In a bowl, mix together the strawberries and sugar. Put in the refrigerator for about 30 minutes.
The Biscuit
Preheat oven to 425 degrees Fahrenheit. Line baking sheets with parchment paper.
Place the buttermilk in a large measuring cup into a freezer for 10 minutes. After the buttermilk is cold, add butter into the cup and stir.
In a large bowl, mix together the flour, sugar, baking powder and salt.
Add the buttermilk mixture into the bowl and stir together gently with your hand. Do not overmix.
Sprinkle flour onto a clean surface. Place the dough on it and pat to a 1 inch thick rectangle.
Fold the dough like a letter (into thirds) and pat to a 1 inch thick rectangle. Cut into small squares and place on baking sheet.
Bake for 13-17 minutes until the top is golden brown. If you are making the shot glass, you will have extra biscuits.
The Whipped Cream
Put sugar in a food processor or a chopper until in becomes fine, not powdered, in texture. About 1-2 minutes.
In a bowl of a stand mixer, combine heavy cream, fine sugar and vanilla on a low speed for about 1 minute. Then increase the speed to medium and whip until soft peak.