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Melt together the butter and olive oil in a large pot over medium heat.
Add the onion, thyme, and sage, cook until fragrant, about 5 minutes.
Add the butternut squash, toss, and cook 1-2 minutes.
Mix in the flour and cook until golden, about 1 minute.
Add the broth, beer/cider, and season with salt and pepper.
Bring to a simmer, reduce the heat to medium, and cook, uncovered, until the butternut squash is tender, about 15 minutes.
Remove the soup from the stove. Puree in a blender or use an immersion blender.
Return the soup to the stove and set over low heat.
Stir in the milk, broccoli, cheddar cheese, and brie, cooking until melted and creamy.
Add the cayenne.
Ladle the soup into bowls and top with a little extra cheddar or a wedge of brie.