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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Ring founder Jamie Siminoff joins Guy on the Advice Line, where they answer questions from three founders about balancing short- and long-term goals.

Today, we meet Vico, an industrial designer in southern California who's launching a crowdfunding campaign for his patented ergonomic desk. Then Iyin, a Baltimore-based product specialist seeking to balance accessibility and profitability for her ethically-sourced chocolate brand. And Franchesca, an Atlanta area educator deliberating whether to pursue small-business certifications for her motivational classroom posters.

Thank you to the founders of ErgoFlex Desk, Luji's Chocolate, and Thrive12 for being a part of a show.

If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298.

And be sure to listen to Ring’s founding story as told by Jamie on the show in 2020.

This episode was produced by Carla Esteves with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Neal Rauch.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Amy Errett had a successful career in finance and venture capital before taking a leap into an entirely new business: hair color. When her wife complained about the indignities of coloring her hair at home, Amy realized the sector was ripe for a makeover. At age 56, she dove into the minutiae of dyes and developers, launching her own formula in 2013, and naming it after her daughter. Madison Reed’s early successes were marred by a management meltdown, when Amy had to break with three of her co-founders—an experience she describes as one of the most difficult of her life. Today Madison Reed is available in thousands of stores across the US, and runs nearly 100 of its own salons.

This episode was produced by Sam Paulson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research by Iman Maani. Our engineers were Patrick Murray and Kwesi Lee.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.