Season your beef generously with salt and black pepper. Heat olive oil in your Dutch oven or a skillet over medium-high heat. Sear the roast for 3-4 minutes on each side until a deep golden-brown crust forms. This locks in the flavors. Remove the roast from the pan and set it aside.
Lower the heat and add onions, carrots, celery, and garlic to the pan. Sauté for 4-5 minutes until softened. Stir in tomato paste and cook for an additional minute.
Place the beef back into the pot, along with fresh thyme, rosemary, and bay leaves. Pour in beef broth and optional red wine. Ensure the liquid covers about three-fourths of the roast. Cover and cook on low for 6-8 hours in a slow cooker, 3-4 hours in the oven at 325°F, or for 90 minutes in a pressure cooker.
Boil the potatoes in salted water until tender, about 15-20 minutes. Drain and mash the potatoes using a potato masher or hand mixer. Incorporate butter, warm cream, garlic powder, salt, and pepper until smooth and creamy.
Shred the pot roast with two forks directly in the pot, discarding any fatty pieces. Remove the herbs and bay leaves. Pile a generous scoop of mashed potatoes onto the plate, top with the pot roast, and drizzle with the rich gravy from the pot.