When you get two talented, intelligent people who see a need in the market, have a great business plan and vision there isn’t much they can’t do, especially when it comes to Ben Chestnut and Dan Kurzius; co-founders of Mailchimp.

Mailchimp has been a leading email marketing service for close to 14 years, with 8 million small business customers, with an email send rate of 15 billion per month. After deciding to build an e-greeting site which wasn’t delivering results, they moved into web design. After listening to what their customers wanted (software with the ability to send emails with graphics that are trackable) they built Mailchimp.

Whilst the beginning of their entrepreneurial journey proved unsuccessful in the greeting card world, they used their experience and knowledge to build something even greater.

Before I share Ben Chestnut’s interview that was conducted with Nina Zipkin from Mashable, I just want to talk a little bit more about Mailchimp and why I am a huge brand advocate.

Firstly, Mailchimp have got their branding spot on. Playing on the words “mailchimp” they used a monkey as their logo, which visually talks to you throughout your email marketing process. Mailchimp’s features include creating email lists, setting up autoresponders, creating email templates, hyperlinking images and text, tracking results to see who has clicked on each email and being able to combine lists and see who is the most receptive to your email marketing.

Mailchimp provides the same CRM system as Salesforce however, as a small business it is easier to use, and cost free. You can have up to 2,000 subscribers and send over 12,000 emails completely free of charge. If that isn’t enough to convince you to use Mailchimp, see an interview below to help you take your business from startup to grown up.

Q: Knowing what you know now, what would you have done differently when you were first starting out?

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.

Q: What do you think would have happened had you known this back then?

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?

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.

Q: What are you glad you didn’t know then that you know now?

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?

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!

It’s always refreshing to hear from the likes of Ben, who believed in helping small businesses grow their business, using the right type of email marketing software. To read more about Mailchimp, purchase a copy of my book Think #Digital First.

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