Google CEO Eric Schmidt's venture capital firm describes its investment philosophy as "opportunistic." We're starting to wonder if that refers to the "opportunity" to buy people's silence, judging from how much money is flowing to friends of Schmidt's sometime mistresses.

There's plenty of circumstantial evidence that Schmidt's money has made its way to a third friend of his girlfriends, as rumored. The associate in question, Liz Brown, runs "healing and wellness site" Liiv.com and is a sometime close friend of tell-all-blog-writing business journalist Kate Bohner, Schmidt's ex girlfriend.

Funneling money to Brown is one way for Schmidt to keep her happy, and to ensure she is never inclined to blab whatever she knows about Schmidt's relationship with Bohner.

And she probably knows plenty. Brown and Bohner met when they both lived near Palm Beach, Florida, and were friends when Bohner was seeing Schmidt. It even appears Brown and Schmidt helped coordinate one of Bohner's trips to rehab.

Since then, Brown, a social worker, has made something of a new career, with help from Schmidt's staff and likely with his money: Her Liiv.com is so heavily intertwined with Schmidt's investment firm TomorrowVentures LLC that it would be surprising if there weren't funds changing hands. Liiv prominently lists Court Coursey, who runs TomorrowVentures, as an adviser. Further, the Liiv.com Web domain was registered in Coursey's real name, Gary B. Coursey. In addition, TomorrowVentures has invested in the similarly named Giiv.com, the mobile gifting statup where Coursey is an advisor just as he is at Liiv. And finally Liiv shares its Chief Technology Officer Michael Slaby with Schmidt's TomorrowVentures, where Slaby is listed as Chief Technology Strategist.

Schmidt doesn't like talking about his romance with Bohner; threats from his lawyers prompted Bohner to delete from the internet an addiction recovery memoir that included passages devoted to Schmidt, who was referenced as "Dr. Strangelove."

But Brown would be well versed on the couple's entanglement.

In video interviews, Bohner described Brown as "my wonderwoman" and "my hero." On Bohner's blog, she posted pictures of a boating excursion with her "dear friend" Brown.

Then there's Bohner's recovery memoir, an online project that she plans to turn into a book. It shows Brown was probably intimately involved in putting Bohner into rehab — in a joint effort with Schmidt. To wit: A character in the diaries nicknamed Bianca is portrayed as living in or near Lake Worth, Florida, the Palm Beach-area town where the real-life Brown's charity Turtle Nest Village was based, and where Brown presumably lived. The memoir's illustration of Bianca, above, left, looks like a stylized, younger version of Brown, right.

In Bohner's diary, Bianca/Brown is the one who "offered up the monastery in Thailand" where Bohner ended up detoxing. Bohner wrote: "In one of the last conversations I had before boarding the 8 p.m. flight [en route to Thailand], my soul mate Bianca... grabbed the sides of my face and said rather pointedly, 'you have completely lost the plot of your life.'"

In the original version of the diary, later changed, Bohner had said that Schmidt/Dr. Strangelove was involved in getting her to Thailand, too: "How did I get here? There was the phone call. There was the betrayal. Dr. Strangelove had lied about his involvement in it all."

So Brown probably knows in detail just how deep Schmidt's relationship with Bohner goes. Best to keep her comfortable, then.

And best to keep Coursey comfortable, too. He was, after all, a "dear friend" to Bohner when she was seeing Schmidt. He was even on that aforementioned boat excursion with Bohner and Brown. (Picture of Coursey and Bohner, right, via Bohner's blog.)

Coursey is no doubt well compensated as the Managing Partner of TomorrowVentures, which Schmidt appears to have launched just this past fall. But, aside from his connections to Schmidt's ladyfriends, he is an odd pick to handle Schmidt's money, estimated at around $6 billion in total. He's repeatedly become entangled in nasty lawsuits with people who have hired him in a finance role, according to the website peHUB. WebMD, where Coursey worked, sued him for falsifying monetary documents. And Coursey was fired by Michael Jackson after the singer gave him $2 million for an entrainment startup, which failed, before Jackson hired him as a $60,000 per month financial consultant. Coursey later sued the singer for $25 million.

We reached out to Brown, Coursey and Bohner for comment on Thursday of last week and have not heard back.

In addition to Brown and Coursey, Schmidt's TomorrowVentures money is also flowing to the startup run by Shervin Pishevar, a friend of on-again-off-again Schmidt honey Marcy Simon. Pishevar, whose Social Gaming Network took a $2 million TomorrowVentures investment earlier this summer, likes to get cozy with Simon when a camera is around. He's also a regular in Simon's Twitter stream, including some of her self-described "romantic" moments.

Of course, Schmidt is free to throw his personal funds around as he sees fit. We know of no outside investors in TomorrowVentures, so it's not like there's any misuse of capital. And since throwing investment dollars to your chums is common in Silicon Valley, and especially at Google, the CEO has some plausible deniability around his motives.

But you have to wonder: Does Schmidt want to keep his affairs private or not? He's been confoundingly, repeatedly, defiantly contradictory on this question. First he unleashed his lawyers on Bohner to hush up their relationship, but then he conspicuously threw money at not one but two of her good friends, along with the buddy of his other mistress. He's gotten into snits over reporters' attempts to examine his private life, but then been brazenly public with his girlfriends. He posed for pictures with Bohner, brought her to Burning Man and apparently gave her a pre-release iPhone, the ultimate in Silicon Valley bling. He's continued to publicly mingle with sometime girlfriend Marcy Simon, as well. He's insulted the integrity of bloggers, those gossipy muckrakers of the internet, even as he told people they should prepare to have all embarrassing information about them available on Google ( "If you have something that you don't want anyone to know, maybe you shouldn't be doing it in the first place." ).

It may well be that noxious Google arrogance that's blinded Schmidt to his inconsistent behavior and statements. Or maybe the computer science Ph.D. is too distracted running Google, and churning out $15 billion in annual profits, to come up with a more coherent and considered approach to his messy personal life. Fair enough: As long as the Google gravy train keeps rolling, investors and colleagues are unlikely to care. It's only when it stops that Schmidt will have to ponder whether all the baggage and buddies he's accumulated are assets or liabilities.