Reid Hoffman (pictured), co-founder of LinkedIn, is an investor in Facebook, Paypal, Zynga, and Groupon – and with a net worth of $2.5 billion (£2bn), it’s clear he knows what he’s doing when it comes to business decisions. But one big opportunity that Hoffman missed out on was investing in YouTube, when venture capital firm Sequoia Capital outbid him for a 30% stake in the video-sharing platform in 2005. Sequoia paid $11.5 million for its share.

The LinkedIn mastermind told the New York Times that he wishes he’d pushed harder to get a stake in the company before it became a global sensation, especially as Google snapped up the company for $1.65 billion just a year later, the equivalent of around $2.5 billion (£2bn) today, which would’ve given him quite the windfall.

The biggest missed business opportunities ever