Yet as often as not, Selvin came away empty-handed in meetings with potential investors. Many venture capitalists just weren't ready to stake money on Gay.com.
"We got calls from analysts and reviewers saying 'Your metrics are incredible, but there were one or two partners in the room who were fearful, homophobic, or whatever and made the decision not to invest,"' he recalled.
Four years later, successor firm PlanetOut Partners has grown to four gay- and lesbian-oriented sites and just posted its first profitable quarter. With backing from J.P. Morgan, Flatiron Partners and America Online, as well as advertising from dozens of Fortune 500 companies, the company dominates its niche in a way any high-tech entrepreneur would envy.
Still small by corporate standards — last year, it had revenues of $14 million, with first-quarter earnings of $103,000 equal to what Wal-Mart makes every seven minutes — PlanetOut's success is about more than dollars, backers say.
It has created a business both gay enough for San Francisco and buttoned-down enough for Wall Street.
"These folks at PlanetOut didn't get into this business to become overnight millionaires," said Jerry Colonna, a J.P. Morgan partner who sits on PlanetOut's board of directors and was its first major investor. "They did it because of a deep and abiding passion for creating a successful gay-owned business — and proving that being gay-owned doesn't necessarily mean not successful."
Headquartered in San Francisco's Financial District, in corporate digs that once housed The Gap's online division, PlanetOut Partners is the result of Gay.com's 1999 acquisition of competitor PlanetOut.com. At the time, Gay.com was known primarily for its chat rooms, while PlanetOut carried more original content.
Today, both sites still have their own personalities - Gay.com is the saucy "Queer As Folk" to PlanetOut's more sentimental "Will and Grace" — but offer a similar mix of news, online matchmaking, health and financial advice. Thanks to the acquisitions of OutandAbout.com and Kleptomaniac.com, the sites also offer information about gay-friendly travel destinations and merchandise such as muscle T-shirts, condoms, and DVD's.
The company owes its status partly to the fact that gays and lesbians tend to be particularly active Internet users and more comfortable than heterosexuals with shopping and dating online.
"The draw for me was that it was a way to get 'out' in the community without really risking anything," said Suzanne Armstrong, 33, a PlanetOut.com member from the Canadian city of Calgary who uses the site to meet other women and to get the latest gay news. "It's generally expected that if I am a woman, then I should be looking for a man. So how do you approach someone who you have never met and find out what their sexual preference is without getting beat up?"
The company's two principal sites have 6.9 million registered members, numbers Selvin says make PlanetOut the world's largest media company serving the gay and lesbian market. With its reach and specialized audience, the company has more in common with broadcasters like Black Entertainment Television or Spanish-language network Telemundo than fellow Internet portals like women-oriented iVillage or the now defunct Third Age, which targeted seniors, says Chief Financial Officer Jeff Soukup.
The comparison apparently hasn't been lost on Planet Out's advertisers, which include major corporations ranging from Sears and Nieman Marcus to American Airlines and Visa.
"The fact is they have brought together more people from the community than any other medium to date has," said Mike Wilke, executive director of Commercial Closet Association, a group that monitors gay-oriented advertising. The three largest gay magazines, The Advocate, Out and Girlfriends, magazines, have combined circulation of about 300,000.
The popularity of its dating services helped shield PlanetOut when advertisers slashed their spending, something that spelled death for many Internet startups.
Today, 60 percent of its revenue comes from a subscription-based personals service, launched two years ago, that allows prospective daters to check out each other's profiles and chat.
With revenues projected to hit $24 million this year and expenses holding steady, Selvin is deciding whether it's time to take PlanetOut public. He says it's been great bringing the company into the black, but even more gratifying when conferences seek him out as an expert on online business, instead of CEO of a gay-owned and gay-led business.
"What we do on behalf of the gay and lesbian community is business activism," Selvin said.
Sometimes, he runs into representatives of venture capital firms that decided not to invest in Gay.com early on. He smiles politely, but feels vindicated when they tell him, "Out of all our possible portfolio companies, I wish we had invested in you."