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From 1994 to 2000, Wales was the research director at Chicago Options Associates,[7] a futures and options trading firm in Chicago.[13] By "speculating on interest rate and foreign-currency fluctuations," he had soon earned enough to "support himself and his wife for the rest of their lives," according to Daniel Pink of Wired.[20] During this time, one of the projects Wales undertook was the creation of the web portal Bomis[20] which featured user-generated webrings and that, according to The Atlantic Monthly, "found itself positioned as the Playboy of the Internet."[21] For a time the company sold erotic photographs,[22] and Wales described the site as a "guy-oriented search engine" with a similar market to Maxim.[13] Questions have arisen about the nature of its content.[14][23] Bomis did not become successful, but in March 2000 hosted and provided the initial funding for the Nupedia project.[14][20]

In March 2000, Wales started a peer-reviewed, open-content encyclopedia, Nupedia ("the free encyclopedia"), and hired Larry Sanger to be its editor-in-chief.[13] Nupedia was characterized by an extensive peer-review process designed to make its articles of a quality comparable to that of professional encyclopedias.[24] After Sanger publicly proposed on January 10, 2001, the idea of using a wiki to create an encyclopedia, Wales installed wiki software on a server and authorized Sanger to pursue the project under his supervision. Sanger dubbed the project "Wikipedia" and, with Wales, laid down the founding principles and content, establishing an Internet-based community of contributors during that year. Wikipedia was initially intended to be a wiki-based site for collaboration on early encyclopedic content for submission to Nupedia, but Wikipedia's rapid growth quickly overshadowed Nupedia's development.[7] Sanger worked on and promoted both the Nupedia and Wikipedia projects until Bomis discontinued funding for his position in February 2002;[25] Sanger resigned as editor-in-chief of Nupedia and as "chief organizer" of Wikipedia on March 1.[26][27] Wales has said that he initially was so worried with the concept that he would wake up in the middle of the night, wanting to check the site for vandalism.[28] In the early years, Wales supplied the financial backing for the project.[8] In a 2004 interview with Slashdot, Wales explained his motivations about Wikipedia, "Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge. That's what we're doing."[29]

In mid-2003, Wales set up the Wikimedia Foundation (WMF), a non-profit organization founded in St. Petersburg, Florida, and now based in San Francisco, California.[30][31] Originally chairman of the foundation, Wales has held the honorary title of Chairman Emeritus since 2006. He is now one of eight directors who make up its Board of Trustees.[32] The work he carries out for the foundation has always been unpaid, including his appearances to promote the organization at computer and educational conferences.[22] In a 2007 interview, Wales said that he thought that "donating" Wikipedia to the foundation was both the "dumbest and the smartest" thing he'd done. On the one hand, he noted, Wikipedia was worth US$၃ billion (by his estimation); on the other, donating it made possible the success he achieved.[33]

In March 2008, Wales was accused by former Wikimedia Foundation employee Danny Wool of subsidizing personal expenditures with foundation funds. Wool also stated that Wales had his Wikimedia credit card taken away in part because of his spending habits, though Wales denied this claim.[34] Foundation Chair Florence Devouard and former foundation interim Executive Director Brad Patrick denied any wrongdoing by Wales or the foundation, saying that Wales accounted for every expense and that, for items for which he lacked receipts, he paid out of his own pocket.[35] Later in March 2008, it was alleged by Jeffrey Vernon Merkey that Wales had edited Merkey's Wikipedia entry to make it more favorable in return for donations to the Wikimedia Foundation, an allegation Wales dismissed as "nonsense."[36][37]

In 2004, Wales and then-fellow member of the WMF Board of Trustees Angela Beesley founded the for-profit company Wikia, Inc.[7] Wikia is a wiki farm—a collection of individual wikis on different subjects, all hosted on the same website.[38] Its most popular wikis include Memory Alpha (devoted to Star Trek), WoWWiki (World of Warcraft) and Wookieepedia (Star Wars).[39] Another service offered by Wikia is an open source web search engine named Wikia Search, intended to challenge Google and introduce transparency and public dialogue about how it's created into the search engine's operations.[15] Wales stepped down as Wikia CEO to be replaced by angel investor Gil Penchina, a former vice president and general manager at eBay, on June 5, 2006.[40]

Wales has asserted that he is the sole founder of Wikipedia[12] and has publicly disputed Larry Sanger's designation as a co-founder of Wikipedia, describing the claim as "preposterous" to The Boston Globe in 2006[41] and calling "the whole debate silly" in an April 2009 interview.[42] Sanger was identified as co-founder at least as early as September 2001 by The New York Times[43] and was referred to as a founder alongside Wales in Wikipedia's first press release in January 2002.[44] In August of that year, Wales identified himself as "co-founder" of Wikipedia.[45] In addition to developing Wikipedia in its early phase and guiding the project,[8][11] Sanger was responsible for the idea of applying the wiki concept to the building of a free encyclopedia, and for the name "Wikipedia".[11][46] In a 2005 memoir for Slashdot, Sanger nevertheless ascribed the broader idea to Wales: "To be clear, the idea of an open source, collaborative encyclopedia, open to contribution by ordinary people, was entirely Jimmy's, not mine, and the funding was entirely by Bomis. … The actual development of this encyclopedia was the task he gave me to work on."[47] In response to Wales' view,[48] Sanger posted on his personal webpage many links which appear to confirm his role in founding Wikipedia, all of which described Wales and Sanger as the co-founders.[11][49] In a discussion in March 2007 with Brian Bergstein of the Associated Press, Wales said: "When you write this up please do not uncritically repeat Sanger's absurd claim to be the co-founder of Wikipedia." He added: "I am not bent out of shape about it. The facts are on my side, which is why I bother so little about it."[11] Wales' role in the Wikipedia community has been described as benevolent dictator, constitutional monarch and spiritual leader.[50]

Jimmy Wales 2014 on CeBIT Global Conferences, Wikipedia Zero

In late 2005, Wales edited his own biographical entry on the English Wikipedia. Writer Rogers Cadenhead drew attention to logs showing that in his edits to the page, Wales had removed references to Sanger as the co-founder of Wikipedia.[51] Sanger commented that "having seen edits like this, it does seem that Jimmy is attempting to rewrite history. But this is a futile process because in our brave new world of transparent activity and maximum communication, the truth will out."[23][52] Wales was also observed to have modified references to Bomis in a way that was characterized as downplaying the sexual nature of some of his former company's products.[23] In an article in the July 31, 2006, issue of The New Yorker magazine, Stacy Schiff expanded on this topic, stating that Wales was "caught airbrushing his Wikipedia entry—eighteen times in the past year" and that he was "sensitive about references to the porn traffic on his Web portal".[46] In both cases, Wales argued that his modifications were solely intended to improve the accuracy of the content.[23] He apologized for editing his own biography, a practice generally frowned upon at Wikipedia. Wales said in the Wired interview, "People should not do it, including me. I wish I had not done it."[23]

Wales is a self-avowed "Objectivist to the core", and named his daughter Kira after the heroine in Ayn Rand's debut novel We the Living,[15] although he has said "I think I do a better job—than a lot of people who self-identify as Objectivists—of not pushing my point of view on other people."[60] He ran an electronic mailing list on "Moderated Discussion of Objectivist Philosophy".[61] When asked about Rand by Brian Lamb in his appearance on C-SPAN's Q&A in September 2005, Wales cited "the virtue of independence" as important to him personally. When asked if he could trace "the Ayn Rand connection" to having a political philosophy at the time of the interview, Wales reluctantly labeled himself a libertarian, qualifying his remark by referring to the United States Libertarian Party as "lunatics" and citing "freedom, liberty, basically individual rights, that idea of dealing with other people in a matter that is not initiating force against them" as his guiding principles.[13] An interview with Wales served as the cover feature of the June 2007 issue of the libertarian magazine Reason, in which Wales cited Austrian School economist Friedrich von Hayek's work on price theory and decentralised information The Use of Knowledge in Society as "central" to his thinking about "how to manage the Wikipedia project".[14]