Make the seasoning blend: In a small bowl, combine the cumin, chili powder, pumpkin pie spice, oregano, salt and a few grinds of black pepper. Set aside.
Sear the beef: Heat the olive oil in a large pot over high heat until it begins to swirl. Add the beef cubes and sprinkle with half of the seasoning blend. Cook, stirring intermittently, until the beef is browned on all sides but not cooked through, about 5 minutes. Remove the beef chunks with a slotted spoon and set on a plate
Build the flavor: Reduce the heat to medium and add the onions, bell pepper, garlic, tomato paste and hot sauce. Cook, stirring, until everything turns dark reddish brown, about 10 minutes.
Complete the chili: Add the ground beef and sprinkle with the remaining half of the seasoning blend. Cook, stirring, until the beef is browned, then add the reserved beef chunks back to the pot along with the cornmeal, stock, wine and squash. Bring to a boil, then reduce to a simmer and cook until the chili is thick and the liquid reduced, 40 to 50 minutes. Taste and season with another pinch of salt if needed, but the seasoning blend you've made should have this tasting perfect for you. If using cinnamon, add the stick 20 minutes before the chili is done, then remove before serving. Serve warm.