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Heat 1 tablespoon of oil in a large skillet over medium-high heat. Add the ground beef, cumin, salt, pepper, Italian seasoning and crushed red pepper flakes. Stir to break up the meat and cook until evenly browned, about 8 minutes. Use a slotted spoon to transfer the beef to a paper-towel-lined plate and allow to drain. Do not wipe out the pan.
Add 1 tablespoon of oil to the pan and add the potatoes. Over medium heat, cook the potatoes, turning them until both sides begin to brown and the potatoes are tender, about 15 to 20 minutes. Transfer the potatoes to the plate with the ground beef.
Heat the remaining 1 tablespoon oil in the skillet over medium heat. Add the onion and bell pepper, stirring occasionally. Cook until tender, about 6 minutes.
Add the garlic and stir constantly. Cook until aromatic, about 1 minute. Add the kale and tomatoes. Stir often, cooking until the kale is wilted, about 3 minutes.
Add the ground beef and potatoes back to the pan. Cook until just heated through.