Imagine giving up your equity in a startup early or passing on the opportunity to invest in a friend or family’s business venture, only to watch the business explode in popularity in the coming years. These people could have made millions but a single choice led them in a different direction.
From a guy who theoretically passed up $138 billion to a Facebook employee who left the social network before it went public to appear on the hit TV show The Bachelorette, we have something for everyone. A few decisions seemed like a bad idea but ended up working out even better for the people involved!
Catherine Hettinger: Lost Out On The Fidget Spinner Fortune
We don’t know how much Catherine Hettinger lost out on but it was definitely millions of dollars. Twenty years before the fidget spinner became a massive hit in 2017, Hettinger came up with the idea and patented her invention.
Hettinger patented the “finger spinner” in 1997 but lost the patent in 2005 when she couldn’t afford to pay the $400 renewal fee for her invention. Millions of units have sold in recent years, making the product a massive financial success.
Sahil Lavingia Lost Out On The Pinterest IPO
Sahil Lavingia was employee number two at Pinterest but like the others on our list, he decided to leave the company before it became a wildly successful juggernaut.
In 2011, Lavingia decided he wanted to build his own company, Gumroad, an e-commerce platform he believed would be the next billion-dollar idea. Lavingia made the decision before his shares vested. That means when the company went public with an initial valuation of just north of $10 billion, he didn’t share in the company’s windfall. Gumroad is still around but it has yet to reach the level of success found at Pinterest.
Daniel Kottke Lost Out On Millions From Apple
After graduating from Colombia in 1977, Daniel Kottke started working for Steve Jobs as Apple employee #12. At one point he even shared a house with Jobs and Job’s girlfriend Chrisann Brennan.
Steve Jobs famously refused to grant Kottke stock in the company. It was Apple co-founder Steve Wozniak who eventually gave up some of his own stock for the loyal Apple employee. While he earned a good living at Apple Computer, it was hardly the windfall employee #12 deserved.
Roy Raymond Lost Out On An Empire He Founded!
In 1982, a man named Roy Raymond decided to sell his company, Victoria’s Secret. At the time, he was running six stores and offering a 42-page catalog. He sold the company for $1 million.
In 2018, the company reported revenue of $7.4 billion. While Victoria’s Secret has struggled in recent years, the company would have made Roy Raymond very rich if he had hung on to even a small part of his original company. At the same time, $1 million is nothing to balk at.
Ronald Wayne: $138 Billion
On April 1, 1976, a partnership agreement was signed between three men: Steve Jobs, Steve Wozniak, and Ronald Wayne. Soon, a number of disagreements and arguments broke out between the partners, and Wayne decided to sell his shares.
Wayne sold his 10 percent stake in Apple for just $800. The market capitalization for Apple at the time of this story is $1.38 trillion. Wayne’s share in its entirety would be worth $138 billion in 2020.
Joe Green Turned Down A Lot Of Facebook Money
Joe Green was roommates with Facebook co-founder Mark Zuckerberg during their time at Harvard University. At one point, Zuckerberg offered Green the chance to head up Facebook’s business operations.
Green turned down the position which would have given him about 3% to 4% of Facebook equity. At today’s $652 billion market capitalization, his share would have been worth around $2 billion. Green was given some stock for being an advisor to the company but nothing compared to what he could have netted.
Ali Fedotowsky Left Facebook For ‘The Bachelor’
In 2009, Ali Fedotowsky was offered a chance to be a contestant on the popular TV show, “The Bachelor,” where she would date pilot Jake Pavelka. Ultimately, with her vacation days depleted at the social network, she offered a tearful goodbye and left the show.
Soon after, ABC offered to make Fedotowsky the next Bachelorette. In order to accept, she was forced to leave Facebook. Two years later, Facebook issued its hugely successful IPO. She has managed to stay partially in the spotlight with TV gigs but she may have lost out on a big payday.
Julian Targowski Turned Down Instagram
In 2011, Julian Targowski could have become an early employee at startup Instagram. Instead, he decided to launch his own app.
Later, Targowski would work for DailyBooth, a company that was acquired by Airbnb and shut down a short time later. In a Quora post, Targowski said, “I don’t regret a thing.” He also says he learned a lot about himself by taking on his own project and wouldn’t trade it for anything other than what he experienced.
Robert Cezar Matei Turned Down Instagram, Facebook, And Square
Robert Cezar Matei turned down Facebook to earn his degree at Stanford University. Then he turned down billion-dollar startup Square and eventual Facebook acquisition Instagram. It was Instagram’s position that may have netted Matei the most lucrative opportunity. Initially, he was given the chance to become the company’s second engineer.
Matei later said there were no hard feelings, in fact, he said he was “touched” by a personal letter he received from Instagram co-founder Kevin Systrom after they had met to discuss the opportunity.
Kevin Rose Lost Out On $80 Million
Digg founder Kevin Rose admits that Digg once received an $80 million buyout offer which he says his board turned down, even though he was prepared to let the company go. Reports suggest that those talks involved Google, although he has never confirmed that rumor.
In 2012, Digg, which had quickly declined in popularity, was sold to a company called Betaworks for the paltry fun of $500,000. The platform has never been able to regain the popularity it once held.
Joe Jackson Turned Down Facebook For An Internship
Joe Jackson decided to turn down an offer from Mark Zuckerberg to live in a shared Palo Alto home for the summer. Zuckerberg thought his former classmate would be a great addition to the team but Jackson chose a different path, an internship with JPMorgan Chase.
Speaking to Bloomberg BusinessWeek, Jackson said, “I completely missed the boat.” He says his initial thought when turning down the role was, “This is going to Palo Alto and living in a house with a bunch of kids and programming for a startup that may not go anywhere.”
Spencer Haywood Could Have Owned 10% Of Nike
NBA Hall-of-Famer Spencer Haywood was offered two options by Nike in the 1970s. He could accept a $100,000 payday to promote the company’s shoes or be given a 10% stake in the company.
Haywood took the cash on the advice of his sport’s agent. If he would have taken the equity, his share today would be worth around $11.5 billion. He made a good amount of money during his career but talk about short-sighted thinking on behalf of his agent.
Noah Kagan Lost Out On Hundreds Of Millions
Noah Kagan has made millions of dollars from his own startup, Sumo (Originally SumoMe), but he could have been incredibly wealthy had he not been fired from Facebook when he was just starting out. Kagan was set to receive a $65,000 base and .05% of the company.
With a market valuation of over $665 billion, his shares would have been worth more than $330 million today. Perhaps leaking info about the company to TechCrunch wasn’t a smart decision. In any case, he looks like he’s still having fun and his business is thriving!
Let’s start out by saying Amanda Wixted has likely done very well for herself. She worked for Zynga as an early employee and continued to work for the company through its IPO.
With that being said, Amanda was offered the role of employee #1 on the Instagram team just as Mike and Kevin were starting to work on the app. They met and the meeting was good but Wixted revealed on Quora that she just “couldn’t get excited about a photo-sharing app.” Hindsight is 20/20 and she admits she kicked herself a little bit for not jumping at the chance.
Mike Abbott Turned Down Facebook But Ended Up Just Fine
Mike Abbott turned down Facebook and eventually became Twitter’s head of engineering before jumping over to Apple. He’s made a name for himself and he’s likely not hurting for money but he could have earned millions.
Facebook turned many of its early employees into multi-millionaires and Abbott would have likely been handed a very lucrative payday had he taken the job. Given his own success with some of Silicon Valley’s biggest tech brands, we’re sure he’s not kicking himself too much over his earlier decision.
Nolan Bushnell Could Have Owned One-Third Of Apple
Atari founder Nolan Bushnell made a fortune from his video game console but he could have made a lot more money for just a $50,000 investment in Apple.
Bushnell was one of Steve Jobs’ first bosses and he was approached about becoming an early investor. With a market cap of $1.38 trillion, his stake would be worth more than $400 billion. Sure, it would have been diluted at some point but he certainly left 10’s of billions on the table.
Chris Hill-Scott: $50 million
Chris Hill-Scott was a part-owner in SwiftKey, a company that would eventually sell to Microsoft for $250 million. Chris owned 20% of the company which would have led to a $50 million payday.
What did Hill-Scott get instead of $50 million? A bicycle. He was only with the company for two months when he called it quits while receiving what we’ll now and forever consider the most expensive bike purchase of all time.
Brad Wall Says He Was Cheated Out Of Millions
Engineer Brad Wall played a big part in modernizing Wawa Inc’s dairies. Wall helped rapidly expand the company from 1999 until 2013 when he served as director of construction and design.
During his tenure with the company, Wall, and other employees, were told they could hold onto their company shares until retirement age. However, the company reversed that decision. “Wawa is pretty much dead to me,” Wall said in an interview. “I am one of the ones who lost at least a couple million.”
John Greathouse Could Have Made $1 Billion
John Greathouse is doing fine, he’s a partner at Rincon Venture Partners which has generated hundreds of millions in shareholder value. With that being said, Greathouse lost out on the opportunity to turn $250,000 into $1.1 billion by investing in Uber.
As Greathouse revealed in Entrepreneur, he not only avoided the company’s seed round but also Series A funding. “I never even bothered to listen to [Uber co-founder Travis Kalanick’s] pitch, even though I was repeatedly offered the opportunity.”
Steve Chen Probably Lost Millions At Facebook But That’s Nothing To Him
Steve Chen is on our list because we wanted to highlight someone who missed out on an opportunity to cash in only to see his fortune grow astronomically with his own company.
Chen was working for Facebook and on track to eventually reap the benefits of a future IPO. Instead, he quit the company and founded a little video service called YouTube. The company eventually sold to Google for $1.6 billion. Chen’s estimated net worth today is $350 million.