Too Much Chutzpah?

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How much chutzpah is too much chutzpah? Somehow, I doubt it's a question that Jake Sasseville has ever asked himself. Sasseville is the 22-year-old producer of The Edge with Jake Sasseville, a Manhattan-based late night talk show that debuted last February on 39 ABC affiliates right after Jimmy Kimmel Live. If you want to know how a kid from Maine muscled his way onto late night TV, watch the show here, because that's what The Edge is basically about — it's a show within a show, where viewers not only watch Sasseville interview celebs like Katrina Bowden of 30 Rock, but also witness his struggle to keep his fledgling show on the air by cajoling sponsors like Overstock.com to give him an advance of $30,000 so that he can make payroll (they did, btw). Companies like Overstock, Ford, Bed Head, Denny's, and Air Tran like Sasseville because his whacky and unscripted show speaks to a large and important demographic — 19 to 30-year-olds — and because he integrates sponsors into The Edge in a way that's, well, edgy.

Now, he's set his sights on State Farm as a potential sponsor, but there's just one problem: the suits in Bloomington, IL are reluctant to open their hearts and their wallets. So how far do you go to land a piece of business? "I don't like being told no, so I wanted to get in their back yard and gently bang on their door," says Sasseville. So he went to Bloomington a couple of weeks ago, talked his way into co-hosting a local early morning show, HOI News Daybreak, and announced on air Tuesday that he was holding an open casting call for a new character on his show: State Farm Dude (or possibly Dudette). Think Rupert Jee on Letterman.

Yesterday, he was back on the morning show with clips of the auditions. So what was State Farm's reaction? Sasseville hasn't heard from them yet, but he's optimistic. Earlier this week, before the broadcast, State Farm execs who had heard the buzz about his upcoming on-air appearance, agreed to hear his pitch. "I think I dealt with all their objections," says Sasseville. And that included an offer to cast an actual State Farm agent as State Farm Dude. So will Sasseville's antics pay off? Will State Farm Dude play a major role in season two of The Edge? Stay tuned.

In the meantime, though, what's your take on how much chutzpah is too much chutzpah? What's the craziest thing you've ever done to land a new piece of business, and was it successful, or did it backfire?

Donna Fenn is the author of Upstarts! How Gen Y Entrepreneurs are Rocking the World of Business and 8 Ways You Can Profit From Their Success (McGraw-Hill, 2009), about ways Gen Y is changing the entrepreneurial landscape. @donnafenn