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The most dangerous investor is the “friendly” one. Not aggressive. Not demanding. Helpful. Relaxed. Supportive. And that’s exactly why founders get sloppy. I’ve seen more damage done by friendly capital than hostile term sheets. Why? Because friendliness lowers defenses. A founder hears: “Don’t worry about docs yet.” “We’ll keep this simple.” “You can clean that up later.” It feels safe. It feels aligned. It feels like trust. But trust without structure is just risk with a sm