Jimmy May

Built Under Pressure: A Navy SEAL’s Mindset

He served, he sacrificed, and then he came home to a world that didn't know what to do with him. So he built something that did. In this conversation with Trixy Castro, Jimmy May talks about the hardest transition any veteran faces — and how he turned it into a movement.

Why Winning Doesn’t Fix You

From homelessness to eight company exits across tech, fintech, healthcare, and payments, Jeremy Lessaris turned survival instinct into a repeatable playbook, then had to unlearn the part of it that was quietly running his life. He sat down with Trixy Castro to break down the difference between builders and operators, and the exact moment success stops solving your problems and starts creating new ones.

Built Through Adversity

He earned the nickname 'The Human Highlight Film' on the court — but 15 seasons of navigating injuries, trades, and rebuilds left a story that no highlight reel ever captured. He sat down with Trixy Castro to finally tell it.

Built Beyond Sacrifice

She took Division I tennis discipline into a brand-new arena — building Brow Arc from one location to 30+ nationwide, then launching a clean beauty line on top of it. In this conversation with Trixy, Flora breaks down the single mindset that made all three possible.

Built on Trust

For decades, Mickey Segal has been the person Hollywood's biggest names call when it matters most — not their agent, not their lawyer, but Mickey. In this conversation, he tells the story he's never told publicly.

The Doctor Who Changed the Model

She had the degree, the training, and a clear path through conventional medicine — and she chose something harder. In this conversation with Trixy Castro, Dr. Kristin Oja explains why building Stat Wellness meant questioning everything she was trained to do, and why that was the most courageous clinical decision she ever made.

NASCAR's Next Rookie of the Year

Rookie of the Year at Hickory, a NASCAR Truck Series debut, an Xfinity Series ride — on paper it reads like a fast track. What it leaves out is a kid from Palm Beach Gardens with no racing family, who turned karting into a career on preparation alone, with his father Tony in his corner the whole way. He sat down with Trixy Castro to finally tell it.

Obsession Over Perfection

He's cooked in some of the world's most demanding kitchens — and every one of them shaped a philosophy he's now building an empire on. In this conversation with Trixy Castro, Freddy Money breaks down what obsession over perfection actually looks like from the inside.

What Sales Really Teaches

She started as a sales rep and rose to CEO of Cydcor — one of the most enduring names in direct sales. But Vera Quinn will tell you the most important things she learned about leadership, she learned in the field. In this conversation with Trixy Castro, she makes the case that sales is the best education a CEO can get.

The Man Behind the Ice Cream Everyone's Talking About

By 2025 he was a Harvard Business School case study, his ice cream was in Walmart and Albertsons nationwide, and Snoop Dogg was his partner. What that skips is the decade before it — a Wisconsin grad learning brand strategy on a retail floor, with one earlier snack venture behind him before Happi Co. ever took off. He sat down with Trixy Castro to finally tell it.

Built for Something Bigger

He was never the starter, not on the basketball team, not in the band whose shows he booked. So he named his first company Sixthman, put 400 fans on a cruise with Sister Hazel in 2001, and turned it into roughly 150 sailings before selling to Norwegian Cruise Line. Sitting down with Trixy Castro one hour before 4,600 guests arrived at his newest venue, Andy explains why the best thing he has built is the thing that no longer needs him.

Surrender as Strategy

He built one of the most widely used prayer apps in the world — and the key to making it work was the lesson every entrepreneur resists: surrender. In this conversation with Trixy Castro, Matt Potter breaks down why letting go isn't a weakness and how surrender became the sharpest strategy in his toolkit.

Handcrafted Comeback

He lost everything — and then built two companies at the same time. ShortBarrel Whiskey and DMC Atlanta didn't happen in spite of his lowest point. They happened because of it. In this conversation with Trixy Castro, Adam Dorfman tells the story of the comeback nobody saw coming.