In a large, pot, over medium high heat, sauté the bacon until browned. Remove bacon to a separate bowl, and set aside.
While the bacon is cooking, prepare the beef. Place cubed beef into a large mixing bowl. Season with salt and pepper. Mix in the 1/4 cup flour and toss to evenly coat the meat.
Sear the beef in 2 batches, in the bacon fat. Cook unit the beef is evenly browned, about 3 minutes per side. Add more oil if needed. Once done, place the beef in with the bowl of bacon.
Add wine to the pot, bring to a slow boil over medium high heat, scrape the bottom of the pot to deglaze. Add the mushrooms and simmer for about 10 minutes.
Meanwhile, heat a skillet over medium-high heat, add the 2 tablespoons oil. Add in the carrots, onion, and garlic. Sauté for 5 minutes. Add in the tomato sauce/paste and let cook for another minute or two. Add the vegetable to the soup pot.
Add in the beef broth, bay leave, and thyme. Add in the beef, bacon and potatoes. Stir to combine. Cover and bake at 325 degrees for 1 hour and 45 minutes. Or simmer on the stovetop for the same amount of time.