Following an unsatisfactory collaboration, he left the company the next year and went on to develop websites for China’s Ministry of Foreign Trade and Economic Cooperation.

[11] He became interested in learning the English language as a young boy and began practicing it with English-speaking visitors who frequented the Hangzhou International Hotel.

For nine years, Ma rode 27 km (17 miles) on his bicycle every day to work as a tour guide of Hangzhou for foreigners in order to practice his English.

In 1980, while he was riding his bike to practice English with tourists, he met Ken Morley, who was traveling with his family with the Australia-China Friendship Society.

His cousin was hired, but Ma was rejected on the grounds that he was "too skinny, too short, and in general, protruded a bad physical appearance that may have potentially ended up hurting the restaurant's image and possibly tarnishing its reputation.

The following year, Ma remained relentlessly determined to pursue higher education despite strong opposition from his family, who wanted him to choose a different career path as an alternative option.

Having realized his aspirations to pursue higher education after enrolling at Hangzhou Normal University, Ma's academic performance began to improve substantially as he steadily achieved scholarly excellence over the course of his undergraduate studies.

In recognition of his merits as evinced by his burgeoning academic achievements, Ma distinguished himself scholastically by consistently being ranked as among the top five students in Hangzhou Normal University's foreign language department due to the extensive English-language skills that he honed.

In early 1995, he travelled abroad to the United States on behalf of the Hangzhou municipal government with colleagues who had helped introduce him to the Internet.

[24] From 1998 to 1999, Ma headed an information technology company established by the China International Electronic Commerce Center, a department of the Ministry of Foreign Trade and Economic Cooperation.

In 1999, he quit and returned to Hangzhou with his team to establish Alibaba, a Hangzhou-based business-to-business marketplace site in his apartment with a group of 18 friends.

Eventually, Alibaba began to show signs of profitability three years later as Ma wanted to improve the global e-commerce system.

As Ma with his distinct profile stands out among his entrepreneurial contemporaries throughout the Chinese high-technology industry, many of whom typically have a foundational background in computer engineering and science as part of their formal academic training and educational makeup.

Instead, Ma parlayed his educational background to use in an entrepreneurial context by fashioning himself as a promoter, businessman, manager, administrator, and organizer who possessed the soft skills, emotional capacity, and personality with a knack for leading and employing specialists of expert ability from every conceivable technical domain.

In September 2014, it was reported that Alibaba was raising over $25 billion in an initial public offering (IPO) on the New York Stock Exchange.

[32] On 8 September 2017, to celebrate Alibaba's 18th year of its establishment, Ma appeared on stage and gave a Michael Jackson-inspired performance.

He also performed a partial rendition of Elton John's 1994 hit single Can You Feel The Love Tonight while being dressed up as a lead heavy metal singer at a 2009 Alibaba birthday event.

[35] Ma denied reports that he was forced to step aside by the Chinese government[36] and stated that he wants to focus on philanthropy through his foundation.

[40] News outlets noted a lack of public appearances from Ma between October 2020 and January 2021, coinciding with a regulatory crackdown on his businesses.

[42] Ma described state banks as operating with a pawn shop mentality and criticized the Basel Accords as a "club for the elderly.

[42] Ant Group had sought to maintain a position as a technology company, although it was deriving approximately 90% of its revenue from financial services.

[43]: 50  This position brought it into conflict with the People's Bank of China (PBOC), which since 2018 had sought to regulate Ant Group as a financial holding company.

[43]: 51  During the IPO, financial regulators became even more concerned about Ant Group due to its high valuation as a tech company, increasing fears of a bubble.

[41][44] In November 2022, Ma was reportedly living a low profile life in Tokyo, Japan, for nearly six months, and occasionally traveling abroad.

[43]: 261  The Chinese government spoke positively of Ant Group's changes, including describing them as improvements in transparency and accountability.

[51] In 2017, Ma made his acting debut with his first kung fu short film Gong Shou Dao, directed by Wen Zhang and produced by Jet Li.

The film stars Ma, Li, Donnie Yen, Wu Jing, Tony Jaa, Jacky Heung, Asashōryū Akinori, Zou Shiming, and Natasha Liu Bordizzo.

[52][53][54] In November 2020, in the finale of Africa’s Business Heroes, Ma was replaced as a judge in the television show, with Alibaba executive Peng Lei taking his place, reportedly "Due to a schedule conflict".

[80][81][82] On 24 September 2014, in an interview with Taobao, Ma attributed the strength of American society to the country being rooted in its Judeo-Christian heritage and expressed his belief in the importance for China to implement a positive value system in order to overcome the aftermath and legacy of the bygone Cultural Revolution.