By now, Alibaba co-founder Jack Ma’s story is the stuff of business legend. He’s a former English teacher who founded the company in his Hangzhou apartment in 1999 and then almost lost it when the first Internet bubble burst in 2002. His company dominates e-commerce in China, but he doesn’t much care for technology. He’s a business celebrity, but at 48 he left the day-to-day management of his sprawling empire to younger talent he called “better equipped to manage an Internet ecosystem like ours.”

Now 50 and worth an estimated $21 billion, according to the Bloomberg Billionaires Index, Jack Ma is getting another closeup by pulling off what may end up the biggest IPO in history when its shares debut on the New York Stock Exchange on Friday. The skinny kid from Hangzhou, with no family connections or even any technical skills (he flunked math) succeeded with sheer determination and doing things his way. As an entrepreneur in China, that meant building his company within the fledgling private sector while steering clear of the strictures and obligations that come from being a state-owned enterprise.

Yet now the same entrepreneur who managed to operate outside of Communist Party confines is raising gobs of money pledging fealty to a new set of masters: the public stock market of the United States, along with the Securities and Exchange Commission that polices it, along with the institutions, analysts and shareholders who clamor for quarterly results, regardless of the long-term plan.

“He is, to employees, a spiritual leader,” said Anthea Yan Zhang, professor at the Jones Graduate School of Business at Rice University. “He will remain a very important figure for Alibaba, but being the leader of a private company is very different [from] being the chair of a public company, listed on the stock exchange in the U.S.”

Shareholders third

And while he’s wooing U.S. investors with a road show spanning the globe, he’s already made his priorities quite clear. “Customers first, employees second, and shareholders third,” he wrote in a letter to investors. It’s a mantra he’s repeated over the years, including during an interview at AllThingsD’s (now Re/code) conference in 2012, when he elaborated, “If the customer is happy, the business is happy, and the shareholders are happy.”

Operating in public will necessarily change the way Ma does business. He could not, for example, simply transfer ownership of $1.7 billion Alipay payments service off Alibaba’s balance sheet as he did to the objection of his biggest shareholders Yahoo and SoftBank, in 2010. Yet those who’ve watched him in action don’t believe he’ll be swayed much by the chattering classes commenting on Alibaba’s open books.

“Jack Ma has a big personality, but he does listen to people’s suggestions; he’s not arrogant,” said Julia Q. Zhu, a former Alibaba exec and founder of Observer Solutions, a China-focused e-commerce advisory firm. That said, she also didn't see him as "a person who will just give up the decision he thinks is right for the company because a shareholder or investor says he should do so.”

Given the complexity of his business itself and the ownership structure, a bet on Alibaba will be a bet on Jack Ma. American investors won't even own Alibaba directly but rather shares in what is called a Variable Interest Entity, which allows Chinese companies in sensitive fields like technology and the Internet to take foreign investment while maintaining total Chinese ownership.

The Alipay decision

Those looking for clues into how Ma will guide Alibaba inevitably go back to that moment in 2010 when he transferred Alipay out of Alibaba to the chagrin of his foreign shareholders. Alipay is the Alibaba-owned payments system that in many ways enabled China’s e-commerce industry by giving consumers the faith to complete purchases online. But it was also a valuable part of Yahoo and SoftBank’s 43 percent stake in the company, and the transfer happened without approval of shareholders or Yahoo’s board.

Financial services are highly regulated by the Chinese government. While shareholders didn’t like it, the move was probably necessary to save it. “If Alibaba had not made that decision, the government might have banned the entire Alipay service,” Zhu said.

“Though it was controversial, they still managed to do it while Alibaba was a private company,” Zhang said. “I don’t think they would be able to do that when it is listed on the New York Stock Exchange.”

One should note that if Yahoo and Softbank were upset about the transfer then, they’re pretty happy with Ma’s strategy now. Both are slated to retain heavy stakes in Alibaba post-IPO, 23 percent for Yahoo and 32.4 percent for SoftBank.

Role model

It’s Ma’s leadership style, rather than his technical prowess, that has gained him fans at home, even among the tech elite on the campus of Tsinghua University in Beijing, a prestigious school often called China's M.I.T.

"He's a role model for a lot of students," said Pan Qingzhong, executive dean of the Schwarzman Scholars, a new program funded by a $100 million grant from the American private equity titan Steve Schwarzman that will bring graduate students from around the world to the Tsinghua campus. "Students love his passion. He's a great communicator. A lot of students try something and then quit. He hasn't quit."

Not lost on Chinese entrepreneurs is how Ma studied and taught English in contrast to the engineering backgrounds of most of his peers. He practices tai chi and claims influences from Buddhism, Taoism and Confucianism.

"His thoughts come from Chinese traditional culture," said Sun Qingfeng, chief executive officer at Shanghai Woo Trading Co., a Shanghai-based designer and manufacturer of silk and cashmere scarves and shawls. He pulled out his iPhone to show a visitor a photo he took of a scroll painting hung from the door of the studio in the lakeside city of Hangzhou -- Ma's hometown -- where the Alibaba founder reportedly practices tai chi.

Ma is also very familiar with the U.S. He famously got his first glimpse of the Internet living with an American family in Seattle in 1995. He’s taken classes at the University of California at Berkeley, where his son is a student, and he owns a home in the Bay Area.

Tilting at the U.S.?

One early question he’ll face once Alibaba is flush with $21 billion or more in cash is how much to invest in expanding to America. On Alibaba’s road show, Ma is promising to become a global company as well as to “expand aggressively” in the U.S.

American e-commerce companies have found China virtually impenetrable; Amazon has spent more than a decade fighting for just 3 percent of the market. But the U.S. presents a similar challenge for Chinese companies. Some critics are already saying that Alibaba has enough to do to grow its business in China’s fast-growing market and defend it from the likes of search giant Baidu and gaming and messaging behemoth Tencent without tilting at a mature market like the U.S.

“I think Alibaba shouldn’t look to go global; there is too much opportunity left in China,” said Joel Backaler, author of the business book "China Goes West." “I think they will try to expand here but the question is at what cost?”

Contributing: Peter S. Goodman in Tianjin, China, and Mark Hanrahan in Hong Kong.