Sauté the vegetables: Heat the olive oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Add the onion and bell pepper and cook for ~4-5 minutes Start Timer, until they begin to soften.
1 Tbsp. olive oil, 1 medium yellow onion, 1 small red bell pepper
Brown the beef: Add the ground beef and season with a little salt and pepper. Cook for 6-8 minutes Start Timer, breaking it into crumbles, until deeply browned. Try not to constantly stir it. Let some of the beef sit against the hot pan long enough to actually brown rather than steam.
1½ lbs. ground beef, 1½ tsp. kosher salt, 1/2 tsp. black pepper
Build the flavor base: Add the garlic and tomato paste. Cook for about 2 minutes Start Timer, stirring frequently, so the tomato paste has time to develop color and fragrance and turn deep red.
4-5 cloves garlic, 3 Tbsp. tomato paste
Season: Add the chili seasoning mix, smoked paprika (more chili powder if desired), and the remaining salt and pepper. Cook for another 30-60 seconds, stirring constantly, until fragrant.
1 (1.48 oz.) packet chili seasoning mix, 1 tsp. smoked paprika
Add everything else: Stir in the Worcestershire sauce, crushed tomatoes, diced tomatoes, beef broth, beans, brown sugar, and cocoa powder. Bring to a gentle boil.
1 Tbsp. worcestershire sauce, 1 (28 oz.) can fire-roasted crushed tomatoes, 1 (14.5 oz.) can fire-roasted diced tomatoes, 1 cup low-sodium beef broth, 1 (15 oz.) can kidney beans, 1 (15 oz.) can pinto or black beans, 1 Tbsp. dark brown sugar, 1 tsp. unsweetened cocoa powder
Simmer: Reduce the heat to medium-low and simmer uncovered for 20-25 minutes Start Timer, stirring occasionally. If you’d like a thicker chili, simmer longer if you have the time! If it becomes too thick, feel free to add a splash of beef broth.
Finish and season: Remove from the heat and stir in 1 teaspoon apple cider vinegar. Taste and add the second teaspoon if needed, along with additional salt or pepper.
1-2 tsp. apple cider vinegar
Serve: Serve with plenty of toppings and cornbread!
Shredded cheddar, sour cream, sliced green onions, finely diced red onion, avocado, cilantro, jalapeños, and/or tortilla chips, Cornbread