There's a theorem of Kaplansky that states that if an element $u$ of a ring has more than one right inverse, then it in fact has infinitely many. I could prove this by assuming $v$ is a right inverse, and then showing that the elements $v+(1-vu)u^n$ are right inverses for all $n$ and distinct.
To see they're distinct, I suppose $v+(1-vu)u^n=v+(1-vu)u^m$ for distinct $n$ and $m$. I suppose $n>m$. Since $u$ is cancellable on the right, this implies $(1-vu)u^{n-m}=1-vu$. Then $(1-vu)u^{n-m-1}u+vu=((1-vu)u^{n-m-1}+v)u=1$, so $u$ has a left inverse, but then $u$ would be a unit, and hence have only one right inverse.
Does the same theorem hold in monoids, or is there some counterexample?