Andy Dunn

Live chat can be just like a sales conversation you would have in-store. Unlike email, chat is immediate and truly two-way, and being at a computer doesn't mean you have to act like a robot. Be friendly, personable and don't stress if you make a few mistakes typing. Above all else, have fun! You're using chat to make people happy, so enjoy the experience.

"The risk not taken is more dangerous than the risk taken," wrote Bonobos Co-Founder and CEO Andy Dunn, explaining his decision to turn down a secure job at a Silicon Valley venture capital firm and team up with Stanford business school classmate Brian Spaly to launch a new kind of men's apparel brand, focused on selling well-fitting pants online. After "creative differences," Spaly left the business in 2009, in what was a mutual though difficult split. But under Dunn's stewardship the company has not only survived, but flourished.

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