APRIL 23--The wife and daughter of a billionaire Silicon Valley titan were the victims of an extortion plot allegedly hatched by the younger woman’s former boyfriend, a Stanford University graduate who threatened to distribute naked photos of his ex unless he received hush money payments, The Smoking Gun has learned.

The shakedown scheme targeted family members of Vinod Khosla, the 59-year-old venture capitalist who co-founded Sun Microsystems. Khosla, who heads his own Sand Hill Road investment firm, is worth $1.5 billion, according to a recent Forbes magazine estimate.

FBI agents last week arrested Douglas Tarlow, 27, in connection with the alleged extortion plot. Tarlow, who dated Khosla’s daughter Nina for about two years, was subsequently released from custody and is scheduled for a U.S. District Court preliminary hearing tomorrow.

Tarlow, pictured at right, allegedly threatened to distribute the naked images 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 a text message to Nina Khosla’s mother--who was sent the nude photos--Tarlow stated, “it seems you’re going to be the mother of the next Paris Hilton,” investigators allege.

The FBI’s investigation of Tarlow is detailed in a court affidavit sworn by Agent Glenn Solomon-Hill, who is assigned to the bureau’s San Francisco office. While the FBI affidavit does not name Tarlow’s alleged targets, TSG has confirmed that the Khoslas are the victims referred to in the document.

In a brief interview yesterday, Nina Khosla, 26, declined to answer questions about the case. “I’d prefer that you didn’t write about that,” said Khosla, who added that her family contacted law enforcement authorities soon after receiving threatening communications.

Tarlow and Nina Khosla, who met in 2007, dated for about two years before breaking up in late-2010. The couple, who studied in Stanford’s Product Design program, started Lokho, a design firm for which Khosla registered a web site in mid-2009. During their relationship, Khosla “voluntarily took nude photos and video,” which she shared with Tarlow, according to Agent Solomon-Hill.

Though their relationship had ended months earlier, Khosla recommended Tarlow for a job with a nonprofit education foundation run by her mother Neeru. A molecular biologist by training, the 59-year-old Neeru Khosla has been described by the San Jose Mercury News as “half of a Silicon Valley power couple.” The Khoslas are seen below.

Neeru Khosla 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 $125,000 salary to work at the CK-12 Foundation.

After about seven months at the organization, Tarlow was fired in February 2012. Neeru Khosla told the FBI that following Tarlow’s termination he “talked about guns to other employees who expressed that they did not feel safe.” As a result, Khosla hired a private security company to guard the foundation’s Palo Alto office “out of concern for the safety of her employees.”

Over the next several months, Tarlow 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, Nina and Neeru Khosla each received a series of texts from Tarlow’s phone number. The messages included several naked photos of Nina Khosla taken during the period she dated Tarlow. One text to Nina asked, “shall I call you Paris?” Another text warned, “expect to see those online in 24 hours. fuck you.”

Neeru Khosla, who was unaware that naked photos of her daughter existed, replied to a text from Tarlow’s number with the question “What do you want for the picture?” She then sought to arrange a meeting with Tarlow, and asked him to return the photos to her daughter. “You sent me that when you were upset and how does she know you wont do that again to someone else with the photos,” wrote Khosla, who added, “I want your copies nothing saved.”

In subsequent communications, Tarlow allegedly sought $72,000, which he claimed the Khosla foundation owed him. A message from Tarlow’s Gmail account directed Neeru Khosla to send the money to a P.O. box in Palo Alto. Tarlow also allegedly wrote to Nina Khosla, asking her, “Would you like to pay me on behalf of [the company]? Their balance is 73k,” reported FBI Agent Solomon-Hill.

In an October 2012 e-mail to Tarlow’s Gmail account, Nina Khosla asked why he was threatening her. A reply e-mail claimed, “not me. No idea what that is.” A second e-mail stated, “please don’t contact me further.”

After being contacted in late-2012 by the Khoslas, FBI agents used grand jury subpoenas sent to Verizon, Google, and Time Warner Cable to link Tarlow to threatening texts and e-mails sent to the two women. However, Tarlow was not arrested at that time.

After more than a year had passed, Tarlow allegedly re-contacted the Khoslas in December 2013 and again threatened to release the naked photos. In a text to Nina Khosla, Tarlow wrote that her mother “doesn’t keep her promises,” noting that “any option besides making you the next Paris would be preferred.” Then, in a reference to Vinod Khosla, Tarlow added, “but one tires” of his “stream of backhanded insults. sorry.” A second text to Nina warned, “some things once released to the world can never be removed.”

In correspondence sent to Nina Khosla (seen above) via an anonymous e-mail service, Tarlow allegedly wrote, “Money is such an unimportant thing except when one has none. Then it hurts not to have any.” Attached to the e-mail were “three nude pictures” of Khosla “provided to Tarlow during their relationship,” according to the FBI affidavit. Referring to Khosla’s mother, Tarlow also allegedly wrote, “guess we’ll have to see how [she] responds to those pictures? maybe it’ll shock her into doing the right thing.”

In the final e-mail cited by investigators, Tarlow allegedly wrote to Neeru Khosla on December 14. He attached “a different nude picture” of her daughter, and asked, “Do you still want to buy these?’

Tarlow did not respond to an e-mail sent to his Gmail account, nor to voicemail messages left on several phone numbers he has used. (13 pages)