A Silicon Valley internet mogul who sold his startup for $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.
However, Gurbaksh Chahal, 34, will not immediately begin serving the sentence because San Francisco Superior Court Judge Tracie Brown cited questions about the evidence while giving him time to appeal her ruling.
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 more than 100 times 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.
Chahal said both women had cheated on him, according to prosecutors.
Chahal's attorney, James Lassart, said in court Friday that his client was denied his right to question the woman during his probation revocation hearing when she failed to attend the proceeding.
"In this instance, the constitution requires that my client be allowed to confront his accuser," Lassart said.
Brown allowed the penthouse video to be admitted as evidence in the probation hearing, and she reviewed it privately before issuing her ruling last month.
Lassart said the judge should not consider the video in her sentencing because it had previously been ruled inadmissible.
The footage has not been played in court or made public.
Assistant District Attorney O'Bryan Kenney called for a sentence of 18 months, saying Chahal had shown no remorse and committed a second act of violence just months after his domestic violence conviction.
"He clearly didn't get the message," Kenney told the judge.
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 highlighted his success and 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 an email or call seeking comment. An email to Chahal's online advertising technology company, Gravity4, was 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.
Brown did not return a message left at his law office.
He 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.
In court documents, Chahal shot back that Khraibut was fired for not doing his work and was seeking publicity.