20VC: Mailchimp’s Ben Chestnut on The Biggest Leadership Lessons Scaling to a $12Bn Acquisition and $1BN+ ARR, The Secret to Happiness, Being a Great Husband and Father & Why 2021 was the Right Time To Sell to Intuit

Posted on 12th December 2022 by Harry

Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the Mailchimp journey to this point. First, Mailchimp was founded as the result of a side project of a design agency Ben and his co-founder, Dan, used to run. Second, Mailchimp is and has always been based in Atalanta, eschewing the notion you have to be in SF or NYC to build a massive business. Then third, they never raised venture funding for the business all the way until their $12BN acquisition. Ben led Mailchimp to over 1,200 employees and millions of global users.

Episode Transcript

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In Today’s Episode with Ben Chestnut We Discuss:

1. From Mama’s Kitchen to the Smell of Business and Founding Mailchimp:

  • How did Ben turn a mediocre agency into the founding of Mailchimp? What was the a-ha moment?
  • At what stage of the business did Ben quit the agency and go all in on Mailchimp? What sign did he need that Mailchimp had true product-market fit?
  • When Ben’s mother died, he bought every flower in the local town to commemorate her. How did Ben’s mother impact the type of father and husband he is today? How did she impact the way that he led Mailchimp as CEO?
  • Ben’s fishing trips with his father played a big role in his early years, what were the single biggest lessons for Ben from his fishing trips with his father?

2. Ben Chestnut: The Leader:

  • How does Ben define the term “high performance” in leadership?
  • What does Ben mean when he says “the secret to happiness is to stay in your lane”?
  • Why would Ben describe himself as the “leader of the misfits”? How did that early experience and labeling impact both the people he hired and the culture he created at Mailchimp?
  • What does Ben mean when he says he used to have a “hands off, eyes off” leadership style? What have been the single biggest drivers in his development as a leader?

3. Ben Chestnut: The Person:

  • Relationship to Money: How does Ben reflect on his relationship to money? How has it changed over time? Why does Ben still to this day buy lottery tickets with his wife?
  • Conquering Fatherhood: What does being a great father to Ben mean? How does Ben attempt to instil the same work ethic and drive when his children are born into immense wealth?
  • The secret to Marriage: What does Ben believe is the core to a successful and thriving marriage? How does Ben view his role in the marriage? How has it changed over time?
  • Potential Lost Identity: A founder’s identity is so closely tied to their company, how did Ben manage the challenge of selling his company but retaining his identity? What did Ben learn about himself through many different acquisition processes?

4. Mailchimp: The Business:

  • Why did Ben never raise venture money in the 21 year journey of Mailchimp?
  • Why did Ben never accept any of the acquisition offers that came before Intuit?
  • How did Ben motivate his team after they knew each acquisition offer was being turned down?
  • Why did Ben decide the acquisition by Intuit was the right decision for the company?
  • How does Ben view his role in the company now and moving forward?

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