In graduate school, Wales taught at two universities; he departed before completing a PhD to take a job in finance and later worked as the research director of Chicago Options Associates.

Wales serves on the Wikimedia Foundation Board of Trustees, the charity that he helped establish to operate Wikipedia, holding its board-appointed "community founder" seat.

[4] His father, Jimmy Sr.,[5] was a grocery store manager, while his mother, Doris Ann (née Dudley), and his grandmother, Erma, ran the House of Learning,[6][7] a small private school in the tradition of the one-room schoolhouse, where Wales and his three siblings received their early education.

"[5][10] During an interview in 2005 with Brian Lamb, Wales described his childhood private school as a "Montessori-influenced philosophy of education", where he "spent lots of hours poring over the Britannica and World Book Encyclopedias".

As an adult, Wales was sharply critical of the government's treatment of the school, citing the "constant interference and bureaucracy and very sort of snobby inspectors from the state" as a formative influence on his political philosophy.

[16] He said that the school was expensive for his family, but that "education was always a passion in my household ... you know, the very traditional approach to knowledge and learning and establishing that as a base for a good life.

During his studies in Alabama, he had become an obsessive player of Multi-User Dungeons (MUDs)—a type of virtual role-playing game—and thereby experienced the potential of computer networks to foster large-scale collaborative projects.

[16][19] Inspired by the successful initial public offering of Netscape in 1995, and having accumulated capital through "speculating on interest-rate and foreign-currency fluctuations",[6] Wales decided to leave the realm of financial trading and became an Internet entrepreneur.

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.

[18][22] Though Wales argued that his modifications were solely intended to improve the accuracy of the content,[22] he apologized for editing his biography, a practice generally discouraged on Wikipedia.

[22][55] In a 2004 interview with Slashdot, Wales outlined his vision for Wikipedia: "Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge.

"[56] Although his formal designation is board member and chairman emeritus of the Wikimedia Foundation, Wales's social capital within the Wikipedia community has accorded him a status that has been characterized as benevolent dictator, constitutional monarch and spiritual leader.

[63] Despite involvement in other projects, Wales has denied intending to reduce his role within Wikipedia, telling The New York Times in 2008 that "Dialing down is not an option for me ... Not to be too dramatic about it, but, 'to create and distribute a free encyclopedia of the highest possible quality to every single person on the planet in their own language,' that's who I am.

[82] 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.

[87] On November 4, 2011, Wales delivered an hour-long address at The Sage Gateshead in the United Kingdom to launch the 2011 Free Thinking Festival on BBC Radio Three.

[92] The topic of discussion was "the age of participation" and the ability of an increasingly large number of citizens to "express their own opinions, pursue their own educations, and launch their own enterprises."

Wales exhorted young people to use social media to try to bring about societal change, and compared government suppression of the Internet to a human rights violation.

[94] In 2017, Wales announced that he was launching an online publication called WikiTribune, to fight fake news through a combination of professional journalists and volunteer contributors.

[98][99][100] Wales founded the charity after receiving a prize from the leader of Dubai, which he felt he could not accept given the strict censorship laws there, but claims he was not allowed to give back.

"[103] When asked by Brian Lamb about Rand's influence on him in his appearance on C-SPAN's Q&A in September 2005, Wales cited integrity and "the virtue of independence" as personally important.

[107] In 2016, Wales and eleven other business leaders signed on to an open letter to American voters urging them not to vote for Donald Trump in that year's presidential election.

[108] In May 2017, Wales said on Quora that he is a centrist and a gradualist, and believes "that slow step-by-step change is better and more sustainable and allows us to test new things with a minimum of difficult disruption in society.

[111][112] Wales cites Austrian School economist Friedrich Hayek's essay, "The Use of Knowledge in Society", which he read as an undergraduate,[18] as "central" to his thinking about "how to manage the Wikipedia project".

[8] Wales reconsidered Hayek's essay in the 1990s while reading about the open source movement, which advocated for the collective development and free distribution of software.

He was particularly moved by "The Cathedral and the Bazaar", an essay which was later adapted into a book of the same name, by one of the founders of the movement, Eric S. Raymond, as it "opened [his] eyes to the possibilities of mass collaboration.

"[18] From his background in finance, and working as a futures and options trader, Wales developed an interest in game theory and the effect of incentives on human collaborative activity.

[114]: 85–90 On May 14, 2014, Wales strongly reacted to the European Court of Justice (ECJ)'s ruling on the right of individuals to request the removal of information from Google's search results.

[116] The May 2014 ECJ ruling required swift action from Google to implement a process that allowed people to directly contact the corporation about the removal of information that they believe is outdated or irrelevant.

"[125] In November 2019, Wales accused Twitter of giving preferential treatment to high-profile figures such as Trump and Elon Musk for not banning or blocking them for their controversial statements.

"[130] During the COVID-19 pandemic, Wales stated on Wikipedia that the consensus in the mainstream media surrounding the lab leak theory seemed to have shifted from "this is highly unlikely, and only conspiracy theorists are pushing this narrative" to "this is one of the plausible hypotheses.