Robinson left basketball partly on the advice of his Princeton coach Pete Carril and pursued a business degree, earning an M.B.A. in Finance from the University of Chicago Graduate School of Business in 1992. Robinson worked in the 1990s as a bond trader. He became a vice president at Continental Illinois Bank and worked there from 1990 to 1992. He was then a vice president, from 1992 to 1999, at Morgan Stanley Dean Witter. Later, he was a managing director and partner at Loop Capital Markets, a minority-owned boutique investment banking firm.