CEO Journeys

Solo episode. No guest. Just me, my story, and why this podcast exists. This show is built on conversations with founders, sales operators, family business owners, and the people who run them. This is the episode where I hand the mic to myself: where I came from, what I've learned along the way, and what made me hit record on this show in the first place. The thread running through every conversation here is the same one running through my own career: the people who win in business, in sales, in marriage, in everything, are the ones willing to look honestly at how they're wired and what it actually takes to grow. That's the conversation I want to keep having, on tape, with people worth learning from. If you've listened to a few episodes and wondered who's behind the questions, this is your answer. If this is your first one, start here. The rest of the show makes more sense once you know where the host is coming from. 

My wife Robin is the calm to my chaos. In this episode, we sit down for the conversation about marriage, mindset, and what it actually takes to keep a household running when one of you is wired like a CEO and the other is not. Robin is a stay-at-home mom to our two daughters, Bethany and Gwen, both 6th graders she homeschools. She runs our household. I run a company. Different jobs. Different temperaments. Same partnership. In this conversation, we go back to where we started. How we grew up. What we learned about growth mindset along the way, and what we got wrong. And what it actually feels like, day to day, to be the easygoing one married to someone running at full throttle. If you're a founder, a CEO, or just a Type-A operator, your spouse has a perspective on you that you don't get to hear out loud very often. This episode is that perspective, and the conversation that comes from finally sitting down to have it on record.

Anthony Bobba the serial entrepreneur! Finance. Insurance. After-intimacy wipes. Yes, really. A serial entrepreneur who's wired to win. Some people sell because they need to. Anthony sells because he can't not. In this episode, he walks us through a career that's moved through finance, insurance, and yes, after-intimacy wipes. The product changes. The operator doesn’t. What makes Anthony interesting isn't the variety. It's what the variety reveals. The category is irrelevant. The competitive instinct is the asset. He picks a market, learns the language, and goes. The win is the win. If you've ever wondered whether great salespeople are made or born, Anthony's case argues for born. Wiring matters. So does loving the scoreboard.

Keith Carley swept the shop floor at Air Compressor Works. Then he ran the company. Then he sold it. The family business arc, told straight. In this episode, Keith walks through what it actually looks like to grow up inside a business his father and uncle built from nothing. The lessons came on the floor: show up early, work harder than anyone else in the room, and the rest sorts itself out. Decades later, Keith took over Air Compressor Works. Years after that, he sold it. The conversation goes where most family-business stories don't: what changes when you stop being the owner and start being the operator inside someone else's structure. Keith is still in the seat, but the equity belongs to a larger partner now. That's a different job. Different incentives. Different conversations at home. If you grew up in a family business, you've thought about the exit. If you're staring down a sale right now, you've thought about it harder. Keith has lived both sides.