This goal unlocks at level 16.
Go to Club Coco and speak to Leah Robertson. She tells you that the club isn't doing so well. Leah thinks everyone goes to Club Venus instead, because of Bobby Blueford and his entourage. You offer to help her to get Bobby Blueford to make an appearance at Club Coco, but she declines. The owner, Carl, would not be happy if he found out she told you the club isn't doing so well.
You now have the option to:
If you choose maybe later, nothing will happen.
If you want you can talk to Barry afterwards.