Cauliflower 'rice' is a staple of the paleo diet. It seemed weird to me at first, but every so often, it's a fun alternative to rice. Again, if you don't think it's for you, just make a pot of rice (1/4 cup / serving). Otherwise, give it a try - you just might like it. Plus when you smother it in this chili, you won't even notice that you're eating a vegetable-based rice.
Cauliflower - Chop off florets. Pulse in a food processor until it reaches a rice-like consistency. (Can be done up to 4 days ahead)
Butternut squash / Bacon / Garlic / Red onion / Green onions - Prep as directed. Keep white and green parts of green onions separate. (Can be done up to 3 days before)
Butternut squash - Toss with olive oil. Salt and pepper generously and roast for 20 to 30 minutes in a 400F (204C) degree oven. (Can be done up to 4 days ahead)
Ground beef - Season with salt and pepper. (Can be done up to 1 day ahead)
Tomatoes - Drain.
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Heat a Dutch oven over medium-high heat. Add in bacon pieces and saute until bacon's browned on the edges. Add in onions, garlic, and white parts of green onion and saute until softened, ~3 minutes. Next add in beef, breaking up into smaller pieces with a wooden spoon. Season to taste with salt and pepper.
Add in cumin, paprika, chili powder, apple cider vinegar, and tomatoes. Stir to mix. Bring to a boil and then simmer for 10 to 12 minutes, letting flavors build and absorb.
Place cauliflower into a microwave-safe bowl. Microwave for 5 minutes, stirring midway through. Mix in butter and season to taste with salt and pepper.
Serve chili topped with butternut squash and chopped green onions. Spoon over your cauliflower rice.