Brown the meats: In your Dutch oven or large pot over medium-high heat, cook the Italian sausage and your second meat choice until no longer pink, breaking it into crumbles (about 7-8 minutes). If there's excessive fat, drain some but leave about 1 tablespoon for flavor.
Add the aromatics: Toss in the diced onion, bell peppers, and jalapeños. Cook until they begin to soften, about 5 minutes. Add the garlic and cook for another 30 seconds until fragrant. (Don't burn the garlic—it gets bitter and will send your chili down a sad path.)
Spice it up: Sprinkle in all your dry spices (chili powder, cumin, oregano, smoked paprika, and cayenne). Stir continuously for about 1 minute to toast the spices and coat everything. Your kitchen should smell amazing right about now.
Add the liquids and tomatoes: Pour in both cans of diced tomatoes with their juices, tomato paste, and broth. Stir to combine everything, scraping any browned bits from the bottom of the pot—that's concentrated flavor!
Bean me up: Add the drained and rinsed beans, brown sugar, and Worcestershire sauce. Stir well to combine all ingredients.
Simmer: For stovetop method, bring to a gentle boil, then reduce heat to low. Cover and simmer for at least 30 minutes, or up to 2 hours for deeper flavor. Stir occasionally to prevent sticking.
Season to taste: Add salt and pepper as needed. Remember that sausage already contains salt, so taste before adding more.
Serve it up: Ladle into bowls and let everyone customize with their choice of toppings.