Guy Raz dives into the stories behind some of the world's best known companies. How I Built This weaves a narrative journey about innovators, entrepreneurs and idealists—and the movements they built. Order the How I Built This book at https://www.guyraz.com/

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

August 25, 2025 01:19:28 16.48 MB ( 59.81 MB less) Downloads: 0

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 overnight
  • How a mispronunciation on the world's biggest podcast turned into a marketing masterstroke
  • How 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. 

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