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1. Heat a large Dutch oven over medium-high heat. Coat pan with cooking spray. Add 1 teaspoon oil; swirl. Sprinkle beef with salt. Add beef to pan; sauté 8 minutes, turning to brown on all sides. Remove beef.
2. Add 2 teaspoons oil to pan. Add onion and bell pepper; sauté 3 minutes. Add tomato paste, garlic, and jalapeño; sauté 2 minutes, stirring constantly. Add wine; bring to a boil, scraping pan. Cook 2 minutes. Return beef to pan.
3. Stir in ancho chile pepper and the next 7 ingredients (through kidney beans), and bring to a boil. Cover, reduce heat to medium, and simmer gently for 1 hour. Add butternut squash and 1 cup carrot, and simmer for 1 hour or until beef is tender. Ladle 1 1/3 cups chili into each of 6 bowls, and top each with 1 tablespoon sour cream and 1 teaspoon cilantro.