Bring a small pot of water to a boil. Add the cashews and let sit for 15 minutes or up to 2 hours. Drain.
In a high-power blender or food processor, combine the cashews, coconut milk, dates, vanilla, pinch of salt, and 2 tablespoons coffee. Blend until completely smooth and the consistency of a thick smoothie.
Evenly divide the remaining coffee among 7-8 popsicle molds. Spoon the cashew mix over the coffee to create a swirl. Insert popsicle sticks, cover the tops of the mold, and freeze until firm, about 4 hours.
To remove the popsicles, run the mold under hot water for 10 seconds and then pull the popsicles out of the molds.
Dip each popsicle in melted chocolate. Store in the freezer.