In a pan, combine olive oil, squash and chopped shallot, and roast over medium heat, stirring every few minutes
While squash is cooking, add broth, apple and all spices to Vitamix, holding the cream back for later
Once squash has been roasted, so that parts have been caramelized, add to Vitamix
Select soup mode on Vitamix, start and allow to complete cycle. If you do not have a soup cycle, blend on high until very smooth and warm.
Open top, being careful, it will be hot, and add cream to soup, and replace top
Switch Vitamix to a low speed and start, slowly increasing speed and blend for another 30 seconds