Originally Posted by Mchaz
Actually it's the opposite. It is easier to push a skinny column of air, but it pumps less volume of air than a fatter column of the same height. The problem with your old pump was probably just a bad design in general.
To the O.P., try looking at pumps that are made to pump high pressures. The Silca Pista comes to mind.
Actually it's the oppsoite. The advantage of the skinnier column of air is that you can get your tire up to a higher pressure.