Being a startup entrepreneur is hard. First, you have to find and execute a great idea (or at least an idea). And second, you have to take care of all the businessy things that come along with creating and operating a company. Things like taxes, payroll, health insurance, incorporation documents, small business insurance, and other important minutia and mandatory idiosyncrasies that make the government make sure it’s okay with whatever it is you’re doing.

But where’s a startup entrepreneur supposed to learn about and acquire all these stamps, documents, and seals of approval? I have no idea! Well, except if you’re a professional services startup with 10 employees or less. Then I have some idea where you can get small business insurance. You can go to Hiscox.

The London Stock Exchange-listed insurance provider that specializes in niche areas of the insurance market (including art collections and kidnapping/ransoms) is extending its services to small businesses in the US. To market its new product, Hiscox commissioned a web series (with a low-to-mid six figure production budget).

Leap Year is a scripted dramedy that tells the story of “five friends and first-time entrepreneurs facing the highs and lows of starting a business.” Or, more specifically, five friends and first-time entrepreneurs get fired, all invest in a shared office space, and all create new startup businesses to compete for $500,000 from a mystery investor.

The program’s executive produced by Wilson Cleveland and CJP Digital (creators of The Temp LIfe, The Webventures of Justin and Alden, Suite 7, and Bestsellers) in association with Happy Little Guillotine FIlms (Yuri and Vlad Baranovsky’s digital production shop behind titles like 7-Eleven’s Road Trip Rally and Break a Leg) and Attention Span Media (the company that brought you Dorm Life and If I Can Dream).

Cleveland created the series, too, while the Baranovsky bros. took care of writing responsibilities. Yuri directed the talented cast of Happy Little Guillotine and Temp Life regulars and a few guest stars, including himself, Alexis Boozer, Wilson Cleveland, Daniela DiIorio, Drew Lanning, Rachel Risen, Craig Bierko, Julie Warner (Doc Hollywood, Crash), Mark Gantt, Guy Kawasaki, Gary Vaynerchuk and Mashable editor Adam Ostrow.

Leap Year debuts its first of 10 weekly episodes on Hulu on June 6, with a six-episode ancillary interview mini-series dubbed #MyStartupStory premiering soon after. The latter will feature successful startup founders – including pete Cashmore (Mashable), Scott Belsky (Behance), Adam Rich (Thrillist), Michael Lazerow (Buddy Media), Josh Williams (Gowalla) and David Karp (Tumblr) – discussing their own small business trials and tribulations.

I recently caught up with Cleveland to tell me how a web series marketing small business insurance to the US from a Bermuda-based London insurance provider came to be.

TF: So, how did Leap Year come about?

Wilson Cleveland: CJP has worked with Hiscox on the PR side for a number of years and was asked to present Hiscox with PR and marketing ideas to promote the launch of its Hiscox Direct service, which offers small business insurance direct and online to professional services startups with 10 employees or less.

The marketing challenge was breaking through an already competitive marketing landscape for small business services. We determined the best strategy for Hiscox to demonstrate its value proposition for startups was to prove it understood the unique risks and challenges every startup faces and could therefore mitigate those risks as a potential insurer.

Hiscox would have to authentically portray the experience of a startup and the highs and lows that follow in order to cut through the clutter. From there we came up with the concept for a series about 5 coworker friends who get fired from corporate life and and decide to make the ‘leap’ to start their own individual businesses.

TF: How did Happy Little Guillotine get involved?

WC: I’ve always loved Yuri’s writing. He wrote the 4th season of The Temp Life and the Suite 7 finale episode I was in with Shannen Doherty.  I was so impressed by the trailer Yuri and the guys from Happy Little Guillotine did for Lovemakers that I brought on that entire team to write, direct and co-produce Leap Year for Hiscox.

TF: How’d you get Guy, Gary, and Adam to make cameos?

WC: Hiscox was already working with Guy and Entrepreneur Magazine on an event but had no reason to know me at all. I took a shot in the dark and sent him an email asking if he’d make a cameo. He responded five minutes later which floored me. The man let us shoot at his house and improv’d one of the funniest lines in the whole show.

To me, Gary Vaynerchuk is the definition of a modern entrepreneur and a hero to the audience we made this show for so I wanted him on the show before we even pitched it to Hiscox. The guy is a machine and nearly impossible to schedule.  As luck would have it, he happened to be in NYC while we were shooting the second leg, for a signing of his new book, The Thank You Economy. We got him for 20 minutes. He was incredibly gracious and makes the perfect cameo later this season.

We wrote Mashable into the storyline and had their real-life editor Adam Ostrow play himself in a key scene.

Startup owners and entrepreneurs in need of insurance and/or entertainment mark your calendars for June 6, and be sure to tune in.

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