Start with the "iced coffee concentrate" that the Pioneer Woman does.
Her recipe is basically 1 lb. of ground coffee, 2 gallons of cold water, steep for 8 hours, strain. You can read the linked article for exact steps and other ideas for your Iced Coffee once you have the concentrate.
I made it with 1/4 lb. of coffee and 2 Quarts of water. I actually just let it steep overnight in the fridge, and I strained it through a coffee filter. Takes a while, so I may make myself a reusable "coffee bag" out of some old silk shirts I have so I don't have to do the straining thing.
Anyway, once I had the concentrate, I was ready.
- Put ice cubes in a blender until they reach the 16-oz line.
- Fill with iced coffee concentrate until the mix of ice and concentrate is at the 16-oz line.
- Add 1/2 Tbsp. Pure Vanilla Extract (no, not the imitation stuff.)
- Add chocolate syrup "until it looks good". I added a couple squirts, maybe 2 Tbsps altogether.
- Blend until the ice is all busted up and you have a shake!
I tell you what, it's so doggone close it's unreal. I did leave out the whipped cream though - I didn't have any, and it doesn't really add anything to the shake except make it pretty.