Waylon was ranked as the #1 junior tennis player in the United States and represented the country in Junior Davis Cup and Junior Grand Slam Competition. By 15, he was competing in professional tournaments and continued his career at the University of Illinois. Next at the University of Miami (Florida) as the #1 ranked singles and doubles player.

Waylon was an inaugural partner of GR8-Group, an innovative company that creates one-of-a-kind products in the ultra-high end luxury travel and experiential industry. He helped grow the company into the leading business in its industry with corporate clients that include members of the Fortune/Global 500 such as American Express and UBS.

After GR8, Waylon transitioned into the venture capital and real estate business full time, where he has completed transactions totaling more than $50 million. Waylon currently serves on the board of Splyce (now part of OverActive Media), one of the world’s leading eSports organizations. He also serves on the board of GR8-Group and the Miami Venture Capital Association.