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In a large pot, heat 1 tbsp of olive oil over medium-high heat. Add ground beef, brown it thoroughly, then remove from the pot and set aside.
In the same pot, add 1 tsp olive oil followed by the potatoes, carrots, onion, and garlic. Sauté for 5 minutes.
Stir in the remaining olive oil and flour. Season with salt, pepper, and garlic powder to form a roux.
Pour in the chicken stock, water, and pickle juice. Bring to a boil, then reduce heat and simmer until potatoes are soft.
Add in the cooked ground beef, diced pickles, fresh dill, shredded cheddar, and sour cream. Stir to combine, and simmer for a few more minutes until the cheese melts and everything is heated through.
Garnish with more fresh dill and serve hot.