Add the olive oil and beef to a skillet over medium heat. Cook the meat, while breaking it up with a wooden spoon, until the meat is cooked through and no longer pink - about 10 minutes.
Once the beef is browned, add the ketchup, mustard and Worcestershire. Then, stir to combine, then remove from heat.
While the beef is cooking, make the dressing. In a bowl, whisk together the mayo, ketchup, mustard, apple cider vinegar and pepper.
Set up a bar with all the toppings, the meat and the dressing and let everyone assemble their own bowl.
Notes
Hint: Pour the mixed Burger Dressing into a squirt bottle to make it easy for topping your bowls.