He attended the London Academy of Music and Dramatic Art from 1977 to 1980 and received an MBA at Gabelli School of Business of Fordham University.

[5] In 2012, he became general partner at Cranemere, investing in middle market private companies in North America, Germany and Austria.

[7] Crosby has been on philanthropic boards, including the Monterey Peninsula Foundation, a charitable organisation that funds education, health, human services, arts, community and environmental projects.

[11] Before his career in banking and private equity, Crosby gained show business experience at an early age by appearing with his father and family on various Christmas television specials from 1965 to 1977 and at the London Palladium in 1976 and 1977.

He has appeared in several films and television programs, including The Hollywood Palace, Friday the 13th, Riding for the Pony Express, and The Private History of a Campaign That Failed.