Bonobos: Andy Dunn (2019)

When Andy Dunn was in business school, his housemate Brian Spaly created a new type of men's pants: stylish, tailored trousers that fit well in both the hips and thighs. Together, they started the men's clothing company Bonobos, which became an instant hit due to the pants' signature flair and innovative e-commerce experience. But within a few years, Andy hit challenging roadblocks, including a struggle with depression and a falling-out with his co-founder and friend. Despite many moments of crisis, Andy steered Bonobos to massive success, and in 2017, it was acquired by Walmart for a reported $310 million.

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