CEO Journeys

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.