Trouble earning some needed cash on your web video series?  You’re not alone.  As The Wall Street Journal reports, and as Silicon Alley Insider so succinctly repeats, not even Google can figure out how to make money with web video. 

The appeal of web video advertising (versus TV) is the potentaial for dynamically placed contextuallyrelevant ads but, so far, not much has seemed to work; text overlays never strike me as particularly well-placed, and graphic overlays also apparently aren’t very effective, but “advertisers consider [pre-roll] highly effective.”

Could this possibly have been the answer we’ve been looking for?  Chris Albrecht at NewTeeVee says the re-emergence of the pre-roll is an indicator of YouTube’s impending migration to the living room.  That makes sense…after all, pre and mid-roll breaks do seem to work well for longer-form content on Hulu, and they’re not even that obtrusive.

YouTube’s (and others’) difficulty generating revenue around video content represents technological and institutional barriers, not a medium unsuitable for advertisers.  A recent survey of Diggnation viewers shows just how powerful niche video content can be for advertisers: 100% of viewers recalled a single sponsor, 93% could name 2 or more, and 48% purchased a product or service, CEO Jim Louderback recently noted via email. Remember the preroll before last Revver video you watched?  Who advertised on the last TV show you watched? 

Monetization of web video content is not quite as straightforward as it has become for most of the web, but innovation that appeals to creators, advertisers, consumers and the not-evil overloards is soon to emerge.  In the meantime, there is a growing opportunity in linking specialized products to targeted video content.

Dynamically inserted is the future of video advertising.  Creative integration of relevant sponsors is the big short-term opportunity.

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