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Combine the cashews, ice, oat milk, cocoa powder, sugar, salt, and vanilla in a high-speed blender. Blend on high speed until the mixture is smooth and creamy, a minute or two.
Combine the chilled coconut cream, aquafaba, ice cubes, agave nectar, and vanilla in a container with a tight-fitting lid. Shake vigorously for about a minute, until the mixture becomes light, fluffy, and doubled in volume.
Squirt chocolate syrup along the inside of your mason jars, swirling it into a fun pattern. Fill the jars with the chocolate milkshake, top generously with the coconut whip, dust lightly with cocoa powder, and insert a fun straw. Serve immediately.