Startup founders are often preached to follow neat frameworks and one-size fits all prescriptions.

Here to say “embrace the mess” is John Cutler. John is a well-respected thought leader in the startup world. He is currently the Senior director responsible for product enablement at Toast. John has previously held the position of product evangelist at Amplitude and numerous product management roles over his fascinating career arc. Most importantly, John is the author of the long running newsletter “The Beautiful Mess” where he posts prolifically to his followers about product development.

This week, John joins Chris and Yaniv to discuss:

John’s fascinating career arc

🔄Reverse Anna Karenina Principle and how it applies to startups

🌀Dysfunctional teams and key anti-patterns associated

🕵️‍♂️Finding the right people

🧠Deriving views from first principles

🌐Non-Silicon Valley Startup operators unique perspective

⏳💔Startups dying slowly vs dying quickly

🚀📚Putting reps in at a startup vs consuming content

This episode is jam-packed with product knowledge and will get you reconsidering your perspectives on startups.

Episode Links

Subscribe to John’s Newsletter: https://cutlefish.substack.com/

Follow John on LinkedIn: https://www.linkedin.com/in/johnpcutler/

The Pact

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Key links

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Learn more about Chris and Yaniv

• Work 1:1 with Chris: http://chrissaad.com/advisory/

• Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/

• Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

Credits

Lovingly handcrafted for the global startup community by:

Editor: Justin McArthur

Associate Producer: Aidan Cousins

Intro Voice: Jeremiah Owyang