Place the four cups of cauliflower into a food processor and pulse a few times, until it resembles grains of rice. Heat the olive oil in a skillet over medium heat. Add the cauliflower rice and cook for about 4-5 minutes, until tender. While this is cooking, you can start preparing the beef.
Mix the chili powder, cumin, paprika, garlic powder, onion powder, salt, and cayenne in a small bowl. Place ground beef in a large nonstick skillet over medium heat. Cook, stirring and breaking the meat apart every few minutes, until beef is browned. If needed, drain off excess fat (leave a little as it will help the spices blend with the meat). Mix in the spice blend and cook for another 1-2 minutes, until mixed thoroughly.
Divide the cauliflower rice and beef evenly between four bowls. Add 5 halved cherry tomatoes, 1/2 cup lettuce, 1/4 cup cheddar cheese, and 1 tbsp guacamole to each bowl (this will total the amounts in the ingredients above across all four bowls). Enjoy!