Leap Year: the joys and risks of start-up life

by Bruce Kasanoff on June 7, 2011

I once raised over $1 million in venture capital with little more than 10 Powerpoint slides. That was the high point. The low point – a year later – was admitting to myself, and my employees, that our start-up was dead.

We all talk a lot about entrepreneurs and the American Dream, but the truth is more complicated than people imagine. Lots of people are entrepreneurs because they have no other option, especially over the past couple of years.

Go ahead – take a ten minute break.

This week, a new web comedy launched, called Leap Year. In a touching and funny way, it tells the story of five friends and their five start-ups.

You might recognize Julie Warner from Crash, or Craig Bierko from Damages. It’s a cut above the typical Web programming, and thankfully lacks the advertising breaks of commercial TV.

The whole series is funded by Hiscox Direct, which sells insurance to – you guessed it – small businesses. But Hiscox is wisely keeping a very low profile, and they are just visible enough on the site so you know who to thank.

A huge gaping hole in the insurance marketplace?

Being the curious and bold type, I phoned up Kevin Kerridge, who runs the Direct business. He used to run the Direct insurance business in the UK, and perfected a process for allowing small firms to obtain quotes and buy a policy online, without ever having to talk with a human being. (But you can if you want to.)

Nothing too exciting about that, right? Wrong. It turns out that until Kerridge arrived in the States, not a single U.S. insurance company sold insurance online to small businesses. None.

It took six months – the regulations are piled high and deep – but last November Hiscox became the first. The next challenge was to figure out a way to get Americans to become aware of the Hiscox name.

No selling. Just a slice of life.

Long story short, Kerridge green-lit Leap Year as a way to just get Hiscox noticed. Google searches already drive business to his online quotes site, and he wasn’t so much interested in getting more short-term sales out of the comedy as he was in starting to build a real brand.

Leap Year offers a slice of the entrepreneur’s life. It wraps the ambition, greed, excitement, camaraderie, exhilaration and terror into one touching and funny package. You care about the characters, and have a week in between episodes to think about how you got yourself into the life of a small business owner.

As a serial entrepreneur, much rings true for me:

- Wife pregnant? (check)
- Start business anyway? (check)
- Wake up sweating at 3 a.m.? (check)
- Thank the heavens above I quit my job? (check)

Life is short. Go for it.

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