It is a matter of good business. You target the customers (members) you want and then you aim to maximise revenue. So, Jack has to judge from the members he would probably preffer not to have here, which ones would not pay the $100. Also how many members he might loose, that he would like to keep, from the new multi times increased rate. Final thoughts, how this would work for potential members, would they pay the fee for something they can not see/judge for a lets say a "test" period? Always accounting also for Jack's reputation.