Begin by heating 2 tablespoons of vegetable oil in the crock pot on the sauté setting until shimmering. Season the beef chuck pieces with salt and pepper, then add them to the pot in a single layer. Sear the meat for about 4–5 minutes, turning occasionally, until each piece is golden brown on all sides.

Once the beef is beautifully browned, stir in 1 chopped onion, 1 diced bell pepper, 1–2 chopped jalapeños, and 3 minced garlic cloves. Sauté the mixture for about 3–4 minutes, or until the veggies soften.

Now, stir in 1 can each of crushed tomatoes, diced tomatoes, and 2 tablespoons of tomato paste, followed by 1 can of drained chili beans or red kidney beans. Add 2 tablespoons of Worcestershire sauce along with 2 teaspoons of ancho chili powder, 1 teaspoon of light brown sugar, and additional spices to taste.

Pour in 2 cups of beef broth and stir gently to ensure all ingredients are well combined.

Cover the crock pot with its lid and set to cook on low for 8 hours or high for about 4 hours, until the beef is tender.

As the cooking time nears its end, taste your chili and adjust seasonings based on your preference.