Of course, once the revenues started to grow, investors lined up behind the MailChimp door. Over the years, Ben had seen

Designer marketing campaigns. In 2014, an announcer on one of the podcast ads accidentally mispronounced MailChimp as MailKimp. The ad was streamed to one million users — but, in character, the company decided to turn the comical mistake into an entire marketing campaign. Soon, entire brands for MailShrimp, FailChips, VeilHymn and a bunch of other Bumblesnuff-Crimpysnitch-esque spinoffs were launched, accompanied by amazingly creative campaigns. Weird? Kind of. Hilarious? Just watch the VeilHymn artist-interview-parody.

Niche social platforms. The company’s adage in the early days was Code, Blog, Tweet, Repeat — simply because this marketing strategy worked. Twitter was a lot less crowded in 2007, and MailChimp was getting real exposure on the network. Similarly, they purchased ads to be played at the beginning of every new episode of a crime podcast called Serial. The podcast is now a hit — having been the first one to hit 5m downloads in the history of podcasts — but buying ads on it was a hipster thing to do back in the day. Hence, cheap.

The main reason why Ben could do it is because MailChimp was a revenue-generating piece of software since day one. Their pricing changed over the years (per email -> monthly subscription -> freemium,) but, unlike products like WhatsApp, it had a very clear revenue model — one that didn’t involve selling your users’ data. Also, it’s crucial to consider that MailChimp was a spinout of the agency Ben used to run, by which it was initially funded.

Ben: “The content that we’re putting out is like… Second chances in life… How do you know when to hold on and when to give up… Those are struggles [small] entrepreneurs are facing all the time. […] We want to help them scale out of the kitchen.”

To investors, the math just didn’t check out. Why serve a highly fragmented, emotional, low-budget small business audience when 30% of them will be out of business in 2 years, and 50% of them will fail within the next 5 years? What Ben understood from personal experience was that even when solo-preneurs fail, they keep their email lists alive, and most of them start something new some time down the road. So MailChimp doesn’t necessarily lose a customer, even when they go out of business temporarily.

Ben: “For us, it was an interesting time. It was the early days of SaaS, nobody was really solving problems with SaaS — or for small business. So we had a nice opportunity to go at it alone. And we just always made loads of money, because we were the only people willing to do email — very unsexy business — for small business — which is also very unsexy.”

The Chimp! Theories behind branding as a be-all-end-all are often cheesy, but the Chimp certainly worked out for Ben. Back in his days as a web designer, he learned that adding a monkey to any marketing design increased its effectiveness. Over the years, the Chimp had become a champion of the brand, throwing goofy comments at users when they log in, disable-able in the ‘party-pooper’ mode in Settings. Seriously, how many other email platforms can you name?

The semi-viral freemium model is the biggest culprit in the Chimp’s success story, and it propelled its growth from 100,000 users to 1m users in just one year. It was novel at the time to give users free access to the entirety of your platform. The explosive success of the freemium model was two-fold: for one, every ‘free’ email sent contained a MailChimp logo in the footnotes, creating a semi-viral loop of organic referrals; since the users had to pay only once they reached a certain number of emails on their list, getting your first paid MailChimp plan acted as a rite of passage you had to ‘earn’ your way to.

The amounts were still negligible. When you’re chasing $30,000 web design projects, a few $50 invoices don’t warrant significant attention. Ironically, it was the increasingly inefficient task of issuing these small invoices that prompted Ben to introduce a monthly subscription model and build a credit card feature for MailChimp — effectively giving birth to one of the first software-as-a-service products ever created.

It sounds corny, but a big part of Ben’s success lies in the fact that he was honest with himself about his own strengths and weaknesses. When Ben’s father bought him a computer, he didn’t teach himself coding — he learned how to draw on a computer program that took 5 floppy disks to run. In fact, he wanted to become a cartoonist as a kid. Is MailChimp an incredible feat of engineering? Perhaps. But its core strength is creativity, and that is, apparently, enough to build a billion-dollar tech company.

How does an internally used background tool turn into a $4.2 billion, industry-spawning behemoth with zero investment? In short, by using every guerrilla tactic in the book:

Ultimately, the Chimp succeeded because it found its way into the hearts of small business owners. Ben’s mom used to run a hairdresser’s salon in their home kitchen, so he knew intimately the kinds of struggles self-employed people run into day-to-day.

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a list of candidate keywords or keyphrases from a document. Although many focus on noun phrases, we are going to keep it simple by using Scikit-Learns CountVectorizer. This allows us to specify the length of the keywords and make them into keyphrases. It also is a nice method for quickly removing stop words.

He knew that small businesses don’t have separate marketing budgets — buying a new TV for your living room or investing into Facebook ads were all funded by the same pocket. He knew that self-employed people are the end users of his product — which makes them emotional as decision makers.

It’s not like Ben was against taking investor money. But the world was still recovering from the dot-com burst, and VCs weren’t exactly eager to throw money at internet companies. Many were wary of the SaaS freemium model — which was novel at the time. Most investors Ben had met argued that MailChimp should go after enterprises — because that’s where the big bucks are — and not small businesses.