Use thinly sliced Inside Round Steak that you tenderize on just one side. Look for these pre-cut thin steaks at the meat counter. Use jarred roasted red peppers for the roasted red pepper strips in the recipe as a shortcut.
In large pot of boiling salted water, blanch rapini until wilted, about 4 minutes. Drain thoroughly. Let cool slightly and coarsely chop. Add to hot large non-stick oven-proof skillet; heat until water has evaporated. Add 1 tbsp of oil and garlic; cook, stirring, over medium-high heat, until garlic is softened about 2 minutes. Set aside.
Tenderize each steak by pounding on one side with meat mallet or heavy fry pan. Spread one side of each steak with about 1/4 tsp of anchovy paste. Divide rapini evenly among each beef steak. Sprinkle each with breadcrumbs and grated Parmesan. Divide roasted red peppers and green olives evenly among steaks.
Roll up each steaks like a jellyroll and tie each with 2 or 3 pieces of butcher twine. Season each lightly with salt and pepper.
Heat remaining oil in pan used to cook the rapini; add beef bundles. Cook over medium-high until golden brown, about 4 minutes. Turn bundles and transfer pan to 400°F oven; cook, turning once, until digital instant read thermometer inserted inside beef bundles reads 140°F, about 12 minutes. Let stand for 5 minutes before serving.