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Step 1
Heat oil in a large skillet over high. Cook beef, breaking up with a spoon, until browned on all sides but not completely cooked through, 6–8 minutes. Transfer to a medium bowl with a slotted spoon, leaving as much fat in pan as possible.
Step 2
Reduce heat to medium and cook onion, bell pepper, and garlic, stirring, until tender but not browned, 6–8 minutes; season with salt and black pepper. Add chili powder, paprika, onion powder, and red pepper and cook, stirring, until fragrant, about 1 minute. Add stock, tomato purée, ketchup, Worcestershire, mustard, molasses, and beef along with any accumulated juices to pan. Bring to a simmer and cook, stirring and scraping up any brown bits, until mixture is thick and saucy (like a ragú or Bolognese), 12–15 minutes; season with salt and pepper.
Step 3
Spoon beef mixture onto rolls. Serve with chips and pickle spears alongside.
Step 4
Do Ahead: Meat mixture can be made 3 days ahead. Cover and chill. Reheat before assembling.