Mailchimp: Ben Chestnut 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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Mailchimp: Ben Chestnut

Mailchimp: Ben Chestnut

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Molly Magnell for NPR
Ben Chestnut is the CEO and co-founder of Mailchimp.
Molly Magnell for NPR

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.

This episode of How I Built This was produced by Liz Metzger and J.C. Howard. Edited by Neva Grant with research help from Liz Metzger. Additional support from Jeff Rogers, Casey Herman, James Delahoussaye, Rachel Faulkner, Julia Carney, Farrah Safari, Janet W. Lee, Analise Ober, and Harrison Vijay Tsui. You can follow us on Twitter @HowIBuiltThis, on Instagram @HowIBuiltThisNPR and email us at hibt@npr.org.

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How I Built This

For all new episodes, go to the How I Built This page on Wondery.com Listen early and ad-free on Wondery+ Listen on Amazon Music