- Will.i.am made a multi-million dollar mistake by passing on Airbnb founder Brian Chesky’s offer to be an early investor, the rapper tells Fortune.
Will.i.am had a feeling nearly a decade and a half ago, but it’s one that he regrets immensely.
Airbnb founder Brian Chesky approached the rapper in the company’s early days with an opportunity to invest up to $200k in a fundraising round, but Will.i.am was skeptical.
“What’s up with concierge? Y’all don’t got that? No,” he told Fortune at SXSW this week. “What’s up with room service? Y’all got that? He’s like, no. I’m like, yeah, I think I’m gonna have to pass on that one.”
Had he taken him up on the offer, Will.i.am would be significantly wealthier. In 2010, Airbnb raised $7.2 million in series A funding. If Will.i.am invested 200k around then, his stake could be worth millions of dollars now. Airbnb went public in 2020 at a $47 billion valuation. Today, it has an over $78 billion market cap.
“Ballin’, I would have been,” Will.i.am joked. “Now, I’m like ballin’—different type, but I’m still ballin’, though.”
While the Black Eyed Peas co-founder admitted to Fortune that skipping on Airbnb was a “bad one,” this is not the first time he has missed out on an investment opportunity; But, he’s taken advantage of other offers.
In 2006, Will.i.am invested in Tesla “before Elon took over,” he told the Drink Champs podcast. He was also an early believer in Beats, the headphones company that was eventually acquired by Apple.
“You’re talking about two companies that changed my life,” Will.i.am said.
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As part of a private investment group, Will.i.am reportedly has stakes in companies like OpenAI and Anthropic.
Will.i.am has a long history as a technology entrepreneur. In 2011, Intel named him their “director of creative innovation.”
“Nearly everything I do involves processors and computers, and when I see an Intel chip I think of all the creative minds involved that help to amplify my own creativity,” Will.i.am said at the time.
His start-up, i.am+, raised $117 million in 2017. But more recently, Will.i.am has set his sights on the future of AI.
“If you are a creator and you see this tool, then it’s a job creator,” he said in 2023. “If you are tied to yesterday and just comfortable with mediocrity, then it’s a job [destroyer].”
Will.i.am founded—and serves as the CEO of—FYI, an AI-driven creative productivity and communication platform that is seeking to redefine the world of radio.
“Making an album is great, but building a station is even greater,” he said.