6 CEOs Share Their Biggest Regrets

Digg, technology
Gregg Segal
4 of 6

My regret: Dropping out of school

Kevin Rose launched his first Internet business as a University of Nevada freshman, left college his sophomore year, and went to work at a Bay Area start-up. As massive amounts of news began to accumulate online, Rose realized how much time Internet users like himself devoted to sorting and sending each other links, and that what the web needed was a centralized site to share these stories--an insight that became Digg. His regret is academic in nature: "I wish I had finished my computer science degree," he told Inc. in 2008. "Sometimes, I’ll be sitting around on a weekend and think, it’d be fun if I could just write up a software app really quickly."