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All in Good Fun

Don't be afraid to lighten up--especially if you're the boss.

This story appears in the May 2008 issue of Entrepreneur. Subscribe »

Before Ranjith Kumaran moved out of his VC firm's incubation space to an office that accommodates his current team of approximately 40 employees, he had acquired a reputation as a boss who cracks jokes--often at his own expense.

The 32-year-old founder of YouSendIt, a Campbell, California, company that lets users quickly send large files over the , had taken a mildly embarrassing story of being politely chastised by his investors and turned it into a war story his team could rally around.

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