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In the late 1990s, Ben Chestnut was a struggling young designer interning at an appliance company, when somebody suggested that he try designing for the internet instead. A few years later, Ben and two co-founders launched a web design agency, only to discover that the service they'd included almost as an afterthought—email marketing—was taking off among their small-business clients. The founders named that service Mailchimp and pivoted to it full-time in 2007, choosing a winking monkey as their mascot, and stumbling onto the Freemium model before it became mainstream. But their most impeccable timing came in 2014, when they decided to sponsor a new podcast called Serial, a move that catapulted the winking monkey into popular culture. Over the years, despite management jitters and a public reckoning over office culture, Mailchimp has remained profitable and self-funded, with revenue of $800 million in 2020.

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