Cook chopped bacon in a wide skillet over medium heat until browned, 10–12 minutes.
Transfer bacon to a plate. Leave about 1 tablespoon drippings in the pan.
Soften onion and shallot in the drippings over medium heat, stirring often, 8–10 minutes.
Stir in garlic, tomato paste, smoked paprika, and red pepper flakes. Cook 1 minute until fragrant.
Deglaze with bourbon, scraping up browned bits, and simmer 2–3 minutes.
Add brown sugar, maple syrup, coffee, vinegar, and the bacon. Simmer on low, stirring often, 35–45 minutes.
Splash in water as needed to keep it gently bubbling and jammy.
Season with salt and black pepper. Adjust sweetness or tang to taste.
Pulse briefly in a food processor for a spreadable texture, or leave chunky. Cool before jarring.