Add chopped bacon and halved brussel sprouts to a cast iron skillet over medium heat. Season with salt and pepper and cook, stirring occasionally, until bacon is cooked and brussel sprouts have begun to brown, about 15 to 20 minutes.
Drizzle 1/2 cup of the balsamic vinegar over bacon and brussels, stir and cook a minute more.
Take off a heat. Transfer to serving platter and drizzle remaining balsamic vinegar over top. Enjoy.
Cut each strip of bacon in half lengthwise. Fry the bacon on medium-high heat until it's partially cooked yet still pliable. (The crispier the bacon, the more difficult it is to weave.)
Remove the bacon from the pan, and set aside. Remove most of the bacon grease from the pan. Leave just enough to coat it.
Cut Brussels sprouts in half lengthwise. Place sprouts, butter, garlic powder, and sea salt into the frying pan. Sauté on medium heat until the sprouts are browned and tender.
Assemble by threading one end of the bacon onto the skewer. Add a Brussels sprout slice, then weave the bacon overtop of the sprout, then back through the skewer. The bacon creates a curved pattern between the sprouts. Slide the bacon, and the sprout, down the skewer, and repeat this process 2-3 more times per skewer leaving enough room at the top to grab the skewer.
Place in a single layer inside a roasting pan. Bake for 5-10 minutes, or until the bacon is fully cooked.