Pop icon will.i.am's smart investment journey

Pop icon will.i.am has revealed that he made a savvy investment in Tesla back in 2006, long before Elon Musk officially took the reins as CEO in 2008. However, he has expressed considerable regret for passing up the opportunity to invest in Airbnb during its formative years.

Investment in Tesla and its growth

In a conversation with Fortune, the musician, whose real name is William Adams, reflected on his early investment in Tesla, stating, "I invested in Tesla in 2006, before Elon took over the company, and he's done great, taking it to where it is. Hopefully, he can figure out a way to get it back to its glory."

The returns on Tesla shares

If will.i.am had retained his Tesla shares since their IPO in June 2010 at $17 – or even earlier at their initial private valuation – he would be sitting on a significant fortune today. Tesla's stock has skyrocketed, reaching an all-time high of approximately $480 in December 2021 and closing just under $249 recently. This translates to a phenomenal more than 200-fold return for those who invested at the IPO price. Early investors, like will.i.am, who bought in before the public offering would have seen even greater gains.

Praise for icons

On the “Drinks Champs” podcast, will.i.am was asked to choose between two icons, Musk and Apple co-founder Steve Jobs. He humorously remarked, “Damn, both of those cats are why my life is nice,” acknowledging the impact both figures have had on his career. He has also credited being part of the Beats by Dre team, which was sold to Apple for $3 billion in 2014, as a major turning point for him.

Musk's impact on Tesla

In further praise for Musk during a 2012 discussion with Singularity University, he lauded Musk’s ability to bring Tesla back from the brink of bankruptcy multiple times, calling him one of the “heroes of this era.”

Investment ventures in tech

Interestingly, this isn't the first time the musician has dabbled in tech investments. He mentioned that he had invested early in Twitter as well, selling his shares after Jack Dorsey’s departure, which also yielded good returns. However, the missed opportunity with Airbnb has haunted him.

The regret of missing out on Airbnb

The Airbnb co-founder and CEO, Brian Chesky, had invited will.i.am to invest up to $200,000 in the company’s early fundraising round. When he learned that Airbnb did not offer standard luxury hotel amenities like concierge services, he hesitated. Frequent travels had led him to favor more lavish accommodations, which ultimately caused him to dismiss the startup.

Reflections on past decisions

Looking back, will.i.am admitted that turning down the Airbnb investment was a significant “wrong decision” and a “bad one.” Since going public in December 2020, Airbnb has soared to a valuation of around $80 billion, meaning even a fractional stake would now be worth millions. He playfully commented, “Ballin’, I would have been; now, I’m like bawlin’,” acknowledging the massive gap between what could have been and his current situation.

Conclusion

As the tech world continues to evolve, will.i.am's story serves as a reminder of both the potential rewards and pitfalls of investment decisions in the fast-moving world of startups and public companies.