JUST MISSED MILLIONS: These People Walked Away From Early Jobs At Billion-Dollar Companies

Ali Fedotowsky

Ali Fedotowsky walked away from Facebook (and probably most of her stock options) when she opted to be ABC’s Bachelorette.

Robert Cezar Matei missed his chance to join early Facebook, Square and Instagram teams.

Missing millions hurts. Some people, like Kevin Systrom, went on to make millions after turning down early start up jobs.

Most live in regret, knowing they let millions of dollars slip through their fingers.

Instagram wanted Amanda Wixted to be its first hire but she was cozy at Zynga.

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.

Ali Fedotowsky left Facebook to become The Bachelorette on ABC. Sadly she and the guy she picked didn't work out.

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.

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 realise 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 left Pinterest just before his one year mark so none of his stock options vested.

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.

Robert Cezar Matei had a chance to be on Instagram's founding team. He walked away from it for Quora.

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.'

Mark Zuckerberg's college roommate and co-creator of Face Mash opted not to join Facebook's founding team.

Joe Jackson also turned down a chance to be on Facebook's founding team when he took an internship with JP Morgan over Facebook's summer house in Palo Alto.

Joshua Inkenbrandt turned down Instagram to become an engineer at Pinterest.

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.'

These guys all turned down Facebook but made millions other ways:

  • 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.

Now check out the investors who missed millions:

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