Indian-American billionaire Vinod Khosla's family was allegedly victim of an extortion plot in which the former boyfriend of Khosla's daughter threatened to distribute her purported nude photos if he was not paid money.
According to a report on the Smoking Gun webiste, Stanford University graduate Douglas Tarlow, 27, was arrested by the FBI last week in connection with the alleged extortion plot.
Khosla, 59, is a prominent venture capitalist who co-founded Sun Microsystems. According to Forbes, his net worth is about USD 1.5 billion.
Tarlow, who had dated Khosla's daughter Nina for about two years, has been released from police custody and is awaiting a preliminary court hearing.
The report said Tarlow allegedly threatened to distribute purported naked images of Nina online, warning in one e-mail that, "Everything is going to reddit. From there, it will be impossible to remove from the internet forever."
In another text message to her mother, Tarlow said, "It seems you're going to be the mother of the next Paris Hilton," according to investigators.
The FBI's investigation of Tarlow is detailed in a court affidavit, which has not named the Khoslas.
However, the Smoking Gun said it has confirmed that the Khoslas are the victims referred to in the document.
In a brief interview, Nina Khosla, 26, declined to answer questions about the case.
"I'd prefer that you didn't write about that," she said, adding that her family contacted law enforcement authorities soon after receiving threatening communications.
Tarlow and Nina met in 2007 and dated for about two years.
The couple, who studied in Stanford’s Product Design programme, started a design firm for which Khosla registered a web site in mid-2009.
During their relationship, Khosla allegedly "voluntarily took nude photos and video," which she shared with Tarlow, according to FBI Special Agent Glenn Solomon-Hill.
After their relationship, Khosla recommended Tarlow for a job with a nonprofit education foundation run by her mother Neeru.
Neeru has told investigators that she "wanted to help Tarlow because he had been close to their family," according to the FBI affidavit, which noted that Tarlow had been promised a USD 125,000 salary.
Tarlow was fired after a few months and he "talked about guns to other employees who expressed that they did not feel safe."
Over the next several months, Tarlow allegedly sent text and e-mail messages to Neeru Khosla complaining that he had been unfairly treated, and that she "owed him money from his tenure at the company," according to the FBI affidavit.
In September 2012, the mother and daughter received several messages from Tarlow's phone number which included naked photos of Nina taken during the period she dated Tarlow. The messages also contained objectionable and obscene texts.
In subsequent communications, Tarlow allegedly sought USD 72,000, which he claimed the Khosla foundation owed him.
In the ultimate e-mail, Tarlow allegedly sent "a different nude picture" of Nina to her mother, and asked, "Do you still want to buy these?"