Heat oven to 350°F. Grease and flour two 9-inch round baking pans.
In the bowl of a stand mixer, stir together sugar, flour, cocoa, baking powder, baking soda and salt in large bowl. Add eggs, milk, oil and vanilla; beat on medium speed for 2 minutes. Stir in boiling water (batter will be thin). Pour batter into prepared pans.
Bake 30 to 35 minutes or until wooden pick inserted in center comes out clean. Cool 10 minutes; remove from pans to wire racks. Cool completely.
While the cake is cooling, make the frosting. In the bowl of stand mixer, beat the butter on medium speed until light and fluffy, about 2-3 minutes. Gradually add the powdered sugar and mix until the frosting is smooth, about 3-4 minutes. Mix in the vanilla. Drizzle in the cooled melted chocolate and beat on medium speed until the frosting is smooth and creamy. Set aside while you make the ganache.
To make the chocolate ganache, add the chocolate to a medium bowl. Heat the cream in a small saucepan over medium heat just until it bubbles around the edges or you can heat it in the microwave. Pour cream over the chocolate chips. Let the mixture stand for 30 seconds, then stir until the chocolate melts and a smooth ganache comes together, about 1-2 minutes. Let the ganache cool for about 5 minutes. Stir again.
To assemble the cake, place one cake on a cake stand or serving platter. Spread frosting over the bottom layer of the cake. You want a thick layer of frosting. Next, slice 1 cup of strawberries lengthwise and place them on top of the frosting. Carefully place the second cake on top of the strawberries and gently press down to help set the cake.
Pour the chocolate ganache over the top of the cake, letting it drip down the sides of the cake. Wait for the ganache to set, about 15 minutes. Remove the stems from 10 pretty strawberries and place them stem side down on the top of the cake. Gently pressing them into the ganache so they will stand up. Cut into slices and serve!