Step 1

Place a medium saucepot over medium-high heat with the beef stock and ancho chilies

Step 2

Bring the liquid to a bubble then reduce heat to medium and simmer for 15 minutes until chilies have softened

Step 3

Transfer mixture to a blender or food processor and -- very carefully, this mixture is very hot! -- puree it until smooth

Step 4

Reserve

Step 5

While the chilies are simmering, place a large, heavy-bottomed pot over medium-high heat with 2 turns of the pan of EVOO, about 2 tablespoons

Step 6

Add the sirloin and cook until golden brown, 6-7 minutes

Step 7

Add the onion, garlic, raisins and spices to the pan, season with salt and pepper, and cook until the veggies are tender, 5-6 minutes

Step 8

Add the tomato paste to the pan and cook until deep golden brown and aromatic, about 1 minute

Step 9

Add the blended stock-chile mixture to the pot and bring the liquids up to a bubble

Step 10

While that's working, in a food processor combine the cilantro, avocado, sour cream, lime zest and juice and a splash of water (a couple of tablespoons)

Step 11

Season the mixture with salt and pepper, and puree until smooth

Step 12

Preheat a broiler or turn a gas burner on high heat and roast the poblano pepper until it is soft and its skin is charred

Step 13

Place the roasted pepper in a bowl, cover tightly with plastic wrap, let cool and chop

Step 14

Place a large skillet over medium heat

Step 15

Add 1 tortilla to the pan and cook about 1 minute per side, until it starts to blister

Step 16

Scatter 1/2 cup pepper jack cheese on top and cook until cheese is melted

Step 17

Top with the chopped poblano pepper and a second tortilla

Step 18

Flip quesadilla and cook for another minute, slice into quarters

Step 19

Add the avocado mixture to the pot of chili, stirring to incorporate

Step 20

Serve the chili garnished with toasted pumpkin seeds and a little cheese with the quesadilla alongside