If you take a cookie and throw it on the ground, you get a range of sizes of crumbs. The details of exactly how you throw the cookie, or if you spin it, aren't terribly important-- there seems to be some kind of self-similar process that determines the distribution of sizes you get. Perhaps if you throw it harder, you may get smaller pieces on the whole, but you'll still get a range of relative sizes in which most pieces are smaller and few are larger, in relation to each other. Stars appear to be similar-- there is some complicated physics that determines the initial mass function, but the details don't seem to matter much because there is already so much going on that you get a kind of statistical outcome. No doubt angular momentum, initial magnetic fields, and metallicity can all be relevant factors, but they don't seem to matter that much unless they are very different from normal (such as the nearly zero metallicity of Big Bang gas, and so forth). What we are ultimately looking for is a kind of self-similar scaling law, not details in all the various different parameters. I don't believe an individual version of such a scaling law argument has been widely accepted, though various suggestions exist. But as with the cookie, you get lots of little pieces, and a few big ones, because there are simply more pathways that lead to small objects than to big ones. More ways to skin those cats, if you will.
Also, I believe the original question is motivated by a misconception about how star formation works. If you think all stars form inside-out, in the sense that they just build up larger and larger cores until the gravity is strong enough to release enough energy to start fusion, which then truncates the formation process and sets the mass of the star, then it is easy to imagine that all stars should have similar masses. But actually, the mass a star will have has normally been determined long before there is any fusion going on, and the mass that is blown away by a wind once fusion originates is not particularly important. Indeed, I'm not even sure where this idea originates that fusion onset begins a stellar wind, there just doesn't seem to be any credible reason why fusion in the center would have anything to do with wind from the surface. But even if that is true, and not simply an astrophysical urban legend (there are surprisingly many of those), the mass that can be driven in a wind is normally not important to the mass of a star (the current solar wind is particularly wimpy, but this is true for much stronger winds as well). It is better to think of the mass as being determined by a formation process that is unaware of the existence of fusion, but which ultimately tags what mass will end up in what star (like the crumbling cookie process does), in something more akin to an outside-in process in which information cascades down from large scales to smaller scales, rather than the other way around.
