Is Mailchimp the Greatest Bootstrapped SaaS Ever?

This post is auto-generated from a public YouTube interview for personal study notes. It is not an endorsement. The transcript is machine-derived and may contain errors; refer to the original video for accuracy.

About this video

This is the story of MailChimp.

Welcome to SaaS Legends, a series where I tell the stories of the founders who built the most iconic software companies, and what you can learn from them.

In this episode I break down how Ben Chestnut and Dan Kurzius accidentally invented freemium, said no to VCs for 20 years, and built one of the most valuable software companies ever created, without following anyone else’s playbook.

About Me: I’m Rob Walling. I’ve been building, growing, and acquiring SaaS companies for nearly two decades.

I’ve started six companies (five of them bootstrapped) and exited multiple times, most notably selling Drip in 2016.

I’ve invested in over 200 startups, and my focus is on helping founders build multimillion-dollar companies without the pressure of the traditional "unicorn or bust" venture capital model.

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