To an outsider, the tech industry can seem completely overwhelming and a little bit baffling. What makes this new guy’s idea so revolutionary? What does that even mean? Does having that name attached to the project truly mean so much? Why on earth do they need such a huge budget? Alternatively, how did they start with such a miniscule budget? There are so many questions, and the outsider often assumes it’s because they’re not in the thick of the tech industry, and simply just don’t have the same understanding as someone on the inside might.
However, even tech mavens can make mistakes. Sure, there are countless stories of people inventing the next big software or device and immediately transforming themselves from a humble worker bee to a multi-billionaire. It’s one of the industries where it’s seemingly easiest to have a rags to riches story. But for every person who has successfully carried through their idea, there are individuals along the way who didn’t truly believe in them, and didn’t think them worthy of their investment.
Now, we’re not pretending that the gentlemen on this list who declined to participate in huge, often multi-billion dollar opportunities, are paupers now. Many are brilliant in their own right and have managed to go on to fund or found countless other ventures. However, they probably still regret turning down that one big fish.
Here are 10 people in the tech industry who missed out on million.
10 Ronald Wayne - Apple
So, there’s this tech company called Apple – you may have heard of it. It’s a giant in the tech industry, and continues to inspire its loyal followers to camp out for the release of any new product. Devotees happily upgrade their tech gear whenever Apple comes out with another new device, and Apple is absolutely raking in the dollars.
Back in the day, Ronald Wayne was Apple’s third co-founder. However, he didn’t quite seem to understand what a success he had on his hands, and a mere two weeks after launching, he sold his 10% stake in apple for $800 dollars. He received an additional payout of $1,500 for totally severing any ownership ties. That’s right – instead of approximately $40 billion, which is what a 10% stake in the tech giant would yield today, he got around $2,000. Whoops!
9 Joe Green - Facebook
Everyone always grows up listening to their parents, and even in their adult years, find themselves turning to mom or dad for advice when it’s needed. Harvard student Joe Green did just that. Green was the college roommate of Facebook’s Mark Zuckerberg, and he was involved in some of Zuckerberg’s early tech experimentation, namely a Hot-or-Not style website (so 2000s!) called Facemash.
Harvard frowned upon their activities, and when Zuckerberg enlisted Green’s help for another project – Facebook – Green must have asked his dad for his opinion, and Papa Green just didn’t think it was a good idea. While there’s no set number regarding what stake Green may have gotten in the company for his early help, according to his own estimates, he may have gotten about 5% - while that doesn’t seem large, given the success of Facebook, it would have boosted his net worth by about $7 billion.
8 James Altucher - Google
Nowadays, Google is basically the only big search engine that people use. Sure, Bing has tried to make an aggressive comeback several times over the years through their marketing campaigns and product placement, but Google is and probably always will be king in the search engine world.
James Altucher would disagree. The venture capitalist was approached by a junior partner at Google, who offered a 20% stake in the company for $1 million (very Dragons’ Den). Altucher decided the opportunity was too small, and declined to fund it. To his credit, he hasn’t gone on to defend or explain away his decision – he’s outright called it “the worst venture capital decision in history.” We’re inclined to agree.
7 Kevin Rose - Digg
Do you remember Digg? It used to be a popular place to scroll through news clippings and read quick little bits. Nowadays, there are countless more streamlined and popular alternatives, but back in the 2000s Digg reigned supreme. The company apparently received several acquisition offers at the height of its popularity, including an alleged $200 million from Google and a confirmed $80 million offer from an unnamed company.
Digg founder Kevin Rose has admitted he would have been willing to sell the company for the asking price, but the Digg board said no. The worst part is, they did end up selling it within a few years, in 2012 – but at that point, the company’s declining popularity meant it went for only $500,000. That board is probably beating themselves up for not accepting the offers while Digg was in its prime.
6 Hewlett-Packard Board - Apple
Okay, so Hewlett-Packard is still manufacturing devices and doing quite well for itself. However, back in the 1970s, they missed out on an absolutely enormous opportunity. You see, a young tech whiz by the name of Steve Wozniak was working for the company in the 1970s. While he was likely a good employee, his biggest contributions came in his spare time, when he created a PC that would eventually become the Apple 1 computer.
Since he was working at HP, Wozniak figured he’d give them the chance to get the product, and asked the executives to manufacture what he had created- not once, not twice, but five times! After begging and begging HP execs to manufacture a product he knew was phenomenal, he decided to leave the company and start his own, alongside Steve Jobs. That’s right – Hewlett-Packard could have had ownership of Apple products, but they missed their chance by turning down a young tech genius.
5 David Cowan - Google
Bessemer Venture Partners, a tech investor, decided to come forward with its mistakes a few years ago by publishing an “anti-portfolio.” What exactly is that? Basically just a list of opportunities or companies that they decided not to invest in which went on to be huge successes. The list is populated by countless huge names such as eBay, Facebook, FedEx and more, but the best story comes from their refusal to invest in Google.
Susan Wojcicki, a friend of Bessemer partner David Cowan, had graciously rented her garage to two young tech geniuses, Sergey Brin and Larry Page. They turned the space into the first office for Google, and Wojcicki, recognizing their talent, tried to introduce Cowan to them. He didn’t even meet them and make a decision – instead, he just totally avoided the garage, and the co-founders working in it, altogether. If he had bothered to converse with the young men, he may very well have made billions on the tech giant over the years.
4 Mark Cuban - Box
Mark Cuban is worth billions, so chance are he isn’t really sweating any missed opportunities, because they’re not going to make or break him. However, there’s one company in particular that could have made him a bundle.
Box, an enterprise cloud company, was started by college student Aaron Levie. Levie pitched Cuban, who initially gave him a $350,000 seed investment for his company. However, Cuban didn’t quite agree with the young tech company’s business model, and after some disagreements, Levie managed to raise enough to buy the billionaire out. Cuban stands by his decision, continuing to comment that he doesn’t agree with Box’s business model, but the company’s success without him proves he may have been able to pocket a nice chunk of change had he stayed.
3 Sahil Lavingia - Pinterest
Who hasn’t spent far too much time pinning recipes, home décor photos, ideas, inspirations and more on popular website Pinterest? Nearly everyone – women in particular – has been guilty of wasting a bit too much time on the addictive site. However, Sahil Lavingia wasn’t quite as committed. He was the second employee of Pinterest, which has expanded dramatically since then, but the teenaged worker decided it just wasn’t for him.
He left after about 11 months – an even bigger mistake, because had he gotten to the year mark, some of his stock options would have vested. However, Lavingia seems to be pretty tech savvy on his own, and at only 19 became CEO of a start-up called Gumroad. His newest company isn’t worth anywhere near Pinterest’s approximately $4 billion valuation, but who knows – it could be the next big thing.
2 Nolan Bushnell - Apple
Nolan Bushnell, the founder of Atari, holds the distinction of being one of Steve Jobs’ first bosses – something that Jobs quickly gave up when he went into business for himself alongside buddy Steve Wozniak. Jobs was evidently impressed by some of the ways Bushnell conducted business, and when he was starting Apple, offered Bushnell a chance to invest a mere $50,000 in seed money in the company.
If Bushnell had agreed to invest in his former employee, he would have been the owner of 1/3 of the tech giant. 1/3 of Apple’s approximate current valuation of $480 billion? That’s a whole lot of dough.
1 Jerry Yang - Microsoft & Yahoo
When you think of a Yahoo CEO nowadays, most people immediately picture current CEO Marissa Mayer, the former Google exec and strong woman in the male-dominated world of tech. However, before Mayer’s time, CEO Jerry Yang was approached by Microsoft. The offer definitely wasn’t a small amount of change, like some of the early investments in tech giants – Microsoft was already an established firm, and they offered him a $31 a share, $44.6 billion offer.
Given the way that Yahoo declined for several years after that, Microsoft’s offer may very well have been the lifeline they needed. While Mayer seems to be steering the company back to relevancy as of late, had Yang accepted the offer, he very well could have dramatically changed the future of Yahoo.
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