Chicago real estate mogul Sean Conlon lends his capital and mentorship to novice property flippers struggling to pull troubled projects back into the black. In this series premiere, Sean partners with Berta, a real estate broker who started flipping condos on the side. She invested all her savings into her latest project, a large 1912 two-unit row house. But unreliable partners and her own negligence led to little progress after nine months. Now, Berta is left to right the mistakes her partners made while trying to dig herself out of financial ruin. Will Sean be able to help this sinking ship, or will Berta prove to be too inexperienced to stand at the helm?

Sean teams up with Mark and Bryan, two best friends who built a business based on quick and easy flips. But now they’ve run into a problem. They bought the wrong house at auction and it’s much bigger and in much worse condition than they planned for. Will Sean be able to prevent this one mistake from bringing down the duo’s whole business?

Sean teams up with Larry and Chantill, a couple from Chicago's South Side who see real estate as their ticket to success. Their latest flip was supposed to be a major moneymaker, but they put their trust in the wrong people and are now in dire straits. Will Sean be able to salvage the project or will a dramatic confrontation put everything at risk?

Sean meets Kai and Bernette, a duo whose reckless house-buying spree has left them cash-strapped. Though once-successful flipper Bernette was hit hard in the housing crash of 2008, the couple has re-entered the real estate market with little regard for past mistakes. Can Sean teach them how to manage their money or will history repeat itself?

Caren and her husband Nic have a good track record as home flippers, but their first attempt at building a house from the ground up is causing them serious problems. The couple have only just started construction on the elaborately designed, luxury four-bedroom house, but Sean is shocked to learn that it's already $100,000 over budget. Caren, an award-winning interior designer, seems reluctant to compromise on any of her big ideas or her costly finishes. Sean sets out to get the project back on track but teaching Caren to build for profit, not just for prestige, proves a real challenge.

Marcello, an ambitious young developer with a checkered past, is racing to make a fortune in Chicago Real Estate. His latest project-an abandoned hundred-year-old Graystone-is under threat of demolition. He desperately needs an injection of cash and expertise to help save it. Sean thinks the house has enormous potential and there's a big profit to be made from flipping it. However, he soon discovers that this beast of a renovation may be the least of his challenges.