Heat the oven to 375 degrees and line a baking sheet with parchment paper.
In a large bowl, combine the ground beef, cheddar cheese, breadcrumbs, egg, ketchup, mustard, onion, garlic powder, salt, and pepper. Mix gently with your hands until just combined.
Shape the mixture into a loaf about 8 inches long and place it on the prepared baking sheet.
Toss the potato fries with olive oil, salt, and pepper on a second baking sheet and spread them in a single layer.
Place both sheets in the oven. Bake the meatloaf for 45 to 50 minutes until it reaches 160 degrees inside. Bake the fries for 30 to 35 minutes, turning once, until golden and crisp.
Let the meatloaf rest for 5 minutes, then slice and serve with the pickled vegetables and hot fries.