Bomis, Inc. (/ˈbɒmɪs/, from Bitter Old Men in Suits;[14] rhyming with "promise")[15] was a dot-com company best known for supporting the creations of free-content online-encyclopedia projects Nupedia and Wikipedia.

[20] The site subsequently focused on content geared to a male audience, including information on sporting activities, automobiles, and women.

[27] Bomis created Nupedia as a free online encyclopedia (with content submitted by experts) but it had a tedious, slow review process.

[33] Since Wikipedia was a drain on Bomis' resources, Wales and philosophy graduate student Larry Sanger decided to fund the project as a nonprofit.

[31][45] Jimmy Wales left a study track at Indiana University as a PhD candidate to work in finance before completing his doctoral dissertation.

[2][28] Wales co-founded Bomis in 1996,[53] with business associates Tim Shell,[5][24][32] and his then-manager Michael Davis,[16][17][18] as a for-profit corporation with joint ownership.

[17][27] Its 2000 staff included programmer Toan Vo, Andrew McCague and system administrator Jason Richey;[17] Wales employed his high-school friend and best man in his second wedding, Terry Foote,[47][48] as advertising director.

[60] The most successful time for Bomis was during its venture as a member of the NBC web portal NBCi; this collapsed at the end of the dot-com bubble.

[21][22][23] Working from the Open Directory Project,[66] Bomis created and maintained hundreds of webrings on topics related to lad culture.

[73] Sheila Jeffreys noted in her Beauty and Misogyny that in 2004 Bomis maintained "The Lipstick Fetish Ring", which helped users with a particular attraction to women in makeup.

[24][75] Advertising generated revenue which enabled the company to fund other websites,[5][76][77] and the site published suggestive pictures of professional models.

[4][57] The website included a segment devoted to erotic images, "Bomis Babes",[6][7] and a feature enabled users to submit recommended links to other sites appealing to a male audience.

[46] Peer-to-peer services provided by the site helped users find other websites about female celebrities, including Anna Kournikova and Pamela Anderson.

[40] Wales referred to the site's softcore pornography as "glamour photography",[36][43][45][80][81] and Bomis became familiar to Internet users for its erotic images.

[82][83][84] During this period Wales was photographed steering a yacht with a peaked cap, posing as a sea captain with a female professional model on either side of him.

[1][60][85] A subscription section, Bomis Premium,[4] provided access to adult content and erotic material;[5][24][25] A three-day trial was US$2.95.

[16] Larry Sanger met Jimmy Wales through an e-mail communication group about philosophy and objectivism,[12][20][58] and joined Bomis in May, 1999.

[95] At that time, Bomis was attempting to obtain advertising revenue for Nupedia[94] and the company was optimistic that it could fund the project with ad space on Nupedia.com.

[34][101] Nupedia was encumbered by its peer-review system,[28][29] a seven-step process[91][99] of review and copyediting,[12] and Wikipedia grew at a faster rate.

[88] Although Wales thought advertising was a possibility, the Wikipedia community was opposed to business development[17][42][104] and Internet marketing was difficult in 2002.

[109] The Wikimedia Foundation board of trustees was initially composed of Bomis' three founders: Jimmy Wales and his two business partners, Michael Davis and Tim Shell.

[58][95] In November 2004 he told the St. Petersburg Times he no longer controlled Bomis' day-to-day operations, but retained ownership as a shareholder.

"[8] Larry Sanger said, "It does seem that Jimmy is attempting to rewrite history",[6][25] and began a discussion on the talk page of Wales' biography about historical revisionism.

"[30][39] Bomis was called the "Playboy of the Internet" by The Atlantic,[42] and the sobriquet was subsequently used by publications including The Sunday Times,[43] The Daily Telegraph,[33] MSN Money,[118] Wired,[119] The Torch Magazine,[99] and the 2007 book The Cult of the Amateur by Andrew Keen.

[44] Wales considered the "Playboy of the Internet" nickname inappropriate,[119] although he was asked in interviews if his time at Bomis made him a "porn king".

[120][122] Wales, interviewed in the film, called the characterization inaccurate and explained that his company responded to content demand from customers.

"[31] Jeff Howe wrote in his 2008 book, Crowdsourcing: How the Power of the Crowd is Driving the Future of Business, about "one of Wales's less altruistic ventures, a Web portal called Bomis.com that featured, among other items, soft-core pornography.

"[45] In his 2008 book, The Future of the Internet and How to Stop It, legal scholar Jonathan Zittrain wrote that "Bomis helped people find 'erotic photography', and earned money through advertising as well as subscription fees for premium content.