How I Built This with Guy Raz (July 2021) Ben Chestnut: From Side Business to $12 Billion – The Accidental Triumph of Mailchimp
6 snips
Aug 25, 2025 
Ben Chestnut, co-founder of Mailchimp, started with a side business that evolved into a $12 billion success. He discusses a surprising spreadsheet that tripled their revenue overnight and a mispronunciation on a major podcast that became a clever marketing strategy. Ben also shares transformative leadership lessons learned through miscommunications and the creation of a supportive company culture. His journey underscores the power of innovative marketing and the challenges of navigating rapid growth in the tech industry.
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Side Project Became Core Product
- MailChimp began as a side project inside a web design agency called Rocket Science Group that charged hourly for client work.
- Ben Chestnut and partners built an internal emailing tool to avoid awful enterprise software and it became MailChimp.
Spreadsheet Changed The Business
- Seeing MailChimp's recurring revenue on a spreadsheet in 2005 made them consider abandoning consulting.
- That visibility revealed SaaS was more sustainable than unpredictable agency cycles.
Use Freemium To Build A Long Funnel
- Use freemium to remove commitment barriers for small businesses and build a long conversion funnel.
- Offer useful free tiers so customers can grow, then monetize when their needs scale.
