(July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp / How I Built This with Guy Raz

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.

Follow How I Built This:

Follow Guy Raz:

Instagram → @guy.raz

Website → guyraz.com

iRobot: Colin Angle. How The Roomba Became a Household Icon

Colin Angle didn’t start out trying to clean people’s floors. He started out trying to shape the future–with robots. In the early days of iRobot, there was no business model. No steady funding. No clear customer. Just a belief that...

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Advice Line with Steve Ells of Chipotle

Today’s callers: Rebecca from Australia wants to make her small-batch spirits stand out in a crowded market. Then, Sri from England wonders how to balance commercial and humanitarian interests for her heated mats. And John from...

9 apr 2026 2568 sec.
Wingstop: Antonio Swad. A Brilliant Idea — And a Nail-Biting Exit

A lot of founders spend their lives chasing one big idea. Antonio Swad had two. The first? Migrating chicken wings from the Happy Hour buffet to the center of the plate. The second? Building a pizza business that catered to a very...

6 apr 2026 4735 sec.