All Episodes

August 25, 2025 79 mins

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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