Grab a medium sized bowl from it's home. Dump in the flour salt and pepper and use a fork or whisk to mix together until well blended. Add in the cubed steak and toss around until every bit of red is covered in a dusting and you've got what looks like a ton of bubble gum flavored marshmallows (but don't confuse them because I don't think it would be very tasty).
In a large pot or dutch oven, heat the oil until shimmering over medium high heat. Grab some of the cubed meat, (about a third) and shake off any excess flour. Carefully add to hot oil being sure not to overcrowd the pot. Let each be for a minute or two until browned, the flip and wait. Repeat until all sides are browned. Using a slotted spoon, remove the nicely browned meat chunks and pile up in a large bowl or plate. Repeat this process until all meat has been nicely browned.
While your pot of oil is still hot, add in the onions (if it's looking a little dry, you can add in a bit more oil) and turn the heat down to medium. Give a sprinkle of salt and pepper to them now and grab a spoon and stir them a bit. Let the onions cook, while stirring every now and then until they start to turn translucent.
Once the onions have cooked down a bit, add in the bell pepper, poblano and smashed garlic (if you ended up mincing your garlic, add it in right after you add the spices, otherwise you may end up burning the tiny particles of flavor). Again, give a nice sprinkle of salt and pepper to the pot. Let it all cook down, stirring when you're not having a taste of your margarita (by the way, you should be drinking a margarita) until the peppers begin to soften (they don't need to be soft and mush because it's going to simmer away on the stove top for a bit).
In between cooking down the vegetables and enjoying a margarita, mix together your spices. Grab a small bowl and combine the chili powder through the red pepper flakes. Mix them together.
Once your peppers have softened, pour in that beautiful spice blend and stir. Give a big ol' stir to everything to make sure you've got every bit of onion and pepper and garlic coated with those fragrant spices. You want to keep it moving so you don't burn any spices. Heating the spices for a couple minutes like this will help to bloom them and bring out lots of great flavor.
After a couple minutes, pour in some of your brewed coffee (about a 1/2 cup) and it will sizzle and steam. Take this opportunity to go in and scrape the bottom of the pot with your spoon. Get every last bit up off the bottom and mixed into the coffee and vegetables. Then, go ahead and add in almost the rest of the coffee, saving about a 1/4 cup (you'll see why next).
Carefully pour the can of tomatoes in (especially if you've got white countertops). Before disposing of your can, rinse it out with the reserved coffee. Add the caffeine water to your empty can, swirl it about to clean off any tomato residue and then add to the soon to be simmering pot.
Finally, add in the beans and the chipotle peppers. Grab your plate of browned beef and add them to the pot along with any liquid that has seeped out. Combine it all nicely with your spoon and crank the heat to high. When it begins to boil, put the lid on and turn the heat down low. Let it simmer away for 2 hours, giving it a stir every now and then (if you forget, it won't be the end of the world). This will make all the delicious fat in the steak melt into the chili, the flavors will meld and your meat will turn very tender. Use this two hour window to clean up, make a pitcher of margaritas, prep any condiments you want to serve it with and chop your chocolate.
After the 2 hours are up, if you're still standing, turn off the heat and remove the lid. Sprinkle over the dark chocolate and let it melt in as you slowly stir the giant pot of chili. Taste and season with salt and pepper to your liking.
Serve with chips or cornbread, sour cream or greek yogurt, cheese, avocado, more chopped chocolate…you get the idea…it's chili.