To make the dressing. Add the apple cider to a medium sauce pot and bring to a boil, boil for about 15 to 20 minutes or until the cider has reduced to about 1/3 cup and is thick and syrupy. Remove from the heat and stir in the honey, apple cider vinegar, olive oil, cayenne (if using), salt and pepper. Set aside
While you work on the dressing preheat the oven to 400 degrees F. and start the kale.
Add the kale to a large bowl. Add 2 tablespoons olive oil, 2 tablespoons parmesan cheese and a pinch of salt and pepper. Toss well and massage the kale with your hands for a good 1 to 2 minutes. Spread on a baking sheet and bake for 15-18 minutes, tossing 1-2 times while cooking, until crispy. Remove and place in a large bowl, set aside.
While the kale gets crispy start working on the squash. In a small bowl combine the chili powder, cinnamon, cayenne, brown sugar, salt and pepper. Mix to combine.
Peel and chop the squash, but reserve the seeds and add to bowl of water. Using your hands separate the seeds form the orange goopy flesh. Place the seeds in a paper towel and pat dry. Set the seeds aside.
Add the squash to a sheet pan and drizzle on a tablespoon or so of olive oil. Sprinkle with about half the spice mixture and toss well. Bake for 20 minutes, remove from the oven and add the chopped apples and pecans and add a sprinkle more of the seasoning and then toss it all together. Bake for another 15-25 minutes, or until the squash and apples are tender.
Now grab the seeds and place them in a small baking dish. Add 2 teaspoons olive oil and the remaining seasoning. Toss well and bake for about 10 minutes or until lightly golden and toasted, but watch carefully, they will burn quickly. Set aside.
Now add the roasted, butternut squash, apples and pecans to the crispy kale. Toss.
Heat a medium skillet on medium heat, add a tablespoon butter. Sandwich the the brie between 2 slices of bread. Add the sandwiches to the skillet and cook for 3 to 5 minutes on both sides or until the bread is toasted and the brie is melted. Remove and let sit a couple minutes and then chop into cubes.
Divide the salad among plates and top with the croutons, roasted seeds and a drizzle of the apple cider dressing. EAT!