Heat the olive oil in a large pot over medium heat. Add the ground beef and cook until browned, breaking it up with a spoon as it cooks.
Add the onion and garlic to the pot. Cook for 3 to 4 minutes until the onion softens.
Stir in the butternut squash, apples, and thyme. Cook for another 2 minutes to combine the flavors.
Pour in the beef broth and diced tomatoes. Bring the mixture to a boil, then reduce to a simmer.
Cover and cook for 20 to 25 minutes until the squash is tender.
Season with salt and pepper to taste before serving.