Investors hitting on investees, dates disguised as business meetings, founders' wives getting hit on: The boys club of tech investing sounds barely more enlightened than the casting couches of Hollywood. And now one lecherous venture capitalist risks becoming the poster boy for tech's sleazier side.

BetaBeat today takes a look at the slimy side of being a woman in Silicon Alley finance. "I once scheduled a meeting with someone and it turned out to be a date," one told the site. Another " met with a Silicon Valley investor who followed up with an invitation to his hotel room via a midnight text message—'and he was married!'"

The story then focuses on Charlie O'Donnell, a principal at First Round Capital. He's never accused of trading investment dollars for sex, of harassment, or of inappropriate touching. He's described by some female friends as having provided women with encouragement, key introductions, and jobs. But his aggressive come-ons have clearly gotten out of hand. To wit:

  • One female founder recounted talking to her girlfriends about O'Donnell making a pass, and it turned out five of the seven women present had been hit on by him, including one who had this story from her college days: "I was the president of my investment club and this guy came to speak. He was bald and he worked at GM and he came up to me afterward and asked me out to dinner, and made it seem like it kind of was a mentoring thing, but it was a date, and it was really weird and really uncomfortable."
  • "What seemed to grate on many of Mr. O'Donnell's targets was the sense that... expecting a meeting, they'd found themselves on a date."
  • "'I once scheduled a meeting with someone and it turned out to be a date,' one well-connected female techie told Betabeat. That someone was Mr. O'Donnell. One female founder was 'asked out to dinner on the pretense of it being a meeting, but it turned out to be a date' with a local venture capitalist, who followed up with an extended series of flirtatious text messages. That man also turned out to be Mr. O'Donnell."
  • "We heard other complaints, similarly mild-flirting over Facebook, flirting over late night Gchat, flirting over email."
  • " A male founder-turned-VC was particularly irked because Mr. O'Donnell had hit on his wife."
  • Two women who had initially emailed BetaBeat to defend O'Donnell - he sent a mass email to supporters after being asked about his pickup attempts - "acknowledged that Mr. O'Donnell 'has a problem,' as one put it."
  • "One woman complained to Josh Kopelman, the managing director at First Round. When Mr. O'Donnell was confronted, he tried to guess who had complained-and guessed wrong."
  • "Another well-connected woman in the New York tech scene said she has spoken to Mr. O'Donnell about toning it down. 'A few women who have offered their guidance and feedback to him only to be met with defensiveness and a refusal to hear it,' she said."

Given the relative paucity of women in the upper echelons of tech, and his own professed concern over it—O'Donnell recently hosted a ladies only tech lunch—why would he stubbornly insist on acting like a sleazebag? Well, venture capital is a hits driven business, and O'Donnell isn't getting enitrely negative feedback. "I want to meet @ceonyc [O'Donnell]!!" braying exhibitionist Julia Allison tweeted."I'm kind of all for flirting," a female software entrepreneur told BetaBeat by way of advice for O'Donnell's professional/personal prospects. "Human social behavior is what it is," another woman said, referring to the atmosphere for females in tech.

As any VC knows, it only takes one big hit to make all the failed attempts worth it. And, sadly, O'Donnell is all but guaranteed to find some success with his brazen blurring of work and pleasure, so long as there's lots of money to be made in his line of work, and so long as he's got loads of cash behind him.

[Photo of O'Donnell via Flickr]