The answer is that I usually buy in relatively short but will sometimes buy in for more if the situation is right. One reason I mentioned is that, by buying in short, you leave the option of buying in for more later. By buying in deep immediately, you pigeon-hole yourself, because you are not allowed to take chips back off the table. I also explained some factors that make me think buying in short can be advantageous. The question was a little outside the scope of the talk, so I first explained the question to the audience; hopefully my readers here will know what buying in short and deep means.
In no-limit holdem, there is a small mathematical advantage to having a shorter stack. This is for two reasons:
Reason 1. Most players with big stacks will not even bother trying to play well against players with short stacks. They maximize their EV by focusing their strategy on playing well against other players with big stacks. This means they will be exposing themselves to being exploited by you if you have a short stack.
Reason 2. If you are all-in against two or more deeper-stacked opponents, one of your opponents might fold a hand that would have won, allowing you to take the pot. Or, you might get to keep a hand that you would have folded if you were not all-in.
This second point was made by Sklansky in his tournament strategy book. Although I originally thought it was a very significant factor, I have come to think it's less important than the first reason I list here. Situations relevant to Reason 1 are fairly common. An example would be if you buy in for $500 and everyone else is playing behind $2k-$5k. They will simply not mind paying you off for $500 if they think they have a chance to win $2k+ from another player. Situations relevant to Reason 2 are comparatively rare. A lot of uncommon factors all have to fall into place. You would need to get all-in with a hand that would have come in second place. The first place player would then need to fold after you are all-in. Even when this does happen, it might actually have hurt you to be all-in, because it's possible you would have won a bigger pot if you had been able to wager more. Because of this it's not entirely clear that being all-in is really mathematically advantageous at all.
During the talk I also mentioned that in my experience, players got used to me playing a short stack, and so when I did have a big stack, they tended to underestimate me. I was able to take advantage of that. (In truth, this probably argues for buying in deep more often, but I didn't bring that up during the talk.)
Against very good opponents I believe it is actually best to buy in short, mostly for Reason 1. Against very weak opponents, it is probably better to have a deep stack, because this allows you to take full advantage of your skill differential. This is especially true if your weaker opponents happen to have deeper stacks than your stronger opponents at a certain table; this is likely to be a temporary situation, but it is usually worth taking advantage of.
Against normal opponents, it's tough to say which is better, but I prefer to buy in short because it allows me the option of staying short stacked if the table becomes tougher.
Frankly, this last consideration is much more important if you are in a situation like I was in as a prop, where you do not always have the option to leave a table if the game is very tough. As a prop, I valued having the option to have a short stack against tough opponents; for most people, the better option is to just leave the game. I didn't think to mention this during the talk, but I think it's an important point.
There is actually a third reason to buy in short that I didn't mention during the talk.
Reason 3. Having a deep stack is stressful and draining. As a prop player, I valued my ability to keep the game as low-stress as possible, because I did not have the option to just leave. It is very difficult to focus intently on poker for eight straight hours; by buying in short, I allowed myself some mental breaks during the day. Most players who are not in the abnormal prop situation should probably buy-in deeper against moderately weak opponents. However, there is something to be said for pacing yourself at the poker table by keeping the stress level low.
In no-limit holdem, there is a small mathematical advantage to having a shorter stack. This is for two reasons:
Reason 1. Most players with big stacks will not even bother trying to play well against players with short stacks. They maximize their EV by focusing their strategy on playing well against other players with big stacks. This means they will be exposing themselves to being exploited by you if you have a short stack.
Reason 2. If you are all-in against two or more deeper-stacked opponents, one of your opponents might fold a hand that would have won, allowing you to take the pot. Or, you might get to keep a hand that you would have folded if you were not all-in.
This second point was made by Sklansky in his tournament strategy book. Although I originally thought it was a very significant factor, I have come to think it's less important than the first reason I list here. Situations relevant to Reason 1 are fairly common. An example would be if you buy in for $500 and everyone else is playing behind $2k-$5k. They will simply not mind paying you off for $500 if they think they have a chance to win $2k+ from another player. Situations relevant to Reason 2 are comparatively rare. A lot of uncommon factors all have to fall into place. You would need to get all-in with a hand that would have come in second place. The first place player would then need to fold after you are all-in. Even when this does happen, it might actually have hurt you to be all-in, because it's possible you would have won a bigger pot if you had been able to wager more. Because of this it's not entirely clear that being all-in is really mathematically advantageous at all.
During the talk I also mentioned that in my experience, players got used to me playing a short stack, and so when I did have a big stack, they tended to underestimate me. I was able to take advantage of that. (In truth, this probably argues for buying in deep more often, but I didn't bring that up during the talk.)
Against very good opponents I believe it is actually best to buy in short, mostly for Reason 1. Against very weak opponents, it is probably better to have a deep stack, because this allows you to take full advantage of your skill differential. This is especially true if your weaker opponents happen to have deeper stacks than your stronger opponents at a certain table; this is likely to be a temporary situation, but it is usually worth taking advantage of.
Against normal opponents, it's tough to say which is better, but I prefer to buy in short because it allows me the option of staying short stacked if the table becomes tougher.
Frankly, this last consideration is much more important if you are in a situation like I was in as a prop, where you do not always have the option to leave a table if the game is very tough. As a prop, I valued having the option to have a short stack against tough opponents; for most people, the better option is to just leave the game. I didn't think to mention this during the talk, but I think it's an important point.
There is actually a third reason to buy in short that I didn't mention during the talk.
Reason 3. Having a deep stack is stressful and draining. As a prop player, I valued my ability to keep the game as low-stress as possible, because I did not have the option to just leave. It is very difficult to focus intently on poker for eight straight hours; by buying in short, I allowed myself some mental breaks during the day. Most players who are not in the abnormal prop situation should probably buy-in deeper against moderately weak opponents. However, there is something to be said for pacing yourself at the poker table by keeping the stress level low.