E-40 recently discussed his evolution from a founding father of the Bay Area’s hyphy movement to an angel investor. During a new episode of Shannon Sharpe’s FOX Sports podcast “Club Shay Shay,” the Hall of Fame NFL tight end asked E-40 if his proximity to Silicon Valley influenced his decision to begin investing in startup companies.

The Bay Area rapper from Vallejo, revealed that while distance did play a small factor in getting involved, rapper Chamillionaire was the catalyst. Between 2012-2013, right around the time he released two trilogy albums: The Block Brochure: Welcome to the Soil, E-40’s interest in investing piqued.

“I didn’t really know too much about it,” he told Sharpe. “I was like how you do it?” By then, Chamillionaire had already seen returns after investing early on in companies like Maker Studios, which was acquired by Disney for $500 million, home security company Ring, which Amazon purchased for $1 billion, and ride sharing app Lyft, among others.

“Chamillionaire hit a couple of times,” E-40 said. “By the time I got in, it’s like 2016. It’s 2021 now, I’m between 45-48 startup companies deep.”

“A lot of people don’t know I’m an early stage investor in Clubhouse, one of the hottest things out right now,” he continued. “That thing valuated at a billion within months and it looks like it gon’ be five billion by the end of the summer.”

Chamillionaire launched a video sharing social networking app of his own in 2018 called Convoz. One of his first investors: E-40. The two friends, who can often be seen sitting courtside together at Golden State Warriors games, also teamed up in 2019 to award $100,000 to a startup founded by a woman or a minority. The winner of the competition, Pierre Laguerre, founded Fleeting — an app that links certified class A & B drivers to trucking companies.