Matt Wellington yearns for a freedom that his current job and boss don't permit. He has plans to start a real estate company with his brother in their hometown of Grant City. Matt's brother, Allan, has a slight addition to the plan. Despite Matt's resistance, Allan insists on including their younger sister, Charlotte, in the company. Two years after starting, money dries up, and pressure sets in. Matt finds himself headed off to unclog toilets in rentals and patch drywall in flips because no one wants to work for him and not get paid. When the tension between the siblings becomes combustible, Matt hires Reggie Singer who is a coach for RISE. Set over four different meetings over a year, Reggie guides the Wellington siblings through their personal conflicts and business plateaus in resources, inspiration, systems, and engagement.