When does "don't raise money until you actually need it" stop being discipline and start costing you the company? (I will not promote)

No raise, no debt and I keep every point of equity. My costs are basically a few AI platform subscriptions right now, and that goes a long way, so there's nothing forcing my hand yet. My logic is simple: raising early isn't free money, it's another responsibility I don't need yet. Investors, updates, expectations, a lot of extra things to consider all while there are plenty of people bootstrapping the whole way and either kept 100% or sell the whole thing for a massive exit. So where's the actual line? When has "raise only when you need it" burned someone you know, or saved them?