Jack Ma
Illustration by Tracie Ching for TIME

Jack Ma, The Capitalist

The Alibaba founder combined an entrepreneur’s ambition with political savvy in China to pull off the biggest Wall Street debut in history

By Rana Foroohar

When the opening bell of the New York Stock Exchange rang out on Sept. 19, it marked the biggest IPO the world had ever seen — bigger than Facebook’s or General Motors’. This new Wall Street juggernaut, based 7,000 miles away in Hangzhou, China, is Alibaba. Its founder and chairman, 50-year-old Jack Ma, is now challenging some of the most powerful companies on the Internet, including Amazon, eBay and PayPal. And he is doing so by melding Western entrepreneurship with a canny—and sometimes controversial—sense of how to profit in the world’s most populous nation.

As with so many Chinese enterprises, comprehending the enormity of Ma’s creation requires thinking on a different scale. Alibaba is used by more than a third of China—some 500 million people—making it easily one of the largest e-commerce companies in the world. Those customers come to Alibaba to shop in the electronic malls it operates, where some 8.5 million merchants, large and small, ply their goods.

Increasingly, Chinese pay for those goods—and conduct all kinds of other transactions—using Alipay, a PayPal-like service affiliated with Alibaba that is now one of China’s most important financial entities. In fiscal year 2014, Alibaba generated $8.5 billion in revenue, nearly half of it profit. And Alibaba’s $25 billion IPO made Ma one of the world’s wealthiest individuals.

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But even those figures obscure the significance of Alibaba’s rise and the extent to which it has been propelled by Ma’s deft understanding of how to do business in his homeland. Since it began in 1999 by linking Chinese manufacturers with foreign and domestic buyers, Alibaba has played a crucial role in China’s digital opening to the West. Having previously worked in the Ministry of Trade, Ma was able to ensure support from the Communist Party government and take on bigger competitors in China’s private sector. His innovations were not just technical but also diplomatic and strategic.

Like many Chinese, Ma comes from almost nothing: he is the son of traditional storytelling performers who taught himself English by tagging alongside tourists at a local hotel. Later he became a teacher and traveled to the U.S. Searching the World Wide Web for information on Chinese beer and coming up dry, he vowed to bring China online, at a time when only 1% of the population was on the web.

A few years later, Ma started Alibaba in his apartment with 17 friends. His first employee was his wife, who now looks after the couple’s two children. Zhang Yin has claimed that she fell for Ma despite his unexceptional looks because he had the capacity to do things other men couldn’t. Friends have also been drawn to that ambition. “Jack had the biggest dreams of anyone I’ve ever known,” says Porter Erisman, an American adman who left his job at Ogilvy & Mather in Beijing to work for Ma early on. “You’d come up with a goal, and he’d immediately ask you to triple it.”

A consummate spinner of corporate narrative, Ma is full of Shaolin-monk-style sound bites. “eBay is a shark in the ocean. We are a crocodile in the Yangtze,” he famously proclaimed. “If we fight in the ocean, we will lose. But if we fight in the river, we will win.” Ma claims to base his management technique on Chinese martial-arts teachings, encouraging employees to adopt nicknames from kung fu novels. (His own, Feng Qingyang, is a nod to an aggressive master swordsman.)

Like the best martial artists, he is capable of turning weakness into strength. In the years before Alibaba went public, for instance, Ma leveraged his freedom from Wall Street pressure on quarterly earnings to keep his site free for a long time, building market share. Obliged to show shareholders progress on profit margins, eBay watched as Alibaba scooped up business.

Ma became more enmeshed with Silicon Valley in 2005. That’s when Yahoo, run by founder Jerry Yang at the time, decided to buy a large stake in Alibaba for $1 billion. Yang, who first met Ma at the Trade Ministry, told Time that he remembered him as “highly curious about the Internet industry and obviously very entrepreneurially minded.” Yahoo wanted a piece of Alibaba because of its market position in China, but also because of Ma.

Yahoo wanted a piece of Alibaba because of its market position in China, but also because of Ma.

The marriage fell apart, though, as Ma tangled with Yahoo’s new management. As Alibaba’s market share took off, it became clear that he’d given away too much of his company for far too little. “If he had waited even a year, Jack would have gotten a lot more,” says Gary Rieschel, a venture capitalist who ran the Japanese conglomerate SoftBank’s investments in Asia outside of Japan, including Alibaba, from 2000 to 2009. He eventually gathered together a group including local princeling investors close to the party elite to buy out half of Yahoo’s stake.

Those relationships are a reminder that Ma couldn’t have produced his achievements without Beijing’s approval. His ties to the party apparatus are a key advantage over foreign rivals, which don’t compete on the same playing field in China’s closed Internet ecosystem. Alibaba operates not only in retail but also in heavily state-dominated and -protected areas like finance. (When Alibaba started offering money-market accounts, $90 billion poured in.)

That’s good not only for Ma and Alibaba but also for the Communist Party. China has come under increasing criticism for its closed financial sector, which holds the private savings of citizens in state-owned banks at minuscule interest levels, then taps that money for state-run projects—many of which have floundered as China’s growth has slowed. Allowing someone like Ma to offer even a slightly better interest rate without real reform helps placate ordinary citizens in a nation where the ruling elite is mindful of the potential for social unrest.

Yet Ma’s skill in co-opting government support has exacted a price, particularly as he seeks both capital and customers on a global stage. He came under media fire, for example, for a 2013 interview with the South China Morning Post in which he appeared to suggest that the government’s actions in the 1989 Tiananmen massacre were justified. Ma’s media representative says the reporting was incorrect and the journalist “misunderstood” his statement. Ma has also said he thought a controversial decision a decade ago by Yahoo to turn over personal information about a Chinese journalist to the Chinese government was justified because “local laws must be obeyed.”

Those forays into seemingly authoritarian views—and a circumscribed approach to shareholder rights—set him apart from some of his counterparts in Silicon Valley. “The thing you have to remember about Jack Ma is that he is a proxy for a certain set of party interests. If the ruling cadres in Beijing didn’t want Alibaba to exist, it wouldn’t,” says Anne Stevenson-Yang, a co-founder of J Capital Research, an independent financial-research firm specializing in China.

Apart from the issue of Alibaba’s independence from Beijing, a more fundamental question looms: Can Ma replicate his Chinese success elsewhere? While it’s unlikely that many Americans or Europeans will do their Christmas shopping on one of Alibaba’s websites anytime soon, Ma is almost certain to use some of his cash hoard to start acquiring Western media and entertainment properties.

Apart from the issue of Alibaba’s independence from Beijing, a more fundamental question looms: Can Ma replicate his Chinese success elsewhere?

Alibaba will also try to grab the dominant market position in other emerging economies like Brazil, India and Russia. Back in China, Alibaba is planning to launch a Chinese version of Netflix and has announced expansions into consumer credit, insurance and mobile apps.

That puts Hangzhou’s homegrown giant in competition with basically all the U.S. Internet heavyweights. Ma says he want to build not an empire but rather an ecosystem, which is less likely to be toppled. Either way, he isn’t looking to bide his time or hide his brilliance, as an old Deng Xiaoping proverb recommends.

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