Robbe Pearson earned seven letters from 1986 to 1989 in soccer and tennis, captaining two years on the tennis team. Robbe was often named Prep Athlete of the Week and earned conference and All-State recognition in soccer. Robbe helped Cedarburg High School appear in its first state soccer tournament during his senior year and held scoring titles with 23 goals and 18 assists. 

After high school, Robbe attended and competed in soccer and tennis at West Point Prep School. While at West Point Prep, he lettered four times in soccer, was named MVP as a sophomore, was twice named All-Conference Athlete, and served as captain his senior year. He was recognized as Male Athlete of the Year in 1990 and was recently honored as West Point Soccer Captain of the Decade for the 1990s.

After his military career, he became a member of the 1996 Milwaukee Rampage, the 1997-98 Milwaukee Wave, the 2000 National Open Cup Vice Champion Bavarian Soccer Team, and the 2001 US National Amateur Cup Champion Bavarian Soccer Team.

In 2008 Robbe received a Master’s degree from Kellogg School of Business at Northwestern University.