The economic structure of the industry of cycling coaches has yet to be the subject of any apparent published inquiry. This study describes the basic characteristics of practicing cycling coaches and presents economic models of the determinants of commercial success for individual coaches. Data were collected through an independent survey of current and former U.S.A. Cycling (USAC) coaches in 2010 (N = 386). Results of ordinary least squares and negative-binomial regression models suggest that coaching and competitive experience are associated with larger clienteles, but formal human capital investments do not generally add to a coach’s ability to garner more clients. Additionally, the study also explored the effects of reputation and experiential learning by using three subgroups of sport levels for dependent variables (i.e., recreational, developmental, and ProAm). These client groupings displayed different patterns of associated coach characteristics.