Set the pressure cooker to the saute function and heat the olive oil. Sprinkle the steak tips in salt and pepper and sear them on all sides, working in batches if necessary, for about 5 minutes or until browned. Remove the beef.
Deglaze the bottom of the pot with the red wine, and scrape up any browned bits (While you’re at it, pour yourself a glass; you deserve it). Turn off the saute function and stir in all of the remaining ingredients (except the toppings). Mix well and lock the lid in place.
Cook the chili on high pressure for 25 minutes (it will take about 10 minutes for the pressure to rise). When done, carefully quick release the steam and unlock the lid. If the chili still looks a little too watery for your tastes, feel free to switch to the saute function again and let it simmer for a few minutes with the lid off.
Serve in bowls, topped with slices of fresh avocado, shredded cheese, and dollops of nonfat Greek yogurt.