To a large pan, add olive oil and onion and sauté on a medium-low heat until softened, about 2-3 minutes. Add beef and cook until browned, about 5 minutes, stirring and breaking the meat up with a wooden spoon. Once browned, drain and discard excess grease.
To pan of browned beef, add red pepper, minced garlic, ground coriander, ground cumin, red pepper flakes, and chipotle powder, and cook for an additional 1 minute. Stir in chopped tomatoes, tomato puree, beef bone broth, red wine, coconut aminos, salt, and pepper.
Reduce heat to low and simmer until sauce has thickened, about 30-40 minutes, stirring occasionally. Taste and adjust seasonings as necessary.
Spoon chili into bowls and serve with chopped fresh cilantro and sour cream over cauliflower rice.