Heat a large skillet over medium heat and add the olive oil. Once it's hot, add the ground beef, garlic cloves, salt and pepper. Break the mixture apart with a spoon and cook until browned, stirring over and breaking the pieces into crumbles, for about 6 to 8 minutes. Turn off the heat and sprinkle about 2 ounces of the cheddar over the beef so it slightly melts. You can serve this salad with the beef hot or room temp - so if necessary, you can make this a bit ahead of time!