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In a large sauté pan, heat olive oil over medium-high heat. Season beef with salt and pepper and sauté 3-4 minutes on each side to get a brown sear. Remove from pan and place in a slow cooker.
In the same pan, add onion and additional olive oil if needed. Sauté until lightly browned and soft. Add garlic and cook for 30 seconds. Deglaze pan with Herbs of Naples balsamic, 1/4 cup of wine and Worcestershire sauce. Stirring to remove all bits and flavor from the bottom of the pan. Cook until just beginning to boil. Remove from heat and add to the slow cooker.
To the slow cooker, add carrots, potatoes, remaining wine and the balsamic. In a small bowl, whisk the flour and 1/2 cup of broth to create a slurry. Pour into the slow cooker and add remaining broth until all is covered in liquid. Place the lid and cook for 6-8 hours on low until meat is pull-apart done. Place meat on a platter and vegetables around the meat. Pour over gravy and garnish with parsley before serving.
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