Behavior Gap Radio

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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