After winning a dream-home lottery, Boris is looking to invest in a business to run with his children. Arlene helps him, his son Anton, and his son-in-law Steven, make this life changing choice.

Arlene helps sisters Sheri-Anne and Charlene search for a stepping-stone business to help them towards their long term entrepreneurship goal of owning a nursing home.

Charlyn from Brampton, ON., has excelled at her job, but has stalled in her career, & is looking to become an entrepreneur. Arlene Dickinson introduces her to 3 carefully selected businesses for sale.

Arlene helps Indiana Pacers guard Cory Joseph and his sister Danielle search for a small business that will support him and his family after he retires from the NBA.