Indiana
Tony Adragna
Business leader. Basketball coach. Husband & dad.
I lead operations for a national vacation company by day and the Greenwood Christian Academy boys' basketball program by night, and I write about what each one teaches me about the other. The best thing on my resume? My wife, Jess and our three kids.
The Coach
Building a program
In 2025 I became Head Boys' Basketball Coach at Greenwood Christian Academy. In our first season together, the we won the sectional championship and advanced to the regional round, playing our best basketball when it counted most.
Basketball has shaped my whole life: point guard and senior-year captain at Southport, almost a decade coaching in the Southport program, and founder of IU Film Room, a film-breakdown site for Indiana basketball fans.
Coaching timeline
- '13 Southport Middle SchoolFirst head coaching job. Broke the school wins record by year three
- '16 Southport High School staffAssistant: scouting, player development, gameplanning
- '19 IU Film RoomFounded a film-study site covering IU basketball
- '25 Greenwood Christian AcademyHead Boys' Basketball Coach
The Business Leader
Leadership is leadership
I'm Senior Vice President of Operations at Keyholder Vacations, where I lead the teams and systems behind our guests' vacations. It is the parent company of where I spent six years as President at DVC Rental Store, the largest Disney Vacation Club point-rental broker in the country.
Everything I know about leading people I learned in a gym first: connect before you correct, communicate with clarity and the right tone, mesh different personalities into one culture, and lead every person the way they need to be led.
Connection first
People don't follow titles. They follow leaders who know them, invest in them, and keep an open door.
Culture is daily
A winning culture doesn't happen by accident. It's built through intentional, consistent action every single day.
Empathy + accountability
Understanding what someone is going through and holding them to a standard aren't opposites. The best leaders do both.
The Family
The home team
I met Jess in the summer of 2007, before my junior year of high school, and finally worked up the nerve to ask her out that winter. We married in May 2015. Growing up alongside my high school sweetheart has been one of the greatest gifts of my life.
Family means everything to me. No matter what else I accomplish, these four will always come first.
Starting five
- #1 JessMy better half in every way. Married May 2015
- #2 Giovanni "Gio"Born 2020. Full of personality, curiosity, and heart
- #3 Luciana "Luci"Born 2021. Marches to the beat of her own drum
- #4 Lorenzo "Enzo"Born 2024. The sweetest, most laid-back addition
From the Blog
Notes on leadership
Lessons from the gym, the office, and everywhere in between.
Leadership Lessons from Curt Cignetti
Nine lessons from Coach Cignetti's candid, transparent approach, from building culture to leading with integrity.
Read post →The Best Quotes From Over 20 Leadership Books
A notes dump from 20+ of the best leadership books I've read: the quotes and lessons that stuck with me.
Read post →How Coaching High Schoolers Has Helped Me Lead a Company
What six years of high school basketball coaching taught me about leading a company: connection, communication, and empathy.
Read post →