Brown ground beef until fully cooked and no longer pink in a 6 quart Dutch oven or soup pot over medium high heat, crumbling beef with a wooden spoon while it is cooking. Drain off fat from beef in a colander and set aside.
Return Dutch oven or pot to burner and add olive oil. Once the olive oil is heated, add green pepper and onions. Saute until vegetables are tender, stirring frequently (about 3 to 4 minutes). Add garlic and cook until fragrant (about 30 seconds).
Return ground beef to pot and stir to combine.
Pour in the beer and stir to scrape the bottom of the pot to remove any browned bits.
Add beef broth, diced tomatoes, tomato paste, chili powder, red pepper flakes, oregano, cumin, salt, pepper, and bay leaves. Stir to combine.
Bring to just a boil, then reduce heat as necessary to maintain a simmer. Cover and simmer for 1 hour, stirring occasionally.
Remove the lid and stir in the beans. Simmer (uncovered) for 20 minutes, stirring occasionally. Remove and discard bay leaves before serving.