Make the chili powder; place the chilis in a cast-iron skillet and toast over medium heat, turning periodically, until very fragrant, about 3 minutes. Remove to a plate and cut into small strips with scissors once cool. Meanwhile, toast cumin seeds in the hot pan, stirring, until fragrant, about a minute. Transfer to a small bowl and let cool. Using a clean spice grinder or coffee grinder, or mortar and pestle, grind chilis into powder; you will likely need to work in batches. Do the same to the cooled cumin seed, as well as the Mexican oregano if necessary. Stir in garlic powder and reserve. The mix will likely not be as fine as store-bought chili powder, nor does it need to be.
Set a large Dutch oven over medium heat. Once hot, stir remaining cumin seed until fragrant, about a minute. Crush as above, and set aside. Increase heat to high and add 2Tbs of Harvest Olive Wood-Smoked Olive Oil. Working in small batches, cook beef until nicely browned on all sides. Transfer batches to a bowl with a slotted spoon, adding more oil if necessary between batches.
Reduce heat to medium, and cook onions in reserved oil and beef drippings for about 10 minutes or until they are soft and lightly browned. Add crushed cumin, reserved guajillo chili powder, paprika, Mexican oregano, thyme, garlic, a good pinch of Kosher salt, and a few grinds of fresh black pepper; cook, stirring, for about a minute or until fragrant. Add broth and beer and scrape up any brown bits with a wooden spoon before adding tomatoes (breaking up with the back of a wooden spoon if necessary), guajillos, and beef. Increase heat to high and allow to come to boil, then reduce heat to low and add chocolate once a gentle and consistent simmer has been reached.
Cover pot partway and continue to simmer at least 2 hours, or until beef is very tender; like most stews, the longer the better, although you may need to add splashes of water to keep it from drying out. Remove stewed guajillos before serving.
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