Soak two cups of beans overnight in cold water. If you’re a bad planner, you can quick soak them for 90 minutes in steaming water. But it’s best to gently soak them in cold water overnight. Drain and rinse beans.
Bring a large pot of water to a simmer (no salt) and add soaked beans. Turn heat down so water is barely at a simmer. Simmer beans for 75-90 minutes until they are tender.
Drain beans and rinse again, set aside.
In a sturdy pot, add olive oil over medium heat. Add diced potato and onion. Cook for about 8 minutes until veggies soften. Season with salt and pepper.
Add garlic, chili powder, cumin, and paprika to the pot and stir. Cook for 30 seconds.
Add diced tomatoes, vegetable stock and browned Italian sausage, bring chili to a slight simmer. Turn heat down to low again and let simmer for 10- 15 minutes, stirring occasionally.
Add beans back into chili and season chili with salt and pepper to taste. Keep chili warm until you serve it. Serve chili topped with grated cheese, pickled jalapenos, and chopped chives.