Whisk together flour, baking powder, salt, and sugar in a medium bowl. Set aside.
In a separate medium bowl, whisk together eggs, milk and vanilla. Whisk egg mixture into flour mixture until combined. Whisk in melted butter and shortening.
Fold in chocolate chips.
Preheat a waffle iron and spray with cooking spray. Add 1/2 cup to 2/3 cup of batter to the waffle iron to create your first waffle. Cook until golden brown.
When you’ve made it through half of the batter, stir in cocoa powder. Continue making waffles until all the batter has been used.
Divide the waffles between 2 plates, making sure both get both types of waffles. Drizzle over chocolate sauce, smashed raspberry compote and fresh raspberries. Serve immediately.