Born in Greenwich, Connecticut to billionaire financier and fund manager Gerald Tsai, and model and actress Marlyn C. Tsai, Tsai attended Brunswick School in Greenwich, Connecticut and graduated in 1993. Tsai began his career in finance at the young age of 11, working for his father, where he was tasked with analyzing investment opportunities for the Tsai family foundation. At age 16, Tsai took a course at New York Institute of Finance on securities analysis.
Tsai attended Vermont's Middlebury College, where he graduated with a Bachelor of Arts degree in Philosophy and International Politics. He is a member of the Middlebury College Arts Council and previously served as a Young Alumni Advisor
Tsai is President and Chief Investment Officer of Tsai Capital Corporation, an SEC-registered, global equity manager headquartered in New York City. He founded the company in 1997 at the age of 22 and serves as Chairperson of the firm's Advisory Committee Tsai has written articles about art as an investment, including commentary in Investment and Pensions Europe "about investing in art as an alternative assets class", and "Back Door to China," specifically advocating investment in Chinese contemporary art, for Worth. Bloomberg, L.P. notes that he "has also been interviewed on Bloomberg Radio, China Money Network, Fox Business, [and] The Street.com TV", and "has written extensively about investing in emerging markets".
In 2014, Tsai launched Tsai Ventures, the venture capital arm of Tsai Capital. CrowdTangle, a Tsai Ventures portfolio company, was acquired by Facebook on Nov. 11, 2016. CrowdTangle is a four-year-old tool used by publishers like Vox, BuzzFeed, and Mic to see what's trending on social media and to track how their content is shared in real-time. Founded in 2012, CrowdTangle had raised $2.2 million in venture funding from Tsai Ventures and other venture capital firms.
Tsai is an avid art collector and first focused on contemporary Chinese art, which he accurately predicted would rise in value. Tsai is the world's largest collector of works by Ai Weiwei.
Tsai attributes his love of art to his father who collected works by Alexander Archipenko, Alexander Calder and Joan Mitchell. Through the Stockamp Tsai Collection, Tsai regularly contributes artwork to museums. These museums have included the Metropolitan Museum of Art in New York, the Pérez Art Museum Miami, the Victoria and Albert Museum in London and the National Gallery of Victoria in Melbourne.
Prior to deciding to build a collection around Ai, Tsai collected contemporary Chinese art broadly, beginning in 2003. Tsai traveled to China and acquired some 50 works by artists including Fang Lijun, Liu Xiaodong, Xie Nanxing, Zhang Huan and Zhang Xiaogang. In September 2004, Tsai published an article in Worth Magazine arguing that contemporary Chinese art was undervalued. In 2005, Tsai reiterated that contemporary Chinese art was undervalued, particularly when compared with contemporary Mexican artists.
Tsai adheres to a well-defined methodology in making art acquisitions, balancing instinct and analysis. Tsai has expressed interest in collecting the work of David Hammons and Berlinde De Bruyckere. Tsai prefers that the artwork he buys stays undervalued for as long as possible. Tsai stated, "It's like buying shares in a company that you know will be worth more in five or ten years. The last thing we want is for the stock to go up as we start buying." Tsai has been critical of art speculators looking to buy art for short-term financial gain.
Tsai is a benefactor of numerous nonprofit organizations, both domestically and internationally. These organizations include the World Monuments Fund, Hirshhorn Museum and Sculpture Garden, The Metropolitan Museum of Art, the Serpentine Galleries and the Solomon R. Guggenheim Museum. Tsai is also a member of the Middlebury College Arts Council, which is a select group of 32 alumni and parents appointed by the president of Middlebury College to work in partnership with the Office of Advancement and the College's arts programs and Museum of Art.
In addition to Tsai being the son of a famous investor, his grandmother, Ruth Tsai, was a pioneer for women in Shanghai. During World War II, she was the only woman to trade on the floor of the Shanghai Stock Exchange until Japanese troops occupied the Shanghai International Settlement on December 8, 1941 and trading was abruptly halted. Tsai is married to André Stockamp.