i agree that there are winners and losers in a capitalist society, but what makes me an anarchist (and not a capitalist) is that i define winning and losing by your membership in the proletariat, and not by your material conditions. stated more clearly, the losers in a capitalist society are the people that go to work and the winners are those that evade wage slavery. i need control over my tools of production, but material conditions and wealth generation have no value to me.
in my political value system, somebody on welfare is winning if they manage to survive in a way that allows them to accomplish their goals (which are personal and defined strictly by the individual, not enforced by collectivist institutions like free markets), which the person on welfare is often able to do, while somebody that goes to work at a good job every day and generates large amounts of wealth and lives in a house they own is losing if they can't accomplish their goals because they don't have time and hate their life because it's tedious and boring. an artist is winning if they can create the art they want, not if they sell it; the doctor or lawyer is losing if they can't do what they want, even if they have millions of dollars to their net worth.
freedom is valuable. wealth is not valuable. those that are free are winning; those that are wealthy are usually losing. wealth rarely presupposes freedom, and more often creates conditions of enslavement.
something i share in common with capitalists is that i don't have a lot of respect for losers, but i flip the definition of winning and losing on it's head, relative to how a capitalist would define it.
i thought about this a lot in the 00s and realized that i have a choice between letting society enslave me into bourgeois excess (which is losing) or finding some way to escape the bourgeois condition by enslaving the society, instead. it's how capitalism operates; you're a slave or you're a slave master. there's no middle point. i have to support unions if i want to find some way to abolish capitalism, but i know that unionized workers are the biggest slaves and the biggest losers of them all.
i am lucky enough to live in an advanced enough form of capitalism that i have some way out and i've taken advantage of it. i'm not dragged out of my home and chained to a factory.
yet.