Heat the olive oil in a large Dutch Oven over medium-high heat. Add bell pepper and sauté for 2 minutes until the peppers start to soften. Add the beef and cook until browned, stirring occasionally. Should take 3 minutes. Transfer the beef and peppers to a plate. Set aside.

In the same Dutch oven heat the tablespoon of olive oil. Add the onion, carrots and celery to the pot and sauté for 3 to 5 minutes until onion is soft and translucent. Stir in the garlic and cook for 30 seconds until aromatic.

Sprinkle the flour over the veggies and stir. Add in the Worcestershire sauce, hot sauce and season with salt and pepper. Stir well and cook for 1 minute to remove the raw flour taste.

Stir in the beef broth bring to a boil. If preferred, add a beef bouillon crumbled up for extra beef flavor. Turn the heat down to low and simmer for 15 minutes until vegetables are tender.

Use an immersion blender to blend the soup until smooth or use a blender, if needed.

Add the heavy cream, cheddar cheese, provolone cheese and stir well. Simmer for another 5 minutes, then add about half the beef and pepper mixture into the soup and remove from heat.

Preheat the oven to 400°F. Line a baking sheet with parchment paper.

Drizzle the croutons with the olive oil and season with salt and pepper. Toss to combine. Place the croutons in a single layer on the prepared baking sheet and transfer to the oven. Bake for 7 to 10 minutes until crisp and golden.

Ladle soup into bowls and top with the remaining beef and pepper mixture. Finally top with croutons and serve.