Preheat oven to 425 degrees. Bring a medium pot of salted water to a boil. Add potatoes and boil until fork tender, about 10 minutes. Drain potatoes. Place potatoes onto a cutting board then gently smash (we used the base of a heavy glass Pyrex measuring cup) until each potato reaches about half its thickness, being careful to keep the potato intact. Drizzle about 2 tablespoons of olive oil onto a baking tray, then gently transfer each smashed potato onto the baking tray with a spatula. Generously brush the remaining olive oil atop the potatoes then sprinkle with salt and pepper. Place tray of potatoes in the heated oven and bake for 15 minutes. Flip the potatoes, season salt and pepper and bake an additional 10 more minutes the tops are until golden brown and crispy. Serve immediately.