Will.i.am Regrets Turning Down $200K Airbnb Investment in Its Early Days: “That Was a Big One” [Video]

Will.i.am recently opened up about a major missed investment opportunity that still haunts him. The musician and entrepreneur revealed that he had the chance to invest $200,000 in Airbnb before the company launched in 2008, but ultimately passed on the offer. Reflecting on his decision, Will.i.am expressed regret, calling it a “bad one.”

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In an interview, Will.i.am shared the conversation he had with Airbnb co-founder Brian Chesky, who had approached him with the investment opportunity. Chesky, eager to secure funding, offered Will.i.am a chance to get in on the early rounds. However, Will.i.am was skeptical.

“Brian Chesky was like, ‘Yo, we got $200,000 left in this round. You want to get in it?’ I’m like, ‘Yo, what’s up with concierge? Y’all don’t got that?’ No. ‘What about 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.'”

Looking back, Will.i.am acknowledges his misjudgment.

“Wrong! Did I make the wrong decision? That was a bad one,” he admitted. “That was a big one. Oh, you know, ask him. Every time you see Brian Chesky, be like, ‘Yo, if Will would have put in that 200k, what would that be worth right now?'”

Despite the missed opportunity, Will.i.am remains optimistic, saying, “I’m still balling though. Different type, I’m still balling.”