Holeman advanced through the East Coast ranks and took many NSSA and Eastern Surfing Association titles before he turned pro in 1984, receiving the rookie of the year award.
He started John Holeman Surf School in Satellite Beach to coach other surfers. In August of 2021, Holeman renamed his surf school to Air360 Surf School. Holeman currently works with beginners to intermediate surfers. Holeman is now retired from surf coaching.