Put the heavy cream in your stand mixer and whip until soft peaks form.
In a separate bowl, mix together the condensed milk, bourbon, and cocoa powder until it is smooth.
Fold the condensed milk mixture into the whipped cream until it is fully combined. Crumble in the chocolate chip cookies and mix again.
Pour this mixture into a parchment-lined loaf pan, it should be nice and fluffy.
Freeze for 12 hours before using. It should take a few minutes to warm up, but then be nice and scoopable.