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.

]]>https://thewindingroadshow.com/Riverside.fm (https://riverside.com)Sat, 05 Sep 2026 08:28:38 GMTThu, 03 Sep 2026 16:04:10 GMT60Brad Habansky<p>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.<br /><br /><br />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.<br /></p>episodicBrad Habanskybradhabansky@me.comnoFirst up: 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.

]]>7f681585-4e2d-402c-9ea3-347a35cfd19cThu, 03 Sep 2026 16:09:29 GMT<p>First up: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/stephentkaufman/" target="_blank"><b>Stephen Kaufman</b></a>, Chief Strategy and Alliances Officer at <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/company/syndigo/" target="_blank"><b>Syndigo</b></a>, 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.</p>no00:45:43Stephen Kaufman on the Detours That Built a Careerfull