First, make the simple syrup by heating the Chambord and sugar in a small saucepan, and slowly reducing (should take about 7-10 minutes).  Let it cool slightly.

Make the Chambord whipped cream as well.  Stir together the cold whipping cream, Chambord, sugar (go light!), and vanilla in a large bowl, then use a stand mixer or hand mixer to whip until the cream has slight peaks (but that don't hold).  Taste and add any more sugar or Chambord as needed, then continue to whip until the cream has peaks (but the tips bend and curl).

Finally, make your cocktail.  Prepare the espresso shots.  In a traditional Irish Coffee glass or similar (they look something like this), add boiling water to just under halfway in the glass, then add the espresso, whiskey, and Chambord simple syrup to the glass.  

Top with the Chambord whipped cream and garnish with chocolate shavings.