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Cheong also gained attention in the watch community through sharing his insights and perspectives online. For years he has exchanged thoughts and opinions with manufacturers and other collectors on websites such as WatchProSite, ThePuristS, and Horomundi Horology-Switzerland. Cheong was part of the first team of unpaid Internet columnists in Timezone.com, and thePurists.com. Although he has never worked in the industry, his knowledge anthology in the field—its history, models, brands and technology—goes beyond that of many professionals, and the Internet has helped him gain influence.

In 2011, Cheong was appointed the first non-commercial ambassador for the Fondation de la Haute Horlogerie.

In April 2008, investigative French journalists from Economie LeHepDo Paris described Cheong as one of the hidden influences in an already highly covert industry. He was to become part of the formative committee of the Grand Prix Haute Horology in Asia, and later a juror in the Geneva GPHH.

Cheong's horologic pursuits went from collecting and reviewing, to a phase of influencing the market, through being a moderator for Harry Winston Inc, in 2003 to 2005. His next step was influencing the watchmaking industry itself, after having built a collection dating from 1975 to 2003. He bought watches that were art pieces, and not trade-named pieces, which were at that time, considered more as liquid assets. Subsequently, he became renowned for creating public interest in what he coined as “independent watch makers”, whose focus was making watches from their own perspectives and desires, rather than for market demands. Because of his efforts, he was unwittingly integrated into the industry and given due recognition, and lauded as a “personality”. Television appearances followed, on channels such as Discovery Channel and CNN, amidst other international channels from Germany, France, China and Japan.

To some, Cheong is a "pioneering customer of the unique, academic, often controversial and almost always misunderstood". Cheong helped formulate the transparent jury system, and, a new carefully audited and numbered voting system for Grand Prix d'Horlogerie de Geneve in 2002, a contest among high-end watch manufacturers. Subsequently, he also helped to bring the annual Grand Prix d'Horlogerie de Geneve to Asia. He is the first non-industry “civilian” chairman of the board, as well as one of the eight jurors from around the world.

Cheong first came under the spotlight in 1998, when he acquired the most expensive watch made by a then-unknown watchmaker, Vianney Halter. This was part of the Goldpfeil Independent Watchmaking Project, where artists made watches for Goldpfeil. It was priced at US$98,000, and called the “camera”. Cheong considered it the most outstanding piece, and gambled that he had spotted what he felt to be a real artist. Later in 2004, he would also acquire Halter's personal watch, then called the Halter Barnes watch, for US$189,000. In return for Cheong's continued support of him starting from when he was still relatively unknown, Halter thanked him in his speech when he won the Best Watchmaker Prize at the Grand Prix d’Horlogerie de Genève in 2011: “Every day, Bernard Cheong shows on various Internet forums that you don’t have to be mad to like my work. Although it does help! He clearly transmitted a little of this madness to the jury, for which I am grateful”.

Since 1998, Cheong has regularly been invited to speak at financial conferences about wristwatches as portable assets. He was well rewarded for his work of investing in innovative and obscure brands, which later became mainstream and increased in value, such as his Panerai collection. He reportedly finds watches to be much more promising, lasting and meaningful investments than wines, cars or jewelry. Subsequently, he has been sought after by watch collectors, connoisseurs, reviewers and investors to name the "next new wave". His focus on investing and sometimes vague connections to the watchmaking industry are however not always well-received within the collectors community, for example causing many stirs on the well-respected PuristPro forums.

Although he is a partner of Lifeline Medical Group, one of the largest medical groups in Singapore, Cheong is better known as an active party animal among high society circles as an eclectic watch collector and horologist, and is often seen at events with his wife, Dolly Ong, whom he married in 1989. In 2003, he was listed in Asia Tatler’s Top 300 list.

Cheong became a medical doctor in 1982 after receiving a degree in medicine and surgery from NUS in Singapore. His earlier days were spent practicing medicine in hospitals in Singapore, and India. He subsequently became a specialist medical officer in emergency medicine, orthopaedics, paediatrics, and internal medicine before he resigned to set up his own firm. In 1987, he founded Lifeline Medical Group (YTL Community), which he expanded into one of Singapore's five largest medical groups during his twenty-three years as CEO and partner. There are currently nine general practitioner clinics, and one aesthetic clinic, and cooperative associations with nineteen specialists under the Lifeline Medical Group chain.

Throughout the 1980s and 1990s, as Cheong grew his business, he expanded his watch collection, particularly those of academic and cultural relevance. In 1993, he directed his attention to marine chronometers and military clocks from 1940 to 1945, and in the following year, trained himself with a focus on pocket watches and their historical significance. His close friendships with innovative watchmakers, such as Rolf W. Schnyder, Vianney Halter, Maximillian Busser and the late Gunther Blumlein, in his early years of collecting gave him an unusual heritage of connections deep within the watch industry.

Cheong began watch collecting in 1973, when his parents gave him a Flyback Seiko Chronograph.

Bernard Cheong (born April 10, 1958) is a watch collector and horologist, medical doctor, and the CEO and partner of Lifeline Medical Group (YTL Community), in Singapore. Cheong was appointed the first collector and non-watchmaking industry ambassador for the Fondation de la Haute Horlogerie in 2011, a foundation in Geneva, Switzerland to promote and develop fine watchmaking internationally.