Ben Chestnut on Building Mailchimp, Selling to Intuit and Finding Contentment

In this December 2022 interview, Mailchimp co-founder Ben Chestnut talks with Harry Stebbings about building a bootstrapped company, its sale to Intuit, leadership and family. His financial and business descriptions are his own account of events and his perspective as a founder and seller.

Chestnut wanted to be a designer and sold small drawings and other items as a child. At design school he discovered that computer rendering suited him better than making physical models, and an internship led him into web design.

Mailchimp began as a side project of the founders’ web-design agency, built for a few customers who needed email newsletters. They made it self-service with credit-card payment partly because handling many small checks was inconvenient. It grew organically while the agency remained their main focus.

After hearing about recurring income, Chestnut compared the revenue of the side project and agency in a spreadsheet. He says Mailchimp was growing while agency revenue was flat or falling, so the founders chose to focus on software. He recalls Mailchimp then making at most a few hundred thousand dollars a year, not millions.

He says freemium became an unexpected growth lever after years of seeking a single breakthrough. According to his recollection, the user base reached one million within a year and doubled the following year. Those historical figures are his account, not independently verified data in the interview.

His mother ran a hair salon from the family kitchen, and he watched her serve customers and earn a living. Chestnut connects that experience to his respect for business owners’ ambitions; he preferred not to describe customers publicly as “small” even when that was a useful internal category.

Fishing trips with his father taught him patience, he recalls. His father often took the long route and quietly waited when Chestnut struggled to keep up. Watching his father lead soldiers also showed him that a leader could be firm in one setting and warm in another.

He says his father reserved praise for moments of growth and taught him that feeling pressure need not prevent a calm outward response. Chestnut shares these memories as personal influences, not as a general rule for dealing with stress.

Chestnut defines high performance less as demanding a goal at any cost than as identifying habits that prevent progress. He describes improving sleep and daily routines when he wanted to get fitter. This is his individual experience, not medical advice or a guaranteed approach.

He says he tries to “stay in his lane”: offer advice when asked without taking responsibility for another person’s decisions. He acknowledges that a founder of an early startup may need to absorb more problems than a leader of a mature organization.

In Mailchimp’s early years he hired creative people and gave them room, with co-founder Dan helping assess work ethic. As the company grew, a coach told him his style was “hands off, eyes off.” He worked toward staying hands off while keeping clearer goals, measures and accountability.

Chestnut wanted to evolve into an operational leader, but eventually recognized that other executives were better at some operational tasks. He says he found more energy connecting ideas among creative people and began relying on the senior team in areas where he was weaker.

When founders seek his advice, he often shares his own mistakes and listens rather than prescribing a solution. He remembers feeling isolated in Atlanta’s earlier startup ecosystem and says hearing that others had struggled can be reassuring.

Chestnut describes growing up as one of few Asian students in his school and being treated as a misfit. Listening to others who felt excluded helped him attend to feelings, he says. He also recognizes that his direct, stoic manner can appear cold, leaving him conflicted about praise for his emotional intelligence.

He says bullying made him determined to prove himself but also sensitive to feeling pushed or disrespected. In business that could produce resilience and independence, yet also make compromise and organizational politics harder. These are his reflections on his own experience.

Asked whether refusing venture funding cost Mailchimp a larger outcome, Chestnut says the counterfactual cannot be known. He is proud that he and the team built the business on their own terms, while recognizing that stubbornness was not always beneficial.

He recalls an earlier potential buyer predicting that his identity would eventually separate from the company. Years later, deaths among friends and family prompted him to think differently about life and work. At the time of the interview he was still at Mailchimp, focused more on innovation and advising, and says the transition was ongoing.

An adviser told him that a CEO’s days are made of habits and that meetings, messages and routines would gradually disappear after a sale. Chestnut found that idea helpful as he began to notice the change. He says Mailchimp’s gradual growth also gave him and co-founder Dan time to adjust.

Publicity initially mattered to him as validation, but he says repeated rejection taught him to focus on paying customers instead. Later the company sought more visibility partly to recruit. He encouraged staff to remember that magazine covers celebrated past achievements, while the product still needed to evolve.

He recalls employees drawing on a magazine cover of his face and turning the joke into an internal art display. Chestnut says he welcomed it as a sign of a culture able to laugh at its leader. This is his description of the company’s culture.

The founders had listened to potential acquirers before, and one earlier process progressed far enough that the senior team began preparing for a sale. When the offers did not meet Chestnut’s expectations, the team was disappointed. He says the process also distracted the company for months.

As he considered telling leaders he would never repeat the process, an adviser introduced Intuit. Chestnut says conversations with Alex Chriss stood out because of a shared understanding of small-business customers. He believed combining with Intuit could supply resources for Mailchimp’s next stage.

He says the courtship and diligence lasted about a year and that the decision remained difficult. The episode description reports a roughly $12 billion announced acquisition value in 2021; that transaction value is not the founders’ individual after-tax cash proceeds.

Chestnut says Mailchimp was already highly profitable and approaching $1 billion in annual recurring revenue when the acquisition occurred. He describes wealth as arriving gradually rather than all at once. ARR is a recurring-revenue measure, not the same thing as realized annual cash revenue or the sale price.

He says he wanted his children to see him helping customers rather than merely making money. He also realized that expecting them to become entrepreneurs like him would be unfair; he wants them to have independence to choose their own paths.

His children learned more about the family’s wealth after a classmate brought in a magazine featuring him. Chestnut says he hopes they learn from how their parents behave, especially by being earnest and helpful. He does not present this as a guaranteed way to raise children with wealth.

In the quick-fire round he mentions reading Thich Nhat Hanh and says philosophical books are helping him reconsider old habits. With fewer scheduled obligations, caring for a new dog has become part of his mornings.

Asked about weight loss, he describes walking, cycling and reducing sugary drinks. He also recounts an older relative’s belief about the cause of his diabetes; that anecdote does not establish a medical cause or a general treatment. Chestnut presents the changes as his own experience.

He and his wife still joke about a lottery ticket she once misread as a large win when they were young. He says they continue to buy tickets occasionally for the memory, not because the story is an investment strategy.

On marriage, Chestnut says he has learned not to treat every disagreement as something to win. He tries to listen to why his wife is saying something and recognizes that he is not always right. He offers a personal observation, not a formula for every couple.

He wants his children to have balance, love, independence and self-sufficiency, along with self-awareness and an ability to improve gradually. He also hopes technology startups can thrive beyond the traditional hubs, as Mailchimp did in Atlanta.

Looking ahead five years, Chestnut says he wants to explore his own mind and learn to be content rather than constantly wanting more. He tells a story about a founder whose satisfaction with a yacht vanished when a larger one arrived, illustrating his concern about comparison.

Harry thanks Chestnut for the conversation, and Chestnut thanks him in return.