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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"The only validation I need is a paying customer."
Ben emphasizes the importance of customer satisfaction over public recognition as a measure of success.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.