The phrase “branded entertainment Web series” typically brings several thoughts to mind. Such as: “awful” or “no one watches them” or “a 20-minute webisode about salad dressing—really?”
So 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. The series, sponsored by Hiscox , features a fictional tech startup competing for funding from a mystery investor.
Last season, Leap Year featured name actors such as Julie Warner (Tommy Boy) and Craig Bierko (Damages). The show generated five million views over its 10 episodes, despite not having the backing of a major media company.
This time around, Eliza Dushku  of Buffy the Vampire Slayer and Tru Calling fame, as well as Steven Weber (Wings, The Shining) will appear in several episodes, the first of which debuts today on Hulu. Each episode will be 20 minutes in length, compared to eight minutes last year.
How do you attract Hollywood talent to branded entertainment? Or a more pertinent question is, how did you make it not suck?
“The difference here is, this isn’t a product oriented show,” said Hunter Hoffmann, head of U.S. communications at Hiscox. “There are only so many ways you can go with that. With this show, people were attracted to it for its entertainment value.”
Indeed, while Hiscox did create several companion videos featuring interviews with entrepreneurs like Mashable founder Peter Cashmore, Leap Year was developed to be a traditional scripted drama/comedy evoking startups' lives and themes—highly relevant in today’s economy.
“We have a client that values the importance of storytelling but at its core, Leap Year is a celebration of entrepreneurship,” said Wilson Cleveland, executive producer, CJP Digital Media (Cleveland also stars in the show). “I think we strike a nice balance between maintaining authenticity where it counts and being entertaining—which is critical when the brand's goal is to amplify credibility and demonstrate experience in areas relevant to specific audiences.”
Hiscox is planning an extensive online campaign tied to the new season, including Web video, display and search ads. “Business insurance can be one of those vague areas, and this has really helped us with our brand awareness,” said Hoffmann.