In a large Dutch oven, heat 1 Tablespoon of oil over medium-high heat.
Once your oil is hot add in ground meat and cook breaking up with a wooden spoon until nicely browned, about 6-8 minutes.
Add in garlic and sauté until fragrant, about 1 minute.
Set cooked meat aside on a plate.
In that same heated pot, add in remaining oil and all vegetables, then sauté the veggies until they carmelize a bit, about 5 minutes.
Add browned meat back into your pot along with the roasted tomatoes, marinara sauce, broth and dried oregano. Sea salt and pepper to taste, about a 1/4 teaspoon each.
Stir to combine well.
Bring your chili to a boil, and once it starts to bubble reduce the heat and let simmer on low until thick and bubbly, about 30-45 minutes.
Once the chili is ready, add your pizza toppings.
Start with an even layer of shredded mozzarella, then arrange the pepperoni slices and sprinkle with parmesan cheese as shown.
Cover with a lid and continue to cook on low until cheese is nice and melty, about 3-4 minutes.
Serve while hot and enjoy!