I always wonder whether you're better off trying to talk an entrepreneur out of it, try to talk them deeper into it, or just try to be neutral yet supportive.

I always wonder whether you're better off trying to talk an entrepreneur out of it, try to talk them deeper into it, or just try to be neutral yet supportive. On the one hand, good entrepreneurs are supposed to be relentless and ones that are likely to give up should give up earlier rather than later. On the other hand, we've all heard stories of that brink that many entrepreneurs blindly stumbled onto, missed going off the cliff of failure purely by chance, and came out as huge winners. Substance or not, perhaps my words could be the ones that could make the difference from falling off the edge? These are the games that PG plays on a regular basis at great scale, with his own money no less. Any thoughts on what the best strategy is, and why?