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There’s security in working for a large tech company: The salary is usually pretty solid and the benefits are top-tier. But that hasn’t stopped many entrepreneurship-minded employees from walking away to found their own companies over the years. (Even some who have been caught in the recent rounds of tech layoffs have set out to found their own startups.)
The degrees of success, of course, vary. But every now and then, one knocks it out of the park, starting a business that becomes another indispensable tech destination or tool. And every now and then, these founders create something that becomes bigger than the place they left.
Here’s a look at seven founders who took a leap of faith and saw tremendous success as a result.
Evan Williams
Williams joined Google in 2003, when the company acquired Pyra Labs, a company he had co-founded in 1999. Designed to make project management software, it became known for its note-taking feature, called Blogger (which helped blogs take off). He stayed with Google for a year-and-a-half, but left to once again explore the startup space. In 2006, Williams, Biz Stone, and others founded Obvious Corp., which spun off a social-networking project called Twitter into its own company in 2007.
Williams was co-founder and a board member (and CEO from 2008 to 2010). Two years after stepping down as CEO of Twitter, he created the publishing platform Medium, which he ran for 10 years. (Williams sold his 30-percent ownership share in Twitter in 2017 and left the board in 2019.) These days, he’s working on his next project: Mozi, which helps people foster in-person connections with their social circle.
Kevin Systrom
Systrom worked at Google, helping to build Gmail and other tools early in his career. On weekends, though, he spent his time building an app called Burbn which let people share location-aware photos and notes. One enthusiastic early user was Mike Krieger. The two eventually began working together to create what would become Instagram. Systrom was growing frustrated at Google and eventually decided to leave so he and Krieger could focus on Instagram full time. The company was sold to Facebook in April 2012 for $1 billion.
Assaf Rappaport
Rappaport co-founded Wiz, a security startup that, earlier this year, agreed to be acquired by Google for $32 billion. Before that, though, Rappaport spent four years at Microsoft after it acquired Adallom, a cloud access security broker he had co-founded in 2012. He ran Microsoft’s Cloud Security Group, but by 2019 was ready for something new. The following year, he launched Wiz, which raised a $100-million Series A round by the end of that year. He initially turned down Google’s offer for the company and was considering an IPO, but when Google raised the offer amount earlier this year, he said yes. The deal is expected to close next year.
Jason Kilar
From 1997 through 2006, Kilar was an executive at Amazon, including his last role as SVP of worldwide application software. He left after nine years to co-found a new streaming company called Hulu in 2007, becoming its CEO. Within two quarters, the company was profitable. Today, after a dizzying series of deals since its launch, Hulu is fully owned by Disney.
Ilya Sutskever
Sutskever’s first job was at a research company called DNNResearch, which was acquired by Google in 2013. He spent two years with the tech giant, working in the Google Brain AI division, before departing in 2015 to co-found and take the role of chief scientist at OpenAI. That went well until November 2023, when he was one of the board members who voted to fire CEO Sam Altman. Days later, he reversed course, signing onto an employee letter demanding Altman’s return and expressing regret for his “participation in the board’s actions.” He left the company the following June to launch Safe Superintelligence, which raised $1 billion in just three months and another $2 billion in April of this year, valuing the company at $32 billion.
Brian Acton
After working in product testing rolls at Apple and Adobe, Acton joined Yahoo in 1996. He spent nine years at the then-web giant as a computer engineer. While there, he met and worked alongside Jan Koum. The two left in 2007. After being turned down for a job at Facebook, they began work on WhatsApp in 2009. Five years later, they sold the messaging app to Facebook for roughly $19 billion.
Tony Fadell
Fadell initially made a name for himself at Apple, where he helped design the infrastructure for the iPod. He’s known as the “Father of the iPod” and co-creator of the iPhone. Hardware, firmware, and accessories were all under his supervision from 2006 through 2008. He left that year and, in 2009, launched Nest Labs. Its first product, the Nest Learning Thermostat, was wildly successful after launch. And in 2014, Google acquired the company for $3.2 billion. These days, Fadell oversees a venture fund called Build Collective.
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Chris Morris
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.jpg "Dan Roselli and Sara Garcés-Roselli (right and left of screen) are the founders of RevTech Labs, which offers an accelerator program for Charlotte startups. “Charlotte has one of the steepest growth curves for entrepreneurs in the country,” said Dan, pictured here with the program’s most recent cohort.")