How 'Leap Year' built a web show for social savvy TV actors

By Natan Edelsburg Comment

Wilson Cleveland isn’t the average show creator and actor. His career includes being a publicist, working at Goldman Sachs and now creating, writing and starring in Hiscox’s ‘Leap Year‘ — which premieres its second season today. The Hulu show — produced by CJP Digital Media and Happy Little Guillotine Films — “follows the founders of startup C3D as they scramble to build and launch their ‘Skype™ with holograms’ technology.” We spoke to Cleveland about the roles he created and how he’s using the startup world and social media industry to spread word about his show.

We caught up him at #MashCon where he was premiering a trailer of season two and filming interviews for My Startup Story, the companion editorial element they produce for Hiscox that covers top entrepreneurs’ startup stories. TVPlus‘s Randy Shiozaki and Storify‘s Burt Herman are among the interviewees. Throughout season one, Cleveland also smartly incorporated well-known tech and social media people into the storyline, a tool that also helped build buzz around the show.

One of the biggest TV actors that will show up in season two is Aaron Sorkin-favorite, Josh Malina. Malina, who made a name for himself on Sports Night, has most recently been on ABC’s Scandal. Malina is the only TV actor I’ve come across who’s actively using GetGlue as well. Most recently, he was watching Veep. We spoke to Cleveland about plans for his show to be on traditional TV and how he’s attracted TV talent.

Lost Remote: Are you trying to get the show on linear TV? If so, why?

Wilson Cleveland: I’ve gotten that question a lot since we announced that Leap Year season 2 episodes would run closer to the 22-minute mark. We’re fortunate to have been presented a few initial opportunities, primarily for international television but it’s never been an intentional goal. As long as there’s benefit for Hiscox, which owns Leap Year, any opportunity is welcome and appreciated.

LR: How did you get TV actors like Josh Malina to participate?

Cleveland: I think the stigma surrounding online projects has dwindled significantly among film and TV circles. In fact, every Leap Year guest star this season known for their film or TV work had already either created their own or been part of an original online series. Actors are drawn to good material. I credit our writers Vlad and Yuri Varanovsky for consistently creating stories and characters specifically for actors like Josh Malina, Emma Caulfield, Eliza Dushku, Craig Bierko, Steven Weber and Julie Warner want to play.

LR: How do you use social for the show? Do you think social TV is important?

Cleveland: Social is a huge component of how we built and continue to build the audience for Leap Year. The show and its presenting sponsor, Hiscox Insurance has an active presence on every major social platform. Leap Year doesn’t have an advertising budget a typical network series has, so social is as critical for discovery as it is for audience engagement and development. Of Leap Year’s 40k+ social media followers, 66% were self-identified as being among Hiscox’s target audience.