In a medium pot, heat the olive oil over medium-high heat. Add the 4 quartered tomatoes, 4 cloves of minced garlic, ½ teaspoon of black pepper, and ½ teaspoon of salt to the pot.
Lower the heat to medium and cook, stirring often until the fresh tomatoes bread down, about 15 minutes.
Add to roasted red pepper and cook on medium heat for another 10 minutes.
Add the chicken stock to the pot and bring the contents to a boil. Then, reduce the heat to medium-low and simmer uncovered for 5 minutes.
Remove the pot from the heat and add the contents of the soup to a blender. Carefully blend the soup until smooth.Important Note: To avoid splattering and overflowing, do this in batches. Place the blended soup back into the pot on the stovetop. Turn the heat to medium-low and slowly add in the 1 cup of finely chopped gouda cheese in small batches, ensuring to stir with a large spoon as you continue to add in the cheese.
Once all the cheese is added, slowly pour in the ½ cup of heavy whipping cream, ensuring you continue to stir.
Continue to cook the soup on medium-low heat for 7-10 minutes, stirring often, until all the cheese has melted.
Add the soup mixture back to the blender and puree for 1 minute.
Return the soup back to the pot and serve. Garnish with fresh basil, cracked pepper, and a splash of heavy whipping cream.