In a measuring cup, whisk together the almond milk, heavy cream, vanilla, and xanthan gum (if using). Sweeten to taste.
Divide the chocolate chips among 10 popsicle molds. Pour in some of the cream mixture, filling each popsicle about 1/3 of the way up (you will have some left). Cover and insert the popsicle sticks. Freeze until solid, about 1-2 hours.
Pour half of the coffee into the remaining cream mixture to form your latte base. In a second cup, combine the remaining coffee with sweetener to taste.
Remove the popsicles from the freezer and take off the cover. Divide the latte base between the molds, filing each to about the 2/3 mark. Cover and return to the freezer for another hour or two, or until frozen.
Remove the popsicles form the freezer and take over the cover. Divide the sweetened coffee among the molds. Cover and return to the freezer for at least 2 hours, or until ready to serve.