During my time on the product design team at Mailchimp in 2018, one of my most memorable conversations was with CEO & Co-founder Ben Chestnut.
In the early days of starting Mailchimp, Ben spent most of his time on design and brand. Ben comes from a design background having studied industrial design. Coming out of school, he wanted to become a web designer although ended up getting a job doing banner ad design.
During our conversation, he outlined his principles for designing the first version of Mailchimp in 2001.
Ben Chestnut designed the initial version of Mailchimp, shown below. When reflecting on it, he says he spent almost no time designing it.
“Most of everything you see in this version of the website was spare parts from previous web design projects. One of the failed side projects we worked on was an e-greeting site and one of the most popular greetings was a monkey. So when we needed a logo for Mailchimp, I just pulled the monkey out of the parts bin from that project and put a hat on him. Constantly working with clients, I didn’t have time to create anything from scratch.” — Ben Chestnut
“Growing up, I watched my mother run her hair salon from the kitchen. But this business didn’t scale. As a startup builder, you don’t want to start a salon in your kitchen with dreams of one day building a large salon with many hairdressers. Instead, you want to come up with the shampoo that gets sold to millions of people.”
When Ben started out years ago, he looked at companies like IBM as an inspiration for what he could one day build. The business Ben Chestnut started with Dan Kurzius before Mailchimp was a web design agency. The problem with their web design agency was that it had a model similar to his mother’s hair salon. All of their projects were one-off gigs. Every client needed something different. The idea for Mailchimp came when the team decided to systematize their workflow.
“After 7 years or so of working on different consulting projects, we started to notice similar challenges across all of our web design projects. So we started to build a system to automate each project. Mailchimp was different from our other projects because it was self-serve. Before we had to pitch and sell to clients. But Mailchimp enabled us to generate new account sign-ups as we slept. People could go in and use the service themselves. It was the one project that scaled.” — Ben Chestnut
Another one of Ben’s guiding design principles was functional design.
“When we were getting started 20 years ago, the web was still fairly new. Often, you could tell designers were porting their style from their 2D offline work. So their work wasn’t native to the internet. They would use a lot of plug-ins like Flash. We would often joke about how people would use too much Flash; we called them Flash-holes!” — Ben Chestnut
In the early days, surprise and delight naturally came from Ben’s personality.
“The reason designing with personality worked for us was because our target customer was small businesses and running a small business can be stressful. So when they would log in to Mailchimp and would see small touches of personality, they would often write to us and tell us how much they loved it.” — Ben Chestnut
Not only did the personality of the brand help with attracting new customers, but many early employees at Mailchimp also said the personality of the brand is what drew them to the company.
One of the hardest lessons Ben has learned was the importance of momentum.
“In the beginning before Mailchimp, we started as a web design agency and designed hundreds of websites. I was the designer for these websites, but I also was responsible for invoicing clients. So I got to see which projects were profitable and which ones we lost money on. Analytically, I was then able to look at all of the projects we did over the year. I found the only projects that were profitable were the ones that were about two weeks long. I then researched why our two week long projects were profitable and found a research study online that said human attention span only lasts around two weeks. That was a really, really big key for us. I have a lot of battle scars from learning that important lesson. If you have a 6 month project, that’s okay, just make sure you are doing two week sprints. I used to say ‘necessity is the mother of all invention’. When you know you only have two weeks left to finish a project, you can get really creative.” — Ben Chestnut
Ben believes that if a new platform is emerging, it’s important to be there on the ground floor before everyone else crowds it up.
“Designers have all the skills they need to design an app that people love. The only other thing you need to mix into that formula is luck and timing. For Mailchimp, we got laid off and we started an internet company at a time when Software as a Service was on the rise. During this time, people were moving their work from doing it on their PC to the internet. That was a transformational wave of change. We just happened to be riding that wave.” — Ben Chestnut
Ben’s advice was if you ever see something new coming out and it looks like a wave, explore it. Ben has learned the importance of identifying waves in the industry, then dropping everything he’s doing to ride a wave for as long as he can. Because you never know when you’re going to get another wave.
Another key lesson I learned during my conversation with Ben was the importance of listening to customers while building your product. Before creating Mailchimp while running his web design agency, he noticed many of the customers were asking for help with email marketing. So they created a simple tool as a side project to help those customers. Over the course of many months, they noticed that this side project was earning more revenue than their core business. So they decided to listen to their customers and pivot towards building an email marketing platform.
“We would visit, email and call customers to ask what they thought about the product and would write all of their feedback on a whiteboard. We even put a toll free number on the Mailchimp website and asked customers to call in with their most requested features. This became our to-do list. As a designer at heart, in the early days, I would think hard about how I could steer the design ship. But what I’ve learned is its really the customers that steer everything. Design responds to what the customers need. In the end, it’s all about customers.” — Ben Chestnut