Lucky in love the second time around, they have raised and educated eight children between them – sometimes working two jobs each to make ends meet. Along the way, saving for their own future seems to have fallen between the cracks – and now with the reality of retirement looming in the next 10 years, these two realize they have a lot of catching up to do! They have pulled together $5,000 (money that should have gone to repair Denise’s car) and are hoping for a big return to kick-start their retirement nest egg. They could play it safe and leave their hard earned savings in the bank, or they could roll the dice and hand it over to one of two, unique dealmakers who will have just 30 days to make it grow. Do they entrust the poker shark on a $500-a-ticket gala tournament where they would split the winnings? Or one of North America’s top vintage purveyors, buying and selling stunning gowns for big bucks?