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Heat 3 Tbsp. oil in a large stock pot or Dutch oven over medium-high heat. Once hot, add onions; cook 6 to 7 minutes, until soft. Stir in tomato paste, garlic, fennel seeds, and chili flakes; cook 3 minutes, stirring occasionally, until the tomato paste turns brick-red and begins to caramelize.
Add tomatoes and salt; stir to combine. Simmer 8 to 10 minutes, until tomatoes start to break down and release their juices.
Carefully transfer tomato mixture to a high power blender. Add silken tofu, 1/2 cup fresh basil leaves, and 1/2 cup water. Blend on HIGH speed until smooth and creamy, about 1 minute. With blender running, slowly stream in remaining 1/4 cup olive oil. (Note: If your blender is not large enough to hold the full batch of soup, blend the tomato mixture in two separate batches.)Pour blended soup back into pot and reduce heat to low.
Prepare Zesty Tomato-Corn Salsa by combining cherry tomatoes, corn, and 1/4 cup chopped basil in a medium bowl. Stir in red wine vinegar, 2 Tbsp. olive oil, and a pinch of salt.
Ladle soup into 5 bowls, and spoon salsa overtop. Finish each bowl with a light drizzle of olive oil and cracked black pepper.