The year was 1994. "Friends" had just premiered, Bill Clinton was president, and online dating – if it happened at all – was a sketchy proposition. A startup called Match.com was trying to persuade the romantically inclined that the World Wide Web (as it was then known) was a hot spot to meet potential mates. Fran Maier, who had a background in marketing, joined Match.com to bring a woman's perspective to the burgeoning field. Her first decision? Nix the question about body weight. Listen to our conversation, where she talks about the highs and lows of building Internet companies over the past three decades -- and the big mistake she made with Match.com, that she'd like other women entrepreneurs to learn from. She's currently the CEO of BabyQuip.com, a baby gear rental platform.

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