One Great Question

Callie Murray is not a clean LinkedIn narrative. She'll tell you that herself. She's got an HR company, a historical fiction novel just released, and a family that went from three kids to seven overnight when she and her husband David finalized the adoption of a sibling group of four through foster care. All in the same season. All at the same time. And somehow she still showed up for a TV intervi...

Jeremy Cowart is one of the most celebrated photographers and creative minds alive. He's also genuinely terrified about where AI is headed. And that tension, being all in on something that scares you, turns out to be one of the most honest things you'll hear a creative say out loud in 2026. In this episode, Jeremy and I dig into what it means to be an artist in the age of artificial intelligence,...

Jason Wahler grew up in Southern California, became a household name on Laguna Beach and The Hills, fought a very public battle with addiction, and somewhere in the middle of all of it found the thing that actually mattered. A pillow fight with his kids on a random Tuesday night. Crying laughing. Nobody watching. Nowhere else to be. In this episode, Jason and I dig into what it looks like to rebui...

Charles Lee arrived in the US at five years old with very little English, moved to Koreatown in Los Angeles, watched his parents build a restaurant that became an institution and cost them their marriage, dropped out of college twice, and somehow ended up advising Toyota, Google, and Sequoia. He'll be the first to tell you he still doesn't feel like he's arrived. And that honesty is exactly what m...

Matt Chenard lost $1.2 million dollars, his wife's nursing job, their life savings, and nearly his health. And he'll tell you straight up, it was the best thing that ever happened to him. Not because he's a masochist. Because it was the moment he finally stopped confusing a good thing for the ultimate thing. In this episode, Matt and I dig into what it actually means to build a life around mission...

Chris Ducker built companies with nearly 600 employees, hit his first million dollar year, and was completely done. Not celebrating. Done. And then he did it again in 2021, this time landing in anxiety, depression, and phase three adrenal failure with cortisol completely flatlined. The long way back didn't start in a boardroom. It started with an hour a day in the woods, no AirPods, no podcast, no...

Most people were told the same thing growing up. Keep work and friendship separate. Don't mix business and pleasure. Play it safe. Sam Primm heard all of that and quietly decided to do the opposite. Sam has 3.5 million followers, 2000 real estate deals, and a team of 55 people, about 15 of whom he's known since elementary school. His business partner Lucas has been his best friend for 25 years. Th...

Most people chase success without ever asking what it's actually going to cost them. Mike Kim did the work, wrote the books, built the brand, and got close enough to the mountain to realize he was climbing the wrong one. In this episode, Mike and I dig into what it really takes to become who you're meant to be, and why the price of that journey is almost always your pride. We talk about why consis...

Hey friends, we are back with another episode of One Great Question, and this one went somewhere I didn't expect, which is honestly my favorite kind of conversation. Nigel Darius is one of those rare humans who is an author, keynote speaker, spoken word artist, and creative director, but more than any of those titles, he's just one of the best hangs you'll ever have. He grew up poor in rural West...

What if the most powerful thing you could do for your career wasn't a strategy, it was a question? In Episode 10 of One Great Question , Carl sits down with Andrew Averso, a multi-disciplinary creative who has reinvented himself across music, fashion, brand identity, and now his own creative house, Averso Co. What unfolds is a raw, honest conversation about the real cost of "success," why there's...

This final episode answers a practical question:  Now what? After a full season of exploring curiosity and leadership, this conversation zooms out to look at the end goal. Not abstract philosophy, but real life.  Most people spend the majority of their waking hours at work.  If that time is consistently  confusing, draining, or joyless, something is broken. In this episode, we...

The leadership industry is worth hundreds of billions of dollars, yet most leaders still feel unsure, lonely, and overwhelmed. That disconnect is not accidental. In this episode, we challenge the idea that leadership is complex, mysterious, or reserved for experts with answers. Using stories from kitchens, soccer fields, bookstores, and boardrooms, we break leadership down into something far more...

Most leaders think profit comes from speed. This episode argues the opposite. In this conversation, we unpack a simple but demanding idea: the real profit is found in the pause. When leaders slow down long enough to ask what is unclear, anxiety drops and performance improves. When they do not, lazy language creates confusion, scattered effort, and quiet burnout. Through stories of broken friendshi...

Most companies do not have a people problem. They have an orientation problem. In this episode, we unpack why smart, capable people feel lost, anxious, and overwhelmed at work, even in healthy organizations. The issue is not motivation or talent. It is a lack of clarity around where someone is in the process and what comes next. We explore why growth creates chaos, why chaos creates anxiety, and h...

Burnout isn’t about working too hard, it’s about not knowing why your work matters . In this episode, we dive into the power of asking the right question: “Does my job matter?” is a lazy question, it seeks reassurance. “Why does my job matter?” is a demanding question, it creates clarity, responsibility, and real meaning. We’ll uncover how purpose shows up in everyday work, why money alone can’t f...

Most disappointment at work doesn’t start with bad intentions. It starts with unclear expectations. This episode explores why teams, relationships, and organizations fall apart when no one defines the rules of the game. Using stories from childhood playgrounds, leadership failures, and real workplace dynamics, we unpack how unclear wins, missing deadlines, and unspoken assumptions quietly turn int...

Great ideas are easy to fall in love with. Turning them into something real is where most teams get stuck. This episode explores the quiet tension between vision and execution, and why so many promising ideas either die too quickly or exhaust the people responsible for making them happen. We unpack a simple but powerful shift: treating ideas as possibilities, not mandates, and separating who you a...

This episode sets the foundation for everything that follows. We start with a simple, uncomfortable question: why are we here? Not as a productivity exercise or a branding hook, but as an honest invitation into better conversations. Most questions are assumptions in disguise. Asking better questions changes how we work, lead, relate, and live. This podcast offers a framework built around seven cor...

Most conflict is not caused by bad intentions. It happens when curiosity disappears. This episode explores a deceptively simple question that changes everything: When was the last time you asked a real question? From a surprising John Lennon and Yoko Ono story to a real-time conflict that forced us to change where we were filming mid-recording (haha), we examine how connection is built or broken i...