Add the banana and milk to a blender and blend until smooth.

Meanwhile, mix the cocoa powder and maple syrup together until it forms a “wet” chocolate syrup. Add the vanilla and stir well. Then add this syrup to the blender and continue blending until combined.

At this point, the shake will be super thick with a soft-serve/smoothie consistency, to make it a little more like a milkshake (and to keep it cold), add about ½ a cup of ice cubes and blend well. Serve in hipster Mason jars or stick a straw in the blender and slurp it up!