Under his leadership, Rockfish experienced rapid growth and earned acclaim not only for its client work but also for incubating successful software ventures, most notably YouEarnedIt, which was later acquired by Vista Equity in 2018. In 2011, following several years of rapid expansion, Rockfish was acquired by London based, WPP, the world’s largest buyer of media.

In 2022, Kenny founded CourtAvenue, a strategically assembled group of companies operating at the nexus of digital transformation, artificial intelligence, commerce, and creative technology. CourtAvenue recently won AdWeek's Fastest Growing Agency in America and was ranked as the 58th fastest private growing company on the Inc. 500.

An entrepreneur and investor with four successful exits, Kenny’s active companies include Court Avenue.com, WeModify.com, GiganticPlayground.com, Botscrew.com, Genjo.ai and WorkTango.com.