
Add 2 tablespoons of the olive oil to a large, heavy-bottomed pot with a tight fitting lid over medium-high heat (I use a 5-qt Dutch oven). Use paper towel to pat the surface of the beef as dry as possible, then season generously with about 2 teaspoons kosher salt and ground black pepper as desired. Once the oil in the pot is shimmering hot, carefully add in the seasoned beef – work in batches as needed to avoid overcrowding the pot. Cook 2-3 minutes per side, until nicely browned. Transfer the browned beef to a plate and set aside.
If needed, add the remaining 1 tablespoon of olive oil to the same pot used to brown the beef. Once the oil is hot and shimmering, add in the yellow onions, bell/poblano peppers, and jalapenos, seasoning with 1 teaspoon kosher salt and ground black pepper as desired. Stir to combine. Cook, stirring occasionally, until softened and fragrant, about 5 minutes. Once softened, add the garlic and tomato paste to the pot, stirring to coat the veggies. Cook until fragrant and browned, about 2-3 minutes longer.
Nestle the browned beef from Step 1 into the vegetables, then add all remaining ingredients into the pot – the chili spices, apple cider vinegar, pure maple syrup, Worcestershire sauce, diced tomatoes, tomato sauce, and beans. Stir in the beef stock – start with 1 ½ cups and increase to 2 as needed or desired. Bring the mixture to a boil, then reduce heat to maintain a steady simmer. Cover and simmer 2 ½ – 3 hours, stirring occasionally, until the beef is fall-apart tender. The braised beef chili will be ready once the meat is fork-tender, or you can easily break it apart with a wooden spoon.
Portion the braised beef chili into bowls, serving with your favorite chili toppings: shredded pepper jack or cheese of choice, smashed avocado or guacamole, chopped cilantro, thinly sliced jalapeño, crushed tortilla chips, etc. Enjoy!