Preheat your oven to 350°F (180°C).
In a large bowl, combine all the meatloaf ingredients (ground beef, breadcrumbs, onion, garlic, egg, ketchup, brown sugar, Worcestershire sauce, oregano, salt, and pepper) and mix well.
Shape the meatloaf mixture into a ring to fit snugly inside a greased Bundt pan.
Bake the meatloaf for 45-50 minutes, or until cooked through.
While the meatloaf bakes, boil the chopped potatoes in a pot of salted water until tender. Drain the water and mash the potatoes with milk, butter, salt, and pepper.
Once the meatloaf is cooked, take it out of the oven and let it rest for 10 minutes.
Carefully transfer the meatloaf to a serving platter.
Top the meatloaf with the prepared mashed potatoes.
Serve hot and enjoy!
