Episode 5: Navigating the Beautiful Mess with John Cutler

Episode 5

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In this episode of “Productly Speaking”, we discuss John Cutler’s journey into product management, his contributions to the product management community through The Beautiful Mess, and his thoughts on self-gaslighting and the doubt loop. We also talk about his audience, where he finds his inspiration from, his thoughts on getting started creating content for the PM community, and the different voices that are already out there. This is an exciting discussion that’s like drinking a large cup of bulletproof coffee with a side of wisdom, resilience, and a dash of humour.

Guest Bio

John Cutler focuses on the messy overlaps and patterns of product—The Beautiful Mess (the title of his newsletter). Until recently, John supported product teams at Toast as Senior Director, Product Enablement. Prior to Toast, he was a product evangelist and coach at Amplitude where he interacted with diverse product teams and product leaders from around the world. There are few people in the world that have this kind of exposure, and if you follow John’s writing over the last couple years I’m sure you can see the influence of this perspective. He has a background in product management and UX research, including B2B SaaS companies like Zendesk, Pendo, and AppFolio, and before that B2C, ad-tech, banking, and media. John is a prolific (or some might say obsessive) writer, with almost a thousand posts spread across various newsletters, blogs, and Medium.

Key Points

00:00Introduction 01:10Episode Introduction 02:54John’s journey into product management 03:42Last Call 06:26Nickelodeon 06:55The Power Point sweatshop 08:35The origin of “The Beautiful Mess” 09:48Pendo, Raleigh Raw, and Bulletproof Coffee 10:41The audience of “The Beautiful Mess” 11:38Cutler as a Service 12:03Readers’ influence on John’s career 13:19How John’s writing has been perceieved by his employers 14:09Sharing overly generic stories in the product world 15:22The problem with relying on the “leaders” of product management 17:12On proving your craft externally 18:21Maturity models 20:31Getting started creating content for the product community 22:54LinkedIn and the voices you’ll hear out there 24:10Self-gaslighting and the doubt loop 27:38How John comes up with new topics week over week 32:19What John is interested in writing about next 33:34Where John gets his inspiration 34:36The Final Question 35:48Episode Wrap Up 39:45Outro

Call to Action

Let us know what your takeaways were — what comments made you think? What new thoughts did you have listening to the podcast?


“This relationship people have with their current employer causes a lot of people to share overly generic things. They don’t feel like they can talk about specifics, unless their company happens to be a company that welcomes people talking about specifics. And what that means is we have this sort of Instagram version of product management.”

John Cutler

“There’s just like this leadership industrial complex, it’s this almost toxic stoicism of bite your lip, don’t complain, it’s just you, you can self-improve your way out of it all the time.”

John Cutler

“It’s ok to have fun.”

John Cutler

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Season 1Episode 5