Add heavy whipping cream and powdered sugar in a mixing bowl and beat with an electric mixer for 5-6 minutes or until stiff. Place whipped topping into a piping bag fitted with a star tip. Set aside.
½ cup heavy whipping cream, 2 tbsp powdered sugar
Add ice, coffee, chocolate chips, and chocolate syrup into a blender. Blend until thick, about 30 seconds.
2 tbsp chocolate syrup, 2 tbsp espresso chocolate chips, 4 cup ice, 2 cup coffee
Pour into glasses and top with whipped topping and chocolate syrup. Serve immediately.