Season beef with salt and pepper. Heat oil and butter in a heavy cast iron skillet over medium heat until hot but not smoking. Add the beef cubes and sear the meat until browned on all sides, but not fully cooked, about 4 minutes total. Remove from the pan and set aside. Lower the heat to medium low, add the onion, red pepper, carrots, mushrooms, oregano and half the parsley and basil to the skillet. Sauté for 5 minutes, or until the onion is transparent and the vegetables are beginning to soften, adding a little more oil if needed. Add the garlic and the beef back to the pan and cook for 2 minutes. Raise the heat to medium, add the wine and allow it to reduce by half. Add the crushed tomatoes, beef broth, tomato paste, cherry tomatoes, capers and red pepper flakes. Season with salt and pepper; stir well to combine. Partially cover the pot with a lid and allow to simmer over low heat for 30 to 40 minutes, or until sauce has reduced and thickened and the vegetables are tender. Stir in the olives and remaining parsley and basil.