A while back, one of our favorite entrepreneurs, Ben Chestnut, was interviewed on the How I Built This Podcast with Guy Raz.

Ben is the co-founder and former CEO of Mailchimp, the famously fun & quirky online marketing/newsletter platform. Also, the carrier pigeon that shared this message with you. In 2021, he and his partner, Dan Kurzius, sold Mailchimp to Intuit for $12 billion in cash and stock. To put that into context, that’s triple the amount that Disney paid George Lucas for the Star Wars franchise.

Two ideas emerged in the podcast that made us stop and think:

First, Mailchimp was an early pioneer in the “Freemium” model. Not in the free trial sense, but in the sense that Mailchimp would let you start using their software for free. Then, only when your email subscribers reached a certain (large) number, would you have to pay. 

This meant Mailchimp got paid only IF AND WHEN their customers were successful, increasing their incentive to create software that made people actually succeed.

This is what NN Taleb calls having “Skin In The Game.” And it worked.

Secondly, they sought to be just as freaky as their customers.

In the early days, Mailchimp’s average customer wasn't your typical buttoned-up, corporate type. They were more akin to small business creatives. Having edgy customers meant they too had to be edgy, so they hired people who had a bit of freak in them as well. This made the company culture (and the Mailchimp brand) not only quirky and unique, but also more relatable to their core customers. Not to mention, it made them stand out from competitors.

The thing to remember is, it's easy (especially in business) to put on a facade. But when we're true to ourselves and our customers, magical things can happen. Ben and Dan understood this better than most. Instead of relying on a team of high-priced consultants to tell them what to do, they listened to intuition and followed their guts.

The lesson here is that in a world of sameness, it’s OK to keep our quirks. In fact, it may very well be what our customers love most about us.