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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.

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Watch the full Ben Chestnut interview

Every time a customer cancels, you tell yourself a story about why.

Most of the time, that story is wrong.

Rob Walling break down the biggest churn patterns I’ve seen kill SaaS companies and how to figure out which ones you can actually fix.

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The SaaS Playbook, Free Sample Chapter

TinySeed Accelerator

AI is changing SaaS, but not everything.

Rob Walling breaks down the 5 fundamentals that still determine whether your business survives, and why ignoring them means no amount of AI will save you.

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MicroConf Mastermind Matching Program (Applications are open in the Fall)

Senior Place

Rob Walling has seen 5 B2B SaaS marketing strategies work over and over, and in this video, he breaks down how AI is changing each one in 2026, what's different (and what's not), and how to prioritize based on your product.

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MicroConf Connect

Grab a free sample chapter of the SaaS Playbook

The SaaS Playbook

Most SaaS founders hit a wall and can't figure out why they won't grow.

After working with thousands of founders and investing in over 230 SaaS companies, I've found the same root cause almost every time: a gap in one of four core skills every SaaS needs to survive.

In this video I'll break down what those skills are and what to do if you're missing one.

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Episode 807 | The “Core Four” SaaS Skills and Knowing When You Should Find a Co-founder (A Rob Solo Adventure)

Episode 811 | When to Delegate the “Core Four SaaS Skills,” Freemium Retention Rates, and More Listener Questions (A Rob Solo Adventure)

Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit

TinySeed Portfolio