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The Bootstrapped Billionaire, Ben Chestnut
Building Mailchimp Into a $12 Billion Business
Justin Gordon
January 05, 2025
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Ben Chestnut, Founder of Mailchimp
Ben Chestnut didn’t dream of building a $12 billion company.
He just wanted to help small businesses with email.
But in 2001, a side hustle became Mailchimp, a company bootstrapped from day one.
Two decades later, he sold it for billions without taking a dime of venture capital.
How did he do it?
Free readers will learn how Ben turned a small idea into Mailchimp’s early success.
Paid subscribers will get the full story: the key takeaways, pivotal moments, and strategies that turned Mailchimp into a $12 billion juggernaut.
Let’s get to it.
Key Takeaways from Ben Chestnut of Mailchimp
Don’t have time to read the whole piece?
Here’s what you need to know from Ben Chestnut, the founder of Mailchimp, tying his lessons into ones we’ve previously learned from other founders we’ve covered:
Early Days
Ben Chestnut grew up in a creative household:
His brother was a painter and a musician
His sister was into graphic arts
His dad was an aspiring writer and computer programmer (on top of serving seven tours in Vietnam as a codebreaker)
His mom ran a hair salon in their kitchen
Early on, Ben started developing his entrepreneurial skills, building a budding empire as a cartoonist at just 10 years old:
I was into cartooning I thought I wanted to be a cartoonist when I grew up. I would steal Post-it notes from my sisters and my brother and make little cartoons and I would take them to school and show them off.
I'd flip them on the bus and the kids would gather round and say “my god that's so cool“ and then I started to sell them. I turned it into a business. I would stay up late at night, I should have been doing my math homework, but I would make these cartoons and sell them for like 50 cents, which is so stupid, I was really bad at math, so I would take these to school and they'd love them.
They're like little stick figures that ran across the screen, you know, bouncing balls, and people loved it and they wanted more so I'd like make a car come in and run over the people, and that's awesome, do more and more and more, so I had to make like jets come in and drop bombs on the cars and the cars would explode and little tires would bounce around on the screen and they wanted more and I found myself, I was 10 or something, and I was already dealing with a-hole clients, like really demanding, I was just 10 and I couldn't wake up in the morning. I didn't want to get on the bus anymore so I got out of it and I just totally got out of the business.
Amazing lol.
From there, Ben sold candy, a much better product, as well as comic books.
In college, he thought he wanted to design cars and, after a couple of years at the University of Georgia, Ben transferred to Georgia Tech in 1994 where he studied industrial design.
Interning at an industrial design company in Iowa, Ben, after discovering he was bad at building models as a designer, received what he described as “life changing advice.”
Another designer at the firm told Ben to look at web design instead of industrial design, sending him down a path that eventually led to riches.
But Ben was far from that point then.
It was 1996 and he started reading technical books at Barnes & Noble to teach himself how to build websites.
Working at Cox Interactive Media around this time, he hired his future co-founder, Dan Kurzius.
When their unit at the company folded in April 2000, Ben was laid off, while Dan stayed at the company for the time being.
Ben used this opportunity to become a freelance website builder, starting an agency called Rocket Science Group with a friend, Mark Armstrong.
My business partner and I went out, and we got clients. We went knocking on doors down the hall from our office, and we got paying projects. We got a $13,000 project and a $32,000 project before even getting a business license. So I was ready to go.
They were off to the races.
But, as with any agency, it was a grind.
Dan joined the agency along with Mark and Ben, but the best the agency ever did was between $200k and $300k per year.
Ben described the experience as “always barely scraping by,” but a side project created during this time seemed promising.
This side project would turn into a $12 billion company and eventually the largest bootstrapped exit on record.
Here’s how it happened.
Starting Mailchimp
In the Spring of 2000, Dan’s father’s bakery went bankrupt and Ben’s older sister lost her hair salon.
These experiences sprung the idea for an email marketing service to allow small business owners to connect with their most loyal customers.
The service was built from Ben and Dan’s past work on an e-greetings site, something they built on the side from their agency:
We had built this failed business. It was an e-greetings website and the only reason we built that was we saw a press release that said Blue Mountain Greetings was acquired by Excite for $600 million.
So we were like “well, let's do that.” So we built an e-greetings website. It did okay, it didn't really make us rich at all, but the spare parts from the e-greetings website, we found that code again, and we repurposed it and built our own email newsletter tool just to make it easier for me to copy paste content and hit send. Then our clients loved it and we kept using it more and more.
In 2001, after launching the product to the public, Ben set up some Google AdWords campaigns and, in his words, "basically forgot about it."
But by 2005, the newsletter tool had grown significantly:
In 2005, we noticed it was a better business than our web-dev agency (it was growing faster than us humans, and its recurring revenue was basically keeping us afloat) so we decided to take all of 2006 to wind down the agency business and beef up Mailchimp’s features. We officially hit the “reset button” in 2007 and became a product company.
What happened when they went all-in on the product company?
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