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Toss cubed beef with ½ cup red wine, generous kosher salt, and black pepper. Marinate at least 2 hours, preferably overnight.
In a cast-iron Dutch oven, heat olive oil. Sauté carrots, onion, and whole garlic clove. Season with salt and pepper. Remove vegetables, tie them in cheesecloth, and set aside.
In the same pot, sear beef in batches until deeply browned on all sides. Remove and repeat until all beef is browned.
Return beef to the pot. Add enough stock (or water) to just cover, plus a splash of red wine.
Strain diced tomatoes over a bowl. Tie tomato solids in cheesecloth and add to the pot. Pour tomato juice directly into the stew.
Tie rosemary, bay, thyme, and oregano in cheesecloth to make a bouquet garni. Add both herb bouquet and vegetable sachet to the pot.
Cover and gently simmer 2-3 hours, until beef is starting to become tender.
Remove beef and all sachets; discard bouquet garni. Strain liquid back into the pot. Add strained vegetables and tomatoes back into the stock. Blend the liquid until smooth using an immersion blender.
Return beef to the pot and simmer another 1 hour, or until very tender.
Add potatoes, mushrooms, and a generous amount of salt. Simmer 30 minutes, until potatoes are fully cooked.
Adjust seasoning and serve hot with crostini