In a large stock pot, heat the olive oil over medium heat.
2 tablespoons olive oil
Add the butternut squash, onion, and garlic. Season the vegetables with chili powder, cumin, kosher salt, ground chipotle, black pepper, and cayenne pepper. Sauté until the squash is tender, about 10 minutes.
Add in the beans, diced tomatoes, and tomato sauce, scraping any browned bits from the bottom. Bring the mixture to a boil. Reduce to a simmer and cook, covered, for 20 minutes. Taste and add more salt and pepper to taste.
Butternut squash: Six cups of butternut squash is roughly half of a medium-sized butternut squash. The squash goes in raw after being peeled, deseeded, and cubed into 1-inch pieces.