Trim excess fat from the steak and cut into 1-inch cubes. Season the steak pieces with salt and pepper, then thread each onto a skewer or hold with tongs for easy wrapping.
Wrap each steak cube with a slice of bacon, securing with toothpicks if necessary. Ensure the bacon overlaps slightly for a snug wrap.
Heat the skillet over medium-high heat and add olive oil. Place the bacon-wrapped steak bites in the pan, seam side down if applicable, and cook for about 5-7 minutes, turning occasionally, until the bacon is golden brown and crispy on all sides.
Use tongs to turn the bites as they sear, listening for a sizzling sound and observing a caramelized, brown crust forming on the bacon and edges of the steak.
Continue cooking until the bacon is crisp and the steak reaches your preferred internal temperature (around 130°F for medium rare). Remove from heat and let rest for 2 minutes.
Serve immediately, garnished with additional salt and pepper if desired. The bites should have a crispy exterior with a tender, juicy interior, showcasing a shiny, caramelized surface.
