Husband & Father
I met Jessica in the summer of 2007, heading into my junior year of high school. We talked here and there through the summer and fall, and that winter I finally decided to shoot my shot and ask her out. Best shot I ever took. We married in May 2015, and growing up alongside my high school sweetheart has been one of the greatest gifts of my life.
In February 2020, after a painful pregnancy loss and months of trying, we welcomed our first child, Giovanni. Gio is full of personality, curiosity, and heart. Luciana followed in December 2021, and her personality is second to none; she marches to the beat of her own drum and we wouldn't have it any other way. Our third, Lorenzo (Enzo to everyone who knows him) arrived in August 2024 and has been the sweetest addition: laid back, expressive, and quickly developing his own little personality.
Family means everything to me. No matter what else I accomplish, they will always come first.
Business Leader
Entrepreneurship is in my blood. My dad has owned and operated his own house painting business my entire life (and still does!). My own first venture came at age four, when I'd put on a suit and tie, take people's rocks out of their driveways, then knock on their door and sell them their rocks back for a penny each. Closing rate: surprisingly high.
In 2019 I joined DVC Rental Store, the largest Disney Vacation Club point-rental broker in the United States, to run digital marketing, and kept raising my hand for more until I was overseeing operations too. In 2020, in the middle of a pandemic that froze the travel industry, I was named President. Leading a team of more than 20 people through that season taught me more about leadership than any book could, though I read plenty of those too.
In January 2026 I stepped into a new challenge as Senior Vice President of Operations at Keyholder Vacations, where I lead the people, processes, and systems that power our guests' vacations.
Basketball Coach
I grew up a point guard at Southport High School, on one of the best high school basketball scenes in the entire country. Three years on varsity, captain my senior year, and a basketball junkie ever since. At Indiana University I majored in sports broadcasting to stay close to the game, covering IU basketball as a student journalist, including rushing the court after The Shot against Kentucky.
I started coaching at Southport Middle School in 2013 at age 23. My first team won three games. By year three, we broke the school's wins record. From there I moved up to the Southport High School staff, assisting across grades 7-12: practices, scouting, player development. I stepped away after the 2019 season to focus on family and career, and scratched the basketball itch by founding IU Film Room, a site dedicated to breaking down film on IU basketball.
In 2025, I got the call I'd been waiting for: Head Boys' Basketball Coach at Greenwood Christian Academy. In our first season together, the Cougars won the 2026 IHSAA Class A sectional championship and advanced to regionals, playing our best basketball when it mattered most. We're just getting started.
Why I Write
This site is where the two halves of my life meet. Coaching made me a better executive; leading a company made me a better coach. I write about leadership: the lessons in the books, the ones in the gym, and the ones my kids teach me for free.
Want to talk leadership, coaching, or hoops? Email me at antadrag@gmail.com or find me on X at @CoachAdragna.