Internet mogul Gurbaksh Chahal 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 on Friday to a year in jail for violating his probation in a domestic violence case.

The Indian American’s rise from a high school dropout to a 25-year-old Internet mogul also landed him on Extra in segments touting him as a highly eligible bachelor. That image began crumbling when prosecutors charged him with dozens of felonies in 2013, saying surveillance footage from his San Francisco penthouse showed him punching and kicking his girlfriend 117 times and trying to smother her with a pillow.

b’Source: PTI’

Chahal avoided prison, receiving probation instead, after the woman stopped cooperating with authorities and a judge said the video could not be used as evidence. He violated his probation by allegedly kicking another girlfriend, who also didn’t help with the case, prosecutors say. Video of the first attack made it into San Francisco Superior Court, where a judge was set to sentence the 34-year-old today.

Chahal has defended himself against the initial charges, saying he lost his temper but did not hit his girlfriend 117 times. And his attorneys have attacked the second woman’s credibility, saying she got into a sham marriage to get a US visa and had been drinking the night she said Chahal hit her. 

Chahal’s legal woes extend beyond the criminal cases. Two former employees have sued him for discrimination, painting him as a bullying boss who thought little of women traits hard to combat in the male-dominated world of Silicon Valley, experts say.

Faced with the initial 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 that The Wall Street Journal reported.

Westly, who was on the board of a company Chahal founded, suggested the businessman reach out to 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.

b’Source: Twitter’

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 USD 250,000. Westly, said in a statement that he doesn’t comment on ongoing legal cases but that domestic violence in any form is inexcusable.

In prosecuting Chahal, the district attorney’s office faced a setback when a judge ruled that police illegally seized the surveillance footage from the mogul’s penthouse. But prosecutors pressed ahead, and Chahal pleaded guilty in 2014 to misdemeanor charges of battery and domestic violence battery.

A different judge revoked his probation last month after prosecutors say he repeatedly kicked another girlfriend in the same penthouse in 2014 and then dissuaded her from talking by threatening to report her to immigration authorities. 

Chahal accused both women of cheating on him, prosecutors say. The judge allowed prosecutors to introduce the video after they argued it showed a pattern of abusive behaviour. She reviewed it before issuing her ruling but has not released it publicly.