People say “oversized” when they mean uncomfortable. Those aren’t the same thing. If a position matters, it should be uncomfortable when it moves against you. Otherwise it probably doesn’t matter enough. The line isn’t discomfort. It’s bankruptcy. Can I be very wrong, sit through an ugly drawdown, and still be fine? I’ve lived the extreme version of that question. My startup was effectively my entire net worth for yrs. One outcome. It worked, but I had a lever. I could go to work every day and affect the result. As an investor you don’t get that. Someone else executes and you sit there. So concentration has to be underwritten differently. The survival test should be stricter, not looser. And the part most people skip entirely is whether they survive being wrong about everything at once. Positions that look independent usually aren’t. If they’d all break for the same reason, you don’t have five positions. You have one. That’s the real constraint. Not how big any single one feels. If it passes, I want my best ideas to matter. Diversifying them into irrelevance to sleep better defeats the point.