In a large, oven-proof pot, sauté bacon over medium heat until golden brown and fat is released. Using a slotted spoon, remove bacon to a separate bowl.
While bacon is cooking, place beef in a large mixing bowl and season with 1 1/2 tsp salt and 1 tsp black pepper. Sprinkle beef with 1/4 cup flour and toss to combine and evenly coat beef. Transfer beef in 2 batches into the hot bacon fat and cook over med/high heat, until beef is browned (3 min per side). Add olive oil if needed. Transfer browned beef to the bowl with bacon.
Add 2 cups wine to the pot and bring to a boil, scraping the bottom to deglaze the pot. Add sliced mushrooms and simmer over medium heat about 10 min.
Meanwhile, heat a large non-stick skillet over medium/high heat and add 2 Tbsp olive oil. Add sliced carrots, diced onion, and 4 chopped garlic cloves, and saute 4 min. Add 1 Tbsp tomato paste and saute another minute. Transfer veggies to the soup pot.
Add 4 cups beef broth, 2 bay leaves, 1/2 tsp dried thyme, 1 tsp salt, and 1/2 tsp pepper. Return beef and bacon to the pot then add potatoes. Stir to combine and make sure potatoes are submerged in liquid. Cover with lid and bake at 325˚F oven for 1 hour and 45 min.