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Scott Belsky on the “messy middle” and when to quit on your startup

April 07, 2025

Scott reflects on the time in every startup’s life that he calls the “messy middle”:

“The messy middle is when you feel like you’re working amidst constant anxiety, ambiguity, uncertainty, and oftentimes anonymity — no one even knows or cares about what you’re doing. And that can go on for some period time.”

He offers advice for founders trying to get through this period:

“I think a big part of it is endurance and learning how to keep your team motivated. I feel like one of the greatest competitive advantages of startups is simply sticking together long enough to figure it out. How do you keep a team together long enough to figure it out? It’s culture, genuine affection for one another, celebrating small wins… Recognize that without your voice telling the story, it’s almost like your team is in the backseat with the windows blacked out driving cross country… You have to narrate the journey, and I find that the CEOs that are really good at this have a disproportionate advantage in their company success. They just continue that motivation and momentum.”

But if your startup is a zombie company, it’s ok to quit sometimes. Life is short. Scott says the most common question he gets from founders going through the messy middle is, “Do I stick with it or do I quit?”

Scott’s answer is a simple conviction test:

“You had a lot of conviction in the idea… Then you went and learned a lot of truth. From what you’ve learned, have you gained or lost conviction? If you’ve gained conviction, but you’re still struggling and you’re still in the messy middle, it’s par for the course. Do all the tricks I just shared and more to figure it out. But if you’ve lost conviction, there is no pride in continuing — quit.”