“We had almost a full 20% [of Netflix],” Arnault said recently, reflecting back on the investment decision during the Legend podcast. “Yes, I sold too early. We made a very good investment, but since then I think it’s increased 10-fold.” 

In 1999, Arnault began by buying up a chunk of Netflix for $30 million through his private family holding company, Groupe Arnault, just two years after the entertainment company’s inception. It was Netflix’s largest investor at the time, when the company was still mailing out DVDs as a service. The French fashion magnate owned nearly a fifth of the entire company, which was already a “huge success” at the time, and cashed out most of his stock four years later when Netflix boasted a market cap of $500 million. Now, Netflix is valued at $300 billion—600 times higher than when he sold most of his stake. 

He didn’t reveal exactly why he sold his shares at that moment, but if he didn’t, his stake could have been worth up to $60 billion today. 

It’s just a dent in Bernard Arnault’s $157 billion fortune

For most, this missed opportunity would be seen as a life-changing blunder. But Arnault, worth $157 billion, says it’s only part of the game. “I always sell too early,” he admitted. 

And Netflix wasn’t his only what-if investment. 

The 77-year-old CEO previously owned stock in $5 trillion tech giant Apple, once again sold too early, but this time admitted in 2018 that he “should have kept them until today.” 

Arnault also recounted investing in a U.S. fund that liquidated during the dot-com crash, and when it dissolved, received a “good bundle” of Google shares, which were valued at  €2 to €3 at the time (or $2.28 to $3.42 today). At that point, he didn’t know what the company was—it was a stroke of luck, landing a deal he had “absolutely nothing to do with.” 

Arnault said he’s since sold those shares and still made a hefty profit, but the company’s shares have since ceased to rise, highlighting that there is no golden timeline for the right moment to sell—all it takes is a market correction to send shares tumbling, or a breakout earnings report to shoot them up.

The leaders who have lost out on billions selling early 

Arnault is hardly alone in leaving billions on the table.

Around fifty years ago, a trio of founders created one of the world’s most lucrative companies: Apple. And in the decades since, many have tuned in for the successes of late cofounder Steve Jobs and computing visionary Steve Wozniak. 

But Apple’s little-known third founder, Ronald G. Wayne, has largely been out of the picture following his early exit. Wayne received a 10% stake for his work in formalizing the tech business, but less than two weeks later, he sold his shares for $800. 

If he had held onto his shares today, he would have nearly $499.5 billion to his name. However, Wayne said he had no regrets—he still made ends meet, even if it meant renting out a part of his property or cashing in his monthly Social Security check.

“If I stayed at Apple I would have probably ended up the richest man in the cemetery,” the now 91-year-old recalled to CNN.

Palantir and PayPal cofounder Peter Thiel also missed out on billions by selling shares before their peak. 

In 2004, just months after Mark Zuckerberg created the social media platform, Thiel forked over $500,000 for a 10% stake in the budding company. That investment valued Facebook at $4.9 million, at the time—but just once decade later, he sold off a majority of his stake for $400 million. It’s still a sum that most would gawk at, but if he had held onto those shares today, he would own about $11.85 billion worth of Meta. 

Looking back, the entrepreneur believes he underestimated Facebook’s original market of college students: “I think investors always have a bias to invest in things they themselves use and they undervalue things they don’t use so there aren’t many investors who are in college,” Thiel said during a This Week in Startups panel in 2015.

Then there are the founders who sold their own companies long before they flew the coop. In 2012, Instagram’s 20-something-year-old creators, Kevin Systrom and Mike Krieger, decided to sell their brainchild to Facebook in a $1 billion deal. The duo said that they sold in part because Zuckerberg allowed them to stay at the company, serving as Instagram’s CEO and CTO roles until 2018.

But the payday wasn’t rewarding. Even though Systrom got about $400 million from the deal, while Krieger walked away with roughly $100 million, they could have been billionaires if they kept their stock, as Instagram’s valuation shot up to about $114 billion in 2024, according to Kantar. 

“I think the biggest lesson…coming into a fair amount of money pretty quickly, was that money itself is no end,” Systrom said during a panel at SXSW in 2019. “It doesn’t make you happy. It doesn’t solve health problems. It can help in those things.”