Preheat your oven to 425°
In a small dish, combine 2 tablespoons of brown sugar, 1 teaspoon of garlic powder, 1 teaspoon of onion powder, 1 teaspoon of salt, 1/2 teaspoon of chili powder or paprika and a pinch of black pepper and set aside for now
Light brush the bottom of a large cast iron skillet with olive oil and set aside for now
Dry the tenderloin with paper towels
Rub the brown sugar mixture over the entire tenderloin
Arrange 10 slices of bacon in a continuous single layer on a flat surface and place the seasoned tenderloin in the center
Starting at one end, carefully wrap the tenderloin by crossing the ends of the bacon slices over the top alternating left and right so that they overlap a bit and completely cover the tenderloin top to bottom
Carefully place the bacon wrapped tenderloin into the prepped skillet seam side down
Roast in a 425° oven for 30-35 minutes or until the internal temperature reaches 145°
Transfer the tenderloin onto a cutting board to rest for 5-10 minutes before slicing