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Why Jack Ma's Second Act Will Be Tougher Than His First

Alibaba's Jack Ma thumped eBay and has the world's biggest e-commerce site. Now, he's looking to whup Silicon Valley.
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In the aftermath of the recent U.S. election, as notables from near and far (and really far) made their pilgrimages to Trump Tower hoping to figure out what this most unexpected presidency might look like, these two made the oddest of couples: the tall, elaborately coiffed president-elect and the elfin CEO of the most famous company in China, a country candidate Donald Trump had repeatedly excoriated on the campaign trail as a trade villain.

In the extraordinary life of Ma Yun, known to most people in the West as Jack Ma, this meet and greet on steroids was yet another of many extraordinary moments. Ma, the founder and executive chairman of the Alibaba Group, had come to Manhattan to tell Trump he wanted to help American entrepreneurs sell their goods directly into China—using, of course, his e-commerce site to connect buyers to sellers. As Ma was speaking to the assembled press, Trump at one point leaned into the microphone and chirped, “He loves this country.”

A few seconds later, Trump realized he might have erred. Proclaiming to the world that the most globally visible businessman in a country run by an authoritarian regime that is, at best, a strategic rival of Washington’s “loves” the United States might not be good for Ma back home. So Trump, towering over his tiny counterpart, awkwardly interjected, “He loves China too,” as Ma grinned but said nothing.

That the two men hit it off that day—and friends of each say they did—is not surprising. Ma, like Trump, is brash and blunt, by the standards set for Chinese businessmen, out there.” Every year, for example, Ma hosts an annual meeting of “Aliren” (Alibaba people) from all over the world at the company’s headquarters in Hangzhou, about 100 miles south of Shanghai. Employees and customers alike come to hear Ma evangelize for the brand. And evangelize he does, making impassioned speeches about what the company has accomplished each year, as well as what it has failed to do. He invites celebrities and politicians and businesspeople. Arnold Schwarzenegger came while he was governor of California. I’ve seen Ma ably translate a Q&A session with then–U.S. Ambassador to China Jon Huntsman, and I’ve seen him share that stage with the CEO of eBay, a company he gleefully drove out of China when Meg Whitman (now running Hewlett-Packard) was in charge.

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