“When things get tough and dark — which is frequent when you’re an entrepreneurship — I

5 min readDec 6, 2020

When hiring, Ben is looking for ‘humble educators’ who are ‘so good they invite criticism.’ He wants people who are confident enough in their own abilities that they don’t have a problem having their views challenged or explaining difficult concepts in a simple way. If a person cannot dumb down their message, Ben says, they’re not a good fit for MailChimp.

Ben’s motto is love what you do vs. the traditional do what you love. He says that eventually all passions fade away if you turn them into profession, and the only way to keep your sense of purpose is by learning to appreciate the craft you’re good at.

Could MailChimp have grown even faster if it had taken VC money? Perhaps. But it’s also likely that the corporate-obsessed investors would have gradually chipped away MailChimp’s culture of creativity and innovation, which made the company special in the first place.

Ben confirmed he’s rejected a billion-dollar acquisition offer from an unspecified company. In his defense, he says that “a billion dollars isn’t that much more than a few hundred million.”

Ben: “I’ve been in this business for 19 years. So I’ve had waves of competitors taking in money and I’ve gone through those stages of grief where I say ‘oh my God, they’re gonna kill me now.’ The funding gets bigger and bigger… and nothing seems to happen. We just keep our laser focus […] and we’re good.”

Of course, once the revenues started to grow, investors lined up behind the MailChimp door. Over the years, Ben had seen dozens of competitors take millions in funding with hopes of outgrowing the company. Each VC-backed competitor could mean that Ben had made a terrible mistake staying self-funded. As of 2020, however, MailChimp still sits comfortably with a 60% share of the email industry.

The low-profile co-founder, Dan Kurzius, does regular anonymous visits to the small businesses that use MailChimp — from yoga studios to warehouses. This way, the company gets invaluable feedback — like the fact that many businesses use MailChimp as a CRM and not an email tool. It does make things a little weird when the biggest critics later learn they’ve been talking to the co-founder at MailChimp events.

For Ben, a blend of cigarette smoke and hair spray is the smell of business. It’s because his mom used to run a hair salon in their kitchen, and that’s how Ben was exposed to entrepreneurship as a kid.

Ben’s first hire and (supposedly technical) co-founder, Dan Kurzius, lied about knowing how to code on his interview. After he got the job, he put together the prototype for MailChimp using “HTML for Dummies” books. Dan tried so hard he actually produced (or stole) clean, functional code which amazed Ben. Only 10 years later did the co-founder tell Ben about his improvisation.

One of Ben’s favorite books is Viktor Frankl’s Man’s Search for Meaning. Frankl was a psychiatrist who survived a concentration camp during Holocaust. In the book, he documents how prisoners find meaning and purpose even in the most inhumane conditions.

“When things get tough and dark — which is frequent when you’re an entrepreneurship — I

Written by Mollanr