Mailchimp co-founder on how he nearly killed off the monkey and introducing original content

Chestnut started the Atlanta-based company as a side project while doing web consulting by day. He had been laid off from a dot com in 2000 and so he started Rocket Science Group, where he found that its clients had a common thread – they all needed email marketing.

“So, we built this email marketing tool... and during the night we worked on Mailchimp on the side,” Chestnut told The Drum. "We had built this tool to send email marketing for all of those clients, and we were getting tired of logging in, manually copy-pasting their Word documents, manually uploading their images. We just felt like, good grief, anybody can do this, why do we have to do this manually and charge them billable hours? Let’s just add a credit card system on it and let them do it themselves.”

Chestnut and his co-founders, Dan Kurzius and Mark Armstrong, found that they could have fun with Mailchimp as a side project. Chestnut and Kurzius bought out Armstrong in 2008.

“Mailchimp was sort of our creative outlet,” said Chestnut. “I would build a website and the marketing materials and just have fun with the monkey jokes. I would drop monkey business puns everywhere. I still remember a zoologist called and said ‘chimps are actually apes.’

“My co-founder was having also a lot of fun with the design. He was dropping Easter eggs into the app. Mailchimp was sort of a creative playground for us. That really made it take off online. It got a little viral because of the fun…it was just a stress reliever for us.”

After five years of treating it as a side project, they realized that the consulting business was losing steam, but Mailchimp business was increasing. So, they pivoted and focused on software. “We had a big official vote, all three of us, and we voted to go all-in on software,” said Chestnut.

Keep the chimp or lose the customers

In 2007, Mailchimp became a legitimate business and one that Chestnut said he almost doomed by suggesting a name change.

“I gathered [the team] in my office and I said, ‘first order of business is that we should probably kill this monkey brand because it’s not serious enough…it should probably be more corporate, more safe looking. They just about had a revolt. They said, ‘the chimp is why we joined…that personality and the fun’.”

Chestnut handed over branding to his growing team and they had a good time with it. “I guess that’s the big message there – you can have fun with your brand and it will go a long way.”

So the mascot, named Freddie, stayed. Freddie rose out of an e-greeting card Chestnut had designed for the growing business before it went in another direction. His titled cap and winking smile have been a mainstay, though the design has been slightly altered over the years. Still, that chimp has kept them in business thanks to his cheeky humor.

“Small businesses, turns out, really love the levity, because running a small business is kind of miserable sometimes. Over the years we’ve kind of scaled back. With mobile design, you have to simplify a lot. We took him away and we would get really angry customers writing in saying ‘he was the only joy in my day.’ Which is kind of sad, but kind of cool. We had to bring back elements of the chimp for small businesses,” said Chestnut.

Continuing to listen to customers

Through its growth cycles, Chestnut and his team have always listened to their SMB customers. They have helped keep Mailchimp unique in voice and offerings, but Chestnut stated that it has been a challenge at times, especially when they had Freddie at the top of the app stating things like ‘I’m not wearing any pants’.

“The British really did not like that joke. They asked for an option to turn off all jokes. But we had to have the last laugh, so we called it ‘party pooper mode’. It was always a delicate balance. People would take screenshots and say ‘this was inappropriate’ or ‘this is too goofy.’

With that balance in mind, Mailchimp continued to gain strength. “When you start a small business it’s all about building your brand. When Mailchimp has such a strong brand it’s like ‘you get me, you get what I’m going through right now’,” he said.

Mailchimp always counted on solid word-of-mouth for its success, but a few years ago, it decided to go for a bigger advertising push. Unfortunately, they couldn’t get any agencies interested, until they were mentioned before a Serial podcast. Someone mispronounced the company as ‘MailKimp’ and that went viral.

“After one call, Droga5 said they wanted to work with us. They said they wanted to take that whole ‘MailKimp’ thing to another level,” said Chestnut. Droga5 made films, activations, songs and products with names like ‘JailBlimp’ and 'KaleLimp' plus 'FailChips' and 'SnailPrimp'. “My favorite was ‘MailShrimp’. It was a song, you can queue it up on Alexa. I love that song,” said Chestnut.

The company essentially reinvented itself with its all-in-one marketing platform and original programming site, which concerned some customers and employees at first.

“I got more and more questions from new employees and new customers saying, ‘hey, does this mean you’re going to change your name? Isn’t ‘mail’ going to hold you back?’ We did hire Interbrand to find out if we should change our name. They did a really good study, they talked to a bunch of customers, many in the UK, and also a whole bunch of non-customers – the recommendation was don’t change the name. I got feedback that it’s a lovable brand. Some said, ‘I don’t know what Mailchimp does, but if the salesman knocked on my door, I’d open it. It’s quirky and trustworthy’,” said Chestnut.

Growth might mean that it’s more difficult to remind people that they started as a three-person small business, but Chestnut stays in the public eye, keeping what he calls the ‘Mailchimpy’ voice and tone active through talks, writing, tweets and a blog.

The company also has a few rules. They never say ‘small ‘for small business, because every small business, he says, has big dreams. Also, they use contractions in writing and speech to be more human. “We have this concept of a parts bin where you experiment and fail, but you don’t consider it a failure. You just throw it in the parts bin because you’ll probably use it later for other projects,” explains Chestnut.

The addition of the new platforms have helped the company reach new customers and create buzz. “This is a way to add a dimension to our relationship with our customers… Creating this original content allows us to make Mailchimp a brand that can be relevant to people when they’re washing their dishes or driving to work, or they need a break from work. Mailchimp can now provide real value for our customers and for people who may one day become our customers," said Mark DiCristina, who has been with the company for a decade and was recently named head of brand and Mailchimp Studios.

With the new platforms and broadened focus, Mailchimp is entering what Chestnut calls ‘Act Two’, he wants to prove that they can repeat the success they had in Act One.

“Our customers will tell us if our brand is still useful,” he concluded.