Li cut his deal-making teeth building Star TV into Asia's first satellite broadcasting service with a loan from his father, Asia's richest man Li Ka-shing. He then sold it to global media tycoon Rupert Murdoch's News Corp for US$950 million in 1995 and turned his attention to the Internet.
He sparked a frenzied buying spree for Hong Kong technology stocks in April 1999 when he announced he would turn sleepy telecommunications equipment distributor "Tricom Holdings" into Asia's premier Internet company under the name PCCW.
The stock had recorded a 1,286 percent gain in a single day.
Since then, his business acumen and background easily won him a US$12 billion loan in 2000 to help buy Cable & Wireless HKT.
On August 2000, Li was seen as a saviour when his flagship PCCW outbid rival Singapore Telecommunications for HKT in a US$28.5 billion deal, Asia's largest corporate takeover, he was dubbed "Superboy" by the local media.
However, as local euphoria surrounding HKT's takeover waned and global tech and telecom shares tanked, shareholders' praise soon turned to criticism.
Li suffered embarrassment on March 2001 when a newspaper revealed he had never earned a degree from California's prestigious Stanford University, contrary to PCCW's claims.
He endured another setback on February 2003 when PCCW made an approach to acquire Britain's Cable & Wireless, which was rebuffed. PCCW later denied making a formal offer, which has led to an investigation by the Hong Kong stock exchange.
Li gave up his spot as PCCW's chief executive officer on July 25, 2003 but remains as chairman and executive director. Jack So, who left his chairman position at Hong Kong subway operator MTR Corp, took up the job of group managing director of PCCW.
Li is a governor of the World Economic Forum for Information Technologies and Telecommunications, a member of the Center for Strategic and International Studies' International Councillors' Group in Washington DC, and a member of the International Advisory Board of the Center for International Development at Harvard University.
He is also a member of the Global Information Infrastructure Commission and the United Nations Information and Communication Technology Advisory Group.