Finely chop Bittersweet Chocolate (6 ounce). Divide the large Egg (3) into egg yolks and egg whites. Make sure all ingredients are at room temperature.
In a large bowl, sift and combine All-Purpose Flour (2 cup), Unsweetened Cocoa Powder (1/2 cup), Brown Sugar (1/4 cup), Baking Powder (2 teaspoon), Baking Soda (1 teaspoon) and Kosher Salt (1 teaspoon).
In another large bowl, whisk together egg yolks, Buttermilk (2 cup), Olive Oil (1/2 cup), and Vanilla Extract (1 teaspoon).
Fold the dry ingredients into the wet ingredients in 3 batches. Do not overbeat. Mix until thoroughly combined.
Using a standing mixer beat egg whites until soft peaks form, 5 to 7 minutes.
Gently fold in the egg whites into the batter, until no white streaks remain.
Heat your waffle maker until it is very hot. Spray with Vegetable Oil Cooking Spray (to taste). Pour ½ cup of the batter onto your well-oiled waffle maker. Cook until it is cooked through.
Transfer them onto a baking sheet and let them cool.
Place Mascarpone Cheese (8 ounce) in the bowl of a standing mixer fitted with a paddle attachment, and whip it for 1 minute.
Slowly add Heavy Cream (3/4 cup), Powdered Confectioners Sugar (1/4 cup) and Vanilla Extract (1 teaspoon) in the bowl and whip the mixture until it turns light and fluffy.
Place the first waffle onto a plate and spread ¼ cup of the mascarpone whipped cream onto it.
Place the second one on top of the first one, and again, spread ¼ cup mascarpone whipped cream. Repeat this process two more times.
Top it off with Fresh Raspberries (1/2 cup) and sprinkle with Powdered Confectioners Sugar (1 tablespoon). Serve with coffee or tea and enjoy!