Behavior Gap Radio

We’ve all heard it: “More money, more problems.” But what if that’s only one way to see it? In this episode, I share a conversation with Rabbi Shira Stutman that helped shift my perspective from viewing money as a burden to seeing it as a tool for possibility. It’s a simple lens change… but it might just change everything, especially if you’ve ever felt guilty, ashamed, or stressed about wanting more.

This isn’t just about money.

It’s about how we see the world:

Problems… or possibilities?

A real email exchange about a home repair gone wrong reveals something deeper: how writing without curiosity—especially when we’re certain we’re right—can turn a simple message into emotional kindling.

If you're frustrated by bottlenecks in your projects, teams, or creative work... look closer. It might be you. In this episode, Carl shares why that's actually good news—and how entrepreneurship, at its best, is a brutal but beautiful path to personal growth.

We all say money can't buy happiness. But deep down, are we hoping it can remove our unhappiness? In this episode, Carl flips the script—and asks what hole we're really trying to fill.

In this episode of Behavior Gap Radio, Carl explores a deceptively simple question: What are you solving for? Whether it’s a mountain bike race, a business idea, or a client conversation, knowing the answer shapes everything—your tools, your preparation, and even your motivation. Carl shares how asking this question (and noticing when the answer changes) has guided his life over the past few years—and how it might do the same for you.

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In this episode of Behavior Gap Radio, Carl takes us inside a classroom exercise that never fails to surprise him—and might surprise you, too. What’s the first thought or feeling that comes to mind when you see a dollar sign? From dumpster diving as a kid to growing up surrounded by wealth but told “we’re not like them,” Carl shares powerful stories about the money scripts we carry. This episode is an invitation to notice the story, feel the emotion, and maybe even write it down and throw it in the fire.

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In this episode of Behavior Gap Radio, Carl shares a quote that hit him like a ton of bricks: “Sooner or later, you’re going to have to give up all hope for a better past.” What does that mean when it comes to money? A lot, actually. Carl dives into how we carry old stories—some ours, some inherited—and how they quietly shape our present. This one’s an invitation to drop the stick, stop rewriting the past, and finally move forward with clarity and compassion.

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In this episode of Behavior Gap Radio, Carl shares a sketch—and a story—from his upcoming book, Your Money: Reimagining Wealth Through Simple Sketches, about the power of perspective. Whether it’s a rafting trip gone sideways or a financial challenge that feels overwhelming, sometimes the only way through is up. Carl invites us to rise above the chaos—walk the riverbank, take a breath, talk to a friend—and see the forest, not just the trees.

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Feeling stuck in a loop? Like every day is just… the same? In this episode, Carl explores what happens when purpose goes missing—and why the smallest spark can change everything. From “bullshit jobs” to freshman soccer referees, this one’s about reclaiming meaning in ordinary moments. You don’t need a big dramatic change. But you do need to decide not to throw in the towel.

What’s more heroic—dying for something or living for it? In this episode of Behavior Gap Radio, Carl explores why it’s often harder (and more meaningful) to show up in the quiet, inconvenient moments than it is to make one grand gesture. From NBA legend John Stockton’s quiet consistency to the daily act of texting a grieving friend, this is a reminder that true courage might just be found in the boring stuff… like doing the dishes.

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Ever felt that spark when watching someone do something incredible—like you're catching a glimpse of pure passion in action?

That feeling isn't random. It's a clue, a breadcrumb, guiding you toward what makes you come alive. In this episode of Behavior Gap Radio, Carl reveals exactly how to decode these moments, uncover your own passion, and turn inspiration into action.

Because the world doesn't need more people just getting by—it needs you to Find Your Fire.

Ever grab an electric fence? Carl has—and he says that’s exactly what money conversations can feel like when we don’t expect emotions. In this short episode of Behavior Gap Radio, he shares one simple idea that might change how you talk about money forever: expect feelings. Because money isn’t just numbers… it’s identity, power, fear, and love. When you expect the emotional charge, you won’t be shocked. You’ll be ready.

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Ever found yourself spiraling into a story before you even know what’s happening? In this episode of Behavior Gap Radio, Carl shares a powerful tool he picked up from a conversation with Henry Shukman: SOS—Sensations Over Stories. When money decisions trigger anxiety, the key isn’t to analyze the story… it’s to drop into the body. Carl unpacks how this simple practice of noticing sensations can shift everything—even if the facts stay the same.

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When life feels out of control—markets crashing, job uncertainty, financial stress—Carl shares the most reliable response: a flight to simplicity. In this episode of Behavior Gap Radio, he explains how shrinking the problem and focusing on what you can control (even something as small as a single breath) helps restore calm and clarity. It's not about fixing everything. It's about finding solid ground—one square inch at a time—and starting from there.

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Ever nailed your morning routine only to find yourself doom-scrolling by 2:47 p.m.? In this episode of Behavior Gap Radio, Carl unpacks why we fall off track—even when we know better—and how the real solution isn’t a hack or shortcut… it’s practice. The kind that stings. The kind that invites us to notice, realign, and try again. Again and again. This is about treating creative work—and entrepreneurship—as a spiritual practice. One where the noticing is the win, the fall never ends, and the way forward is simple (but not easy): practice.

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In this episode of Behavior Gap Radio, Carl explores the strange magic of urgency and asks a simple question: What are you waiting for? Whether it’s sending that email, raising your fees, or finally writing the thing you’ve been thinking about for years, the time between idea and action doesn’t have to be so long. Carl shares real stories—his own and those of others—to show how much time we waste waiting for the “right” moment. Spoiler: This is your sign. Do the thing.

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In this episode of Behavior Gap Radio, Carl shares his most tactical money decision-making tool: the Financial Pause. Forget budgets and spreadsheets—this is about noticing what you're feeling before you act. Carl walks through a four-step process that starts with tuning into your body and ends with making choices from a calm, centered place. It’s simple, powerful, and might just save you from making a financial decision you’ll regret.

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In this gentle reminder from Behavior Gap Radio, Carl shares what to do when someone comes to you feeling nervous, scared, or uncertain—and thinks action is the answer. Instead of rushing to give advice, Carl encourages us to slow down, lead with empathy, and ask thoughtful questions. Because often, the wisest answers come not from us but from the person sitting across from us—if we’re willing to create the space for them to emerge.

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In this quiet but powerful episode of Behavior Gap Radio, Carl shares a simple phrase that might just rearrange the furniture in your brain: We live in the feeling of our thinking. Not our circumstances. Not the email. Not the number on the statement. Carl unpacks how noticing our thoughts—not fixing or fighting them—can shift everything. It’s not self-help. It’s not mindset hacks. It’s just awareness. And it changes things.

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In this episode of Behavior Gap Radio, Carl comes in hot with a wake-up call about the hidden cost of distractions. He shares shocking stats about how often we're interrupted, how much time we lose to switching tasks, and why most knowledge workers only get two hours of deep work a day—on a good day. But this isn't just finger-pointing. It's Carl confronting his own habits and offering two tiny experiments to help us all reclaim our time: install RescueTime and schedule just two 90-minute distraction-free work blocks. No shame. No blame. Just a deep, empathetic punch in th...

In this episode, Carl takes on the wild, stretchy nature of time—why we can procrastinate for months on a task that only takes minutes. He explores Parkinson’s Law, the mental weight of unfinished tasks, and the surprising productivity gains of adding constraints. With practical tools like the two-minute rule and a three-hour workday experiment, Carl invites you to test the "time illusion" for yourself and reclaim your attention, energy, and calendar.

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In this episode, Carl explores a powerful framework for navigating creative and financial risk: understanding whether you're playing a luck-based or skill-based game. Drawing on insights from Michael Mauboussin’s book, The Success Equation, Carl explains why sharpening your decision-making process is essential in luck-driven environments—like markets or venture capital—while skill-building is key in more predictable terrain. Knowing the difference just might change the way you approach your next big move.

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In this episode, Carl shares a personal experiment in breaking free from the “dopamine machine”—those tempting websites and distractions that quietly steal our time. He talks about using defensive measures like locking down access, creating space between stimulus and response, and replacing old habits with more meaningful activities. Along the way, he reflects on meditation, addiction, and the surprising power of simply noticing what we feel instead of trying to suppress it.

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In this episode, Carl explores what he believes is the greatest risk of all—not failure, but waking up one day and realizing we haven’t been the person we hoped to be. He reflects on daily regrets, the subtle ways distraction can derail our intentions, and why ignoring that quiet sense of misalignment only makes it worse. Most importantly, he offers a gentle reminder: notice the feeling, use it to course-correct, and begin again.

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In this episode, Carl dives into one of his most-quoted ideas: "Risk is what's left over after you think you've thought of everything." He unpacks the concept of residual risk, why it matters in everything from investing to skiing, and how small, safe-to-fail actions can help us navigate uncertainty. Plus, he explores the idea of general resilience—the kind of strength that helps you deal with the unknown unknowns.

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In this episode of Behavior Gap Radio, Carl shares a simple but powerful idea: When something feels too scary—whether it’s launching a business, writing a book, or making a big change—just make it smaller. He introduces the concept of microactions: tiny steps that feel almost too small to matter but are exactly what we need to get unstuck and start moving.

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In this episode of Behavior Gap Radio, Carl shares a powerful mindset for navigating uncertainty—whether it’s a looming recession or just a vague feeling of unease. Borrowing from his backcountry experience, he introduces the idea of a “flight to simplicity” as a way to reduce exposure to risk. From creative businesses to household budgets, Carl walks through practical ways to make things simpler, delay big decisions, and regain clarity—especially around the margins.

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In this episode of Behavior Gap Radio, Carl explores the terrifying beauty of doing work no one asked for. He challenges the conventional path of chasing demand and instead makes a case for following the quiet compulsion to create—especially when it feels scary, uncertain, or totally invalidated. If you’ve ever felt called to make something simply because it lights you up, this one's for you.

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In this episode of Behavior Gap Radio, Carl questions the very idea of financial "problems." What if most of what we worry about isn’t actually a problem at all—just imagined futures that may never happen? He explores how shifting our mindset (and maybe even our language) can help us stop spinning in thought and start doing the simple things that actually move us forward.

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In this episode of Behavior Gap Radio, Carl shares one of the most powerful tools he's ever created: The Overnight Test. Through stories of stocks, cabins, businesses, and even old clothes, Carl explores how this simple mental exercise helps reveal when we’re making emotional decisions disguised as financial ones. If you’ve ever struggled to let go of something—just because it’s always been there—this one’s for you.

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In this short and powerful episode of Behavior Gap Radio, Carl offers just one thought—“If you don’t know who you are, money is a very expensive way to find out.” Then he invites you to sit with it. No answers, no unpacking—just space to let the idea settle and do its work.

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In this episode of Behavior Gap Radio, Carl reflects on the challenge of communicating hard truths with people we care about. Inspired by a principle from Buddhism, he explores the delicate balance between saying what is kind, true, and necessary. Through personal stories and honest introspection—especially around parenting—Carl unpacks how even well-intentioned kindness can sometimes be a misapplied avoidance of discomfort. This episode is a thoughtful invitation to approach tough conversations with clarity, courage, and compassion.

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In this episode of Behavior Gap Radio, Carl reads a new essay from his upcoming book, Your Money: Reimagining Wealth Through Simple Sketches. The essay is titled You Can’t Hedge Yesterday, and it uses a simple circle sketch to illustrate a powerful truth: The time to prepare is before the crisis, not after. Carl reflects on how we often react to past events with elaborate solutions that can’t change what’s already happened—and why true resilience comes from preparation, not panic.

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In this episode of Behavior Gap Radio, Carl explores what Henry Shukman calls the fundamental investigation of a lifetime: the search for our identity. Drawing from Shukman’s book One Blade of Grass, Lao Tzu’s wisdom, and reflections from thinkers like David Whyte and Jim Collins, Carl unpacks the power of asking, "Who am I? and What do I want?" He shares how this practice can create distance from reactive emotions, like grumpiness, and helps align our time, energy, and money with what truly matters.

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In this episode of Behavior Gap Radio, Carl shares a deeply personal story about a recent argument with his wife over money—one sparked by the language he used. He unpacks how the phrase "beast of burden" shaped his mindset around financial pressure, risk, and creative work, and how words carry unintended weight in conversations about money. Through this reflection, Carl explores the power of language, the emotional charge behind financial discussions, and the importance of reexamining the narratives we tell ourselves.

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What do you truly want? In this episode of Behavior Gap Radio, Carl Richards continues the conversation on the two fundamental questions that shape financial decisions—and life itself: Who are you? And what’s important to you? He explores how our desires evolve, how cultural and social influences shape what we think we want, and why living with these questions (rather than rushing to answer them) leads to better-aligned choices. If you’ve ever felt pulled in different directions by expectations, trends, or habits, this episode is for you.

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