Andy Dunn was the Christopher Columbus of digitally-native brands. Although not technically the first to launch, Bonobos was the most well-known brand that started online and sold direct-to-consumer. With Dunn at the helm, and frequently writing Medium articles, Bonobos built its reputation as the pioneer in the consumer space. It deserves plenty of credit as a result. But like the saying “pioneers take the arrows, settlers take the land,” Bonobos made a number of key mistakes that its followers would and/or should have learned from. It built its own ecommerce and logistics infrastructure, at a significant cost. It raised an immense amount of money to do so—nearly $130 million over six years, which was spent in a much cheaper customer acquisition landscape with not the most impressive results—a revenue to spending ratio of only 2:1. It sold to Walmart for $310 million, just over its previous private round valuation and for about two times revenue.

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