Lightly whip the cream with the vanilla syrup in a bowl and have on standby.
In a cocktail shaker, combine the cold brew coffee, milk, chile syrup, chocolate sauce and ice, then shake until frothed and combined. Pour into an ice-filled glass, top with vanilla whipped cream to cover and dust with the cinnamon and cayenne pepper.
Cold Brew Coffee:
Mix the ground coffee with the water in a large container. Cover and allow to sit at room temperature for 8 hours or overnight.
Line a fine-mesh strainer with cheesecloth and set over a pitcher or other container. Pour the coffee/water mixture through the strainer, allowing all the liquid to run through. Discard the grounds. Refrigerate and use as needed.