He graduated from the University of Toronto with the highest honours in his class, and received the university's Governor General's Award for his thesis. He enrolled at the Massachusetts Institute of Technology to begin doctoral studies in engineering. In 1967, he completed a PhD in astrophysics from MIT.
In 1967, after completing his PhD, Sherman purchased the Empire Group of Companies from the executor of the estate of his aunt and uncle, Beverley and Louis Lloyd Winter, as both had died 17 days apart in November 1965, leaving four orphaned young children: Paul Timothy, Jeffrey Andrew, Kerry Joel Dexter, and Dana Charles. Empire had been the first to secure the compulsory rights to manufacture Hoffmann-La Roche's Valium (diazepam) in Canada, and was one of Canada's largest manufacturers of Pfizer's Vibramycin (doxycycline), Upjohn Company's Orinase (tolbutamide), and the dietary sweetener saccharin. The estate allowed Sherman to buy a majority stake in the company and run it only on the condition that the four Winter children be allowed to work for the company when they reached 21, with the option to buy 5 percent stakes in the company two years later, with 15-year royalties on four of its patented products. The agreement would be voided if Sherman sold Empire.