Add the olive oil to a large pan over medium-high heat. Add onion and garlic. Cook for 3-5 minutes, stirring occasionally until fragrant.
Add the ground beef to the pot, breaking apart and cook until brown.
Add chili powder, cumin, sugar, oregano, salt, black pepper and cayenne pepper. Stir until well combined.
Add remaining ingredients to the pan. Simmer for 5 minutes and then spoon the chili into a 4-5 quart slow cooker.
Cook on low heat for 8 hours.
Top with your toppings of choice: avocado, cheese, sour cream/greek yogurt, oyster crackers, etc.