Heat 1 tablespoon of olive oil in a large cast-iron skillet over medium-high heat until shimmering.
Add the sliced bell peppers and onions to the skillet. Sauté for 6-8 minutes until the vegetables are tender and exhibit char marks. Remove vegetables from the skillet and set aside.
Increase heat to high and add the remaining 1 tablespoon of olive oil.
Place the thinly sliced ribeye in the skillet in a single layer. Season with salt and black pepper. Sear for 2-3 minutes without moving to develop a crust, then flip and cook for another 1-2 minutes.
Add the minced garlic and Worcestershire sauce to the beef. Toss to incorporate and cook for 60 seconds.
Return the sautéed peppers and onions to the skillet. Toss the mixture together to ensure even heat distribution.
Divide the mixture into four distinct piles within the skillet. Place two slices of provolone cheese over each pile.
Cover the skillet with a lid for 1 minute or until the cheese is fully melted and bubbly.
Transfer each cheesy portion to a bowl and serve immediately.