A multimillionaire tech mogul violated his probation for a domestic violence conviction when he reportedly attacked a woman one year after viciously beating his ex-girlfriend with kicks and punches 117 times.
Entrepreneur Gurbaksh Chahal, 31, was ordered to surrender his passports by San Francisco Judge Tracie Brown and is set to be sentenced on August 12.
Video of him attacking a different woman in 2013 is now being used against him in the second case.
He faces up to a year in jail or his probation could be extended, according to the San Francisco Chronicle.
Chahal's legal problems first started in 2013 when his then-girlfriend called 911 after he allegedly attacked her inside his luxurious Rincon Hill penthouse.
He was recorded on surveillance footage in his bedroom punching and kicking the woman, who was not publicly identified, 117 times and smothering her with a pillow for 20 seconds on August 5, 2013.
Scroll down for video
Jail?: Multimillionaire tech mogul Gurbaksh Chahal (above), 31, violated his probation for a 2013 domestic violence conviction. He is set to be sentenced on August 12 in San Francisco
In 2013 he was caught on camera inside his penthouse viciously beating his ex-girlfriend with kicks and punches 117 times. Nearly a year later, another woman accused Chahal (above) of attacking her
She stated she was unable to breathe,' San Francisco Police Officer Anh Nguyen testified at the preliminary hearing against Chahal, who was once deemed one of the planet’s “richest and fittest guys” by Men's Health magazine.
'She stated that he said, 'I'm going to kill you' four times. She stated she was in fear for her life.'
At the time, prosecutors charged him with 47 felony counts of domestic-violence related offenses.
However, a judge ruled that the video could not be used in court because authorities obtained it without a search warrant and it was unlawfully seized.
Chahal, who was the CEO of RadiumOne at the time, struck a deal in April 2014 with prosecutors that allowed him to plead guilty to misdemeanor battery charges.
The deal allowed him not to serve any time in jail, as he agreed to be on probation for three years, serve 25 hours of community service and attend a year-long domestic violence rehabilitation course.
Chahal (above with President Obama) struck a plea deal with prosecutors and was placed on probation for three years for the 2013 attack
A judge now ruled Chalal violated the 2013 probation with the alleged 2014 attack on a different woman who he was also dating
The guilty plea forced him out of his position at RadiumOne, but he went on and founded another advertising company, Gravity4.
On Friday, Brown ruled that the shocking video from 2013 could be entered into evidence in determining whether Chahal violated his probation for a second alleged attack with a different woman.
Prosecutors say he attacked another woman, whom he was dating, inside his bedroom of the same penthouse on the morning of September 17, 2014.
That woman, who he met in Las Vegas, told authorities that Chahal viciously kicked her repeatedly 10 times before threatening to report her to immigration officials when she discussed taking a restraining order out against him.
'The defendant knew he was in trouble and immediately rallied the troops and used the enormous resources at his disposal,' Assistant District Attorney O'Bryan Kenney said in court Friday of Chahal.
She fled back to South Korea and has not appeared in court during the probation revocation hearings.
Kenney argued that the video from 2013 showed a pattern of abuse by Chahal, who had sold two advertising companies he had founded for more than $300 million by the age of 25.
Authorities claim that Chahal, who was once called one of America's most eligible bachelors, accused both women of infidelity and became incensed.
'I think it's very important you find that video admissible, and you should watch it,' Kenney told the judge in remarks. 'In the very room, in the very bed where he did it before ... the pattern here is unmistakable.'
Since the second alleged victim returned to South Korea, both the prosecution and defense cases are hurt.
Chahal handed over his CEO role at Gravity4 to his sister, Kamal Kaur, last week
Chahal's attorney, James Lassart, argued that his client had a constitutional right to confront her in the probation hearing.
'Her word isn't very good. ... She refused to come,' Lassart said while, calling the woman 'unstable' and 'deceitful,' the Chronicle reported.
Kenney asked the judge to put the CEO in jail without bail after her ruling, but she declined.
According to TechCrunch, Chahal handed over his CEO role at Gravity4 to his sister, Kamal Kaur.
He has been removed from the company's leadership page and replaced by his sister who is listed as CEO.
She has previously held leadership roles at his other companies, including RadiumOne, where she worked as Vice President of mobile before they sold it to Yahoo in 2007.
Chahal's attorney, James Lassart, provided the following statement to TechCrunch:
'The CEO switch-up comes as Chahal waits to hear whether he'll face jail time or an extended probation period after violating his probation.
'Chahal pleaded guilty to misdemeanor assault charges after attacking a woman in his apartment in 2013 and was placed on three years' probation.
'A second woman accused Chahal of assaulting her in September 2014, and a San Francisco judge decided last week that there was enough evidence of the attack to determine Chahal had violated his probation.'