Wang Xiaolai was a member of the merchant elite originally from the Ningbo area and rose to hold numerous prominent social, political and financial positions during and beyond Republican-era Shanghai. He was born into one of the wealthier families of Shengxian County (嵊縣), today’s Shengzhou County (嵊州), in the northeastern province of Zhejiang. His traditional family background and home-tutored classical Chinese studies would have had him continue along the scholar-gentry trajectory as he passed in 1898 the first degree of imperial examinations of the Qing dynasty, xiucai (秀才).
The changes in political regimes and social landscapes of the late Qing Empire however, would have Wang Xiaolai decide differently. He became a member of the anti-Manchu Restoration Society, the Guangfuhui (光復會) and after the Anqing uprising in 1907 sought refuge in Shanghai where, as a merchant, he engaged in the commerce of tea, silkworms and silk to name a few of his early activities. In 1915, Wang Xiaolai was one of the seven founding members of the Shanghai Commercial and Savings Bank, along with Chen Guangfu (陳光甫).
As president of the Zhabei Chamber of Commerce, and then chairman of the powerful Shanghai Chamber of Commerce, in which he served for fifteen years, he was in a central position to interact not only with Chinese Chambers of Commerce from all provinces across the country but also with visiting European and North American Chambers of Commerce and Trade delegations. His leading position as a Shanghai entrepreneur, with close ties to the Guomindang (KMT) and the Green Gang, Qing Bang (青幫), put him at the very heart of the financial, industrial and business networks of Shanghai.
In 1926, at the request and invitation of the Guangdong National government, Wang Xiaolai travelled to Canton as the representative appointed by the Shanghai General Chamber of Commerce to secure for the government the support of the Shanghai merchants. Indeed, he was a key Shanghai figure in the negotiations and mediations with the Canton merchants.
He also endeavored to improve the life of the ordinary man by not only promoting but actively participating in charitable works, such as in the construction of the Zhixiang Hospital (芷湘醫院) in Zhejiang, which he had funded and built in 1919 with his brothers; it stands today as one of the principal hospitals in the province. He played a major role in the boycott against Japanese goods in 1931-32, was the chairman of the Chinese Ratepayers' Association, and one of the 19 members appointed to the Shanghai Municipal Council.
In 1949, after having taken refuge in Hong Kong when the communists arrived in Shanghai, Wang Xiaolai returned to Shanghai upon the invitation of Zhou Enlai to continue his efforts in China’s course toward renewal and modernity.