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

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

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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Lyft: John Zimmer

Lyft: John Zimmer

Ridesharing wasn't a thing 12 years ago when John Zimmer was in college. But a class on green cities got him thinking about the glut of underused cars on the road, and eventually led him to co-found Lyft, a company that has helped make ridesharing a way of life. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

13 Feb 201739min

Kate Spade: Kate & Andy Spade

Kate Spade: Kate & Andy Spade

A 1991 conversation at a Mexican restaurant led Kate & Andy Spade to ask, "What's missing in designer handbags?" Kate's answer was a simple modern-shaped handbag that launched the iconic fashion brand: Kate Spade. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

6 Feb 201739min

Virgin: Richard Branson

Virgin: Richard Branson

Richard Branson took a record shop and built it into a label, a bank, an airline, space tourism, and 200 other businesses — all under the name Virgin. But the serial entrepreneur has also had his share of failures. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

30 Jan 201733min

Zappos: Tony Hsieh

Zappos: Tony Hsieh

Computer scientist Tony Hsieh made millions off the dot-com boom. But he didn't make his mark until he built Zappos — a customer service company that "happens to sell shoes." Now Zappos is worth over a billion dollars and known for its completely unorthodox management style. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

23 Jan 201728min

Honest Tea: Seth Goldman

Honest Tea: Seth Goldman

In 1997, after going for a long run, Seth Goldman was frustrated with the sugar-filled drinks at the corner market. So he brewed up a beverage in his kitchen, and turned it into Honest Tea. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

16 Jan 201729min

Drybar: Alli Webb

Drybar: Alli Webb

A decade ago, full-time mom Alli Webb noticed a gap in the beauty market: there was nowhere that just focused on blow-drying hair. Now with 70 locations, Drybar is testament to Webb's motto: Focus on one thing and be the best at it. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

9 Jan 201732min

Zumba: Beto Perez & Alberto Perlman

Zumba: Beto Perez & Alberto Perlman

Zumba began as a mistake: aerobics teacher Beto Perez brought the wrong music to class, then improvised a dance routine to go with it. For his students, it was more fun than work — and it eventually grew into one of the biggest fitness brands in the world. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

2 Jan 201737min

Warby Parker: Dave Gilboa & Neil Blumenthal

Warby Parker: Dave Gilboa & Neil Blumenthal

In 2008, it was nearly impossible to buy a fashionable, affordable pair of glasses online. That simple frustration inspired the idea behind Warby Parker – and disrupted the eyewear industry. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

26 Dec 201630min

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