Are anions stronger bases than (different) neutral molecules?

I need to compare the basicity of 2 molecules: a negatively charged $\ce{O}$ attached to a *t*-butyl (*t*-butoxide), and a neutral $\ce{N}$ with 3 ethyls attached to it (triethylamine).


These are completely different molecules, so by instinct, I would say that the one with the negative charge is probably more basic. But, is there a more formal way of figuring it out (not experimentally)?


