In a glass measuring cup, whisk together bourbon, honey, red pepper, garlic, lime juice, 1/4 teaspoon salt and 1/8 teaspoon pepper. Put the steak in a baking pan or 1-gallon zip top plastic bag; add the bourbon and honey mixture, turn the steak over to coat. Let the steak marinate in the fridge for at least 30 minutes or overnight.
Heat oven to 425°F. In a medium bowl, toss potatoes, olive oil, 1/4 teaspoon salt and 1/8 teaspoon pepper until well coated. Spread potato halves in a single layer on a rimmed baking sheet. Roast potatoes, turning once, until tender and deep golden brown, 25 to 30 minutes.
Meanwhile, place steak on grill pan over medium-high heat (or directly on the grill over medium heat; cover grill.) Cook 10 to 14 minutes for desired doneness, turning once. Remove from grill pan (or grill) and cover loosely with foil; let rest 5 minutes. Cut steak diagonally across grain into thin slices.
While the steak is resting, transfer the marinade into a small saucepan and boil over medium heat until slightly thickened, about 3 minutes. Serve the steak with the roasted potatoes and a drizzle of sauce.