First, we should note that Wixted is plenty successful. She joined Zynga as an early employee and stayed through its IPO. But she probably could have made even MORE millions if she had left for Instagram when it offered in 2010.
Wixted writes about her missed opportunity on Quora:
"In June 2010, Mike and Kevin were just getting started on their mobile web app which they called Burbn. I was a lead engineer on the mobile team at Zynga at the time. Mike contacted me about coming on board as their first hire. We met, and they showed me their ideas for where they were thinking of heading with Burbn: a photo-sharing mobile app.
... It was a great team fit, but I just couldn't get excited about a photo-sharing app. I felt, and I still feel, that I need to be working on more complicated things, so I've stayed in the games space...Of course, I'm kicking myself now. Hindsight is 20/20 and all."
Photo: Amanda Wixted
In 2009, Ali Fedotowsky faced a dilemma. She was a contestant on The Bachelor dating pilot Jake Palveka.
In a tearful goodbye, she left Palveka to return to her job at Facebook. Fedotowsky had run out of vacation days while filming the show and didn't want to miss out on millions.
But when ABC offered to make her its Bachelorette, Fedotowsky left her sales rep gig at Facebook, probably along with her stock options. She joined the company in July 2009 and left around March 2010.
Fedotowsky's engagement to contestant Roberto Martinez ended a few months ago and while Facebook didn't re-hire her, she's now a host on NBC's 1st Look.
Julian Targowski was offered a role at Instagram last October but walked away to launch his own app.
He says he wasn't even interested in the offer because he was loyal to his own team.
"I don't regret a thing," he says on Quora. "You realize a lot of things about yourself (how content you are with your current situation, how hard you're working, where you want to be in the next few years, etc) when things like this happen."
Sahil Lavingia has a buzzy startup now that's raised $8 million from Silicon Valley investors, Gumroad. To start Gumroad, Lavingia had to walk away from his position as the #2 employee at Pinterest.
His timing could have been better. Lavingia left Pinterest about one month shy of his 1 year mark at the company. That means none of his stock options vested.
Hopefully he'll make it back on Gumroad. Meanwhile, Pinterest's valuation is skyrocketing.
Gumroad only has 3 full-time employees. Last month it only had one, founder Sahil Lavingia (second from left).
Robert Cezar Matei has missed a few golden opportunities. First he turned down an opportunity to work for Facebook and decided to stay at Stanford instead. Then he failed to be impressed by Jack Dorsey's Square and turned down an early opportunity there.
But his most costly decision may have been turning down Instagram. He was offered a job as Instagram's 2nd engineer and the founders had only made one other offer prior.
"When I was deciding where to work next, they made me build a follow recommendation algorithm using their API. I guess they liked it," he writes. "We talked about their vision. We had sake in the Tenderloin at 1 in the morning. Kevin crafted a lovely letter, peppered with shared experiences and pictures, as he did for every offer. I was touched."
Instead, Matei went to Quora. He was more passionate about its vision and the position.
"If you're in the Valley for any amount of time, you'll have missed opportunities," writes Matei. "Whatever. Opportunities were rarely as close as they might seem in hindsight. There are a million ways my life could have turned out worse, too."
When Joe Green was at Harvard, he was roommates with Mark Zuckerberg. He and Zuckerberg created Face Mash together, which got the pair in trouble with the university.
Green's father, a professor at UCLA, cautioned him not to work with Zuckerberg anymore. So when Zuckerberg asked him to head up Facebook's business operations, he declined. The position would have granted him about 3 or 4 percent of the company, Green estimates, which would have made him worth about $3 billion.
He still scored some Facebook stock for being an advisor to the company and he later cofounded Causes and NationBuilder, companies other early Facebookers backed.
He tells Bloomberg BusinessWeek, “Every once in a while you can have a moment of bitterness but in general I've been so blessed with what I have been able to do."
When Facebook was taking off and Zuckerberg rented a house in Palo Alto for the summer, he invited Harvard classmate Joe Jackson to come with him.
Instead, Jackson went to New York for a J.P. Morgan Chase internship.
“I completely missed the boat," he tells Bloomberg BusinessWeek of his missed Facebook stock options. "I wasn’t thinking about it as ‘This could be my chance to be rich and famous.' It was more like, ‘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."
Like Wixted, we should note that Inkenbrandt will be just fine. He chose Pinterest over Instagram, which should yield a decent multi-million payout of its own.
But with Instagram, he could have been a millionaire already. Inkenbrandt writes on Quora:
"I chose to work at Pinterest over Instagram. It was not an easy decision by any means because I really like Instagram and the guys who built it. I'll keep my reasons for choosing Pinterest to myself, but I will say that I don't regret the decision."
Kevin Systrom turned down Facebook and later sold his company, Instagram, to Zuckerberg for $1 billion.
Mike Abbott became Twitter's head of engineering
Steve Chen worked for Facebook for a few months then founded YouTube, which he sold to Google for $1.6 billion.
Photo: HarcoRutgers, Flickr.com
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