In a large bowl, mix together dry ingredients: all-purpose flour, cocoa powder, brown sugar, baking powder, baking soda, salt, ancho chile powder and cinnamon.
In a measuring cup or medium bowl, measure out milk, crack in the egg and pour in the olive oil and vanilla extract; whisk until smooth.
Make a make-shift double-boiler by setting a glass or stainless-steel bowl over a pot of simmering water. Add the chocolate and butter to the bowl; when melted, stir the two together until smooth. Pour the melted chocolate into the milk mixture and whisk. The chocolate will be striated throughout the milk - not to worry!
Create a well in the dry ingredients and pour in the liquid ingredients. Combine until just mixed, being sure not to over mix.
Coat both sides of your waffle iron with cooking spray or rub it with olive oil. Fill each cavity with about 1/2 cup of batter and cook until golden brown, about 2 to 3 minutes (or according to the waffle maker's instructions - each one seems to be slightly different).
Serve with a generous scoop of your favorite ice cream. I think strawberry ice cream works pretty well.