Benzinga and Yahoo Finance LLC may earn commission or revenue on some items through the links below.

They say hindsight is 20/20, but for Will.i.am, it might just be worth billions. The Black Eyed Peas frontman and tech investor had the chance to ride Tesla's stock to astronomical heights—but instead, he watched from the sidelines as Elon Musk transformed the company into an electric empire.

A Missed Jackpot

In 2006, Will.i.am bet on the company before Musk officially took the reins. “I invested in Tesla in 2006, before Elon [Musk] took over the company, and he's done great, taking it to where it is,” he recently told Fortune. “Hopefully, he can figure out a way to get it back to its glory.”

Don't Miss:

• Inspired by Uber and Airbnb – Deloitte's fastest-growing software company is transforming 7 billion smartphones into income-generating assets – with $1,000 you can invest at just $0.26/share!
• Arrived Home's Private Credit Fund’s has historically paid an annualized dividend yield of 8.1%*, which provides access to a pool of short-term loans backed by residential real estate with just a $100 minimum.

Tesla's stock debuted in 2010 at $17 per share—$1.13 after stock splits. On Dec. 17, it peaked at around $480. That means an early investor who held onto their shares would have made over 420 times their initial investment. Even at its current $282 per share as of April 2, that's a 200x return. Had Will.i.am kept his stake, his net worth might look very different today.

While Tesla's meteoric rise turned early believers into multi-millionaires, it hasn't been all smooth driving. Industry experts are divided over the stock's future.

According to Bloomberg, Tesla's dominance is slipping, with EV competitors like BYD and legacy automakers like Ford and General Motors ramping up production. But not everyone agrees. ARK Invest's Cathie Wood remains bullish, projecting a $2,000 per share valuation by 2027, citing Tesla's advancements in AI and full self-driving capabilities.

Trending: BlackRock is calling 2025 the year of alternative assets. One firm from NYC has quietly built a group of 60,000+ investors who have all joined in on an alt asset class previously exclusive to billionaires like Bezos and Gates.

Adding to the turbulence, a 2024 report from the National Highway Traffic Safety Administration highlighted concerns about Tesla's Autopilot system, linking it to multiple accidents. Meanwhile, Musk’s political controversies have contributed to a decline in Tesla’s brand perception and sales.

Will.i.am's investing track record has been a mix of wins and "what-ifs." He was an early backer of Pinterest, Dropbox, OpenAI, and Anthropic. He even bought into X before selling when Jack Dorsey left—dodging Musk's chaotic takeover. But one decision stings the most.

“I invested in Twitter early on. When Jack [Dorsey] left, I sold it. Made good there,” he said. Yet, the one that haunts him? Airbnb.

See Also: This platform is reshaping how you invest in private companies — and you can be a part of it for $0.18 per share.

When Airbnb co-founder and CEO Brian Chesky invited him to invest $200,000 in an early round, he turned it down because Airbnb lacked luxury services like room service. Today, the company is valued at around $80 billion.

"That 200K could have ballooned to nearly $80 million. “Ballin’, I would have been. Now, I’m like bawlin.” Will.i.am teased.

His regret echoes past investment blunders. In the 1970s, Ronald Wayne sold his 10% stake in Apple for $800—shares that would now be worth billions, according to Cult of Mac. Warren Buffett has also admitted to skipping Google and Amazon early on, proving that the brightest minds can miss a golden ticket.

Read Next:

• If there was a new fund backed by Jeff Bezos offering a 7-9% target yield with monthly dividends would you invest in it?
• Warren Buffett once said, "If you don't find a way to make money while you sleep, you will work until you die." Here’s how you can earn passive income with just $100.

This article Will.i.am Says Passing on Airbnb Was a '$80 Million Wrong Decision'—'Ballin', I Would Have Been, Now I'm Like Bawlin' originally appeared on Benzinga.com