HEAT olive oil in a medium pot over medium. Add garlic and onion. Cook until onion is soft, about 3 min. Add tomato paste, chopped fresh sage, salt and cayenne. Pour in vegetable broth and butternut squash.
BOIL, then reduce heat to medium-low and simmer until squash is very tender, 15 to 20 min. Use a hand blender to purée soup.
LADLE soup into bowls. Garnish with fried crisp bacon and sage leaves, if desired.