Photo via Born Rich
In 1987, a 20-something Roman Abramovich married his first of two wives, Olga Yurevna Lysova. Here's how Wikipedia describes their short-lived union (they divorced in 1990):
A 2,000-ruble wedding present from Olga's parents (about £1,000 or $2,000 at that time) was invested by Abramovich in smuggling of black market goods or contraband to sell in Moscow in or around December 1987. Abramovich soon doubled, then tripled, the investment, his confidence growing with each success in this smuggling business. Soon he progressed to making plastic toys (including plastic sailors) and started up an automobile parts cooperative. He attended the Gubkin Institute of Oil and Gas in Moscow (where he sold retreaded car tires as a sideline), then traded commodities for Runicom, a Swiss trading company.
In 1988, as [the political movement] Perestroika opened up opportunities for entrepreneurs in the Soviet Union, Abramovich got a chance to legitimize his underworld business. He and Olga set up a company making dolls. "It brought success almost immediately," says Olga. Due to his business acumen, within a few years his wealth spread from oil conglomerates to pig farms and he also started investing in other businesses. Abramovich set up and liquidated at least 20 companies during the early 1990s, in sectors as diverse as tire retreading and bodyguard recruitment.