The Contractor Roundtable is a free monthly meetup for construction operators who want real conversation with people who actually get it.
In a year that changed everything, Jason and his wife left it all behind and traveled the country.
He walked the Camino de Santiago — a pilgrimage that strips away the noise and forces you to ask what actually matters.
He came home with clarity he hadn’t had in years.
He didn’t want to go back into operations. He wanted to help other construction leaders build what he spent decades learning the hard way.
That’s why Waypoint Advisory exists.
Over 37 years in and around construction. A business he built, grew, and ultimately had to learn hard lessons from. Years inside another company’s operations, identifying gaps and rebuilding structure. And a framework — the 5 Waypoints — built from lived experience on job sites, in payroll meetings, and in the honest moments when a leader has to decide what kind of company they’re actually building.
He works with a limited number of operators at a time. Because this work is personal, and it should be.
