Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp

If you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog. 

When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over. 

After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head."

“After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.”

Mentioned in this episode: Intuit, Wolt, DoorDash, LinkedIn, Dan Kurzius, Salesforce, ExactTarget, Pardot, Constant Contact, Rackspace, Free by Chris Anderson, Wired Magazine, Charles Hudson, the Freemium Summit, Drew Houston, Dropbox, Evernote, Phil Libin, TechCrunch, Brian Kane, Catalyst Partners, Georgia Pacific, Scott Cook, Bing Gordon, Vinay Hiremath, Loom, Joe Thomas, Caltrain, Flickr, Saturday Night Live, Droga5, Cannes Film Festival, Strava, Twitter, LinkedIn, Nvidia, Glean, Rubrik, Amazon AWS, and Mechnical Turk.

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What is Grit?

Grit explores what it takes to create, build, and scale world-class organizations. It features weekly episodes highlighting the leaders who are pushing their companies to make a difference. This series is hosted by Joubin Mirzadegan, go to market operating partner at Kleiner Perkins, a venture capital firm investing in history-making founders.