Preheat oven to 325°F. Grease two 9x5-inch loaf pans.
Sift flour and cocoa together.
Chop up chocolate squares and melt in double broiler or low microwave setting, being very careful not to burn the chocolate. Stir in the espresso powder.
In bowl of stand mixer, beat coconut oil with 1/2 cup sugar until fluffy. Add butter and beat well.
Add remaining sugar, salt, and vanilla; beat at high speed for 5 minutes.
Lower speed and beat in eggs, one at a time.
Beat in flour mixture, then, beat in the cream. Stir in the melted chocolate mixture.
Pour into pans. Rap pans on counter to release any trapped air.
Bake 40 - 50 minutes (depending on your oven and altitude), or until a toothpick come out clean when inserted in center of cakes.
Cool 15 minutes before removing cakes from pans to a wire rack to cool completely.
Drizzle caramel glaze over cut slices.
For the Glaze
In a small, deep, heavy saucepan, bring sugar, water, corn syrup, and cream of tarter to a boil over high heat. Cook, stirring frequently, until mixture turns amber in color and registers 340°F on candy thermometer.
Remove from heat. Add butter, whisking constantly until melted.
Whisk in cream. The mixture will bubble violently.
Using whisk, stir in the bourbon, vanilla, and salt until combined.
Let cool completely. Store leftover in a covered container at room temperature for up to a week.
