Startups come and go, meaning that those in the tech world often face the dilmemma of pick at which company where they’ll actually be successful in the future.
- Major tech executives who have turned down lucrative offers include Instagram’s Kevin Systrom and Bachelorette’s Ali Fedotowsky.
- Here are some other big names in Silicon Valley who may have missed out on millions from opportunities they turned down.
Ali Fedotowsky walked away from Facebook when she opted to be ABC’s Bachelorette.
Robert Cezar Matei missed his chance to join early Facebook, Square and Instagram teams.
It’s impossible to know which startup is going to become the next billion dollar success story, and the risk of letting a golden opportunity slip through your fingers is something that tech workers grapple with every day.
While some who turn down lucrative offers still achieve success — Instagram’s co-founder Kevin Systrom is a prime example — others may come to live in regret.
Here are how some Silicon Valley techies missed opportunities to make millions at companies like Facebook and Instagram:
Instagram wanted Amanda Wixted to be its first hire but she was cozy at Zynga.
First, we should note that Amanda 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 came calling in 2010.
Wixted wrote about her missed opportunity back in 2012 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.
Wixted went on to found the company Meteor Grove Software, and served as CTO for the e-learning app Homer.
Ali Fedotowsky left Facebook to become the lead on ABC’s “The Bachelorette.” 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. Two years after her March 2010 departure, Facebook had a massive IPO that turned many of its employees into millionaires.
Fedotowsky’s engagement to contestant Roberto Martinez ended shortly after the show aired and while Facebook didn’t re-hire her, she went on to be a host on NBC’s “1st Look.”
Now, Fedotowsky is married to TV and radio host Kevin Manno and writes a blog called Ali Luvs.
Julian Targowski was offered a role at Instagram in 2011, but walked away to launch his own app.
Julian Targowski was offered a role at Instagram in October 2011, 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.”
Targowski went on to work at a startup called DailyBooth, which was acquired by Airbnb in 2012 but closed down soon after.
Sahil Lavingia left Pinterest just before his one year mark, so none of his stock options vested.
Sahil Lavingia has a startup called Gumroad, a payment company launched in 2012 at 19 years old. But to start Gumroad, Lavingia had to walk away from his position as the No. 2 employee at Pinterest.
His timing could have been better (or worse): Lavingia left Pinterest about one month shy of his one-year mark at the company, which means none of his stock in Pinterest had vested.
Hopefully he’ll make it back on Gumroad. Meanwhile, Pinterest is valued around $12 billion.
Robert Cezar Matei had a chance to be on Instagram’s founding team, but 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 wasn’t impressed by 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 second engineer. Plus, 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 wrote on Quora. “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, where he worked on product and growth.
He said was more passionate about Quora’s 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 FaceMash, Joe Green, opted not to join Facebook’s founding team.
When Joe Green was at Harvard, he was roommates with Mark Zuckerberg. He and Zuckerberg created FaceMash 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% 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 co-founded Causes and NationBuilder, companies other early Facebookers backed.
Green has also served as president of FWD.us, an investor in Asana, and an entrepreneur-in-residence at Andreessen Horowitz. He continues to serve as an executive board member at Causes today.
Joe Jackson also turned down a chance to be on Facebook’s founding team when he took an internship with JPMorgan instead of hanging out at Facebook’s summer house in Palo Alto.
Spencer Platt / Getty Images
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 JPMorgan Chase internship.
“I completely missed the boat,” he told 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.'”
Joshua Inkenbrandt turned down Instagram to become an engineer at Pinterest.
Inkenbrandt chose Pinterest over Instagram, a decision made at a time when Pinterest was nowhere near its $12 billion valuation of today.
Inkenbrandt wrote 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.”
Inkenbrandt left Pinterest in 2016, and has co-founded an app called Clutch for sharing video game clips.
These guys all turned down Facebook, but they 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.