Brown the meat: Heat olive oil in a heavy Dutch oven over medium-high heat. Add cubed beef (in batches) and sear until browned on all sides. Remove and set aside.
Sauté the aromatics: In the same pot, add onion and cook until soft and golden, about 5 minutes. Stir in garlic and cook another 1–2 minutes.
Toast the spices: Add chili powder, smoked paprika, cumin, cayenne, oregano, salt, and pepper. Stir constantly for 1 minute to bloom the spices.
Deglaze with beer: Pour in the dark beer, scraping up browned bits from the bottom of the pot. Let simmer for 2 minutes.
Build the base: Stir in tomato paste, crushed tomatoes (if using), Worcestershire sauce, and apple cider vinegar. Mix well.
Add broth and beef: Return seared beef cubes to the pot. Pour in beef broth and bring to a gentle boil.
Simmer low and slow: Reduce heat to low, cover partially, and simmer for 2–3 hours, stirring occasionally, until beef is tender and sauce is thick.
Taste and adjust: Add more salt, pepper, or cayenne to your liking. If chili feels too thick, splash in extra broth.
Serve hot: Ladle into bowls and garnish with onions, cheese, or cilantro.