The Winding Road Show

Brad Habansky
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Every episode, we sit down with an executive near the end of their career to trace the real path that got them there, not the highlight reel, but the layoffs, detours, and unplanned turns that ended up mattering most. Inspired by Wayne Dyer's idea that there are no wrong roads to anywhere, each conversation is a guided look back: what a guest thought success would look like starting out, the moment that changed everything, and the pattern they'd tell their younger self to watch for.

Episodes

  1. 3d ago

    Udo Rauch on the Career You Could Have Never Planned

    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

  2. Sep 3

    Stephen Kaufman on the Detours That Built a Career

    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.

  • 2 Episodes

About

Every episode, we sit down with an executive near the end of their career to trace the real path that got them there, not the highlight reel, but the layoffs, detours, and unplanned turns that ended up mattering most. Inspired by Wayne Dyer's idea that there are no wrong roads to anywhere, each conversation is a guided look back: what a guest thought success would look like starting out, the moment that changed everything, and the pattern they'd tell their younger self to watch for.

Information

  • Creator
    Brad Habansky
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © 2026 Brad Habansky
  • Show Website
    The Winding Road Show