Boil the Potatoes: In a large pot, add chopped Yukon Gold potatoes and cover them with cold water. Bring to a boil over medium-high heat and cook until fork-tender, about 15-20 minutes. Drain and let sit to steam and dry out before mashing.

Prepare the Cowboy Butter: In a medium saucepan, melt salted butter over medium heat. Add minced garlic, paprika, Worcestershire sauce, green onions, black pepper, and red pepper flakes. Whisk until well combined, cooking for 2-3 minutes until aromatic.

Cook the Steak Bites: Season steak with salt on all sides. Heat a skillet over medium-high heat, drizzle in olive oil, and add steak cubes. Sear for about 2-3 minutes on each side until browned and medium-rare.

Mash the Potatoes: Return drained potatoes to the pot over low heat, adding heavy cream and salted butter to taste. Smash until creamy, season with salt if needed, and keep warm.

Assemble and Serve: Place steak bites in a dish and drizzle with cowboy butter. Serve smashed potatoes on the side.