Employees cycle past the headquarters of Chinese e-commerce giant Alibaba Group in Hangzhou, East China's Zhejiang Province, June 25, 2014. Photo: IC

Softbank President Masayoshi Son (left) hugs Alibaba Group Chairman Jack Ma Yun during the Softbank World 2014 annual forum in Tokyo on July 15, 2014. Photo: AFP

Masayoshi Son's nose for an investment has turned a $20 million start-up punt on Alibaba into a stake worth maybe $50 billion or more as the Chinese e-commerce giant co-founded and led by Jack Ma Yun heads to what could be the biggest US tech IPO of all time.

Son, CEO of Japanese telecoms firm SoftBank Corp, also put money into a young Yahoo Inc, co-founded by Jerry Yang, in 1995, and Yahoo's subsequent investment in Alibaba saw Ma, Son and Yang build Alibaba Group Holding Ltd into one of the world's biggest Internet companies as China's e-commerce market took off.

Under pressure from investors, Yang quit Yahoo in early 2012 and gave up his seat on Alibaba's board. He is now a founding partner of AME Cloud Ventures, a San Francisco venture fund.

But this month, the three poster boys for Asian technology entrepreneurship, bound by a shared ambition and a taste for sushi and golf, are set to be reunited on Alibaba's board following the firm's long-awaited New York IPO.

For potential IPO investors, the reunion - Yang will be an independent director, while Son will be a director and Ma the executive chairman - is likely to further tighten Ma's control over the company as Son and Yang tend to follow his direction, former Alibaba, SoftBank and Yahoo insiders said.

SoftBank has a 34 percent stake in Alibaba, and Yahoo owns 23 percent. Son has said SoftBank doesn't plan to sell down its Alibaba stake in the IPO, while Yahoo may sell up to about 16.5 percent of Alibaba.

"Mr Ten Times"

The son of a pachinko parlor operator, Son has risen to the top of Forbes' Japan rich-list, forging SoftBank into a tech titan worth $84 billion, making it Japan's second-most valuable listed company behind Toyota Motor Corp.

SoftBank increased its stake in Yahoo in 1996, buying into the US firm's IPO to become its primary shareholder. The stake has since been whittled down to almost nothing, but the two remain Yahoo Japan Corp's biggest investors, each holding more than one-third of the Japanese firm.

In 2000, Son met Ma, an elfin and outspoken former English teacher from Hangzhou, capital of East China's Zhejiang Province. The two, who often joke about being both short and smart, according to a person close to Son, saw each other as kindred spirits. Their shared drive helped Alibaba grow from just 18 people working out of an apartment to a company with more than 22,000 employees and global ambitions.

David Wei, a former CEO of alibaba.com and co-founder of Vision Knight Capital, recalled how he nicknamed Son "Mr Ten Times."

"Every time I explained any business plan or model, Masa's first reaction was to say, 'David, can this be 10 times bigger?'" said Wei. "In the cases I managed to answer, he would ask again, 'What about 10 times more?'"

When Ma first heard that Son was in China sniffing out potential investments, he e-mailed him and snagged some brief "face time." After just five minutes of listening to Ma riffing on his vision, Son extended the meeting and ended up investing 2 billion yen (about $20 million at the time) in Ma's company.

When Alibaba launched its Taobao consumer-to-consumer marketplace in 2003, Son donated his wristwatch to be sold on the new site and, as the pair met more frequently, Ma developed a love for Japanese food.

Yahoo joins in

Ma first met Yang in the late 1990s, when he was working for the government and acted as Yang's official guide to the Great Wall. By 2005, their friendship had developed and the idea of Yahoo investing in Alibaba came up.

Yang contacted Ma at the prompting of senior Yahoo executives who were trying to figure out how best to get a foothold in the China market, said a former Yahoo executive familiar with the Alibaba transaction.

"Jerry was reluctant at first because it was very difficult to do business with Chinese entrepreneurs," he said. "(Yang and Ma) spent a lot of time together, they had to get to know each other, build a relationship."

Ma kept Son in the loop in the months running up to Yahoo's investment.

The final decision - with Yahoo buying a 40 percent stake in Alibaba for more than $1 billion - was made at a Pebble Beach golfing retreat.

Son, who can also show a domineering streak, was reluctant to reduce the size of his valuable Alibaba "insider" stake by selling to Yahoo, but Ma eventually won him over.

"The only place where there was a challenge (to Ma) was about taking the initial investment from Yahoo. Son's biggest point was that he didn't want to sell anything to Yahoo," said another person whose firm invested in Alibaba. "As part of that deal insiders had to sell 40 percent of their stake, and Masa fought that tooth and nail."

With Yahoo on the board and its money and China operations in Alibaba's hands, the Ma, Son and Yang triumvirate envisioned an alliance between their three companies that could one day knock Google out of China, said people close to them.

However, while Yang's investment in Alibaba was lauded as one of his best decisions at Yahoo, the stake was big enough to rankle Beijing, which feared the US firm held too much sway over Alibaba, people familiar with the matter said.

Yahoo China's search engine was subject to local restrictions in line with official policy overseeing the Chinese Internet.

Ma and Yang, however, remained close even after Ma split Alipay, an online payment subsidiary, from Alibaba in 2011 without the board's approval, said people who know the two men. Yang was reluctant to challenge Ma over the move, sitting on his hands rather than addressing the issue, the people said.

More recently, Yang has been instrumental in helping Alibaba get a foothold in Silicon Valley as the Chinese group increases its overseas investments.

He introduced Alibaba to Tango, a mobile messaging app-maker in which he was already invested. Alibaba later paid $215 million for a stake.

Son, too, has supported Ma - who sits on SoftBank's board - particularly when Alibaba last year traded blows with the Hong Kong Stock Exchange over a controversial listing structure.

Having his two key allies back on Alibaba's board will further cement Ma's grip on the company even as the IPO opens Alibaba up for outside investors.