Gurbaksh Chahal’s rise from a high school dropout to a 25-year-old Internet mogul who sold his startup for $300 million landed him on “The Oprah Winfrey Show” and “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. 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.

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“What makes Silicon Valley more challenging than other areas is … it has a macho culture that is deeply embedded,” said Deborah Rhode, a law professor at Stanford University who teaches gender equity law. “There are very few women in leadership positions.”