Ben Chestnut's operating philosophy at Mailchimp was that the company needed to reinvent itself every three years to adapt to changing customer tastes and technology needs.

Ben Chestnut never considered taking Mailchimp public, viewing it as a "greater hell" because he wanted to run the company his own way without answering to the market.

The founder of Glean and Rubrik told Ben Chestnut that while Rubrik had to reinvent itself every 3-4 years, the current pace of AI innovation requires Glean to reinvent itself every six months.