With a mechanical engineering background Dale's early experiences began in manufacturing operations. He later moved into process engineering and finally product development where he spent much of his time on computers doing product visualization and CAD/CaM. This would finally lead him into the animation and CG industry.

In 1995 Dale founded Raintree Media, a Miami based studio specializing in branded entertainment for Fortune brands. Raintree produced brand interactive entertainment for many of the nation's largest companies. Dale built the company providing CG animation, commercials, videos and interactive CD's.

In 1997 Dale wrote, produced and directed the Mac/PC game "Lost Island of Alanna", promoted by Coca-Cola. Lost Island of Alanna was awarded Best Free Computer Game of 1998 by PC Gamer Magazine and had a total distribution of 2 million CD's. In 1998 Dale launched another PC title Time Tremors and in 1999 he again gained acclaimed success with the award winning online game "Powerade NHL Challenge". Dale also designed and produced a non-released game title for the Microsoft Xbox Console.

Finally, in 2001 Dale began working independently as a strategic business and production consultant though he continued to produce branded entertainment; most recently in 2004 for the Miller Brewing Company and Playboy Magazine.

In addition to working with Fortune Brands, over the last decade Dale has also worked with Madison Avenue advertising agencies providing business integration consulting and derivation concepts. Companies include Bates Advertising, CCG, DVC Worldwide, McKinney & Silver and The GEM Group.

In 2001, as the CEO of award winning studio Raintree Media, Mr. Leary was presented the Award of Excellence by Ernst and Young for exceptional entrepreneurial achievement and at the age of 32 was appointed to the Florida Business Advisory Council.