Butter a 9” tube pan and then dust bottom and sides liberally with cocoa powder. Knock out excess and set aside.
In a medium, heavy-bottom saucepan over low heat, heat the coffee and the bourbon. When it’s warm, add the chocolate and the butter. Stir constantly until smooth. Remove from heat and allow to cool down slightly.
By hand, stir in the sugar until well combined. Let stand for five minutes. Transfer to the bowl of an electric mixer.
Sift together the flour, baking soda and salt. With the mixer on slow speed, add the flour mixture to the chocolate mixture IN FOUR ADDITIONS. Mix only until each addition is incorporated. Add the eggs and vanilla and beat on low/medium speed until batter is smooth.
Pour into the prepared tube pan. Bake until cake tester in the center comes out barely clean, about 1 1/2 hours. Cool completely in the pan. After removing from pan to a cake plate, dust top with confectioners’ sugar. Nice to serve with a dollop of flavored whipped cream or, better yet, Hawaiian Vanilla Bean ice cream (or any vanilla bean ice cream if you’re not lucky enough to live in Hawai‘i!)