HOW MAILCHIMP (FINALLY) MADE IT

MailChimp’s path was never easy or straightforward. That’s why there’s so much to learn from it

Keep Your Eye on New Opportunities

Since its early days as Rocket Science Group, the company has shifted from specialized web development for many kinds of big corporate customers (first tech companies, then travel companies, and then real estate companies) to, finally, email marketing software for startups.

Be a Hoarder

Early on, Chestnut and Kurzius worked on a failed e-greetings project and then shelved it for years. When small businesses started asking them for help with email, their solution was in that project that they’d set aside. Chestnut still encourages staffers to save such ideas. “Anytime there’s been a threat or an opportunity,” he says, “we have parts i n the bins that we could just assemble really fast. That speed is so important.”

Free Is Your Friend

MailChimp’s tipping point, in Chestnut’s view, came when it introduced a freemium model, which lets customers use MailChimp’s s ervices for free. Initially, Chestnut wanted to give away one product (collecting subscribers) and charge for another (sending emails), but “it was really, really difficult to break our product into two pieces,” he recalls. So the company decided to “just make the whole thing free.” Customer numbers shot up. So did MailChimp’s revenue.

Above All, Stick to It

It took more than five years for MailChimp to find its sweet spot, and about a decade for Chestnut to feel like it was starting to succeed. That experience influences how he chooses which founders he mentors now. “If they say, ‘These hackathons are hard. Do you have advice on how to build a deck?’ I don’t want to talk to them,” he says. “When they’ve hit some really tough time—struggling to deal with a partner who’s uncooperative, the real struggles of the small-business owner—those are the ones that I invite in.”