Company: Microsoft (2000 - Present)
Biggest asshole moment: Snatching an employee’s iPhone, pretend to stomp it, and making several unflattering remarks about the person during a private company meeting.
A gaggle of Microsoft employees, as well as the general public, agree on one thing: Steve Ballmer is a nut job. If he's not screeching and frolicking on stage (reference his Dance Monkeyboy video), then he's putting his employees on blast for owning Apple products. This year's approval rating surveys from Glassdoor (29 percent) and GeekWire (40 percent) showed that employees voted him the worst tech CEO. And since taking over for Bill Gates at the turn of the century, the polarizing Ballmer has earned a rep amongst workers and investors as the arrogant egomaniac responsible for massive layoffs and losing billions. The KIN failure speaks for itself. When you take into consideration his long list of insane public outbursts, poor vision, and lack of leadership, it's no wonder Microsoft continues to struggle.