Soak chia seeds in 3 tablespoons water for 10 minutes.
Combine coconut milk, avocado, peanut butter, chia seeds, coconut oil, cocoa powder, ice cubes, and 1/4 cup water in a blender. Blend until smooth. Top with cocoa nibs and cinnamon.
Add almond milk, strawberries, and blueberries to a high-powered blender, such as a Vitamix®. Blend on High for 45 seconds. Turn blender off; add protein powder. Blend for 15 seconds more.
Pour mixture into a glass, top with sugar-free whipped topping and sugar-free chocolate chips.