Jarrett Chirico had a racket in his hand at three years old. By 11, he was at the Bollettieri Academy on a full scholarship. By 16, he was the top-ranked junior in America, playing all four Junior Grand Slams.

Today he builds racquets programs at private clubs and turns them into the highest-revenue departments in the building. He took Baltimore Country Club from $7,000 a month to nearly $100,000. He grew Royal Oaks Country Club from $1 million to over $2.5 million a year in racquets revenue, without raising prices. In 2022, he founded the Directors Club of America, a network of over 1,300 leaders across 400+ clubs.

In January 2026, Jarrett moved to North Hills Club in Raleigh to take on his next challenge: 22 tennis courts, 6 pickleball courts, and 3 padel courts.

In this conversation, we get into:

• Growing up at Bollettieri, playing Grand Slams, and the decision not to go pro
• Playing World Team Tennis for the Philadelphia Freedoms, coached by Billie Jean King
• The $7K-to-$100K turnaround at Baltimore Country Club and the $1M-to-$2.5M run at Royal Oaks
• Building the largest pickleball program in the Northeast (1,000 players a week) and pioneering clay court pickleball
• Why his crossover rates hit 80%+ when the industry average is 30%
• Founding the Directors Club of America and building a network of 1,300 directors
• The move to North Hills and what padel looks like from a director's chair

If you run programs at a club, manage a racquets facility, or want to understand what separates the best directors in the country from everyone else, this one's for you.

ABOUT COURTSIDE

CourtSide is a podcast about the business side of racquet sports. Long-form conversations with the owners, directors, and head pros shaping tennis, pickleball, padel, and squash. Hosted by Evan Dechtman, founder of TopSpin Digital.

New episodes every two weeks. Subscribe so you don't miss one.

Want to be a guest? Book your spot: https://topspindigital.co/courtside/book

Email Evan directly: evan@topspindigital.co

Full show notes: https://topspindigital.co/courtside

TopSpin Digital: https://topspindigital.co

HEARD Digital Marketing: https://heardmarketing.io

CONNECT WITH JARRETT CHIRICO

The Directors Club of America: https://www.thedirectorsclubofamerica.com

North Hills Club: https://www.northhillsclub.com

LinkedIn: https://www.linkedin.com/in/jarrett-chirico-dca-b7712649

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