Vinod Khosla (right), the cofounder of Sun Microsystems and titan venture capitalist, values his privacy. He's also a billionaire—so if you're his daughter's scumbag ex-boyfriend, you might think he's just the right guy to threaten with naked pictures of her.

An affidavit obtained by The Smoking Gun details the scheme: after a romantic (and working) relationship between Stanford sweethearts Douglas Tarlow (left) and Nina Khosla (right) disintegrated, Tarlow started waving around naked pictures the latter had voluntarily shared with him. He'd briefly worked for Neeru Khosla, Vinod's wife and Nina's mother, and claimed he was owed tens of thousands of dollars after being fired.

The offer was simple: pay up, or your daughter's naked JPEGs are going on Reddit:

Both mother and daughter were repeatedly harassed with the lewd shots via text and email. Maybe he figured Khosla, with a net worth of roughly $1.5 billion and a deep understanding of the social web, would be quick to shut him up with money. What he didn't expect is that messing with a superbly rich person's family is a superbly quick way to get the FBI all over you. Tarlow is currently facing federal extortion charges.

Perhaps Khosla's next investment will be Snapchat.