Heat 3 tablespoons olive oil in a heavy-bottomed pot or Dutch oven over medium-high heat. Season the chuck roast with 2 teaspoons salt and 1 teaspoon pepper.

Add the beef in batches, browning the meat on all sides, about 5-6 minutes per batch. Remove the browned meat and set aside.

To the same pot, add 1 large diced yellow onion, 2 jalapeno peppers, and 6 minced garlic cloves. Cook, stirring occasionally until softened, for about 4-5 minutes.

Add 2 tablespoons chili powder, 1 tablespoon smoked paprika, 1 tablespoon cumin, 1 tablespoon brown sugar, 2 teaspoons dried oregano, 1 teaspoon coriander, ½ tablespoon cocoa powder, 2 chopped chipotles in adobo, and 1 tablespoon tomato paste. Stir to combine.

Add the beef back to the pot, then add 1 (28-ounce) can crushed tomatoes and 4 cups beef broth. Stir to combine.

Bring to a boil, then reduce the heat to low. Cover the pot and simmer for 2-3 hours, stirring occasionally, until the meat is tender and the chili has thickened. If the chili gets too thick, add more broth as needed.