doesn’t come from shame, it comes from remembering who you are.

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In episode six of Your Wise Money Friend, Carl explores what it means to honor someone's dreams—big, small, wild, or vague—without judgment. A wise money friend doesn’t roll their eyes or ask, “When are you going to get a real job?” They lean in and say, “Tell me more.” This episode is about learning to hold space for dreams—our own and others’—with curiosity, not criticism. Because dreaming isn’t naive, it’s trust.

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In episode five of Your Wise Money Friend, Carl reflects on how true wisdom isn’t pushy. A wise money friend doesn’t rush your process or pressure your decisions—they wait with you. Because they know money decisions are rarely urgent, and often about something much deeper: identity, emotion, and transition.

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In episode four of Your Wise Money Friend, Carl shares how a wise money friend helps you pause, not to stop you, but to give you space. Space between the impulse and the action. Space to breathe, to feel, and to choose. Because the point isn’t control—it’s clarity. And that little pause? That’s where alignment begins.

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In episode three of Your Wise Money Friend, Carl reminds us that to a wise money friend, your story is never just about money. They listen between the lines—because behind every financial decision is something deeper: fear, joy, dreams, love. A wise money friend knows it’s all connected, and that’s where the real conversation begins.

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In episode two of Your Wise Money Friend, Carl explores the idea that wisdom isn’t about being right—it’s about being present. A wise money friend won’t hand you a to-do list or correct your choices. Instead, they ask the deeper questions that help you see yourself more clearly. Because the goal isn’t certainty, it’s clarity.

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In this special 1,300th episode, Carl kicks off a new series called Your Wise Money Friend. Episode one starts with a simple but powerful idea: A wise money friend doesn’t shame you. They don’t scold, lecture, or judge—they lean in with curiosity. Instead of asking, “Can you afford it?” They ask, “Tell me more.” Because real wisdom isn’t about telling you what to do—it’s about helping you explore why.

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In this kickoff episode, Carl introduces a new series called Your Wise Money Friend—a collection of short, gentle reflections to help you pause, notice your money patterns, and choose on purpose. No hype. No shame. Just tiny moments of clarity, like a quiet walk with someone who really gets it. Because money isn’t just math, it’s meaning.

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It’s not about what you spent—it’s about what you felt. In this field episode from Los Angeles, Carl shares a shift in how he thinks about money decisions. Whether it’s a new truck or a fancy coffee, the real question isn’t “Can you afford it?” It’s “What are you hoping this will do for you?” Because every financial choice has a feeling underneath it—and that’s where the real insight lives.

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Money isn’t math—it’s practice. In this episode, Carl reframes every financial decision as a chance to get more aligned with who you really are. Not perfect. Just intentional. Not based on someone else’s rules, but rooted in your own values. One choice at a time.

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