PlanetOut's biggest online competitor is Gay.com, also based in San Francisco. Both have attracted venture capital. PlanetOut last fall pulled in $16.4 million from America Online, Mayfield Fund and others during a second round of financing. This spring, Gay.com nailed $23 million from investors including Chase Capital Partners and Times Company Digital, a unit of the New York Times Co.

It was there that she first met PlanetOut founder Tom Rielly. A former marketing executive in Silicon Valley, Rielly got an early version of PlanetOut running on the Microsoft network after receiving seed money from AOL. By August 1996, he and his small and very young team of 20 employees and contractors were facing a critical deadline: Within three weeks, they were going to launch PlanetOut on AOL.

PHOTO, Color, Audrey Shehyn for USA TODAY; PHOTO, Color, James Kegley for USA TODAY; Caption: 'Wicked smart': [Megan Smith], CEO of PlanetOut, graduated from the Massachusetts Institute of Technology with engineering degrees before helping to launch the Web portal for gays and lesbians. Conferring: Megan Smith, right, talks with Deanne Loonin of Boston at PlanetOut's booth at the Millennium March in Washington, D.C.