#80. Revisiting Mailchimp: From Bootstrapping to Ben Chestnut's Life After the $12B Exit
Editor's Note: As I celebrate the 4-year anniversary 🎉✨ of this newsletter, I am revisiting some of the most impactful pieces I've written. Over the last few weeks I have revisited Imposter syndrome: = Superpower: 4 Years Later, and Two Years of Growth: Revisiting "Mindset" for a Changing World.
Today, I'm reflecting on my 2021 piece about Ben Chestnut, the founder of Mailchimp, and his remarkable journey from bootstrapping the startup to a $12 billion acquisition.
Last Month, Ben Chestnut had an interview with Kleiner Perkins which provided fresh perspective on his 20 year journey building Mailchimp to exit, so it is the perfect time to examine what has changed - and what timeless lessons remain.
The Original Article: #19. Mailchimp: Lessons in Business – Ben Chestnut - Bootstrapping to $12 billion.
The Original Story: Bootstrapping to $12 Billion
In October 2021, I wrote about Mailchimp's extraordinary journey from a side project to a $12 billion acquisition by Intuit. Mailchimp was founded by Ben Chestnut after him and two colleagues were laid off due to the dot-com bubble .
The story resonated with many readers because it challenged conventional wisdom about startup funding and growth.
The core lessons I highlighted then remain powerful today:
Listen to Your Customers: Mailchimp began as a solution to problems their web design clients were facing with email marketing.
Follow the Data: The founders pivoted to focus on Mailchimp when they saw it growing while their consultancy business was flat.
Trust Your Instincts: They rejected VC funding that would have pushed them away from serving small businesses.
Ride Multiple Waves of Good Fortune: Mailchimp skilfully leveraged emerging trends like freemium models, cloud computing, and social media.
At the time of writing that article, the acquisition had just been announced. What we didn't know then was how the story would continue—how would Ben Chestnut adapt to life after selling his 20-year labour of love?
New Insights: Life After the Exit
In a recent podcast interview with Kleiner Perkins (March 2025), Ben Chestnut shared candid reflections about the acquisition and its aftermath that add fascinating dimensions to the Mailchimp story.
The Decision to Sell
While my original article focused on the business achievement, Chestnut's interview reveals the deeply personal factors behind the decision to sell:
Personal Losses: The passing of his parents shifted his priorities and perspective
Pandemic Pressures: Increased competition and challenges during the pandemic influenced timing
Team Considerations: His executive team's enthusiasm and the implementation of a phantom equity program played a significant role
Avoiding Going Public: Chestnut strongly opposed taking Mailchimp public, preferring Intuit's acquisition
Perhaps most interestingly, Chestnut admits he almost didn't sell because he wanted to hit $1 billion in Annual Recurring Revenue himself—a revealing glimpse into the entrepreneurial mindset that both drives success and can sometimes stand in its way.
The Psychological Journey
The interview offers rare insight into the psychological aspects of building and selling a company:
Gradual Wealth: Unlike many founders who experience sudden wealth, Chestnut's financial success came gradually over 20 years, helping him maintain perspective
Competitive Drive: He acknowledges being fuelled by a chip on his shoulder, stemming from being underestimated
Finding Closure: The sale brought a sense of peace, allowing him to relinquish the constant need to prove himself
Adjusting to "Normal" Life: Breaking habits like constantly checking email and learning to live without being "on stage" as CEO required significant adjustment
Technology's Accelerating Pace
One of Chestnut's most thought-provoking observations concerns the accelerating pace of change in technology:
"Earlier in the tech industry I realized we need to reinvent ourselves every 3 years, customers' taste change and their technology needs changing every 3 years, so I had to keep Mailchimp very nimble. Now things are accelerating really faster."
He expresses relief at not having to navigate today's tech landscape, particularly the AI revolution, noting that while Mailchimp needed reinvention every 3 years, today's companies might need to reinvent themselves every 6 months.
Lessons for Today's Entrepreneurs
Reflecting on both the original story and these new insights, several enhanced lessons emerge for entrepreneurs:
1. Define Success on Your Own Terms
While the $12 billion exit is impressive, Chestnut's satisfaction came from building something meaningful over two decades. He describes feeling "completely fulfilled" after selling, with no desire to start another business.
2. Prepare for the Emotional Journey
Beyond the business challenges, entrepreneurship is deeply emotional. Chestnut described the acquisition process itself as "very stressful" despite the positive outcome. The psychological aspects of building, scaling, and potentially exiting a business deserve as much attention as the business mechanics.
3. Build Sustainable Resilience
Chestnut defines grit as the ability to persevere through hardships without complaining—just doing the job. This sustainable approach to resilience helped Mailchimp weather numerous challenges over two decades, from server crashes to changing market dynamics.
4. Consider the Full Lifecycle
Most entrepreneurial stories focus on the growth phase, but Chestnut's reflections reveal the importance of thinking about your entire journey, including a potential exit and life afterward. His thoughtful approach to the acquisition and subsequent transition offers valuable lessons for founders at all stages.
Building a Business vs. Building a Life
Perhaps the most profound insight from Chestnut's interview is the relationship between building a business and building a life. His description of post-exit life—focused on family, exercise, and personal interests—suggests that the true measure of entrepreneurial success may be the ability to create something meaningful while maintaining the capacity to enjoy life beyond your creation.
In an age of hustle culture and glorified burnout, Chestnut's journey offers a refreshingly balanced perspective. His story demonstrates that remarkable business success doesn't have to come at the expense of personal fulfilment—and that sometimes, knowing when to let go is as important as knowing when to hold on.
Looking Forward
As we consider the implications of both Mailchimp's extraordinary growth and Chestnut's reflections after the exit, I'm curious:
How are you balancing the drive to build something remarkable with the need for personal sustainability?
What would "success on your own terms" look like for your entrepreneurial journey or career?
How are you preparing for the increasing pace of change in your industry?
I'd love to hear your thoughts on these questions, as well as your own reflections on the Mailchimp story and its evolving lessons.
Until next time.
Nero
The Best is Yet to Come
If you missed the original article, you can find Mailchimp: Lessons in Business – Ben Chestnut - Bootstrapping to $12 billion in the October 2021 issue of this newsletter.
If you enjoyed this article, you would also enjoy What Does It Take to Build a Successful Startup? and Sam Walton Made in America. My Story.
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