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(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp

August 25, 2025
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How I Built This with Guy Raz

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In 2001, three web designers built a quirky email tool called Mailchimp. It wasn’t their main business. It wasn’t even meant to make real money. For years, Ben Chestnut and his partners survived on web-design gigs, while Mailchimp earned just enough to cover lunch. Then…one surprising spreadsheet changed everything. In this episode, Ben reveals:The decision that tripled their revenue overnightHow a mispronunciation on the world's biggest podcast turned into a marketing masterstrokeHow a painful wake-up call about leadership reshaped the company’s culture Listen now to hear how guerrilla billboards, a monkey logo, and a string of improbable breaks built one of the most recognizable names in tech.  Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.