Most professionals will be laid off, fired, or ousted at some point in their careers—it’s a universal, soul-crushing experience shared by even the greatest of leaders, including Oprah Winfrey, Steve Jobs, and Mike Bloomberg. The CEO of the billion-dollar software company Scope3, Brian O’Kelley, spent most of his 20s job-hopping after getting fired over and over again.
“For many of us who are entrepreneurs, we don’t listen to anybody, and we just make a bunch of mistakes,” O’Kelley tells Fortune’s Orianna Rosa Royle. “I go back to myself in my 20s, I wasn’t going to listen to anyone. I thought I knew everything, I burned a lot of bridges, and spent a lot of time learning the hard way.”
After graduating from Princeton University in 1999, the serial entrepreneur was ready to take on the tech industry. O’Kelley’s first defeat came at a little consulting company, where he tried his hand at launching an internet commerce company. It failed, and so he was fired (by his best friend, no less). “It was pretty embarrassing to go to Princeton and six weeks after college, be unemployed on your dad’s sofa.” he recalls.
Unemployed and stuck living back at his parents’ home, he made some calls to former mentors begging for a job. Luckily, an opportunity swiftly came up, and he jumped to a vice president role at IT consulting firm LogicSpan—but again, the stint was short-lived.
