This teaching case explores the sport of wakeboarding to examine how its female practitioners need to become entrepreneurial in order to make a living from the sport. Students ponder the financial pressures of becoming a professional female wakeboarder, and how to sustain momentum once one turns professional. The significance and inter-relationship of sponsorship and self-branding/promotion figure prominently. Costs of competing are high in the best of circumstances, and nearly insurmountable without corporate backing. Obtaining such support requires a healthy degree of marketing oneself. The female riders offer a number of anecdotes and recollections providing salience to issues concerning sustainability and gender inequity. Male riders may earn up to four times more on tour than female riders and there is pressure to adapt to the “boys’ club” to advance one's career. Earning a living through involvement in wakeboarding is difficult for women. Models of entrepreneurism are provided to guide student discussion in developing strategies to overcome issues for female wakeboarders making the sport financially attractive for female competitors.