Wilson Cleveland Talks To NMR About Leap Year Season 2

With four winning nominations from the 33rd Annual Telly Awards and a season premier trailer debuting at Mashable Connect, season two of the original web series “Leap Year” is off to a great start. The second season of “Leap Year” begins Monday, June 18, on YouTube, Hulu, and Mashable.

“Leap Year” shadows five friends as they attempt to start their own tech company while struggling with funding, relationships ,and the dangers of startups. “Leap Year” is written and directed by the Baranovsky brothers of Happy Little Guillotine Films. Bermuda-based specialist insurer Hiscox funds the web series with production by CJP Digital Media.

We got a chance to talk with Wilson Cleveland, who produces and created “Leap Year” in addition to playing Derek Morrison on the web series. Cleveland is also the founder of CJP Digital Media, a new media studio specializing in brand-sponsored online programming.  We spoke with Cleveland about the creative process behind “Leap Year,” working with Mashable, and what we can expect from the upcoming second season:

Matthew Manarino: Leap Year and CJP Media both promote brand-sponsored programming. Does including brands and sponsors in your work ever compromise the creative process of writing and filming “Leap Year”?

Wilson Cleveland: CJP is a marketing/PR firm, so we take a different approach to the concept of ‘branded entertainment’ than an ad agency might. As a marketing discipline, PR exists to communicate or amplify a client’s story either directly or through the media to shape perception. That allows us to focus on the elements of good storytelling versus how to showcase a specific product without being distracting. We produce “Leap Year” for Hiscox Insurance, and they couldn’t be a more ideal partner because they understand the strategy is to focus first on telling a great story. Keep the brand out of the content itself and your audience will be more receptive to the advertising message you surround the content with.

Matthew: After the award winning first season of “Leap Year,” how has the bar been raised for season two, and do you think this season will meet those expectations?

Wilson: The bar has been raised quite a bit, actually. For starters, we increased the length of the episodes from 8-10 minutes to a more TV-length 20-22 minutes. We did that for a few reasons: 1. The request we received most often from fans and viewers last season was to make the episodes longer. 2. Hulu is our primary distribution partner and audiences who typically visit Hulu online or subscribe to Hulu Plus are used to watching longer-form series. 3. Longer episodes equates to more time spent by the audience engaged in content produced for the brand.

Matthew: Being one of the original series streaming at Mashable, how have you found the experience of porting “Leap Year” to this new project by Mashable?

Wilson: Mashable is a perfect distribution partner for “Leap Year.” Their native audience is precisely on target with the audience Hiscox has set out to engage with “Leap Year.”

Matthew: What can we expect from this season of “Leap Year”?

Wilson: You can expect the tone to get a bit more serious. We still have plenty of Vlad and Yuri’s quick-wit comedy, but in order to give justice to the real entrepreneurial experience it can’t be played for laughs 100% of the time. This season, these characters deal with realities every startup founder faces, like balancing work and family; threats from competitors, and issues over money.

You can check out the trailer for season two of “Leap Year” below.