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

Summary Notes


In this episode of "20 VC" with host Harry Stebbings, Ben Chestnut, co-founder of Mailchimp, shares his insights on entrepreneurship, the value of staying in one's lane, and the organic growth of Mailchimp outside the typical tech hubs of San Francisco and New York. Ben discusses Mailchimp's journey from a side project to a self-service email marketing platform that experienced exponential growth through a freemium model, eventually leading to a $12 billion acquisition by Intuit in 2021. He reflects on the influence of his parents on his leadership style, the importance of maintaining humility, and his approach to life post-Mailchimp, emphasizing the desire to explore his mind and achieve contentment without the constant need for more. Harry and Ben also touch on topics like the impact of upbringing on business, the relationship with money, and fostering meaningful family values amidst success.

Summary Notes

Personal Philosophy on Discipline and Success

  • Ben Chestnut believes in the importance of staying focused on one's own goals and responsibilities.
  • He suggests that success requires discipline and control over one's life.
  • Ben expresses a lack of interest in those who do not show the discipline to be successful, implying they may not truly want success.

"The key to happiness is staying in your lane and knowing when people need to be in their lane, don't get in their lane and don't let them get in your lane. To me, if somebody is just not disciplined to take control of their lives and be successful, they must not want it. And I'm not going to bother with it."

This quote highlights the significance of personal boundaries and self-motivation in achieving happiness and success, as seen through Ben's perspective.

Harry Stebbings' Enthusiasm for Ben Chestnut's Story

  • Harry Stebbings admires Ben Chestnut's unconventional path to success.
  • He notes Mailchimp's origins outside major tech hubs, its growth without venture capital, and its large acquisition.
  • Harry appreciates the insight provided by Ben's sister, Lottie, which contributed to the interview's preparation.

"First, they did not build their business from San Francisco or New York, but Atlanta, proving that massive companies can be built from anywhere. Second, they did it with no venture capital at all, despite every venture investor wanting to invest. And then finally, our guest today scaled the company as CEO until their reported $12 billion acquisition by Intuit in 2021."

Harry's quote underscores the unique aspects of Ben's journey with Mailchimp, challenging the norms of the startup world.

Ben Chestnut's Journey to Entrepreneurship

  • Ben always had a passion for design and business, starting from childhood ventures.
  • His transition from industrial to web design was influenced by his lack of dexterity with physical models and a push towards digital design.
  • Ben's discovery of passive income and the realization of Mailchimp's potential marked a turning point in his career.

"I always wanted to be a designer. I loved drawing... Mailchimp is really just the end of a series of pivots... I fell in love with computers... It took me a long time to realize that it was an accidental kind of a business... That was all we needed to say. Let's stop the agency business and let's focus on Mailchimp as a software company."

Ben's quote reflects his natural progression from early entrepreneurial activities to the strategic pivot towards focusing on Mailchimp.

The Realization and Growth of Mailchimp

  • Mailchimp began as a side project to solve a specific problem for a few customers.
  • The decision to make Mailchimp self-serve led to organic growth and the shift to focus solely on the software.
  • Ben and his team discovered the power of freemium, which led to exponential user growth.

"We built it for just a couple of our customers... We made it totally self serve, and it just started to grow organically... We separated it from our agency revenue... Mailchimp was growing, and our agency was flat or declining... We fell into freemium... Within one year, it was a million users."

This quote details the evolution of Mailchimp from a convenient solution for a few to a widely adopted platform, thanks to the freemium model.

Influence of Ben's Mother on His Leadership and Business Approach

  • Ben's mother was an entrepreneur who ran a hair salon from their home, influencing Ben's view on business.
  • He learned to respect the ambitions of small business owners and refrains from calling them "small" due to their potential for growth.
  • Ben's mother's approach to business as a means to an end contrasted with his father's more scalable view.

"She was an entrepreneur... I watched money exchange hands... To me, being born in here in the States, my father is born in the States, he thought about business differently... that's been the DNA of Mailchimp."

Ben's quote reflects how his mother's entrepreneurship and his father's perspective on business shaped his approach to Mailchimp and its customers.

Ben's Relationship with His Father and Its Impact

  • Ben learned patience and the value of taking the scenic route from his father's fishing trips.
  • His father's stoic nature taught Ben about perseverance and leadership without the need for constant praise or reprimand.
  • The dual nature of his father's leadership, both commanding and personable, influenced Ben's own leadership style.

"The lake where we would go fishing was always about 45 minutes to an hour away... Sometimes it's not always better to be faster... I think I learned stuff's going to be hard... He was also in the military... I could see that there are two sides. If you're a leader, you do what you got to do to lead the troops."

This quote encapsulates the life lessons Ben learned from his father, which translated into his own leadership and approach to challenges.

Praise and Struggle

  • Ben Chestnut's father would express pride after Ben overcame a struggle and improved himself.
  • His father saw stress as the norm and believed that a calm demeanor was a sign of leadership.
  • Ben's father would help him silently through challenges and reserve praise for when Ben prevailed.

"And there were times when he would say that he was proud of me. It was usually after me going through some struggle myself."

This quote exemplifies the conditional nature of praise from Ben's father, highlighting that it was earned through personal growth and overcoming adversity.

High Performance in Business and Leadership

  • High performance at Mailchimp wasn't about setting high goals and crushing them at all costs.
  • Ben focused on changing core habits that hindered performance rather than chasing goals directly.
  • He emphasized the importance of addressing the root causes of performance issues.

"It's looking at the roots of what's causing you to not be high performance and changing these core habits that are blocking you."

Ben explains his approach to high performance, which involves identifying and altering fundamental habits that impede success, rather than solely focusing on the end goal.

Discipline and Desire

  • Ben believes that if people truly want something, they will find the discipline to achieve it.
  • He subscribes to the philosophy of staying in one's lane, not interfering in others' problems, and not allowing others to interfere in his.
  • Ben suggests that a lack of discipline indicates a lack of desire for success.

"If people want something bad enough, they figure out that discipline. They just must not want it."

Ben's perspective on discipline is that it is inherently tied to one's desire for success; if the desire is strong enough, individuals will cultivate the necessary discipline.

Staying in Your Lane

  • Ben Chestnut advises not to make other people's problems your own and to offer advice without attachment to its implementation.
  • He believes in maintaining emotional boundaries and allowing others to manage their own issues.

"Everybody has problems. You got problems, I got problems. You bring those problems to my table. Hey, Harry, good for you, man. I'm not going to make it my problem."

Ben emphasizes the importance of emotional boundaries in leadership, suggesting that while he offers advice, he does not take on the responsibility for others' problems.

Evolution of Leadership Style

  • Ben's early leadership style was hands-off and creative-focused, relying on a small team's ability to understand his vision.
  • As Mailchimp grew, he was coached to adopt a "hands-off, eyes-on" approach, which involved being more explicit about goals and relying on managers.
  • He recognized the need to be more operational and hold people accountable as the company scaled.

"And that was the biggest change for me, being trying to be hands off, but eyes on."

Ben describes how his leadership style evolved to include more oversight while still allowing his team autonomy.

Operational Leadership and Self-Awareness

  • Ben transitioned from a creative role to a more operational one, but he was self-aware enough to recognize his limitations.
  • He leaned on senior leadership for operational tasks and stepped back when necessary.

"I started to lean more on operational people, on the senior leadership team, and I was self aware enough to step back in some areas."

This quote highlights Ben's self-awareness in recognizing when to delegate operational responsibilities to others better suited for those tasks.

Advising Other Founders

  • Ben Chestnut acts as a sounding board for other founders, sharing his experiences rather than giving direct advice.
  • He emphasizes the value of relating to others' struggles and not feeling alone in the challenges of entrepreneurship.

"I don't invest. I don't do any kind of angel investing. They just come to me as a therapist."

Ben shares his role as an informal advisor to other founders, where he listens to their challenges and offers empathy based on his own experiences.

Emotional Intelligence (EQ)

  • Ben has been told he has high emotional intelligence (EQ) but also acknowledges that he can appear cold and logical.
  • His EQ stems from his experiences as a quiet loner and leader of misfits, which helped him tune into people's feelings.

"I have been told many times I have a high level of self awareness and a high amount of Eq."

Despite being recognized for his emotional intelligence, Ben admits to having a logical side that can come across as cold or detached.

Negative Traits from Being a Misfit

  • Ben's experiences as a misfit made him ready to defend himself and prove his worth, driving his entrepreneurial success.
  • He acknowledges that this background can lead to stubbornness and a reluctance to concede in illogical situations.

"I think that, for me, being a misfit meant that I was bullied quite a lot, and I was discounted and disrespected quite a lot through my childhood years."

Ben reflects on how being a misfit shaped his defensive nature and determination to prove himself, which influenced his approach to entrepreneurship.

Painful Lessons and Stubbornness

  • Ben values the perspective and focus he gained from being a misfit, which contributed to his success as an entrepreneur.
  • He admits that his stubbornness to do things his way and reject early offers to sell Mailchimp may have had both positive and negative outcomes.

"I think there were times when I think we could have sold the business early. There were a lot of people, a lot of suitors knocking on the door, a lot of investors knocking on the door. I just sort of had this stubbornness that I didn't need, that I didn't want it."

Ben discusses the potential impact of his stubbornness on business decisions, suggesting that it helped him maintain control but may have limited other opportunities.

Personal Philosophy and Identity

  • Ben Chestnut prides himself on doing things his way, akin to Bruce Lee's unique style.
  • He values the individuality in his approach to running his business and sees it as a point of pride.

"I'm really proud to say I did it my way, and I'm really proud of that."

This quote emphasizes the importance of individuality and the satisfaction derived from forging one's own path in business and life.

The Journey of Mailchimp

  • Mailchimp's development spanned over two decades, with Ben Chestnut being intricately involved throughout.
  • The business became a significant part of Ben's identity, similar to how many founders feel about their ventures.

"21? Not that I'm counting anyone."

Ben Chestnut humorously notes the exact duration of his journey with Mailchimp, indicating its deep significance to him.

Identity and Business

  • Ben recounts a conversation where a potential buyer predicted he would eventually sell Mailchimp as his identity evolved.
  • The buyer's perspective was that as Ben aged, he would realize the business was separate from his personal identity.

"But as you get older, you're going to realize that your business is just something that you created and something that you do, but it is not you."

The quote reflects the common evolution of a founder's relationship with their business and the distinction between personal and professional identity.

Reflections on Life and Mortality

  • Ben experienced a shift in perspective in his mid-forties as he faced the mortality of friends and family.
  • This led to a realization that his life was not solely defined by his business.

"Something happens when you're in your mid forty s, all right? It happens to everybody. Their friends and their families start to die."

Ben discusses the life events that cause many to reflect on their priorities and the role their business plays in their life.

Transitioning from CEO

  • Ben has not fully stepped away from Mailchimp but has shifted focus to advisory roles and innovation.
  • He discusses the impact of changing habits post-transition and the guidance he received on this matter.

"Your entire life, your career, your idea as a CEO is composed of nothing but a whole bunch of habits."

This quote highlights the concept that a CEO's life is driven by habits, and a change in role involves altering or losing those habits.

Humility and Publicity

  • Ben maintained humility despite Mailchimp's success and his own recognition.
  • He focused on customer validation over media attention and only sought publicity later for strategic reasons.

"The only validation I need is a paying customer."

Ben emphasizes the importance of customer satisfaction over public recognition as a measure of success.

The Decision to Sell Mailchimp

  • Ben felt a duty to consider acquisition offers and learned from the process.
  • The decision to sell to Intuit was influenced by a shared vision for small businesses and a strategic opportunity for growth.

"It was very compelling. We talked for a year, by the way. The whole thing was an entire year of due diligence and courting each other."

Ben describes the careful and prolonged consideration before deciding to sell Mailchimp, emphasizing the importance of alignment in vision and values.

Relationship with Money

  • Ben's financial situation evolved gradually due to Mailchimp's consistent growth, which allowed him to remain grounded.
  • He focused on setting an example of helping customers for his children rather than emphasizing financial success.

"I just wanted them to be helpful watching me. So, anyways, that relationship with money, I don't know. I was lucky that we eased into it."

Ben reflects on his approach to wealth, which was shaped by a gradual increase in financial success and a desire to instill certain values in his children.

Raising Children in a Different Financial Context

  • Ben grappled with how to instill ambition and hustle in his children given their more privileged upbringing.
  • He realized he shouldn't expect them to follow in his entrepreneurial footsteps but rather to find their own paths.

"I used to worry about that a lot, and then I realized the heart of that was that it was because I wanted them to be an entrepreneur like me."

Ben shares his initial concerns about his children's ambition and the realization that his expectations were influenced by his own entrepreneurial journey.

Parental Expectations and Financial Secrecy

  • Ben Chestnut discusses the importance of allowing children the freedom to become who they want to be, rather than imposing parental expectations.
  • He chose not to discuss the financial success of Mailchimp with his children, aiming to keep them grounded.
  • His children were unaware of Mailchimp's worth until it was pointed out by a classmate.
  • Ben emphasizes that actions, rather than words, teach children about values and lifestyle.

"That's what I want to have for them, some freedom and independence for them to decide."

This quote highlights Ben's desire for his children to have the autonomy to shape their own futures without being burdened by his expectations.

Perception of Wealth and Material Possessions

  • Ben Chestnut shares his love for cars, owning an R8, but doesn't flaunt it as a status symbol.
  • His children do not perceive the R8 as a supercar, reflecting the modest approach Ben takes towards possessions.
  • He values the car for its design and performance rather than as a luxury to show off.

"I have an R8. And I love that R8... But they have no idea that we have this damn. They know it. They know the car, they ride in it with me sometimes, but they just don't think about it that way."

This quote reveals Ben's personal interest in cars and his approach to owning a luxury vehicle without using it as a means to display wealth.

Personal Reading Preferences

  • Ben Chestnut expresses a shift in his reading interests from business books to philosophical ones.
  • He finds reading works by Zen Buddhist monk Thich Nhat Hanh, such as "Peace Is Every Step" and "The Art of Power," therapeutic.
  • The flooding of his basement library led to the disposal of many business books, which he found cathartic.

"And now the only books that are remaining are sort of philosophical ones. Stuff about life."

The quote indicates a turning point in Ben's life where he is more interested in philosophical insights than business strategies.

Daily Routine and Lifestyle

  • Ben Chestnut does not adhere to a typical daily routine and enjoys the lack of structure.
  • He has recently adopted a dog, which has added some regularity to his mornings.
  • Despite stepping back from his business, he continues to wake up early and care for his dog.

"I never had a typical routine ever... Right now, these days, it's more like dealing with no routine."

This quote underscores Ben's preference for a non-routine lifestyle and how his new pet has introduced some consistency to his days.

Weight Loss Journey

  • Ben attributes his weight loss to cycling, walking, and eliminating soda from his diet.
  • He shares a personal anecdote about his great uncle Clarence, who advised him to avoid sugar to prevent health issues.

"Walking is way more effective than people think it is. And I've lost five pounds just walking this darn dog every day."

The quote emphasizes the effectiveness of simple activities like walking in achieving weight loss, which has worked for Ben.

Lottery Ticket Misunderstanding

  • Ben recounts a humorous story about his wife mistaking lottery ticket rules, leading them to believe they had won a large sum of money.
  • Despite the mix-up, they continue to buy lottery tickets and joke about the incident.

"And she scratched off a ten, and she said, 'oh, my God, I won $25,000.' And I was so excited, I almost crashed the car."

This quote captures the excitement and subsequent disappointment of the lottery ticket misunderstanding, illustrating a light-hearted moment in their lives.

Secret to a Happy Marriage

  • Ben Chestnut believes the secret to a happy marriage is not about winning arguments but understanding and listening to one's partner.
  • He learned from observing older couples that the happiest ones were those where husbands did not always insist on being right.

"What I noticed was the happiest couples had husbands who just kept their damn mouths shut."

The quote conveys Ben's observation that active listening and humility contribute to marital happiness.

Desired Traits for Children

  • Ben aims to instill the values of balance, love, independence, self-sufficiency, and self-awareness in his children.
  • He hopes his children will learn adaptability, perseverance, and grit.

"It was bliss. It stands for balance, love, independence, and self sufficiency."

The acronym BLISS encapsulates the core values Ben wishes to pass on to his children.

Changes to the Startup World

  • Ben Chestnut advocates for the decentralization of tech startups, wishing for more geographic diversity beyond Silicon Valley and New York.
  • He appreciates that Mailchimp succeeded outside of these traditional tech hubs.

"I would love it to just be everywhere as tech startups, to not have to be in those two locations."

Ben's quote reflects his vision for a more inclusive and widespread startup ecosystem.

Personal Aspirations and Contentment

  • Ben Chestnut expresses a desire to explore his own mind and understand his thoughts and behaviors.
  • He aspires to reach a state of contentment where he does not crave material possessions.
  • Ben shares a story about a fellow founder who felt inadequate upon seeing a larger yacht, illustrating the futility of comparing wealth.

"I want to explore my own mind. I want to know why I think the way that I do."

The quote reveals Ben's introspective goal to delve deeper into his own psyche and find internal fulfillment.

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