Following short stints at CAA, and as an assistant editor on the film The Last Shot[1] he moved to Portland Oregon to work in Internet technology.

In 1995, while working at One World Internetworking, he started his first online venture, which was initially called The Bi-Weekly Business Internet Report.

[8] In 1995 Kleinman covered Internet World,[9] where a young David Filo and Jerry Yang (still students at Stanford) were publicly showing off, for the first time, their search engine Yahoo!

In January 2005 the podcast would officially launch as DVD Talk Radio with the premiere episode, an Interview with Henry Rollins.

[24] Kleinman was often called on to be a professional source for the home entertainment industry and has been cited as an expert opinion,[25][26] especially in regards to the HD format war.

[33] In 2013 Kleinman received official accreditation from the Beverage Alcohol Resource Group as "Bar Certified",[34] one of the highest certifications for a spirits professional.

[39] From late 2007 to early 2008 Kleinman appeared weekly on KNRK with a segment called "Alternative Movie Picks," showcasing indie films in theaters and on DVD.

From March 2012 to August 2012, Kleinman appeared on KPAM and the Terry Boyd Show with a weekly radio segment called "The Drink Spirits Happy Hour".

In 2011, Kleinman began freelance writing for Tasting Panel Magazine, and debuted with the piece "Pisco, Take Too" in the June 2011 Issue.