I'm Mailchimp Co-founder Ben Chestnut, And This Is How I Work

Photo: Courtesy of Mailchimp

If you’ve ever listened to a podcast, you’ve heard of Mailchimp. (“Mail... kimp?”) We talked to Ben Chestnut, CEO and co-founder of the email newsletter company and marketing platform that grew to half a billion dollars in revenue without ever taking any venture capital. Ben reveals the email habit that ran his early hiring policy.


Location: Atlanta, GA

Current Gig: CEO & co-founder of Mailchimp

Current mobile device: iPhone X

Current computer: Macbook Air

One word that best describes how you work: “Why.” I’m always asking why, and making sure people understand the why behind decisions and strategies.

First of all, tell us a little about your background and how you got to where you are today.

I grew up in a small town in South Georgia. My father was in the military, and my mother ran a hair salon out of our family kitchen. As a kid, I helped out by sweeping up the hair and emptying the ashtrays at the end of the day.

My mother worked very hard. I remember she kept a Rolodex with names and notes about all of her clients. Today, I call it a CRM. I saw firsthand how hard it is to run a small business, and how fulfilling it can be. That still motivates me today — Mailchimp exists to empower small businesses and help them grow.

Take us through a recent workday.

Every day is a little different, but here’s a typical Monday.

5AM: Wake up, check the weather, my calendar and the news on my phone

5:45AM: Have coffee, check email

6:30AM: Cook breakfast for my sons and then walk them to school

8AM: Peloton ride

9AM: Head into the office

10AM: My team briefs me on news for the week

10:30AM: Huddle with the executive team to talk about high-level updates and roadblocks

11AM: Meet with our VP of design to talk about a customer experience project

12PM: Lunch at my desk, then go for a walk on the Atlanta BeltLine

2PM: Meet with our new hires for a “co-founders chat” where Dan and I talk about our company’s history and answer any questions

3PM: Catch up on email

4PM: Send a memo to our employees thanking them for a strong quarter and reminding them of MailChimp’s strategic plan

6PM: Go home for family time

The Mailchimp front desk (Photo: Courtesy of Mailchimp)

What apps, gadgets or tools can’t you live without?

On the personal side, Strava to track my cycling and Audible for audiobooks. At work, I rely on GSuite and Slack. And my favourite tool in general is the OLFA Slimline knife. I used it in design school instead of an X-Acto knife. I keep them at the house and in the car. They’re the handiest little knives!

What’s your workspace setup like?

My workspace is pretty sparse. I have a comfortable meeting area, and on my desk there’s a laptop and Post-it notes. A lot of conversations happen in my office, but the work itself is happening in other people’s offices and we have dedicated spaces for presentations, so I’m able to keep it simple without whiteboards or monitors or gadgets.

What’s your best shortcut or life hack?

Ben’s home screen (Screenshot: Ben Chestnut)

I’m very finicky about how I arrange my apps on my iPhone. The very first home screen is optimised for my morning routine. This screen is *only* the most important apps for my mornings, so I never fill this screen to maximum capacity.

Generally, the most important apps are on the top row and the bottom row, for quick visual identification and access. Medium importance apps are along the side edges, and the rest are in the middle. At the very top row are the apps I use when I first wake up.

Starting at the top left is the weather app, because I need to know how to dress my boys for school and myself for the workday. Then my calendar, so I’m ready for meetings at work. Then it’s the News app, so I know what’s going on in the world. Then Trello, so I can keep up with strategic initiatives.

The bottom row are apps I use for my morning exercise routine: Strava and Apple Music to listen to during workouts. The last two apps are Audible and Podcasts, for my morning drive.

At the very bottom shortcuts dock, I make it a point to keep my camera app in the bottom right corner, so I can find it fast and snap those action shots of my kids, or some wildlife I spotted while on a bike ride. I never have to hunt for that app.

All my other iPhone screens are a complete mess, but that home screen is a thing of beauty.

What’s your best email hack?

In the early days of Mailchimp, I would bucket emails by categories (“design bugs”, “accounting issues”) and use the volume in each of those categories to determine who I needed to hire next. If I had a hundred emails related to design, I knew it was time to hire a design leader.

Take us through an interesting, unusual or finicky process you have in place at work.

I like the “throw your hat over the wall” tactic. It comes from a JFK speech at the dedication of the Aerospace Medical Health Center. The idea is that when you’re embarking on a big project or initiative, sometimes you just have to throw your hat over the wall. Then you’re committed to overcoming any challenges, climbing the wall, and getting to your hat.

For me, that usually means you have to get your MVP out, and figure it out from there.

Who are the people who help you get things done, and how do you rely on them?

My entire executive team. They have ownership over their areas, and I rely on them every day. When I’m on vacation or out of the office at an event, I don’t have to be glued to my phone or worry that I’m missing something important. I know that the team’s got this.

How do you keep track of what you have to do?

Sticky notes.

What’s your favourite side project?

Mountain biking and taking care of my health. This is something I didn’t have time for when we were in the start-up phase of building the business and working all the time. Now I make the time to exercise, eat well, and take care of myself.

What are you currently reading, or what do you recommend?

Multipliers by Liz Wiseman is an excellent book on leadership. I also love How to Read a Book by Mortimer Adler. I’m teaching its tips to my children while they’re young, so they can consume books much faster and have more fun reading.

Who else would you like to see answer these questions?

Kris Tompkins. She’s a former CEO of Patagonia, and she’s a conservationist preserving millions(!) of acres of nature in Chile. You should follow her Instagram.

What’s the best advice you’ve ever received?

My mother used to say, “You become your friends.” It’s true — over time, you start to reflect the people you hang around. This has inspired me to pick really good friends who are role models for me and lift me up.

What’s a problem you’re still trying to solve?

We’ve spent the last year adding new functionality to Mailchimp and becoming a multi-channel marketing platform for small businesses, not just an email company. We’re in the process of repositioning our business, but we have to keep the trains running while we plan new routes for the future.

I recently read a book on this topic called Dual Transformation. Dual transformation is the perfect way to describe our current challenge.

We've asked heroes, experts and flat-out productive people to share their shortcuts, workspaces and routines. Want to suggest someone we should feature or questions we should ask? Let us know.


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