Every conversation starts with a story.

One of ten kids raised by a widowed mother in Mississippi, Gregory has reinvented himself across four industries. He started in auto finance — with Nissan Motor Acceptance, and helped stand up Infiniti Finance when the brand launched — then pivoted into ministry at 33, taking a 60-person church in East Tennessee and, over 25 years, building it into the largest-attended congregation in the Tri-Cities at more than 2,200 people a Sunday. In 2018 he helped a billionaire friend raise $56.6M for an orphanage — bringing in Jack Nicklaus, Gary Player, Peyton Manning and Dan Marino for what became the highest PGA-endorsed fundraiser in history. Then Amazon called. At 57 he started a last-mile logistics company from zero, got his CDL, and today runs an Amazon Delivery Service Partner business with more than 200 employees and a monthly payroll north of $600,000.

Gregory learned to hunt — and, as he tells it, learned to be a man — from the successful businessmen of his boyhood church, who kept a 3,000-acre hunting lease in Mississippi and took him and his four younger brothers into the woods after his father died. Six decades on, the outdoors is still where he resets and where he studies his craft: bird hunting behind pointing dogs, fly fishing the Watauga and South Holston near his East Tennessee home, drifting the Gunnison and the Yellowstone, chasing pheasant in South Dakota and quail at Rio Piedra in South Georgia. He reads biographies and autobiographies constantly, keeps a cigar case loaded with Liga Privadas, and treats a world-class lodge less as a vacation than as a service clinic to reverse- engineer for his own drivers.

Gregory is proof that reinvention isn't reserved for the young — and that the leap only works when it's paired with a plan. He's blunt about the mechanics: faith without a strategy is just a wish, you can't steer a car that isn't moving, and "potential" is the one word he won't let his team use because it means you want it for someone more than they want it for themselves. He gave up an established Austin territory to rebuild his whole company from scratch when Amazon wouldn't transfer him home, laid awake nights sure he'd fail, and did it anyway — because people who didn't make big moves never lived big lives. Underneath the operating lessons is a quieter one he found in marriage counseling: that a man surrounded by a big, close family can still have no one safe to brag to, and that building that circle on purpose is the work.