For the marinade, combine the garlic, adobo sauce, chipotles, dried ancho chili, oregano, cumin, and olive oil in a processor and blend until smooth. Add a little water if needed to fully blend.
In a shallow dish, place steak and rub steak with the marinade. Heavily salt and pepper each side. Cover the plastic wrap and let marinate at room temperature for 30 minutes or in the fridge for up to 12 hours.
Put cast iron skillet on skillet and turn to high. Allow to get hot, about 4 minutes. Add olive oil.
Add steak, pushing down slightly to ensure even contact. Sear for 1 minute. Flip and then sear for another minute. Keep cooking on high, flipping every 30 seconds.
When steak as developed a dark crust and slightly shrunk in size, about 4 minutes total, check for doneness. The meat should feel slightly soft but not squishy. For medium-rare, 120 - 125 F is ideal.
Remove steak to a cutting board and let rest for 10 minutes.