Pour the water into a medium-sized saucepan and set over medium heat. Stir in sugar, and when dissolved, add dried figs. Remove from heat just as mixture begins to boil. Set aside to steep for 30 minutes, then strain into a clean jar and chill, reserving the plumped figs for another use.
To make milkshakes, combine Chameleon Cold-Brew Black Coffee Concentrate and fresh figs in the pitcher of a blender. Blend until mixture is smooth, but still has a few flecks of fig. Add ice cream, fig simple syrup, and rum, and blend just until combined and creamy.