Can you bootstrap your way to scale? Here’s how Mailchimp did it (with a lot of luck on their side)

Reid Hoffman
2 min readMay 24, 2019

I believe that Blitzscaling is the most effective way to build the companies of the future. It’s what I specialize in as an investor at Greylock. But it’s rare that entrepreneurs can blitzscale from day one. It’s hard to prioritize speed over capital efficiency when you have no capital. That means bootstrapping is a key part of the start of almost every entrepreneurial story. But what happens when you need to scale? Can you keep bootstrapping your way to scale during the blitzscaling era?

In this latest episode of Masters of Scale, my guest, Mailchimp Founder/CEO Ben Chestnut, helps me explore this question by sharing Mailchimp’s journey from neglected side project to $600 million in annual revenue. You’ll hear how Mailchimp turned down eager VC backers and rode the waves of cloud computing, social media and “freemium” to build a thriving business without ever taking outside capital. But you’ll also hear me wonder whether the company could have been even bigger, sooner, with the right kind of help.

Along the way, you’ll learn the touching story of why cigarette smoke and perms are still the smell of business for Ben, how eating Fuddrucker’s hamburgers became a symbol of Mailchimp’s early success, and why television legend LeVar Burton illustrates the limitations of venture capital.