Place steaks on a plate and perforate both sides with small holes with a sharp knife
Season both sides of the steaks fairly heavily.
Cover both sides of the steak with olive oil over top of the seasoning. Allow excess oil to pool on the plate but not overflow.
Cover plate with plastic wrap and refrigerate for 2-8 hours.
Before cooking the steaks take them out of the fridge and allow them to come up to room temperature.
Use excess olive oil marinade on the plate to cover the bottom of your cast iron pan. If the excess marinade doesn't suffice to cover add more olive oil until it does.
Turn on the heat and get the cast iron pan to approximately 375° F, just before the olive oil smoke point. Make sure the cast iron has plenty of time to come up to temp as it needs to be ripping hot.
Carefully place steaks into hot oiled pan. For medium cook 4 minutes a side. For medium-well cook 5 minutes a side. For rare cook 3 and a half minutes a side.
Only flip the steak once, try not to press down on it with the spatula as it will push the juices out.
Once your steaks are cooked take them off of the cast iron and allow them to rest on a plate for at least 5 minutes. Resting is very important to lock in the juiciness of the steak. Cutting into the steak too early will cause it to spill all of it's flavorful juices.