Trim the fat from the roast and dice into small, bite-sized cubes. Season with salt and pepper.
Add 1 tablespoon of oil to a large dutch oven over medium heat. Once hot, add the beef, working in batches as needed, and sear. Once the beef is browned on the outside but not cooked through, remove to a plate.
Add the remaining tablespoon of oil to the pot. Once hot, add the onion and cook for 5 minutes, until softened. Stir in the garlic and cook for 30 seconds.
Add the chipotle pepper and tomato paste and stir to combine. Let cook for 2-3 minutes and then stir in the chili powder, paprika, cumin, and oregano. Cook for 1 minute more.
Return the beef to the pot and top with the tomatoes, beef broth, beer, and sugar. Stir to combine.
Bring to a boil, reduce to a simmer, and cook at a low simmer, covered, for 1 ½ hours. Remove the lid and continue cooking for 30 minutes.
Drain and rinse the beans and add to the pot. Cook for 5 minutes to warm.
Taste and season with additional salt, if needed.
Serve hot, topped with cheddar, jalapeno slices, onion, and sour cream.