Heat oil in an large electric skillet or Dutch oven over medium heat.
Cut chuck roast into small bite size pieces, set aside.
Pour flour, salt, pepper and into a sealable large bag and add chuck roast pieces. Shake to coat.
Remove the meat from the bag, shake off excess flour and add to the hot oil.
Cook on medium-high heat until roast pieces are browned on all sides, then add ground beef, chopped onions, bell pepper, jalapeno, and garlic.
Sprinkle cayenne pepper, chili powder, and cumin, into meat mixture and cook until ground beef is cooked completely and veggies are tender.
Pour enchilada sauce, diced tomatoes and kidney beans into the pan. Stir, cover, and continue cooking over low heat and simmer for 45 minutes to an hour until the meat is fork tender, stirring occasionally.
Add chili to individual bowls or bread bowls, if desired, and enjoy.