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5 Notable Tech Entrepreneurs Who Missed out on Huge Opportunities

Ashton Kutcher

Hindsight is 20/20.

Investing in tech startups can be like throwing darts at a target… blindfolded. There’s a certain amount of forecasting and identifying potential successes, but the truth is that no one really knows what’s going to happen with these tech innovations, so much so that people end up missing out on fantastic opportunities.

Nolan Bushnell

Missed out on: Being a one-third owner of Apple

Nolan Bushnell, who founded video game company Atari, turned down the opportunity to invest $50,000 in initial seed money during Apple’s origin years. Bushnell was one of Steve Jobs’ first bosses when the Apple creator first worked the night shift at the video game company prior to branching off to create the first Macintosh. Had Bushnell said yes, he would have owned a third of Apple, a company that is today valued at about $480 billion.

Ashton Kutcher

Missed out on: Being a primary investor in Snapchat

The 70’s Show and Two and a Half Men actor Ashton Kutcher is well-known for putting his money into innovative tech companies. He was at the forefront of investors in the likes of Uber and AirBnb, but one he decided not to tackle was picture-sharing app SnapChat. The social networking app has obviously blossomed massively in recent years, but Kutcher still stands by his point, saying: “I looked at Snapchat’s product and I hated the product. I just thought it was like, a little crickety and a little rickety. It just wasn’t beautiful or elegant. And I have this dumb, personal pet peeve about that, and it really bugged me.” Fair enough.

Kevin Rose

Missed out on: a lot of money from Google.

News aggregation website Digg was (and kind of still is) a hot commodity within the tech space, but there’s no denying that it’s lost a bit of steam with the rise of social networks filling the news-sharing gap. During the height of Digg, Kevin Rose, the company founder, was reportedly approached by Google with an acquisition offer of $200 million. The board turned it down, and a few years later, was only able to sell the company to Betaworks for $500,000.

Enzo Ferrari

Missed out on: Having Lamborghini as his partner.

While exotic sports car company Lamborghini originally focused on producing farm tractors, it’s owner, Feruccio Elio Arturo, was a mechanic and huge sports car fan. In 1958, he bought his first Ferrari and fell in love with it, but found that it had major flaws, thinking it was too noisy, had a poorly designed clutch system, a badly built interior, and was a little too crude for the road. He pointed these out to Enzo Ferrari, the company’s founder, who didn’t take it well, thinking Lamborghini was nothing more than a tractor maker who didn’t understand cars. Offended, Lamborghini decided to make his own range of sports cars. In doing so, he forced Ferrari to make the suggested improvements or get out of business. Had Ferrari listened to Lamborghini, the two could have been partners. At the very least, Ferrari could have had one less competitor in the world.

Hewlett-Packard

Missed out on: Being part of the home PC revolution.

Before striking it big with Apple, co-founder Steve Wozniak worked as a calculator designer for Hwelett-Packard in the 1970s. In his spare time, Wozniak built a computer prototype (which would eventually become the Apple 1 computer), showcased it to the HP execs, and begged them to manufacture it – but they weren’t interested. Wozniak then left HP to start Apple with Steve Jobs, and the Apple 1 laid the groundwork for the home PC revolution.

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