Season the steaks with 1 teaspoon salt and ½ teaspoon pepper.
Heat a large skillet over medium-high heat. Add the oil and sear the steaks on both sides until browned.
Remove the steaks from the skillet and keep warm.
Reduce the heat under the skillet to medium. Add the butter, shallots, mushrooms, and flour. Cook, stirring occasionally 2-3 minutes, making sure to scrape up the browned bits that collected on the bottom of the skillet from searing the steaks.
Season the mushrooms with ½ teaspoon salt, and ½ teaspoon pepper. Add the beef broth to the skillet and stir well to combine.
Cook over medium heat for 3-4 minutes until the sauce thickens slightly.
Turn the heat off under the skillet and add the bourbon, and cider vinegar. Stir well to combine. Return the heat to medium.
Add the seared steaks back into the skillet and spoon the bourbon mushroom sauce over the steaks. Cover and cook the steaks to reach your desired doneness.
To serve, spoon the bourbon mushrooms over the steaks and enjoy!