Democracy will never create a free society, but neither will dictatorship. Democratic societies tend to be more free than dictatorship, but that's not always the case.
If there was an enlightened and rich dictator, he could decide to make weed legal, impose zero taxes, grant freedom of speech. Compared to most of the western world, where weed is mostly illegal, taxation is imposed forcefully and freedom of speech is disappearing - that would be a freer society.
The real way to have a freer society is to decentralise power away. It's not about granting 60 millions people an infinitesimal choice for an outcome shared by everyone. It's about each individual having a different outcome.