Combine flour, salt, black pepper and cayenne pepper. Reserve 1 tablespoon flour mixture. Lightly coat beef with remaining flour mixture.
Heat 1 tablespoon oil in stock pot over medium heat. Brown beef in batches; adding additional 1 tablespoon oil as necessary. Set aside.
Add onions, oregano and fennel seeds to stock pot; cook and stir 2 to 3 minutes or until onions begin to soften.
Add wine to pot; increase heat to medium-high. Cook and stir 1 minute or until browned bits attached to pot are dissolved. Stir in beef broth, tomatoes, tomato paste and reserved flour mixture. Return beef to pot; bring to a boil. Reduce heat; cover tightly and simmer 1-3/4 hours or until beef is fork-tender.
Slice olives into quarters and stir in olives. Cook 2 to 3 minutes or until olives are heated through. Serve with pasta. I used rigatoni.