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Heat heavy cream in a saucepan over medium heat until it is hot, but not boiling. You'll begin to see little bubbles forming around the edges of the pan.
Reduce heat to low. Sift in cocoa powder, powdered sugar, and espresso powder. Whisk well until fully combined and smooth.
Add in chopped chocolate and cubed butter. Stir until melted and mixture is smooth. Stir in vanilla extract.
Pour mixture into a heatproof bowl and cover with plastic wrap so that it is touching the top of the mixture -- this way it won't develop a film on top.
Let frosting cool at room temperature for around 45 minutes -- less for a thinner frosting, and more for a thicker frosting.