As a basketball player for the University of Wisconsin in the late 1980s, Trent Jackson was in on the beginning of the transformation from Big Ten doormat to Final Four contender. Following a basketball career in Europe, he served as CEO of the Boys and Girls Club and later founded the ROUGH Foundation and ROUGH Sportswear to help athletes and other youth through their journeys, no matter how rough. (Jackson is senior director of development at the UW Foundation.)