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Step 1
Cut beef chuck into 1/2 inch cubes.
Step 2
Pour 3 tablespoons of oil into a dutch oven or large pot. Turn the eye on high and allow the oil to heat.
Step 3
Place onion and garlic into the pot and cook for 2 minutes. Reduce the heat to medium-high, then add the beef cubes. Brown the meat, while stirring constantly.
Step 4
Once the meat has browned slightly (with no red showing), lower the temperature to medium.
Step 5
Add Italian seasonings, chili powder, smoked paprika, cumin, brown sugar, vinegar, tomatoes, beans, black pepper, salt, diced jalapenos, and red pepper flakes. Mix well.
Step 6
Simmer for about 10 minutes, then add corn tortilla flour (or masa harina) to help thicken the chili.
Step 7
Cook for another 10 minutes, or until chili thickens.
Step 8
Serve and top with sour cream, shredded cheese, tortilla chips, and avocado slices.