While I think Maher raises legitimate concerns, I do not believe Jesus endorses anything akin to socialism.
Socialism is a political/economic philosophy predicated upon the forced redistribution of wealth. That is, socialism espouses the civil government taking wealth—by force—from some citizens and giving that said wealth to other citizens.
Jesus nowhere endorses such a notion.
Jesus doesn't offer us economic/political theories per se. Rather, He offers us something better. He teaches us about life in His kingdom. He doesn't talk about civil laws. No, He talks about the individual heart. He doesn't talk about government coercion; He talks about inner transformation which comes from following Him and His Way.
Capitalists, socialists, Maher, Democrats, and Republicans...none of them have cornered the market on Jesus.