Twitter/Square's Jack Dorsey in March 2011. Credit: Helena Brown/Wired.com

George Carlin once joked that “advertising sells you things you don’t need and can’t afford that are overpriced and don’t work.” Carlin wasn’t thinking about the internet, but it’s amazing that despite the reliance of social media and the web on advertising revenue, most digital advertising still works that way: obnoxious, unwanted, uninteresting, easily ignored. The more advertising that looks like that, the more the idea of advertising itself becomes disreputable and unwanted.

Jack Dorsey, co-creator of Twitter and Square, thinks we can avoid this problem by building businesses based on “serendipity.” On Sunday, at Techonomy 2011, Dorsey explained his stance in an interview with David Kirkpatrick:

I don’t necessarily think of it as advertising in the traditional sense. It’s, how do we introduce you to something new? How do we introduce you to something that would otherwise be difficult for you to find, but something that you probably have a deep interest in discovering? It’s really just another algorithm, or it’s just more curation, but it’s something that you would find delight in anyway.

Dorsey touches on something here that’s complex but profound: how do you engineer a system that, while not literally random, produces the feeling of serenidipitous discovery, meaning emerging from what seems like meaninglessness?

The answer seems to be in “delight,” a word Dorsey uses often for both Twitter and Square. For Dorsey, technological delight seems to be primarily driven by three factors:

1. Capture user intent. On Twitter, “all of that following, all of that interest expressed, is intent. It’s a signal that you like certain things,” Dorsey says. In “promoted tweets, promoted trends and promoted accounts… you actually see introductions to content, to accounts or to topics that are deeply meaningful to you, because you’ve already expressed interest, you’ve already curated your timeline. And it’s a delightful experience; It feels good.”

   The best example of intent-driven advertising, and a model for Twitter revenue generation, is Google AdWords. When it first launched, Dorsey says, “people were somewhat resistant to having these ads in their search results. But I find, and Google has found, that it makes the search results better. It makes search better. Because [by searching], you are expressing intent again. It’s something that you’re looking for. It’s not a typical banner ad, which is just broadcasting.”

2. AdWords also works because it’s a natural part of the system. You perform a search in order to get results — some of those results come in the form of advertising. With Twitter, says Dorsey, “we wanted to build a business model, we wanted to build a monetization strategy, that felt like it was part of the network… So we have three [promoted] products: the accounts, we have the trends, and we have the tweets. But all three are things that people see every day. And they actually bring more meaning and more definition to whatever you’re looking at.”

   Felix Salmon touches on a similar idea in his short history of (and manifesto for) media advertising when discussing magazine ads:

   Leaf through a glossy fashion magazine like Vogue, and you’ll find dozens of pages of ads at the front of the book, with basically zero editorial content to break them up. If advertisers thought that readers only looked at ads insofar as they were adjacent to editorial, then they would ask for placement opposite editorial. But that’s not what happens: the ads all cluster at the front, the editorial gets relegated to the back, and readers spend more time looking at ads than they do looking at editorial features. In fact, the most avid readers of the editorial shoots are the advertisers, who use them for ideas when they’re planning their next campaign.

   Great magazine advertising doesn’t interrupt, compete with or attach itself to content: it complements and co-exists with it. It’s delightful.

3. Finally, Dorsey says, “what matters most is the user experience. If the user experience fails, then we have the wrong model. But our users have shown — and the advertisers [who] keep coming back — that it’s working, that it is engaging, that it is useful, and that it is delightful.”

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