n a large mixing bowl, toss cubed meat with fine sea salt and ground black pepper.
Heat 2 tablespoons olive oil in a large Dutch oven or stock pot. When oil is hot, add 1/3 diced beef. Cook 3-4 minutes, tossing along the way, until all pieces are a uniform, light brown. Remove to a paper towel lined plate. Discard excess liquid in the pot, but do not rinse out browned bits clinging to the pan.
Repeat this process twice with the remaining diced beef. After removing the last of the excess liquid, add browned beef back to the hot pot and add ground cumin. Stir and continue to brown for an additional 3 minutes.
Add dark beer to deglaze the pan and loosen browned bits from the bottom of the pot. Lower heat to a simmer. Allow beer to absorb into the browned beef. Simmer until almost no liquid remains. Remove beef from the pot. Set aside.
Add remaining 2 tablespoons olive oil to the Dutch oven or stock pot. Add onion. Saute until almost soft, approximately 5 minutes, add garlic, saute an additional 2 minutes.
Add jalapeno, habanero, chipotle and poblano peppers to pot. Continue to saute over medium-high heat until fresh peppers start to soften.
Add crushed tomato and beef stock. Stir and bring to a simmer for 20 minutes.
Using an immersion blender, puree the chili mixture to a smooth sauce. Add beef back to the sauce and simmer on low for at least an hour.
Before serving, stir in maple syrup.
Ladle chili into a bowl and top with sour cream and cheddar cheese. Serve by itself, over rice or with macaroni.
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