MailChimp's Founder on How to Get Your Business from 'Startup to Grown Up'

Ben Chestnut is the CEO and co-founder of MailChimp an Atlanta-based email marketing service that has been around for 14 years and has more than 8 million customers, mostly small businesses, who send out a whopping 15 billion emails each month.

Jason Travis for MailChimp

Of Mailchimp's success, Chestnut often jokes that he and his co-founder Dan Kurzius "Forrest Gump'd our way here." They were first inspired to start a business around email and communication after watching e-greeting site BlueMountain.com get sold to Excite for more than $700 million in the late '90s. They decided to build an e-greetings site but didn't get much traction. The pair's next move was to develop a web-design company, (Chestnut earned his postgraduate degree in industrial design from the Georgia Institute of Technology) and they quickly discovered an exciting trend.

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"All our clients asked for the same thing: software that gave them the ability to send email promotions that included graphics, plus an ability to track results…We realized we already had the parts for that. We built the tool with scrap parts from the failed e-greetings site. We even made the logo out of one of our most popular email cards: a smiling, animated monkey." Chestnut says the experience taught him that opportunity can strike at any moment and that what you thought was a failed experiment can be the foundation of something great.

In addition to helping those small businesses, MailChimp makes it a point to throw support behind likeminded endeavors like the Emerging Women conference, lecture series like CreativeMornings and podcast networks like Radiotopia. The company's name also might be familiar to you if listened to Serial, the true crime podcast from This American Life that had everyone talking last year – they were the breakout hit's sole sponsor.

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Ultimately, Chestnut attributes the company's longevity to its culture and values. "We hire creative misfits who love empowering the underdog. There's a sense of purpose here that makes us want to come to work and build great products."

We caught up with Chestnut to talk about how to ask the right questions, the importance of listening hard and changing fast, and why your leadership style must evolve in concert with your company's growth.

Q: Knowing what you know now, what would you have done differently when you were first starting out?
A: I remember feeling insecure and lost a lot in our startup years. I was constantly studying and reading business books and chasing after the right answers for everything, so I wouldn't look so clueless in front of my team. Instead of looking for the right answers to tell, I wish I had spent more time seeking out the right questions to ask. Specifically, I wish I would've approached everything this way – "at the current stage our business is in right now, what should our priorities be?" It's one thing to know what you should do; it's another thing to know when you should do it. Fortunately, I've always had good people on my team to nudge me in the right direction.

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Q: What do you think would have happened had you known this back then?
A: Frankly, I would've been less of an asshole. Can you print that?

Q: How do you think young entrepreneurs might benefit from this lesson?
A: Eventually, if you succeed in building something truly unique and successful, and if you hang around and keep it going, you'll cross over from startup to grown up. Your leadership style will need to change from quarterbacking employees to coaching new leaders to take your company to the next level. That starts with learning how to listen, and that starts with asking more than telling.

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Q: What are you glad you didn't know then that you know now?
A: At the end of the day, all businesses are composed of the same basic building blocks. It's how you stack them that makes you unique. That knowledge has been incredibly helpful and liberating for me now, but in the early years, I'm afraid that knowing this would've taken away a lot of the fun and experimentation.

Q: What is your best advice for aspiring entrepreneurs?
A: As it grows, your business will go through several stages and each stage requires a different kind of leader. When you feel like you've mastered the stage you're in and can finally feel comfortable with yourself and proud of your capabilities, you're already falling behind. Time to move to the next stage!

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