In a large skillet add bacon and turn heat to medium low. Cook until bacon is golden and begins to crisp. Using a slotted spoon remove the bacon from pan.
Remove all but 1 tbsp of bacon fat from pan and add in olive oil. Turn heat up to medium high. Add Brussels sprouts cut side down to the pan and allow to cook without disturbing for 4-5 minutes or until the sprouts begin to char. Once they are browned, flip the sprouts over and stir continuously until they start to get tender, about 3-4 minutes.
Return cooked bacon to the pan along with maple syrup and ½ tsp of salt and pepper. Stir until sprouts are coated in the maple syrup. Remove maple bacon brussels sprouts from pan and enjoy!