Chill a coupe glass with ice and set aside.
Add all the ingredients into a shaker with ice and shake.
Strain into the chilled coupe.
*Homemade grenadine: Quarter 2 pomegranates, and juice them with an electric masticating juicer. Combine the juice and 1/2 cup granulated sugar in a container, and stir until sugar dissolves. Bottle and store in refrigerator for up to 2 weeks.