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Add all your ingredients to your high speed blender (add the cacao powder last so that it doesn't stick to the bottom). It's important everything is as cold as possible because your blender is going to produce a lot of heat. You will want a smaller blender than a Vitamix here, especially if you're only making one portion.
Blend until super smooth and creamy. You may need to keep scraping down the side to make sure everything gets combined properly. Be patient and keep blending until you get your pudding as smooth as you can. If you need to add more milk, do it gradually. The purpose of this is to keep your pudding as thick as possible, and therefore as filling as possible.
Once blended to your satisfaction, you may wish to refrigerate your pudding (or freeze it) for 30 minutes to chill it right down again. You may wish to eat it straight from the blender cup because it's quite difficult to extract. You can also take your time with a long spoon getting into all the nooks and crannies of the blender cup.