Add the heavy cream into a medium mixing bowl. Beat on medium until soft peaks form.
Add in the powdered sugar and beat until it becomes thick and forms stiff peaks. Place in the fridge until you're ready to use it.
Add the coffee, chocolate ice cream, and 1 T. chocolate syrup in a blender. Blend until the ice cream is completely incorporated and there are no lumps.
Drizzle ½ tablespoon of the remaining chocolate syrup on the sides of a glass.
Pour the milkshake into the glass.
Add the whipped cream into a disposable bag fitted with a 1M tip.
Pipe a tall swirl in the center of the milkshake.
Drizzle the remaining 1 tablespoon of chocolate syrup on the top of the whipped cream.
Top with a chocolate covered espresso bean, if you have one.