Preheat oven to 325 degrees.In a large bowl toss beef in flour and season with salt and pepper.
Heat 1 tablespoon oil in a cast iron pot.Once hot add in beef in batches making sure not to overcrowd the pan. (I did 3 batches)Brown meat on all sides, 2-3 minutes. You may need to add more oil as you go. Take beef out of the pot and set aside.
Add the remaining 1 tablespoon olive oil to the same pot.Add in onion and cook until browned and slightly tender, 2-3 minutes.Add in garlic and cook for an additional minute.
Pour in wine and deglaze the pan. Scraping up the bites on the bottom of the pan.Stir in tomato paste, beef broth and worcestershire sauce. Bring to a simmer.
Add beef back into the pan along with the carrots, bay leaves, thyme and rosemary.Cover and place in the oven. Cook for 1 hour.
Remove from the oven and add in the potatoes stir and cook for an additional 45 minutes to an hour or until the beef is tender.Stir in the balsamic vinegar and the cornstarch slurry (1 tbsp water + 1 tbsp cornstarch), if desired.
Remove the bay leaves and herbs from the pan. Season with salt and pepper to taste. Serve warm!