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Masad: Proactively seeking out pain reduces long-term debt and organizational suffering

Amjad Masad · AI CEO: How To Make A $10M Business With AI Employees (Amjad Masad, CEO of @replit) · Jul 30, 2025 · at 1:03:25

Amjad Masad, CEO of Replit, discusses the company's core operating principle of 'Seek Pain' and how addressing difficult feedback or underperforming employees immediately prevents compounded issues later.

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“And what I tell our team counterintuitively, when you seek pain, you actually reduce it. Because typically what people do is they procrastinate. You have a underperforming employee. You don't want to fire them. You don't want to deal with it. They're annoying. And I just want to just like let them on the side. I'm just going to focus here. But what's going to happen is you're just building up a world of pain because you're not giving them real time feedback. And by the time you have to fire them, they're going to be surprised and maybe they're going to sue the company or something like that. And so anytime you delay pain, you're building up a larger debt of pain. So counterintuitively seeking pain reduces pain, but you have to seek it.”

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