Ben Chestnut: Disruptive design

Mailchimp CEO teaches us how to kill the competition with design-driven products

Marco Santonocito


Ben Chestnut, CEO of Mailchimp, was a speaker at the unSEXY Conference organized by 500 startups.

For those of you who don’t know Mailchimp, it is an email company that has almost 5 million users and has sent approximately 70 billions messages. They bootstrapped the company without any kind of funding.

But how Mailchimp achieved this success?

By killing the competition with design-driven products and if you want to do it, you should follow some rules:

Rule #1: Stop obsessing about the competition

Focus on yourself. If you are obsessed with the competition following all their tweets, reading their blog posts and press releases you are going to start copying them subconsciously. Your startup will never be ahead of the others but it will simply follow them.

Mailchimp started as a side project from a web design company in 2001 (screenshot on the left). They started doodling some monkeys and putting jokes on the website, and this attracted a certain clientel.

Then the company grew over the years and, in 2007, they decided to make a restyle. Ben thought “I got to treat this business seriously now” so, looking at the competition he said “wow, everything is really serious, I should do the same!”.

They dropped out all of the monkeys and made a corporate design. But their customers bolt. Ben got a lot of hate mails where people were complain about the new style.

So, after a while, they decided to get back to their style. They accepted who they are. You don’t come to this kind of conclusion if you are always obsessed with the competition. You should listen to yourself.

Rule #2: Fight really, really weird

Mailchimp marketing team started spending a lot of their budget on Google AdWords but “it was stupid”. So, what they did? They used some unconventional tactics:


They did the math and acquiring a customer via AdWords was always profitable but it cost the same of printing great T-shirts and sending them out to people. For this reason they sent a T-shirt or a hat as a gift to all the users who started using their paying service and sent their first campaign.

They get the 1,000,000 users milestone doing this.

Me and my mailchimp hat

Open APIs

A couple of years ago MailChimp’s team had to decide between hiring a sales guy, or investing in MailChimp’s API by hiring a programmer. They took the API route.

Some companies require you to register, or even pay a fee before you can access their API. MailChimp’s API is open and free, which encourages other developers to link their apps.

They created a sort of ecosystem and in less than one year they got more than 500,000 developers using their APIs.


Freemium has been the best unconventional tactic for MailChimp. They started in 2001 and they took 8 years to get 100,000 users; at that time they decided to launch the freemium business model.

After that, it took 2 years to get to a million users and then 10 months to get 2 millions.

Mailchimp user growth

Rule #3: Always. Be. Creating. (things)

Build fast, build cheap. No project should take longer than 2 weeks.

MailChimp has 3 core products: MailChimp, Mandrill and TinyLetter.

When a developer has an idea for features that may not works so great inside MailChimp or may take longer than 2 weeks to get in, he’s encouraged to go to the Lab and build his app. So over the years MailChimp Developers created a lot of tiny little miniature apps that help different segments of their audience.

All of these apps and tools are miniature opportunities for your customer to have a little user experience. They basically say: “Wow! MailChimp, you really get me!”.

That’s me!… No, I’m kidding ;)