(CNN) -- Entrepreneur and media mogul Jimmy Lai is not afraid of a challenge. He took on Hong Kong media barons to set up his publishing company in 1981 and provoked the wrath of the Chinese government when he spoke out against the 1989 Tiananmen Square crackdown against pro-democracy protesters.
On topics ranging from China to the economic crisis, Jimmy Lai opened up to CNN's Talk Asia.
Despite taking on such formidable opponents, he continues to run a successful publishing company in Hong Kong and Taiwan and remains outspoken defender of a free press and freedom of speech.
"I think when you are not free you don't have dignity. And to me it's not a political issue whether you have democracy or what, it's a moral issue," he told CNN from his offices in Hong Kong.
These days the Chinese Government tend to turn a blind eye to Jimmy Lai, but his criticism of them post Tiananmen -- calling then prime minister Li Peng a "turtle's egg" (an unpleasant insult in China) in an editorial -- precipitated his downfall in the clothing business.
After the controversy he had to sell his stake in Giordano, the clothing company he set up in 1975 or risk the closure of all his shops in mainland China. It cost him millions in lost business opportunities.
He's suffered other business failures; a shopping web site set up during the first dot.com boom was one of a number of causalities when the bubble burst.
Lai, however, remains philosophical about money.
"I think I'm a bit different to other people because I'm actually from a very rich family so I had the riches, I had the sense of it. I was never insecure about money. I was very poor, but I never felt sorry."
Hailing from southern China, Lai's family was wealthy but marginalized by the communist government. After working as a railway porter boy, Lai dabbled in the black market before being smuggled into Hong Kong when just 12 years old, taking a job as a child laborer and earning just over $1 a month.
"You know I was free. I was full of hope. When I saw people in a Rolls Royce, in a Mercedes Benz, there was no envy, there was no jealousy, there was just hope that one day I was the one that will sit there," he told CNN.
"You know the opportunity is there. You know that it is open for you. That was a wonderful society. You know that if you try hard, you will get it."
Lai's can-do attitude and the heady free-market environment have proved to be a winning combination.
However, Lai insists that freedom to make money is not the only thing that inspires him to run his publishing company. He remains politically aware and often an outspoken critic of China at a time when many try a more diplomatic policy of engagement.
"It's the dictatorship that rubs me up the wrong way. It's the freedom that we, the Chinese people, are not allowed to flourish. I think when you are not free you don't have dignity. And to me it's not a political issue whether you have democracy or what, it's a moral issue," he said.
Optimistic, determined, sometimes contrary, Lai is committed to pursuing his business interests in Hong Kong and Taiwan, as both value the freedom of press. He believes Taiwan will be a "very powerful catalyst that will change China".
"In China you have a vacuum of moral infrastructure...It's just the free market and the government. So if the market fail and the government is dragging down with it, what is hold the whole society up?" he said.
"I think if China has to make decisions to take measures which are so painful, without the mandate of the people they can't do it. That will be the beginning of a new China. China will have to go through a political restructuring."