Preheat oven to 300° F. Place Dutch oven on burner and turn to medium-high heat. Coat the bottom with olive oil (roughly 4 Tbsp.). Meanwhile, generously salt and pepper the outside of the roast (I never measure, just make sure the outside is evenly salted/peppered). Once the oil is hot, sear the meat in the Dutch oven, 1-2 minutes per side until brown. Turn off the burner and remove from heat.
2-3 tbsp Salt, divided, ½ tsp Pepper, 1 3-4lb Chuck Roast, Eye of Round Roast, or Similar, 6 tbsp Olive Oil, divided
After the meat has cooked, place the onion, garlic, and potatoes in the Dutch oven on either side of the meat. Sprinkle with about a tablespoon of salt and drizzle olive oil over vegetables (roughly 2 Tbsp.).
6 tbsp Olive Oil, divided, 2 Medium Onions, Cut in Chunks, 4-5 Garlic Cloves, Sliced, 6-8 Red Potatoes, Quartered, 2-3 tbsp Salt, divided
Pour wine (Port is best, but another red sweet wine will work) and beef stock over veggies.
3-4 tbsp Port or Red Wine, 1 ½ c Beef Stock
Cover with oven-safe lid and place in preheated oven for 2-3 hours, depending on thickness of meat. Turn meat after 1 hour. Serve warm and enjoy!