Oct. 20, 2025

The 4 Biggest Execution Mistakes Founders Make

The 4 Biggest Execution Mistakes Founders Make

Think you’re executing well? Think again. Chances are you’re making one of these four common mistakes.


Drawing from Chris’s latest essay and real-world advisory experience, Chris and Yaniv spend this episode breaking down the four biggest execution mistakes you're probably making right now. They explore how to recognize these patterns early, how to apply taste and judgment when scaling, and how to develop the discipline needed to execute with precision.



In this episode, you will:

  • Identify when you’re oversimplifying, and mistaking nuanced, unique use cases for the same problem
  • Understand how overcomplicating your product or process can destroy focus and momentum
  • Learn to categorize problems correctly using the principle of mutually exclusive, collectively exhaustive thinking
  • Apply the concept of “necessary and sufficient” work — doing everything that’s needed and nothing that’s not
  • Recognize that mistiming priorities ends in attempting to do everything at once, but finishing nothing
  • Develop the taste, judgment, and rigor to strike the perfect balance between simplicity and depth
  • Avoid falling into domain dogma; naming, structuring, and communicating ideas clearly for your team and customers



Read Chris’s original LinkedIn post: https://www.linkedin.com/posts/chrissaad_the-big-4-execution-mistakes-youre-probably-activity-7379681603847049216-ApcV



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Key links

Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A 

The Startup Podcast website: https://www.tsp.show/episodes/

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/


Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

Intro Voice: Jeremiah Owyang https://web-strategist.com/