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From 1994 to 2000, Wales served as research director at Chicago Options Associates, a [[futures contract|futures]] and [[stock option|options]] [[stock trader|trading firm]] in [[Chicago, Illinois|Chicago]].<ref name="qanda">{{
cite news
| author = [[Brian Lamb|Lamb, Brian]]
| title = Q&A: Jimmy Wales, Wikipedia founder
| url = http://qanda.org/Transcript/?ProgramID=1042
| work = [[C-SPAN]]
| date = [[2005-09-25]]
| accessdate = 2006-07-11
}}</ref> 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 (magazine)|Wired Magazine]].<ref name=bookstopshere>{{
cite news
| last = Pink
| first = Daniel H.
| title = The Book Stops Here
| url = http://www.wired.com/wired/archive/13.03/wiki.html?pg=3
| publisher = [[Wired (magazine)|Wired]]
| date = [[2005-03-13]]
| accessdate = 2006-10-09
}}</ref> During this time one of the projects Wales undertook was the creation of the [[web portal]] [[Bomis]], a website featuring [[user generated content|user generated]] [[webring]]s that, according to [[The Atlantic Monthly]], meant the site "found itself positioned as the [[Playboy]] of the [[Internet]]".<ref>Poe, Marshall. "[http://www.theatlantic.com/doc/200609/wikipedia/2 The Hive]". ''The Atlantic Monthly'', [[2006-09-01]]. Retrieved on [[2008-01-15]].</ref> For a time the company sold erotic photographs<ref name=accessforall>{{
cite journal
| last = Brennen
| first = Jensen
| title = Access for All
| journal = Chronicle of Philanthropy
| volume = 18
| issue = 18
| publisher = Chronicle of Higher Education, Inc.
| location = USA
| date = [[2006-06-29]]
| accessdate = 2008-01-16
}}</ref> and Wales described the site as having had "a market similar to say [[Maxim (magazine)|Maxim]] magazine. So it's kind of a guy-oriented search engine".<ref name="qanda"/> Although Wales is no longer connected with the company his involvement with Bomis has been criticised with questions frequently asked about the nature of its content.<ref>{{
cite news
| last = Mangu-Ward
| first = Katherine
| date = June 2007
| title = Wikipedia and beyond: Jimmy Wales' sprawling vision
| journal = Reason
| volume = 39
| issue = 2
| pages = 21
| publisher = Reason Foundation
| accessdate = 2008-01-16
}}</ref><ref name="wirednews">{{
cite news
| last = Hansen
| first = Evan
| title = Wikipedia Founder Edits Own Bio
| url = http://www.wired.com/news/culture/0,1284,69880,00.html
| work = [[Wired News]]
| publisher = [[Wired (magazine)|Wired]]
| accessdate = 2006-02-14
}}</ref> Bomis also provided the initial funding for the [[Nupedia]] project.<ref name=bookstopshere>{{
cite web
| last = Pink
| first = Daniel H.
| date = [[2005-03-13]]
| title = The Book Stops Here
| url = http://www.wired.com/wired/archive/13.03/wiki.html?topic=wiki
| publisher = Wired
| accessdate = 2006-10-09