“In the media business, it’s important to make sure your content is fresh,” says Jimmy Lai Chee-ying, chairman of Next Media, Ltd. The Hong Kong entrepreneur is doing just that, as he keeps taking risks and reinventing himself. Spirited into Hong Kong from mainland China when he was 12, Lai worked his way up the job ladder at a garment factory, in due course becoming plant manager. By speculating in the stock market, he turned bonus money into enough cash to start his own clothes-making operation, which eventually became Giordano, a wildly successful casual clothing manufacturer and retailer with stores across East and Southeast Asia. The company became the subject of a 1990 HBS case study.

In 1989, Lai branched out into the media world, starting up Next, an irreverent Cantonese-language magazine that quickly clicked with the public. Six years later, he rolled out Apple Daily, a liberal broadsheet aimed at working-class readers that shook up the more established newspapers, forcing them to scramble to compete. In 1999, Lai dabbled in the Internet, setting up Admart, an online grocer that failed, losing $140 million in just six months. Last year he decamped to Taiwan, a bigger and more competitive market for Chinese-language media. Lai plans to invest $15.5 million to publish a new Mandarin-language magazine, which he predicts will overshadow his Hong Kong readership in five years.

Throughout his journey from refugee to mogul, Lai has been a maverick, consistently criticizing the Chinese government and openly supporting the pro-democracy movement in Hong Kong and the mainland. He isn’t afraid to swim against the current and try new things. “The only way to innovate is through trial and error,” he explains, noting that one of his biggest blunders was to get caught up in the Internet craze with Admart. “I just lost the prudence a businessman should have,” he confesses. “I wouldn’t have gone so deeply into it if the market hadn’t given us such crazy valuations. It was unreal.” Going forward, says Lai, “the Internet will be just an extension of what we do. Our anchor will still be the print medium.”

After Taiwan voters ended more than a half-century of one-party rule in presidential elections last year, Lai knew he had to move to the island. Taiwan, he says, “is the only democracy in Chinese culture.” A fervent promoter of press freedom, he believes that mainland China is on the verge of its own political awakening. “What is happening in Taiwan will have a great impact on China,” he predicts. Leave it to Jimmy Lai to want to be where change is happening the fastest — and where the risks are sky-high.

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