Cut the bacon into ¾-inch pieces. In a medium sauté pan, cook the bacon over medium heat until crisp. Transfer the bacon to drain on a paper towel–lined plate, leaving the bacon fat in the pan. Add the olive oil, and once hot, add the Brussels sprouts. Cook, stirring often, until the sprouts start to brown, about 6–8 minutes. Return the bacon to the pan, drizzle in the maple syrup, and continue cooking until the syrup thickens and the sprouts are browned and caramelized. Season with salt and pepper to taste.