Heat a large pot or skillet (if you're using a crockpot) over medium-high heat with a tablespoon of oil. Liberally season the ground beef with salt and pepper.
Carefully place each pound of ground beef seasoned side down in the oil once it's hot. Add a pinch of salt and pepper to the top side of the beef.
Cook for 3-5 minutes until the bottom develops a dark brown crust. Flip and cook for another 2-3 minutes before crumbling the beef and cooking until no pink remains.
While the beef cooks, add the pineapple, chipotle peppers, garlic, and dry spices to a food processor or blender. Pulse until smooth.
Once the beef is cooked, add the stewed tomatoes, black beans, and chipotle mixture to the pot. Bring to a low boil before reducing the heat to low. Simmer, covered, for 10-20 minutes (or longer if you have the time to let flavors develop).
Top with chopped cilantro, queso fresco, tortilla strips, a dollop of Greek yogurt, or your choice of toppings. Enjoy!