Gurbaksh Chahal: A Silicon Valley Entrepreneur's Journey to Jail

Gurbaksh Chahal attends the Fox Fall Eco-Casino party at The London West Hollywood hotel on September 8, 2008 in West Hollywood, California. Charley Gallay/Getty

In the latest twist to a notorious Silicon Valley tale, a judge on Friday sentenced tech mogul Gurbaksh Chahal to 12 months in the San Francisco County jail, three years after the young titan was arrested and charged with 45 felony counts of domestic violence. Chahal's attorneys immediately moved to appeal, and it's unclear when or whether he will begin the sentence, but the Lamborghini-driving, Vegas-partying playboy who made a fortune in the ad tech business now faces time behind bars for smacking his then-girlfriend 117 times. The exact number is known because the entire beating was captured on a video camera he had set up in his bedroom, above his bed.

Chahal eventually pled guilty in 2014 to two misdemeanors after a judge ruled the video inadmissible. At the time, his sentence—no jail time and freedom to go back into business, which he has done—was met with howls of outrage from women who saw in it the brashest example yet of Silicon Valley's casual misogyny. Five months later, though, Chahal was charged in another domestic violence incident, involving another woman. Under California law, his probation was liable to be revoked, but his legal team fought on. After two years of hearing delays and arguments, a judge in July agreed with the prosecutor to revoke probation.

Chahal's trouble with the law began on August 5, 2013, when San Francisco police officer Anh Nguyen rang the bell and was buzzed up into the penthouse in the city's tony Rincon Hill neighborhood. The officer brushed past the movie-star handsome man who answered the door, looking for a woman who had called 911 to report she was being beaten. Passing floor-to-ceiling windows with splendid views of San Francisco, the officer found the master bedroom, where a headboard was monogrammed with a large "G." Cowering in the master bedroom shower was a bruised, slender brunette named Juliet Kakish, a beautician from Pasadena. She told the officer she was "saved by the bell." Before leaving the room, the officer noticed a tinted glass panel in the ceiling. A video camera was behind it, recording the bed below.

On the drive to the hospital, Kakish told Nguyen that she had been dating the owner of the apartment, internet ad mogul Gurbaksh "G" Chahal, for eight months. That night, according to filings, she said Chahal had beaten her after learning she had gone to Las Vegas with another man: He grabbed her by the hair, threw her on the bed, hit her on the head "many times with his palm" and spit on her. Nguyen later testified at a preliminary hearing in San Francisco Superior Court: "She stated that he said, 'I'm going to kill you' four times. She stated she was in fear for her life."

Within days of Chahal's arrest, Kakish signed an affidavit indicating she did not want to press charges and requesting the police department "terminate its investigation." But prosecutors went forward and charged Chahal with 45 felonies. Based on the recording from the camera above the bed, the prosecutors alleged the mogul hit Kakish 117 times over 30 minutes.

Before that night in August 2013, Chahal had checked all the Silicon Valley Success Boxes: dropout, internet innovator, tens of millions of dollars by age 20, hundreds of millions by 25. An Indian immigrant family's youngest son with an instinct for business, he won the support of middle-aged, male financiers and lawyers, attracted to his ability to create highly valued internet advertising companies. One of them, Silicon Valley venture capitalist named Tim McAdam, told Bloomberg in 2010: "This guy is on track to be a billionaire. He is cut of the mold of a Larry Ellison or Richard Branson. It's not about education, pedigree, or connectedness. It's about the single-mindedness to succeed."

That desire was evident from an early age. Born in 1982 in India's Punjab state, the youngest of four children, Chahal moved to the U.S. with his Sikh parents when he was 3. The family shopped at Goodwill and the Dollar General store, and shared a one-bedroom apartment in a rough part of San Jose, California. "G" and his brother, who wore turbans to school, were taunted mercilessly. At 16, in 1998, he dropped out to start his own digital advertising company, Click Agents. Businesses were just learning how to measure and track consumer behavior online, and within two years, Chahal sold Click Agents for $40 million.

At age 18, he moved out of his parents' home—a revolutionary and wrenching act. "In a typical Indian household, sons never leave their parents," he wrote in a mogul how-to book called The Dream: How I Learned the Risks and Rewards of Entrepreneurship and Made Millions. "They stay with them even after marrying." After discarding his turban—against his parents' wishes—and hitting the gym to shed his teenage chubbiness, he emerged with male-model looks. He then started another company, Blue Lithium, taking advantage of nascent technology that enabled companies to track the behavior of online consumers. Four years later, Yahoo! paid $300 million to buy it from him. Chahal was 25.

By 2008, he was a Valley legend. He appeared on Secret Millionaire, a Fox reality show featuring millionaires bestowing money on deserving strangers. In 2009 the syndicated entertainment program Extra TV named him one America's "most eligible bachelors." Oprah Winfrey interviewed him on a segment of her show she called "Millionaire Moguls."

By the time he sold BlueLithium, Chahal had gained entree into the rarefied world of San Francisco's young capitalists with a Lamborghini (later, a Bentley), a penthouse and an entourage. With all those accoutrements, he then started two more companies, first an online payment system called g-Wallet, and then another digital advertising concern called RadiumOne—his first to attract major venture capitalist backers.

He gave significant sums to the Democratic Party, and was photographed with Barack Obama at a San Francisco dinner. Chahal paid $6.9 million for the Rincon Hill penthouse, installed plasma screen space scenes on the walls and decorated one floor with a zebra rug, tail attached. Soon, his neighbors complained about loud parties and cigar ash dropping from his terrace onto their decks and into their eyes. Eventually the homeowners association sued him, citing "excessive late-night and early-morning noise…including loud music vibrating the ceiling and the sound of loud footsteps and high heel shoes." He settled for an undisclosed amount. The association also banned him from using the building's fitness center for a time because he was in the habit of showing up for work-outs with a boom box.

Despite his success, Chahal shared a trait common among many Valley brogrammers: an adolescent unease around females. In the first years after made his first $40 million, he still couldn't talk to women. He did eventually start dating, but in his book he wrote that while he desired a stable relationship, he was unable to tell whether women wanted him just for his money.

A few months before the 2013 arrest, there were already signs of trouble for "G." In June 2013, Chahal's personal assistant, Rafael Rojas, emailed RadiumOne's then-CFO, Bill Lonergan, complaining that Chahal was trying to get him to break the law. "As you know Gurbaksh has pushed the line before, particularly with prostitutes," Rojas emailed Lonergan. "But now like I told you he is getting into drug use, including trying to get me to get him Adderall and other drugs illegally. He has also tried to get me to drug girls (without them knowing) so to make sure they don't get pregnant." The email doesn't clarify what substance Chahal supposedly thought he could surreptitiously feed females to ward off pregnancy. Rojas concluded: "When I signed up to be an executive assistant I did not agree to be a co-conspirator in these illegal activities." Chahal's attorneys have declined to speak with Newsweek.

Lonergan, a British, bow-tie wearing accounting executive, had been a stalwart in Chahal's business life ever since he signed on as CFO at Blue Lithium in 2004. Before linking up with Chahal, Lonergan had been a partner at accounting giant KPMG in Silicon Valley, eventually consulting on the Hewlett-Packard and Microsoft accounts. In his book, Chahal says he and Lonergan, who is old enough to be his father, had "immense trust and respect for one another," and that "despite the fact that he reported to me I genuinely looked up to him..." Lonergan declined to comment about Chahal.

Five days after Rojas sent that email to Lonergan, Chahal sued Rojas and his personal driver, accusing them of overcharging and stealing $1 million from him. He included the email in his suit and called the statements in them "defamatory." The case was reportedly settled.

When Chahal was charged with 45 felonies involving Kakish, the RadiumOne board supported its CEO and founder. The arrest came at a sensitive time, because the company was trying to go public and preparing for a "bake-off"—finance lingo for a process in which a company seeks investment bankers to underwrite an IPO. According to emails between the board members, the RadiumOne board was concerned that a conviction in the domestic violence case for Chahal could derail the process because of SEC requirements involving disclosure of criminal records.

The board could have jettisoned its CEO; instead, it saved him. Some members, the emails make clear, bought into the notion—eventually advanced by Chahal—that the criminal charges were part of an extortion plot. At the very least, sources say and documents show, they didn't appear to take the domestic violence charges seriously. In one email from the mediation brief, RadiumOne lawyer Robert Latta—a partner with the prominent Silicon Valley firm Wilson, Sonsini, Goodrich & Rosati—advised the board that even a misdemeanor conviction would probably trigger a disclosure requirement in the IPO, but that "it can be argued that passing small bad checks are more relevant to the integrity of an IPO executive than our situation." At another point, Latta emailed Chahal in a tone that seems either menacing or playful: "Seems like [San Francisco District Attorney George] Gascon needs to be visited with some domestic violence." Latta did not respond to Newsweek's requests for comment.

A few months after Chahal's arrest, with the IPO "bake-off" still only in the planning stages, Steve Westly, a Silicon Valley venture capitalist and former California state controller, joined the RadiumOne board. He soon suggested Chahal hire former San Francisco Mayor Willie Brown on the domestic violence case, to help "make it go away." Brown is a phenomenally well-connected, legendary California Democrat, having served 30 years in the California Assembly before being elected the first African-American mayor of San Francisco. In recommending Brown, Westly wrote: "G: I spoke with Mayor Brown this morning and believes that he can help you." He then noted that Brown had helped the District Attorney Gascon get elected. A few days later, Chahal emailed Westly to tell him he'd met with Brown, who wanted $1 million, and that he'd paid him a $250,000 retainer. "Wow. That's pricy [sic] , but probably worth it if he can make it happen," Westly replied.

Steve Westly speaks to guests at the One Center Senior Enrichment Center in Reseda on June 1, 2006, when he was running for governor of the state. Wally Skalij/Los Angeles Times/Getty

Brown admitted he set up a team to work on the case, but Gascon denied meeting with him personally. In March 2014, San Francisco Superior Court Judge Brendan Conroy threw out the incriminating video, after Chahal's team argued police illegally seized it from the apartment. Without that evidence, the prosecutor dropped the 45 felony charges and Chahal later pleaded guilty to misdemeanor domestic violence and battery. He got three years' probation, a one-year domestic violence training program and 25 hours of community service.

Hours later, Chahal emailed RadiumOne Board members under the subject heading "Update of Personal Matter," boasting that he "would've gotten a full dismissal on all charges but that would've likely taken several months in the political/legal system." Lonergan replied by text: "The board has your back completely" and then implored him: "PLEASE do not violate the terms of your settlement agreement with the lady." (A spokeswoman for Lonergan said that by "settlement," he was referring to the plea deal with the prosecutor not a pay-off for the woman Chahal supposedly paid off.)

Willie Brown, former mayor of San Francisco, speaks during a Bloomberg West television interview in San Francisco on August 12, 2014. David Paul Morris/Bloomberg/Getty

Chahal had won a legal victory, and though he had been told to keep quiet, he was unable to resist the lure of social media. He published a blog post with the headline "Can You Handle the Truth?" claiming his own victimhood and suggesting the case was a set-up for extortion. "Celebrities in sports, entertainment and business, and high net worth individuals in general are all potential targets," he wrote. "It was only a matter of time when I would fall prey." He admitted only that he "lost his temper" that night.

Outrage erupted at the light sentence. The Democratic National Committee returned $20,000 Chahal had donated. TechCrunch dropped RadiumOne as a sponsor of a Disrupt New York hackathon. A few days later, the RadiumOne board fired Chahal by conference call. Lonergan immediately took over as CEO, a position he still occupies. Chahal went ballistic, unleashing another tirade online and threatening to sue the board, and then filed a cache of private communications, including the emails quoted above, to a mediator. .

Controversy over domestic violence had driven Chahal out of the company he built. But he was able to almost immediately start another online ad company, Gravity4, in July 2014. Its aim, as the company website puts it, is "to disrupt the software and advertising industries together, by automating a $100 billion industry that is still manually driven." But before that new enterprise was a year old, two ex-employees filed lawsuits against Chahal and his new company. A former male employee alleged wrongful termination and painted a lurid picture of a leader in full breakdown mode. That plaintiff, Yousef Khraibut, was one of Chahal's first Gravity4 hires. At age 16, Khraibut founded Brotips Media, a Mark Cuban-backed online chix-ploitation website that shares social media tips aimed at horny young men, but even he couldn't keep up with his new CEO's style. "Chahal, fueled by a toxic cocktail of prescription drugs, party drugs, alcohol and sycophants, subjected his associates and Gravity4 employees to daily abuse, humiliation, racist taunts, extortionate manipulation, tales of revenge and threats of violence," he claims in the federal lawsuit. Khraibut alleges, among other things, that Chahal was in the habit of surreptitiously watching employees from remote locations; checked out and shared online bikini pictures of prospective female hires; urged that attractive female hires be put on the company's "pussy path"; often referred to "whipping out my 14-incher"—meaning his penis—at work; called women "bitches and ho's"; and described himself as "the Indian Brad Pitt." Neither Chahal nor his attorney responded to Newsweek's questions about these allegations. A judge has sent the Khraibut case to arbitration.

Five months after his plea deal, Chahal had a new girlfriend, Sobeen "Laura" Bae, whom he had met in Vegas, where she worked as a VIP services supervisor at the Bellagio. Khraibut claims Chahal referred to her as "Noodle House." In the early morning hours of September 17, 2014, five months into his three-year probation under terms of the plea deal, Chahal had an altercation with Bae in his San Francisco bedroom. According to a report filed by the San Francisco police, Chahal kicked her in the right leg and thigh multiple times. She went to the hospital that night and was released. She told police Chahal had attacked her before.

Bae also told police Chahal had threatened to report her immigration status to authorities. The police report quoted her describing Chahal's routine drug and alcohol consumption: He "would take 10 to 13 pills, antidepressant and sleeping pills one to two hours before bed. He would also drink alcohol while under the influence of the pills. Usually he is very mellow and becomes almost unconscious at times." She told police Chahal paid for her breast augmentation, and she reimbursed him by donating $5,050 to his charitable Chahal Foundation. Chahal's criminal defense lawyer, James Lassart, did not respond to emails or messages about the case.

The lawsuit says Khraibut eventually fled to Canada, "in fear for his life after Chahal's incessant, violent threats," and "went into hiding for months." On October 6, 2014, San Francisco police obtained a criminal protective order for Khraibut against Chahal after the mogul bragged to Gravity4 employees that he knew people in Eastern Europe who could "take care of" his former underling. Chahal's attorney, Patricia Glaser, told Newsweek she couldn't comment.

As Chahal dealt with his legal matters, the PR fallout landed hard on his former supporters. Last year, women's rights activists Eve Ensler and Gloria Steinem, alerted to the accusations against Chalal by news reports, wrote a letter to Steve Westly, who some have seen as a possible candidate for California governor, chastising him for helping the mogul. "Your work defending this violent abuser in order to personally profit disqualifies you from any public office," they wrote. Brown, the former mayor, was moved to defend himself in a radio interview regarding the startling sum he supposedly requested "to make it go away" and the implication that the board members believed Brown might have influence over the prosecutor's political future. He told San Francisco's KCBS radio that he had returned nearly $200,000 of the retainer, and denied saying he could make it "go away."

Khraibut claims in his discrimination lawsuit that Chahal told him he paid the first domestic violence victim, Juliet Kakish, $2 million. A source close to the case says a Goldman Sachs check from Chahal's account for more than that was paid to her attorney, noted Los Angeles lawyer Mark Geragos, who has represented the likes of Michael Jackson and Winona Ryder. Geragos did not return a call for comment. It is illegal to pay witnesses not to testify, but there is no evidence that happened. In fact, as part of his suit against RadiumOne over his dismissal, Chahal produced a copy of an email from Kakish titled "I love you," dated August 25, 2013, 20 days after the incident. "Baby I just want to know how sorry I am what I caused. I should never have called 911 and I regret every moment of it." The email ends with: "And hopefully soon I can be with you again."

Experts say this email isn't exculpatory. Domestic violence victims often refuse to press charges, even with overwhelming evidence of abuse. California lawyer Gloria Allred has made a career of representing high-profile female victims, including most recently Bill Cosby's accusers, and has no relationship to Chahal's cases. She says it's common practice for prosecutors to go forward without victim cooperation. "Often, victims are reluctant, but are subpoenaed to testify anyway, because battered women's syndrome is something district attorney's offices are used to dealing with."

This Silicon Valley reversal-of-fortune fable hasn't concluded, but for the the young, troubled mogul, the jail sentence is an ominous sign of how his enablers have abandoned him. His penthouse was on the market for $12 million as recently as early this year, After it failed to sell it was de-listed this summer. Late last year, he replied to a few text messages from Newsweek, suggesting he would answer emailed questions, then he stopped replying. Online, he has rebranded himself, putting his name on anodyne blog posts accompanied by photographs of pretty, happy young women and links to his old screeds now lead to a site called "Be Limitless."