01 - Heat olive oil in a large pot or Dutch oven over medium-high heat. Add ground beef and cook until browned, breaking it up with a wooden spoon, about 6 to 8 minutes.
02 - Add diced onion, minced garlic, and diced bell peppers to the pot. Sauté until vegetables are softened, about 5 minutes.
03 - Stir in chili powder, ground cumin, smoked paprika, cayenne pepper, black pepper, and salt. Cook for 1 minute until spices become fragrant.
04 - Mix in tomato paste and cook for another minute to deepen the flavor.
05 - Add crushed tomatoes, kidney beans, black beans, beef broth, dried oregano, and brown sugar. Bring to a simmer, then reduce heat to low, cover, and let simmer for 45 minutes, stirring occasionally. Taste and adjust seasoning if needed.
06 - Preheat your waffle iron according to the manufacturer's instructions while the chili simmers.
07 - In a large mixing bowl, whisk together all-purpose flour, cornmeal, granulated sugar, baking powder, baking soda, and salt.
08 - In a separate bowl, whisk together whole milk, eggs, melted unsalted butter, and sour cream until smooth.
09 - Pour wet ingredients into the dry ingredients and mix until just combined. Do not overmix—some small lumps are fine.
10 - Lightly grease the preheated waffle iron. Pour batter into the waffle iron (about 1/2 to 2/3 cup per waffle, depending on your iron) and cook according to manufacturer's instructions until golden and crisp, about 4 to 5 minutes per batch.
11 - Place a cornbread waffle on each serving plate. Spoon hot beef chili generously over the top. Garnish with shredded cheddar cheese, sliced green onions, fresh cilantro, and a dollop of sour cream if desired.