Rinse the beef chuck pieces thoroughly and drain. Sprinkle them generously using half the adobo con pimiento and ground cumin, then mix well to coat. Set aside to rest for 30 minutes at room temperature.
Set a medium-large sized caldero over medium-high heat and add aceite de achiote. Once the oil is hot, add the seasoned beef and stir to coat it in the oil. Let the meat brown for about 5 minutes, stirring occasionally to ensure even browning on all sides.
Once the beef is browned, add sofrito, tomato paste, and garlic to the pot. Stir everything together so the aromatics can begin to sauté and blend with the meat. Cook for 2 to 3 minutes.
Add the remaining dry seasonings, including the bay leaves, stirring well and let the mixture cook for 2 to 3 minutes, allowing the flavors to meld.
Pour in cooking wine and water. Stir everything together, reduce the heat to low, cover the pot, and let it simmer for 2 hours or until beef is tender.
When the beef is tender, add the potatoes and carrots to the caldero and stir well. Taste the stew and adjust the seasoning if needed. Partially cover the pot and continue cooking on low heat for another 30 to 45 minutes, or until the potatoes are tender and the stew has thickened to your liking.
Finish by sprinkling with cilantro and olives during the last 5 minutes, stirring gently.