Trip was drawn to advertising long before he illustrated and eventually painted. After graduating from the University of North Carolina at Chapel Hill, he first worked as an Art Director with ad agencies Leo Burnett, Chicago, and with Saatchi & Saatchi, New York. But working with and hiring his favorite illustrators through the help of being an Art Director gave him an intoxicating look into their side of creative world. He has illustrated a number of children's books and helped develop characters for animated features and commercials.