When people think of NBA star Shaquille O’Neal and music producer Will.i.am of the Black Eyed Peas, they often think of sports and entertainment icons — Shaq with four NBA championships and an Olympics gold medal; Will.i.am with seven Grammys and a dozen platinum hits.
But they are also prolific AI investors with Shaq an early backer of Google and other tech unicorns, and Will.i.am with stakes in ChatGPT-maker Open AI and its multi-billion dollar rivals.
I recently had a chance to talk with both of them in San Francisco, Shaq at Disrupt 2023 and Will.i.am at Dreamforce 2023, as they shared with me how they came to invest in some of the biggest companies in AI.
Of course, all roads lead back to a handful of power players in Silicon Valley, including Forbes Midas List investors SV Angels founder Ron Conway who was an early backer of Google, Facebook, Twitter and PayPal, and LinkedIn cofounder Reid Hoffman who is a Microsoft board member, Greylock partner and Inflection AI cofounder.
But it’s an interesting tale about how just the right mix of celebrity and grit landed these two at the center of the AI boom.
All about access
As the story goes, Shaq got invited to invest in Google’s Series A in 1999 when his agent Perry Rogers introduced him to Ron Conway. The company went public in 2004 and everyone made a fortune.
To this day, Conway remains a close friend and adviser when it comes to investments. “If a guy like Ron says I like it, I check into it. If he says I don’t like it, I stay away from it,” Shaq told me. “It’s good to have a respectable team that you know is smarter than you.”
Shaq would go on to invest in other tech unicorns like Lyft and Ring which was acquired by Amazon, and the sleep tracker Oura. A fan of startups, he often agrees to endorsement deals by taking stock plus cash and becoming a vocal and visual owner, he said.
“Being Shaq, I can get to anyone, but it’s all about respect,” he told me. He greatly admires Jeff Bezos and Bill Gates, follows them on social media and listens carefully to their advice, but doesn’t often call on them as he still sees himself as a young geeky investor who’s just a novice. And even though his net worth has been estimated in the hundreds of millions of dollars, he still fears the stat that 79% of all professional athletes end up with nothing.
That said, he’s reached a stage in his life where sometimes he’ll make an investment without expecting a traditional return. His latest portfolio company Edsoma is an AI assistant to help kids read. With it he’s hoping to make a real difference in raising literacy levels.
“I wasn’t a good reader. I had ADD and was all over the place,” he said. “When I was forced to read aloud and I stuttered, people laughed at me and brought my confidence all the way down.” The experience weighed heavy on him. He ultimately dropped out of college to join the NBA. But having parents who valued education as a path out of poverty, he made a point of returning to school years later to get his MBA and doctorate.
He sees AI as a game-changer that’s going to making everything easier, including school. “I told my son, if I had the same tools you have like Google Bard or ChatGPT, I would have gone to Princeton,” he said.
Boom boom pow
Raised by a strong mom in the crime-ridden projects of Los Angeles, Will.i.am was drawn to tech from an early age and got into a high school that specialized in science, engineering and mathematics. But he too struggled with attention deficit disorder and wound up leaving school after signing with his first record label at age 17.
By the early 2000s, he had become a worldwide sensation with his band Black Eyed Peas, working with chart-topping artists like Britney Spears and hanging out with tech pioneers like Google cofounder Larry Page. He would then go on to co-create Beats with Dr. Dre and Jimmy Iovine, which was a fashionable headphone maker and music streaming service that Apple bought for $3 billion in 2014.
It was about this time he started to dabble in AI as an entrepreneur. While working on an AI assistant backed by Solina Chau at Horizon Ventures, he was introduced to her portfolio companies Viv Labs, cofounded by Siri developers Adam Cheyer and Dag Kittlaus, and DeepMind, co-founded by Demis Hassabis and Mustafa Suleyman, which Google acquired for about $500 million. By 2015, he was already in the thick of things when Y Combinator launched OpenAI with backing from billionaires Reid Hoffman, Elon Musk, Peter Thiel, Amazon Web Services, and other giants in the industry.
Over the next few years, as everyone tinkered away with natural language processing and machine learning, Will.i.am became close friends with the soon-to-be leading voices in AI. In 2019, Hoffman had him on his Masters of Scale podcast and soon invited him to invest in Inflection AI, a startup that would come to rival OpenAI.
Will.i.am recalled: “One day Reid called me and said, there’s this guy you should meet named Mustafa. I know you’re interested in AI and there’s not that many people from the industry that have the vernacular and understanding of the space. It’ll be great to have you in the fold. You should invest, I am. I’m like, this is an opportunity of a lifetime.” And of course, I knew Mustafa, he said.
He would go on to take stakes in OpenAI, Anthropic, Runaway and Hugging Face through a private investor group, each now with multibillion dollar valuations, and finally returned to school to get his MBA at Harvard. “Class of 2024,” he proudly told me.
His latest venture, FYI,, is an AI-powered productivity app that enables creatives to collaborate and communicate on projects with digital asset management.
Like Shaq, he sees AI leveling the playing field.
“Everything’s about to change and we’re going to witness a societal redefining that will balance inequities. Folks that have been underserved will be able to use these new tools and technologies to solve their problems and create new industries. And yesterday’s industries will topple with the wave of transformation,” he said.
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