Serve these waffles on their own as a fun breakfast or tasty snack, or pair with Sweet-and-Spicy Glazed Pork Belly for a delicious dinner.
Heat 1 tablespoon olive oil in a small skillet over medium heat. Add chiles, season with salt, and cook until softened and slightly golden, about 5 minutes. Remove from heat and set aside.
Preheat a Belgian waffle iron.
In a medium bowl, whisk together flour, cornmeal, baking powder, 1 tablespoon plus 1 teaspoon salt, and cayenne pepper. Add milk, remaining 2/3 cup olive oil, and eggs, and maple syrup, whisking to combine. Do not overmix; batter may be lumpy. Fold in the cheddar cheese and reserved sauteed chiles. Let batter rest at least 30 minutes at room temperature, and up to one hour.
Spray waffle iron with cooking spray. Pour 3/4 cup batter into waffle iron. Cook until golden brown, about 7 minutes. Carefully remove waffle from iron and repeat process with remaining batter. Serve immediately with desired toppings.