The key to this is climbing on a building. Find a large, tall building and climb. You may need to punch a window or two to get people to appear.
Grab someone using
. Then push
+
to throw the person in the air. Move to be in a place where you can catch them using
again. Keep repeating until the achievement unlocks.
You may also want to push
to change your perspective to as wide as possible. This will make the person easier to catch.
Doing this in the first or second story mode level will be the easiest, as the threat level will be low and you won't have to deal with helicopters.