It is possible but difficult. Unless you make up some sort of jig, you pretty much need a lathe. The bullet is hard to hold without damaging it, and lead tends to be "grabby" when you try and drill it.
if you want hollow points I'd reccomend simply buying them.
For a hollowpoint to really do what it is supposed to do it needs to be done just right and also should be jacketed. This is why you have premium self defense rounds (like gold dots) and you have just basic generic hollow points. Both have the same basic principle but premium is better designed and will give you better results.
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