A Silicon Valley internet mogul who made $300 million at the age of 25 and appeared on "The Oprah Winfrey Show" as a highly eligible bachelor was sentenced Friday to a year in jail for violating his probation in a domestic violence case.
Gurbaksh Chahal, now 34, was sentenced by Superior Court Judge Tracie Brown, who gave him time to appeal the decision before starting to serve the sentence.
Brown determined last month that Chahal had violated the probation ordered after he pleaded guilty in 2014 to misdemeanor charges of battery and domestic violence battery.
Prosecutors said surveillance footage from his San Francisco penthouse showed him punching and kicking his girlfriend and trying to smother her with a pillow.
Chahal entered his plea to the reduced charges after the woman stopped cooperating with authorities and a judge said the video could not be used as evidence because it had been improperly obtained.
He was accused of violating his probation by kicking another girlfriend, who also didn't cooperate with prosecutors. His lawyers challenged her credibility by saying she got into a sham marriage to get a U.S. visa and had been drinking on the night of the dispute.
Chahal said both women had cheated on him.
During the previous probation hearing, Brown reviewed the video of the first attack before issuing her ruling. The footage was not made public.
Chahal made $300 million in 2007 when he sold his digital advertising company to Yahoo. A year later, he appeared on "The Oprah Winfrey Show" in a segment that promoted him as a highly eligible bachelor.
Chahal's legal woes extend beyond the criminal case. Two former employees have sued him for discrimination, painting him as a bullying boss who thought little of women.
Patricia Glaser, the lawyer representing Chahal in the lawsuits, did not return emails or phone calls seeking comment. Emails to Chahal's online advertising technology company, Gravity4, were not returned. A message to his Twitter account also went unanswered.
Faced with the initial domestic violence charges, Chahal got help from powerful former San Francisco Mayor Willie Brown and the former chief financial officer for the state of California, Steve Westly, according to one of the lawsuits and emails between Westly and Chahal reported by The Wall Street Journal.
Westly, who was on the board of a company Chahal founded, suggested the businessman reach out to Willie Brown, according to a 2015 lawsuit by Yousef Khraibut, a former Gravity4 employee. Chahal told Khraibut that he paid Brown a $250,000 retainer to exert pressure on the district attorney to dismiss the charges, saying Brown had the "juice" to make them disappear, the lawsuit said.
A woman who answered the phone at Brown's law office said he would not be back until Friday. Brown said in a radio interview last September that he was asked to put together a legal team to defend Chahal but did nothing unethical and returned most of the $250,000.
Westly, whose name has been mentioned as a possible gubernatorial candidate in 2018, said in a statement that he doesn't comment on ongoing legal cases but added that domestic violence in any form is inexcusable.
Khraibut's lawsuit also accuses Chahal of crass behavior, saying he sought male colleagues' opinions of a bikini photo of a prospective female employee and used a vulgar term to describe decisions to let attractive women advance in the hiring process.
In court documents, Chahal shot back that Khraibut was fired for not doing his work and was seeking publicity to get money he wasn't owed.
Bloomberg reported Friday that Chahal used the alter ego "Christian Grey" — the rich and powerful business tycoon in the book "50 Shades of Grey" — to email marketing professionals and humiliate his employees, according to half dozen people familiar with the situation.
NBC Bay Area's Riya Bhattacharjee contributed to this report.