This trophy requires that you fail a request 50 times. Once you fail a request you will be brought to the Punishment mini-game.
You could play the mini-game (a great way to try for the Endurer trophy which requires you to gain 50,000+ point in this) while trying to achieve the trophy as well. But if you are in a rush you can just hit the start button and it will skip the mini-game and bring up the restart menu.
A great stage to boost this trophy is the Hot Stuff request in the King's Cosmos. Once the request starts just pick up as much cold stuff as you can and you will fail relatively quickly. On average it took me about 10 seconds per try.
Once your goal has been met your trophy should pop once you return back to the stage select area.
Hopefully this helps and have fun!