I just finished an excellent biography of Ayn Rand and her philosophy in the context of American political culture. While reading, I couldn't help think of Wales' expressed interest in Objectivism and the next to the last page actually comments on this issue:
One of the many ironies of Rand's career is her latter-day popularity among entrepreneurs who are pioneering new forms of community. Among her high-profile fans as Wikipedia's founder Jimmy Wales, once an active participant in the listserv controversies of the Objectivist Center. A nonprofit that depends on charitable donations, Wikipedia may ultimately put its rival encyclopedias out of business. At the root of Wikipedia are warring sensibilities that seemed to both embody and defy Rand's beliefs. The website's emphasis on individual empowerment, the value of knowledge, and its own risky organizational model reflects Rand's sensibility. But its trust in the wisdom of crowds, celebration of the social nature of knowledge, and faith that many working together will produce something of enduring value contradict Rand's adage "all creation is individual." (Burns 2009, p. 284)