Add 1 1/2 ounces bourbon to each cup of coffee and cinnamon simple syrup to taste. Whisk together 1/2 cup heavy cream and 2 tablespoons cinnamon simple syrup until soft peaks form, top each drink.
For Cinnamon Simple Syrup:
Combine 1 cup water, 1 cup granulated sugar, and 4 cinnamon sticks to a boil. Cool to room temperature before removing cinnamon sticks. Keep refrigerated in an airtight container for 3 weeks.