Since breaking the mold of online entertainment, Cleveland founded UNboxd, his own creative digital studio, where he produces original series for brands, networks, and companies. 

Cleveland, who also founded digital media and branded entertainment studio Unboxd, is one of the jury members for the talent section of the Adweek Watch Awards. If you want to get on his good side, you’ll probably want to emulate some of the actors he thinks are killing it online.

Wilson Cleveland is one of the most humble, yet prolific people working in digital media right now. Starting out as a film and television actor, Cleveland moved on from traditional television to carve out his own successful niche in digital video.

Consumer surveys conducted in Q3 2011 and Q3 2012 revealed aided brand awareness nearly doubled. The campaign also contributed to a 35% increase in product quotes viewed and products purchased online during the same time period.

About to wrap up their second season, this series follows the stories of a group of friends running a tech startup in Silicon Valley. It co-stars such notables as Eliza Dushku, Josh Malina, Craig Bierko, Emma Caulfield and Steven Weber. In a nod to what made their distribution medium viable, Leap Year often features cameos by real tech entrepreneurs, such as Reddit co-founder Alexis Ohanian. The Season 2 finale runs on Monday

what are the chances that a branded entertainment show produced in conjunction with a small business insurance company would work, let alone make it to Web series nirvana, i.e. a second season?  But here comes season two of Leap Year, a show which debuted last year on Hulu, YouTube and a handful of other outlets—with longer episodes, more stars and a slightly bigger budget.

Wilson Cleveland, the executive producer and star of the Silicon Valley dramedy Leap Year on Hulu and the founder of new media studio Unboxd, is this week's guest curator of TVGuide.com's recently launched mobile app.

I sat down with Wilson Cleveland, the producer and actor in the series (Derek) to get a behind the scenes look at the first season, their partnership with Hiscox, and a sneak peak at what’s to come.