[5][6] Prior to joining Zappos, Hsieh co-founded the Internet advertising network LinkExchange, which he sold to Microsoft in 1998 for $265 million.

[13] In 1996, Hsieh started developing the idea for an advertising network called LinkExchange with his college classmates Sanjay Madan and Ali Partovi.

[15] 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.

[18][19][20] After LinkExchange sold to Microsoft, Hsieh co-founded and owned Venture Frogs, an incubator and investment firm, with his business partner, Alfred Lin.

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.

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.

[28] Hsieh loved the game of poker and moved Zappos headquarters to Henderson, Nevada, and eventually to downtown Las Vegas.

[35] 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.

[36] Hsieh was a member of the Harvard University team that won the 1993 ACM International Collegiate Programming Contest in Indianapolis, ranking first of 31 entrants.

Hsieh was known for taking extreme challenges regarding his body, including starving himself of oxygen to induce hypoxia, using nitrous oxide, and fasting to the point where he was under 100 pounds (45 kg).

[51][6] It has been reported that he was visiting family for Thanksgiving, and he either became trapped in a pool shed during the fire,[52] or barricaded himself inside and would not answer the door.

[59][60] The Wall Street Journal reported that according to property records, Hsieh was staying at a house that was possibly owned by a former Zappos employee, Rachael Brown.