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

In this episode of "How I Built This," Guy Raz interviews Ben Chestnut, the co-founder of Mailchimp, exploring the company's journey from a web design business side project to a leading online marketing platform. Chestnut recounts Mailchimp's early days, bootstrapped beginnings, and the pivotal decision to focus on small businesses, which led to significant growth. He shares insights into their creative marketing strategies, including the iconic monkey logo and their early adoption of podcast advertising. Chestnut also discusses the challenges they faced, such as navigating the stigma of email marketing and dealing with internal cultural issues as the company scaled, and also touches on the company's eventual acquisition by Intuit for $12 billion.