Dry the beef with paper towels to remove excess moisture. This helps the browning process.
Heat Dutch oven over medium-high heat. Add the bacon. Brown and remove with a slotted spoon, keeping the rendered bacon fat in the pot.
Add the beef to the pan and work in batches. DO NOT CROWD THE PAN. You want a nice brown sear on both sides, so 6 pieces should do for each round.
After you’ve seared and browned all the beef and set aside, add olive oil to the pot. Add the vegetables (minus the garlic), potatoes and salt. Toss to coat and cook for a few minutes until veggies start to soften, 5 minutes or so.
Add the beef and bacon back into the pot, sprinkle with the flour and 1 tbsp of butter. Toss the meat to coat and cook for 2 minutes to remove that raw flour taste.
Add the Siponey, beef stock, garlic, and the herbs. Simmer on the stove for an hour until nice and thickened.