Ron Knauer grew up in a small Indiana town, in a family where no one had gone to college. When more than 70 people applied for an entry-level job at IBM, Ron knew he probably wasn’t the best candidate on paper. So he found another way to stand out.

That instinct followed him for the next four decades.

Ron went from painting parking lot lines at night to building a career in enterprise sales, eventually working on deals worth hundreds of millions of dollars. But underneath the success was something that never really went away: a chip on his shoulder and a need to keep proving himself.

In this episode of The Winding Road Show, Ron looks back at where that drive came from, how it shaped the way he sold and led, the life-changing deal that changed what was possible for his family, and what all those years of chasing the next win look like from the other side.

As Ron puts it: “Why do the same when you can be different and win more?”

John Mattingly took over his family's construction business from his father, grew it from a dozen employees to nearly 600, and built it through the 2008 housing crash that wiped out most of his competitors. By any outside measure, he's made it.

In this episode, John talks about walking away from a promising path in law to join the family business, what actually happened between him and his dad along the way, and the cost of chasing a goal line that keeps moving — $12 million, then $15 million, then $25 million, then $50 million, and never quite "enough." He's honest about what freedom really means once you own something instead of working for someone else, and what he'd tell himself now about slowing down enough to notice it.

The Winding Road is a show for executives near the end of their careers, looking back at the real path that got them there — not the highlight reel, but the detours, setbacks, and reframes that ended up mattering most. Inspired by Wayne Dyer's I Can See Clearly Now.

Udo Rauch studied physics before building a thirty-year career across technology, enterprise sales, and leadership. Almost none of it went according to plan.

In Episode 2 of The Winding Road Show, I sat down with Udo to talk about the opportunities he never expected, the fear of failure that keeps people from taking a different road, and why trying to control every part of your career doesn't work.

We also talked about the motorcycle accident that changed how he viewed his life, his decision to take a year away from business, learning to play Chopin, getting married and having a daughter later in life, and the Elton John story that shaped his attitude toward failure.

Udo Rauch on the Career You Could Never Have Planned

Stephen Kaufman, Chief Strategy and Alliances Officer at Syndigo — a guy who almost became a lawyer like his dad, ended up teaching Macintosh graphics to union print workers, and built a company he sold for over $100 million. We talk about the calls, tips, and chance conversations that kept opening doors he never planned for — and why he's spent his life learning to notice them.