Hsieh was born in Urbana, Illinois, to Richard and Judy Hsieh, immigrants from Taiwan who met in graduate school at the University of Illinois. Hsieh's family moved to Lucas Valley area of Marin County, California when he was five. His mother was a social worker, and his father a chemical engineer at Chevron Corp. He had two younger brothers, Andy and Dave. Hsieh attended the Branson School.
In 1996, Hsieh started developing the idea for an advertising network called LinkExchange. Members were allowed to advertise their site over LinkExchange's network by displaying banner ads on its website. They launched in March 1996, with Hsieh as CEO, and found their first 30 clients by direct emailing webmasters. The site grew, and within 90 days LinkExchange had over 20,000 participating web pages and had its banner ads displayed over 10 million times. By 1998, the site had over 400,000 members and 5 million ads rotated daily. In November 1998, LinkExchange was sold to Microsoft for $265 million.
After LinkExchange sold to Microsoft, Hsieh co-founded Venture Frogs, an incubator and investment firm, with his business partner, Alfred Lin. The name originated from a dare. One of Hsieh's friends said she would invest everything if they chose "Venture Frogs" as the name, and the pair took her up on the bet, although they had not seen any money as of 2011. They invested in a variety of tech and Internet startups, including Ask Jeeves, OpenTable and Zappos.
In 1999, Nick Swinmurn approached Hsieh and Lin with the idea of selling shoes online. Hsieh was initially skeptical and almost deleted Swinmurn's initial voice mail. After Swinmurn mentioned that "footwear in the US is a $40 billion market, and 5% of that was already being sold by paper mail order catalogs," Hsieh and Lin decided to invest through Venture Frogs. Two months later, Hsieh joined Zappos as the CEO, starting with $1.6 million of total sales in 2000. By 2009, revenues reached $1 billion.
Without a precedent to guide him, Hsieh learned how to make customers feel comfortable and secure with shopping online. Zappos offered free shipping and free returns, sometimes of several pairs. Hsieh rethought Zappos structure and in 2013 it became for a time a holacracy without job titles, reflecting his belief in employees and their ability to self-organize. The company hired only about 1% of all applicants. Named for the Spanish word for shoes, "zapatos," Zappos was often listed in Fortune as one of the best companies to work for, and beyond lucrative salaries and being an inviting place to work it delivered extraordinary customer service.
On July 22, 2009, Amazon announced the acquisition of Zappos.com in a deal valued at approximately $1.2 billion. Hsieh is said to have made at least $214 million from the sale, not including money made through his former investment firm Venture Frogs.
On August 24, 2020, Hsieh retired as the CEO of Zappos after 21 years at the helm.
Hsieh joined JetSuite's board in 2011. He led a $7 million round of investment in the growing private "very light jet" field with that company. The investment allowed JetSuite to add two new Embraer Phenom 100 jets which have two pilots, two engines and safety features equivalent to large commercial passenger jets but weigh less than 10,000 pounds (4,500 kg) and are consequently highly fuel-efficient.
Real estate rejuvenation projects
Downtown Project - Las Vegas
From 2009 until his death, Hsieh, who was still running the downtown Las Vegas-based Zappos.com business, organized a major re-development and revitalization project for downtown Las Vegas, which had been for the most part left behind compared to the Las Vegas Strip's growth. Hsieh originally planned the Downtown Project as a place where Zappos.com employees could live and work, but the project grew beyond that to a vision where thousands of local tech and other entrepreneurs could live and work. Projects funded include The Writer's Block, the first independent bookseller in Las Vegas.
Park City, Utah
After stepping down as CEO of Zappos in August 2020, Hsieh bought multiple properties in Park City, Utah, with a total market value around $56 million.
Hsieh resided primarily in Downtown Las Vegas, and also owned a house in Southern Highlands, Nevada. Hsieh was known for taking extreme challenges regarding his body, including starving himself of oxygen to induce hypoxia and using nitrous oxide as well as a fasting to the point where he was under 100 pounds. Singer Jewel said that she was aware of Hsieh's extreme drug abuse and sent him a letter months before his death to warn him.
On the morning of November 18, 2020, Hsieh was injured in a house fire in New London, Connecticut, although his identity was not revealed at the time. It has been reported that he was visiting family for Thanksgiving, and he either became trapped in the basement during the fire, or barricaded himself inside and would not answer the door. The exact cause of the fire is currently under investigation. He was rescued by firefighters and transported to the Connecticut Burn Center at Bridgeport Hospital to undergo treatment for burns and smoke inhalation, where he died on November 27, two weeks before his 47th birthday. The Connecticut medical examiner determined that Hsieh died from smoke inhalation, and ruled his death was an accident. News sources have suggested that his drug use and nitrous oxide use may have played a role in his death.
According to property records, the Wall Street Journal reported that Hsieh was staying at a house that was possibly owned by a former Zappos employee, Rachael Brown.