We follow the story of Rashard Johnson who was arrested and incarcerated for breaking and entering at only 18 years old. Today, Rashard wants to provide for his young daughter and build a new tiling business. With the help of entrepreneur and business creator Brian Hamilton, Rashard learns how to manage his finances. He also learns valuable marketing lessons from local business owner Lawrence Carpenter. Rashard is able to conquer his fear of rejection and show off his tiling skills.

We follow the story of Derek Francis who got tangled up with the wrong crowd and was incarcerated for possession. Today, Derek has reformed his life, found a new fiancée named Jessica and wants to start a mobile auto repair business. With the help of entrepreneur and business creator Brian Hamilton, Derek develops his business ideas and discovers new ways to retain customers. He also learns valuable marketing lessons from media consultant Joe Woolworth.

We follow the story of Claudia Shivers who was incarcerated for tax fraud. Today, Claudia has learned the error of her ways, repaired broken relationships and wants to take her new coffee business to the next level. With the help of entrepreneur and business creator Brian Hamilton, Claudia hopes to get her coffee into several local retail stores. She also learns valuable web marketing from media consultant Marty Martin. Through her coffee business, Claudia finally feels like her life is back on the right track. English

We follow the story of Brad Maggio who was first incarcerated at only 19 years old and has struggled with narcotics for years. Today, Brad is sober and wants to start a pressure-washing business. With the help of entrepreneur and business creator Brian Hamilton, Brad gets a lesson on how to manage contracts and customer expectations. Along the way, Brad learns how to save money on startup costs, discovers valuable marketing skills, and creates his own video advertisements with content creator JD Roberson. Brad is well on his way to realizing his dream of starting his own business.

We follow the story of Rosemarie McDonald. As a formerly incarcerated single mom, Rosemarie has struggled to provide for herself and her teenage daughter. Today, with the help of entrepreneur and business creator Brian Hamilton, Rosemarie is learning new skills to help make her online clothing business a success. Brian shows Rosemarie how to organize her inventory and he introduces her to a professional clothing designer for a crash course on how to create her own clothing. Later, Brian gives Rosemarie some helpful advice courtesy of a surprise focus group. With her confidence running high, Rosemarie feels like her dreams of financial freedom could finally be within reach.

Rashard Johnson and Brian Hamilton are reunited for the first time since they appeared together on the show for a look back at their experience. Rashard is hoping to start a new life with a new tiling business and Brian is an entrepreneur and business creator who’s helped formerly incarcerated people start new businesses. We’ll watch along as Rashard and Brian relive key moments, provide new insights, and offer behind the scenes commentary on what it takes to build a small business from nothing.