Silicon Valley mogul Gurbaksh Chahal, who founded two advertising companies by the age of 25, is headed back to jail after he was caught punching and kicking his girlfriend more than 100 times.

Chalal, who made $300 million by the age 25, lost an appeal on a judge’s decision to revoke his probation for a domestic violation conviction. Chalal has a history of domestic abuse. In 2013, he was charged with 47 felony counts after he beat his girlfriend at the time. Chalal violated his probation when he beat a second girlfriend and was sentenced to a year in jail.

This week a judge rejected an appeal on that decision and Chalal will be required to report to jail for a one-year term. Chalal’s attorney argued to throw out the conviction on the grounds that the surveillance video used in the courtroom was inadmissible evidence. The video, which has not been made public, allegedly shows Chalal punching and kicking his girlfriend 117 times.

In a statement, San Francisco District Attorney George Gascón said that Chalal was trying to “escape responsibility” for his actions by filing the appeal. “Mr. Chahal sought to escape responsibility for assaulting two women, but today he learned that wealth and privilege will not shield him from consequences,” the attorney said in a statement. “Domestic violence is very serious, and we will always be here to make sure that batterers are held accountable.”

Chalal has also been accused of discrimination in the workplace. At one of his companies, two former employees sued him for discrimination on the basis of their gender.