MicroConf Tactics: Is Mailchimp the Greatest Bootstrapped SaaS Ever?

August 12, 2026 00:23:32
MicroConf Tactics: Is Mailchimp the Greatest Bootstrapped SaaS Ever?
MicroConf On Air
MicroConf Tactics: Is Mailchimp the Greatest Bootstrapped SaaS Ever?

Aug 12 2026 | 00:23:32

/

Show Notes

This is the story of MailChimp.

Welcome to SaaS Legends, a series where Rob Walling tells 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.

Links from the Pod

Subscribe to the Rob Walling YouTube channel

Watch this video on YouTube

Join MicroConf Connect

Watch the full Ben Chestnut interview

Other Episodes

Episode

February 22, 2023 00:54:10
Episode Cover

MicroConf Refresh Episode 64: The 7-Figure To Do List: 31 Tactics To Level-Up Your Business In 60 Minutes or Less with Rob Walling

In this talk from MicroConf Growth US 2022, Rob Walling walks through 31 quick tactics for that get outsized results in your business. The...

Listen

Episode

July 05, 2023 00:15:35
Episode Cover

MicroConf Tactics: Turn Your SaaS Side Hustle into a Full-Time Gig in 2023

Want your side hustle to make more money and go full time? This is how to turn you SaaS side hustle into a full-time...

Listen

Episode

October 22, 2025 00:11:56
Episode Cover

MicroConf Tactics: The BEST Sales Funnel For Your SaaS (new data changed my advice)

In this episode, Rob Walling breaks down data-backed strategies to improve your trial funnel and explains why most SaaS founders should rethink freemium vs....

Listen