Coat the steaks with the cracked pepper and season with salt. Place the olive oil in a cast-iron skillet and heat 1 minute before adding the steaks. Cook over medium heat 3 minutes on each side for medium rare. Remove the steaks to warm serving plates. Drain the excess fat from the pan and carefully add the bourbon, away from the heat. Reduce the heat to low and reduce the bourbon until the pan is nearly dry. Add the red wine, raise the heat to medium, and reduce the half. Add the brown stock, bring to a boil, cook 6 minutes and "finish" by swirling the butter into the sauce. Remove from the heat and divide the sauce among the steaks.