“We sort of Forrest Gumped our way into business.”
– Ben Chestnut, Co-Founder of Mailchimp
More like “Forest Gumped” their way into becoming the largest-ever acquisition of a bootstrapped company!
- Valuation: $12B
- 1,500 Employees When Acquired By Intuit in 2021
- Competitors: Constant Contact, ActiveCampaign, HubSpot, ConvertKit, Beehiiv
Mailchimp Revenue On The Way To $1B
- Launched in 2001
- $525M ARR in 2017
- $600M ARR in 2018
- $750M ARR in 2020
- $800M ARR in 2021
- Acquired By Intuit For $12B in 2021
1. Obtaining First Customers Through Solving a Problem
What if the key to explosive growth lies in addressing the overlooked struggles of your clients? Here’s how Mailchimp did exactly that.
Ben Chestnut and Dan Kurzius didn’t set out to revolutionize email marketing. They ran a web design agency called The Rocket Science Group in the early 2000s.
While running the web design agency, a recurring issue was that their clients struggled with email newsletters.
Read on to see how this issue was found a solution, which became Mailchimp.
The Founders of Mailchimp
Ben Chestnut and Dan Kurzius, the co-founders of Mailchimp, both grew up immersed in the world of small businesses.
Ben spent his childhood helping in his mother’s hair salon, which operated out of their kitchen. He recalled the following, highlighting the early influence of entrepreneurship on his life:
“To me, if I close my eyes and think about business, there’s a smell to it—hairspray and cigarettes.”
-Ben Chestnut (Source: Harry Stebbings interview).
Similarly, Dan assisted in his parents’ bakery, gaining firsthand experience in running a small business. Their early experiences gave them firsthand insight into the challenges faced by small business owners.
Launching The Rocket Science Group
Ben and Dan met in Georgia during college. Their shared backgrounds and entrepreneurial spirits led them to start a web design agency called The Rocket Science Group in 2000.
This venture began during the aftermath of the dot-com bust, a time when many tech companies were struggling.
What’s The Problem They Solved?
In 2001, while working with clients at their agency, they noticed a recurring problem.
Many of their small business clients were having trouble sending email newsletters. Some had no idea how to do it, while others were stuck with complex and expensive enterprise software that was difficult to use.
Instead of ignoring this issue, Ben and Dan saw an opportunity to solve a real problem.
They decided to create an easier way for their clients to send email newsletters. Utilizing spare code from a previous project—an e-greetings website—they developed a simple, user-friendly email marketing tool.
“We built it just to make it easier for me basically to copy, paste content, and hit send.”
-Ben Chestnut, Interview with Rob Walling
Their clients loved the tool, and it quickly gained traction.
As demand grew, processing numerous small checks from clients became time-consuming.
They then implemented a credit card payment system, streamlining revenue collection and making the service more accessible.
Pivoting to Mailchimp—From Web Design to Email Marketing
Their decision to focus on email marketing marked a significant shift from their initial web design services.
This change was driven by their clients’ needs and their desire to provide tangible value.
By addressing a specific problem faced by small businesses, they began to attract more customers organically. This customer-centric approach was foundational to Mailchimp’s growth.
Their focus on simplicity and user experience resonated with small business owners who were underserved by existing solutions.
Standing Out With Creativity
Ben’s passion for creativity played a significant role in how they developed their email marketing tool.
Rob Walling: “If one topic at dinner came up, which topic would you not be able to stop talking about?”
Ben Chestnut: “Creativity.”
They infused creativity into their product design and branding, making their tool not only functional but also enjoyable to use. This unique approach attracted users who appreciated a fresh take on email marketing software.
Focusing Exclusively on Small Businesses
Mailchimp made a strategic decision to concentrate solely on small businesses, deliberately avoiding the midmarket and enterprise sectors. Ben referred to the midmarket as “Death Valley”:
“You can, in our business, have Small Business Mountain or Enterprise Mountain. In the middle, I drew Death Valley. Midmarket is Death Valley—you have clients who have the ambitions of a large business and the budget of a small business. They’re high maintenance.”
—Ben Chestnut (Source: Rob Walling Interview)
Not to mention, focusing on small businesses allowed Mailchimp could offer a self-service model that was scalable and cost-effective.
This approach allowed them to provide high-quality services without the overhead of extensive customer support typically required by larger clients.
Building a Community
Mailchimp fostered a sense of community among its users by supporting initiatives that mattered to small business owners.
They provided educational resources, webinars, and success stories to inspire and inform their audience.
Ben and Dan understood that entrepreneurship could be a lonely journey.
With creating spaces for users to connect and learn from each other, Mailchimp became more than just a service provider—it became a hub for entrepreneurial spirit.
Key Takeaway: Mailchimp began by addressing a specific issue small businesses faced—email marketing. By providing an accessible, user-friendly solution, they successfully transitioned from a web design agency to a thriving platform, proving that solving real customer problems fuels growth.
2. $12B Valuation Bootstrapped… How?
Founders Ben Chestnut and Dan Kurzius chose to bootstrap their company from the very beginning, growing it without any venture capital.
This decision allowed them to maintain complete control over Mailchimp’s vision and growth trajectory, free from the external pressures that often accompany outside funding.
Building a Business During a Tech Downturn
Mailchimp was founded in 2001, during the aftermath of the dot-com bust—a time when the tech industry was experiencing significant turmoil.
Startups were closing, and investor confidence was low. Ben and Dan started Mailchimp as a side project while running their web design agency, The Rocket Science Group.
With limited financial resources, they relied on revenue generated from their clients to fund their operations.
“We were in Atlanta, Georgia, and nobody bothered to fly over until one of our competitors went public. We never needed money. We just made plenty.”
-Ben Chestnut (Source: SaaStr Annual 2022 Interview)
Ben explains Mailchimp to have started as more of a side hustle or project, so the need or want for extra money to build wasn’t necessary.
Choosing Independence Over Investment
As Mailchimp gained traction, venture capitalists began to take notice. Offers of investment started to come in, but Ben and Dan were hesitant to accept. They were cautious about the potential loss of control and the pressures that come with external funding.
“Every time someone knocked and asked to help fund, they gave me someone else’s playbook. As an entrepreneur, I’m sure you all can relate—I wanted to build my own thing my way.”
-Ben Chestnut (Source: MicroConf Interview)
They valued their autonomy and didn’t want to be steered by investors who might not share their vision or understanding of their customers. By declining venture capital, they retained the freedom to make decisions that aligned with their mission of empowering small businesses.
Without external investors, Ben and Dan could focus on long-term goals rather than short-term returns demanded by shareholders. They prioritized customer needs and product quality over rapid scaling.
Ben highlighted the importance of this control:
“I didn’t want to take orders from some nerdy MBA VC to become a copycat—that’s like the worst hell. I wanted to build it my own way.”
-Ben Chestnut (Source: MicroConf Interview)
This independence fostered a culture of innovation within Mailchimp. They weren’t constrained by investor expectations and could experiment with new ideas, such as introducing the freemium model in 2009.
Insane Amount of Growth… Independently
Mailchimp’s bootstrapped journey didn’t hinder its growth; instead, it proved that massive success is achievable without venture capital.
When 2021 rolled around, Mailchimp had grown to over 1,200 employees and was serving millions of customers worldwide.
In that year, the company was acquired by Intuit for $12 billion, marking one of the largest acquisitions of a bootstrapped company in history.
Their success demonstrated the advantages of maintaining control:
- Agility in Decision-Making: Without the need for investor approval, they could swiftly implement strategies that responded to market needs.
- Customer-Centric Focus: They could prioritize the needs of small businesses without conflicting interests from investors seeking higher returns.
- Cultural Integrity: They preserved a company culture that valued creativity, independence, and a personal connection to their customers.
Mailchimp’s journey offers valuable lessons for entrepreneurs:
- Self-Funding Can Drive Success: Relying on revenue and profits to fuel growth can lead to sustainable success without the pressures of external funding.
- Maintain Your Vision: Retaining control allows founders to stay true to their mission and values.
- Customer Focus Pays Off: Prioritizing customer needs over investor demands can build a loyal user base and drive organic growth.
Key Takeaway: Mailchimp’s founders, Ben Chestnut and Dan Kurzius, bootstrapped the company from day one, avoiding venture capital. This allowed them to maintain control over their vision, prioritize customer needs, and grow into a $12 billion company without the external pressures of investors.
3. The Power of a Free Model
One of the most pivotal moments in Mailchimp’s journey to $800 million in revenue was the introduction of the freemium model.
Mailchimp attracted millions of users by adding this, many of whom eventually converted into paying customers. This strategy not only expanded their user base exponentially but also solidified their position as a leader in email marketing.
The Accidental Introduction of Freemium
In 2009, nine years after Mailchimp’s inception, the company faced a significant technical challenge. Ben Chestnut and his team wanted to split Mailchimp into two products: one for email list building (free) and one for sending emails (paid).
However, their lead engineer encountered difficulties due to the complexity of their existing codebase.
Ben talked about freemium, in all honesty at MicroConf:
“We didn’t want to do freemium; we wanted to charge the hell out of people. We wanted to make it free to sign up for the email collection part of Mailchimp, but if you wanted to send emails to your customers, that’s when we’d get you.”
-Ben Chestnut
Their engineer, overwhelmed by the task of splitting the product, proposed an alternative:
“He said, ‘Here’s what I can do for you. Instead of making two products, I’ll make it one, but we can make it free for a certain amount of time.’ And I was like, ‘Well, we’re running out of time; do it.’ That’s it. It was an accident.”
-Ben Chestnut
This accidental shift led to the creation of Mailchimp’s free plan, marking the company’s entry into the freemium model.
Initially, the team didn’t fully grasp the potential of the freemium model. It wasn’t until Ben stumbled upon a book that the concept crystallized:
“I wrote a blog post and saved the draft. Over the weekend, someone put a book on my desk by Chris Anderson called ‘Free: The Future of a Radical Price.’ I was like, ‘That’s what we’re doing!’ So I just said, ‘Mailchimp introduces a freemium plan.'”
-Ben Chestnut (Source: MicroConf Interview)
Accessibility = Growth
The impact of offering a free plan was immediate. Small businesses and individual users who were hesitant to invest in email marketing suddenly had access to a powerful tool at no cost.
This inclusivity resonated with Mailchimp’s mission to empower small businesses.
“Even my kids—every app they download is freemium. Everyone expects it. So if you’re not doing it, you should be considering it for sure.”
-Ben Chestnut (Source: MicroConf Interview)
The freemium model significantly lowered the barrier to entry, allowing millions of users to experience Mailchimp’s platform firsthand.
This massive influx of users led to increased brand recognition and market share.
How To Convert Free Users into Paying Customers
While attracting users is important, converting them into paying customers is the true measure of a successful freemium strategy.
Mailchimp excelled in this area by offering valuable premium features that users naturally gravitated toward as their needs evolved.
Users began with the free plan to test the waters. As their businesses grew, so did their requirements for advanced functionalities like automation, segmentation, and detailed analytics.
Recognizing this progression, Mailchimp designed its pricing tiers to cater to the scaling needs of its users.
“We wanted to make sophisticated marketing tools accessible to everyone. Small businesses should have the same opportunities as big companies to connect with their audiences.”
-Ben Chestnut
Mailchimp effectively nurtured free users into paying customers by aligning their premium offerings with the growing demands of their users. This strategy not only increased revenue but also fostered long-term customer relationships.
The introduction of a freemium model unlocked exponential growth for Mailchimp and solidified its position as an industry leader.
Offering free services attracted a vast user base, many of whom transitioned into paying customers as their needs expanded. This approach demonstrated the effectiveness of freemium in driving user acquisition and revenue growth.
Key Takeaway: Mailchimp’s experience underscores that when executed thoughtfully, the freemium model can be a catalyst for significant success in the SaaS industry. By lowering barriers to entry and providing a clear path for users to grow within the platform, companies can build a loyal customer base and create sustainable revenue streams.
4. From Email Marketing to All-in-One Platform
As we know, Mailchimp began as a simple email marketing service but transformed over time into a comprehensive, all-in-one marketing hub.
This evolution was driven by the need to adapt to customer demands (as does every company in order to grow), and stay competitive in an ever-evolving digital landscape.
When Mailchimp expanded its product offerings beyond email, they made sure they could support small businesses as they grew and faced more complex marketing challenges.
From Email Marketing to a Multi-Channel Platform
In its early days, Mailchimp focused solely on email marketing. The platform’s simplicity allowed small businesses to send newsletters without needing expensive software or technical expertise.
However, as Mailchimp’s user base grew, so did the range of tools its customers wanted.
“As we talked to our customers, it became clear they were juggling many different tools for email, ads, social, and more. We thought—why not bring it all under one roof?”
-Ben Chestnut (Source: SaaStr Annual Interview)
All you have to do is listen to your customers! Mailchimp’s realization that customers were using a patchwork of tools to manage their marketing led to its shift toward becoming a multi-channel platform.
The goal was to simplify marketing processes for small businesses by offering all necessary tools in one place.
Automation and Data-Driven Insights
Automation enabled businesses to send the right message at the right time based on user behavior, significantly improving personalization. This not only streamlined marketing for small business owners but also made it more effective.
At the same time, Mailchimp began offering data-driven insights, allowing businesses to measure the performance of their marketing campaigns.
These analytics empowered users to make informed decisions, improving the overall effectiveness of their outreach efforts.
“We saw the importance of helping businesses not just send emails but really understand how their customers are responding.”
-Ben Chestnut (Source: MicroConf Interview)
With automation and data insights, Mailchimp users were able to scale their marketing efforts and drive more meaningful engagement with their audiences.
Integrating Social Media and Ads
Recognizing the growing importance of social media, Mailchimp expanded its platform to include social media management and advertising.
Businesses could now create, track, and manage Facebook, Instagram, and Google ads directly from Mailchimp. This allowed users to align their social media marketing with their email campaigns for a better strategy.
“It was all about making life easier for the small business owner—managing everything from one place meant less stress and better marketing.”
-Ben Chestnut (Source: SaaStr Annual Interview)
Social media integration made Mailchimp a more attractive option for businesses that needed to manage their entire digital marketing presence efficiently.
It enabled them to streamline workflows and maintain consistency across various channels.
Expanding into E-commerce Solutions
Mailchimp’s growth didn’t stop at email and social media. As e-commerce became increasingly vital for businesses, Mailchimp responded by adding e-commerce tools to its platform.
These tools allowed businesses to integrate their online stores with their marketing efforts, offering features such as abandoned cart emails, product recommendations, and sales tracking.
“We wanted businesses to connect their marketing with real results—sales. Adding e-commerce tools was a natural fit for what our users needed to grow.”
-Ben Chestnut (Source: SaaStr Annual Interview)
The e-commerce integration gave businesses the power to not only communicate with customers but also drive conversions and measure the direct impact of their marketing efforts.
Key Takeaway: Mailchimp’s transition from an email marketing tool to a complete marketing ecosystem was instrumental in its success. By evolving to meet the demands of its users, Mailchimp ensured that businesses could manage everything from email to social media and e-commerce—all within a single platform. This evolution helped cement Mailchimp’s place as a leader in the marketing space, providing small businesses with the tools they needed to succeed in the digital age.
5. Customer-Centric Focus: Prioritizing Feedback and Exceptional Support
Mailchimp’s success wasn’t just a product of its innovative marketing tools but also of its unwavering dedication to understanding and meeting customer needs.
From the start, Ben Chestnut and Dan Kurzius recognized that a business grows when it listens carefully to its users and provides exceptional support.
This customer-centric focus created a loyal user base that contributed to Mailchimp’s sustained growth and strong market position.
Actively Listening to Customers
Mailchimp’s commitment to customer satisfaction was evident in its approach to feedback. Unlike companies that relied solely on internal ideas, Mailchimp made it a point to incorporate user feedback into its product development.
Instead of assuming they knew what small businesses wanted, Ben and Dan actively listened to users, learning about their pain points and unmet needs.
“You don’t just build a product and expect it to be perfect. You have to listen, adapt, and evolve based on real customer experiences.
-Ben Chestnut (Source: SaaStr Annual Interview)
This focus on feedback was essential as the digital marketing landscape changed. Mailchimp’s team didn’t shy away from making iterative adjustments based on customer requests, continuously improving the platform to serve small businesses better.
Whether it was simplifying workflows or adding more customization options, every decision was informed by direct user input.
Innovation Through Feedback
Listening to customer feedback didn’t just help Mailchimp solve problems—it became a fuel for innovation.
As users provided insights into their needs, Mailchimp identified opportunities to expand its services. For example, when users expressed the need for more automation options, Mailchimp responded by building a robust automation system that allowed businesses to streamline their marketing efforts.
This customer-driven approach to innovation kept Mailchimp at the forefront of the email marketing industry. By staying in tune with user demands, Mailchimp avoided becoming outdated and was able to offer features that resonated with its growing audience.
“Some of our best ideas came from our users. They told us what they needed, and we made it happen.”
-Ben Chestnut (Source: SaaStr Annual Interview)
Prioritizing Support
Recognizing that small businesses often lacked the technical resources of larger enterprises, Mailchimp made it a priority to offer accessible, helpful support at every touchpoint.
Whether through detailed knowledge bases, live chat, or email assistance, Mailchimp ensured its users could get the help they needed quickly and effectively.
Ben Chestnut understood that providing reliable support wasn’t just about solving problems—it was about building trust.
Small business owners needed to feel that they were supported by a partner who understood their challenges. This philosophy shaped Mailchimp’s support strategy, creating a strong sense of loyalty among its user base.
“Our job wasn’t just to provide a tool—it was to support people’s dreams and ambitions. And that meant always being there to help.”
-Ben Chestnut (Source: SaaStr Annual Interview)
By investing in its support infrastructure, Mailchimp built lasting relationships with its customers, many of whom became long-term users.
Turning Feedback into Loyalty
Mailchimp’s focus on customer feedback and exceptional support didn’t just result in a better product—it fostered strong loyalty among its users.
Customers who felt heard and supported were more likely to stick with Mailchimp over competitors. This loyalty was critical in Mailchimp’s ability to grow organically, especially in the early days when the company relied on word-of-mouth marketing.
Satisfied users not only stayed with Mailchimp but also became brand advocates, recommending the platform to others. This organic growth allowed Mailchimp to scale without the need for aggressive sales tactics or heavy reliance on paid advertising.
Key Takeaway: Mailchimp’s success in fostering customer loyalty can be directly traced back to its unwavering focus on user needs. By listening closely to feedback, implementing customer-driven innovations, and providing top-tier support, Mailchimp built a brand that small businesses trusted. This customer-centric approach was not only essential to Mailchimp’s growth but also to its longevity in an increasingly competitive landscape.
6. Cultivating a Strong Company Culture Centered on Creativity
As we know, the heart of Mailchimp’s growth is a company culture focused on creativity and innovation.
Co-founders Ben Chestnut and Dan Kurzius cultivated a work environment that empowered employees to think differently and encouraged experimentation.
This approach not only fueled internal productivity but also allowed Mailchimp to develop groundbreaking products that resonated with small businesses.
Creativity is a Core Value
From the beginning, creativity was not just an attribute but a core value of Mailchimp’s culture. Ben Chestnut believed that a company must foster a creative environment if it wants to innovate.
His personal passion for creativity influenced how Mailchimp approached problem-solving and product development.
“Creativity is the thing I can’t stop talking about. It’s at the core of everything we do here,” Ben said during an interview with Rob Walling (Source: MicroConf Interview).
Mailchimp’s work environment encouraged its employees to embrace creativity in their day-to-day tasks. Whether developing a new product feature or designing a marketing campaign, the company gave its team the freedom to explore new ideas and take risks.Â
This emphasis on creativity led to some of Mailchimp’s most innovative features and branding strategies.
Prioritizing Employee Well-Being
Ben and Dan also recognized that supporting employee well-being was crucial to maintaining creativity. Mailchimp developed initiatives to support work-life balance, mental health, and professional development.
The goal was to create an environment where employees felt valued and inspired to do their best work.
Mailchimp’s commitment to its employees was demonstrated through benefits like comprehensive health insurance, flexible work schedules, and opportunities for growth within the company.
This focus on well-being helped foster a motivated workforce, where employees were excited to contribute to Mailchimp’s success.
Creating a Space for Innovation
Mailchimp thrived on innovation, which was fueled by its commitment to creative problem-solving. Employees were encouraged to experiment without fear of failure, knowing that even unsuccessful ideas could lead to new insights.
Ben believed that too much rigidity in a company could stifle innovation, so Mailchimp intentionally maintained a flexible, open-ended approach to its processes.
“We didn’t want to follow a rigid playbook. Creativity needs space to breathe, and at Mailchimp, we built that space for our team to take risks and innovate.”
-Ben Chestnut (Source: SaaStr Annual Interview).
This culture of experimentation was evident in Mailchimp’s marketing campaigns, user experience designs, and product innovations. By giving employees the freedom to explore creative solutions, Mailchimp consistently pushed the boundaries of what a marketing platform could offer.
Quirky Mailchimp
Mailchimp’s quirky and unique brand is a reflection of its internal culture. The company embraced its individuality, which was evident in its branding, messaging, and customer interactions.
The playful and creative tone of Mailchimp’s marketing campaigns resonated with small business owners, many of whom shared similar values of creativity and innovation.
Ben and Dan intentionally crafted Mailchimp’s brand to connect with its core audience—small businesses looking for marketing solutions that were both effective and enjoyable to use.
This approach helped Mailchimp stand out in a crowded market of corporate-style competitors.
“Our brand connected with people because it was authentic. We weren’t trying to be something we’re not—we embraced our quirks and creativity, and that resonated.”
-Ben Chestnut (Source: 20VC Interview).
By aligning its external messaging with its internal culture, Mailchimp created a brand that felt personal and accessible, fostering strong customer loyalty.
Key Takeaway: Mailchimp’s focus on creativity, employee well-being, and innovation was key to its success. By fostering an environment where creativity thrived, the company was able to attract talented employees and build a brand that connected with small businesses. This culture-driven approach allowed Mailchimp to stay innovative while remaining true to its core values.
Why Intuit Acquired Mailchimp for $12 Billion
In 2021, Mailchimp, one of the largest bootstrapped startups in the world, was acquired by Intuit for $12 billion.
This was a monumental moment, not only for Mailchimp but for the SaaS industry as a whole.
The acquisition highlighted both the incredible growth Mailchimp had achieved on its own (bootstrapped) and the strategic alignment between the two companies.
The deal was the result of more than a year of discussions, reflecting Intuit’s commitment to integrating Mailchimp into its platform and the evolution of Mailchimp’s role in the small business world.
But why did Ben Chestnut, a long-time proponent of bootstrapping, finally decide to sell?
The Deal Took One Year
The path to the Intuit acquisition wasn’t quick or simple. It was a long, calculated process that took more than a year to finalize.
Ben Chestnut admitted that although he had never actively sought to sell Mailchimp, he always believed in listening when offers came to the table.
“I never really had a desire to sell, but I always felt it was my duty to listen to people when they wanted to buy,”
-Ben Chestnut (Source: 20VC Interview).
Several companies had knocked on Mailchimp’s door before, and some of these offers went relatively far into the process.
However, none of those deals materialized, and the aftermath of each failed offer left Mailchimp’s leadership team deflated.
As a bootstrapped company, Mailchimp had always maintained a high level of independence, and the senior leadership team, many of whom were drawn to the company specifically because it hadn’t raised external funding, was emotionally invested in remaining independent.
When Intuit reached out, things were different. Their approach and their deep understanding of small businesses made the conversation stand out from previous offers.
Alex Chriss, the Executive Vice President and General Manager of Intuit’s Small Business and Self-Employed Group, brought a perspective on Mailchimp’s potential that resonated with Ben.
“Alex talked about small business in a way no other leader had before. He knew the same stuff that Dan and I knew, and that was rare.”
-Ben Chestnut (Source: 20VC Interview).
This alignment of values and mission was a turning point, prompting Mailchimp’s leadership to take the offer seriously.
Why Intuit Wanted Mailchimp
Intuit’s interest in Mailchimp was clear from the beginning. As a financial software company known for products like QuickBooks and TurboTax, Intuit already had a strong foothold in the small business market.
But they lacked a robust marketing tool to complement their financial services. By acquiring Mailchimp, Intuit could offer its small business customers a one-stop platform, encompassing everything from managing finances to marketing.
Mailchimp’s strengths were exactly what Intuit needed. The company had built a strong brand in email marketing and had grown its product offerings to include full marketing automation.
For Intuit, this meant expanding beyond accounting software into the marketing realm, creating an ecosystem where small businesses could handle nearly every aspect of their business in one place.
The strategic value was undeniable: Intuit wanted to be the go-to solution for small businesses, and Mailchimp’s integration was a natural fit for that vision.
“It felt like this was a refueling moment for us… we could connect, get pumped full of fuel, and then take off with our mission,” Ben shared, describing how the partnership with Intuit was like jet fuel for Mailchimp’s growth (Source: 20VC Interview).
Why Ben Chestnut Finally Agreed to Sell
For over 20 years, Ben Chestnut had remained committed to keeping Mailchimp bootstrapped.
The company grew on its own revenue, without venture capital or outside investors, giving Ben full control over the direction of the company. For Ben, bootstrapping was not just a business decision; it was a matter of principle.
“I always wanted to build my own thing my way. I didn’t want to be a copycat or take orders from some nerdy MBA to become a copycat.”
-Ben Chestnut (Source: 20VC Interview).
However, after decades of bootstrapping success, Ben started to reconsider his approach. Conversations with mentors helped him realize that while Mailchimp was his creation, it didn’t have to define his entire life.
“My mentors told me, ‘One day you’re going to find out that the business is not really you… It’s a tool that enriches your life, but it doesn’t define you.'”Â
-Ben Chestnut (Source: MicroConf Interview).
This shift in thinking, combined with Intuit’s compelling offer, led Ben to see the acquisition as an opportunity for Mailchimp to reach even greater heights.
Intuit’s deep resources and shared mission of supporting small businesses made the decision to sell more about Mailchimp’s future than its past.
The Strategic Fit for Intuit’s Small Business Ecosystem
Intuit’s acquisition of Mailchimp was part of a broader strategy to become the ultimate platform for small businesses. By adding Mailchimp’s marketing automation tools to their financial management solutions, Intuit created a seamless experience for small business owners.
Mailchimp’s capabilities allowed Intuit to offer marketing services that complemented their core products like QuickBooks and TurboTax.
The acquisition gave Intuit the ability to provide a full suite of services for small businesses, covering everything from tax preparation to customer acquisition and marketing campaigns.
This strategic alignment was a win for both companies. Mailchimp could leverage Intuit’s resources to fuel its growth, while Intuit could expand its market share by offering an all-in-one solution for small business owners.
The $12 billion price tag reflected not just Mailchimp’s current value but the long-term potential of integrating its tools into Intuit’s platform. For Intuit, acquiring Mailchimp wasn’t just about adding a new feature—it was about creating an ecosystem that would keep small businesses loyal to their brand for years to come.
Key Takeaway: Mailchimp’s acquisition by Intuit was a landmark deal in the world of SaaS, representing one of the largest exits for a bootstrapped company. The decision to sell wasn’t just about financial gain; it was about aligning with a partner that shared Mailchimp’s vision for empowering small businesses. For Intuit, the acquisition was a strategic move to create a comprehensive platform for small businesses, solidifying their leadership in the market. And for Ben Chestnut, it marked the culmination of a journey that transformed Mailchimp from a side project into a global powerhouse.
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