India, Aug. 23 -- In the 80s, Jackie Shroff was one of the most popular and bankable young actors around. With hits like Hero, Karma, Ram Lakhan, and Tridev, he was among the few stars who could command the masses. But in the 90s, as younger stars took over, Jackie began to take on more supporting roles. He even saw near-financial ruin when his home production, Boom, was a bomb at the box office. Yet, by the mid-2000s, Jackie was among the richest men in Bollywood. And it was not by appearing on camera, but through some extremely smart investment.

In 1994, after the Union Government announced the New Economic Policy of globalisation and liberalisation, international players entered the Indian cable television market. Many media conglomer...