In 1986, Heyward and other investors bought the DIC Enterprises from CLT. Heyward sold a majority interest in DiC to Capital Cities/ABC in 1993. In 2000 with two venture capital firms, Heyward re-purchased DIC Enterprises. On June 20, 2008, Hewyard announced that he was selling DIC Entertainment to Cookie Jar Group.
In 2009, he founded A Squared Entertainment (A2) with his wife, Amy. In 2013 the company merged with Genius Brands to form Genius Brands International, with Heyward serving as CEO.