Episode 267

FROM THE WALL TO WINTERGREEN

In this episode

In this episode of the GreatBase Tennis Podcast, Steve Smith sits down with longtime friend and coach Ryan Fleming for a reflective and practical conversation about tennis, coaching, and leadership. Fleming shares his journey from hitting on a cinder block wall in North Carolina to playing college tennis for Chuck Kriese at Clemson, and eventually finding the GreatBase system, which reshaped his technique, mindset, and career.

They discuss the frustrations of not being taught the fundamentals earlier, how hitting left-handed changed Ryan’s perspective, and the transformative power of clear, fact-based instruction. Ryan also shares insights from his time managing over 100 coaches at TennisBloc and his new role as Director of Racquet Sports at Wintergreen Resort in Virginia. The episode closes with programming ideas for Wintergreen, thoughts on doubles as a development tool, and the value of teaching players and coaches how to truly improve.

show notes

In this episode of the Great Base Tennis Podcast, Steve Smith speaks with Ryan Fleming, a former player turned coach with a remarkable journey through the sport. Ryan shares how his tennis story began in the mountains of Western North Carolina, where he developed his game by hitting for hours against a cinder block wall—an early expression of persistence and passion that would define his career.

The conversation traces his path to Clemson University, where a chance encounter with coach Chuck Creasy led to his recruitment and collegiate career. The demanding environment at Clemson shaped Ryan’s philosophy around athleticism, mental toughness, and preparation—principles that have guided his professional and coaching endeavors.

Ryan reflects on the challenges of life on the professional tour and how injury shifted his focus toward coaching. He discusses how unique training approaches, such as practicing with both dominant and non-dominant hands, influenced his adaptive style and emphasis on mental strategy. Over the years, he has embraced evolving methods in coaching, culminating in the creation of Tennis Block—a program dedicated to providing coaches and players with clear pathways for growth and development.

The episode also highlights Ryan’s new role as director of the Wintergreen Racket Sports Department. His vision emphasizes community engagement, blending pickleball and tennis under one umbrella while ensuring high-quality instruction across all levels of play.

This conversation captures Ryan Fleming’s dedication to fostering talent, his belief in lifelong learning for coaches and players, and his commitment to building a supportive tennis community.

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