If Twitter's transformation from "that micro-blogging service" to publicly traded advertising titan works out, it's going to have a painful tax bill. But there's good news! Twitter is already pulling an Apple and setting itself up with Irish money loopholes.

Apple has saved over $74 billion dollars in American corporate taxes since it started moving assets to Irish shell corporations that consist of little more than an address and paperwork a few decades ago. It's simple corporate "rationality"—taxes in the U.S. are higher than they are elsewhere in the world, so large, clever firms will exercise every legal trick at their disposal to skirt these taxes and pay a much, much lower rate in Ireland. Taxes aren't really supposed to work this way, but they can, and so any company with the means—including Gawker Media—will pay the bare minimum, no matter how much navigating it takes. Ireland doesn't scream disruption, but it's made a name for itself as a Yankee corporate haven. Twitter appears to be the latest high profile tax tourist in the Emerald Isle.

Twitter's Irish outfit isn't a shell. The company employs 100 Dubliners, and is looking to expand. But a look at the documents which gave birth to Twitter in Ireland show other motives for the move there, of all places in the world.

Twitter's offices at 42 Pearse St. in Dublin are registered, for tax purposes, to a "Twitter International Company," the directors of which are either in distant California, or are Irish attorneys at Matheson Ormby Prentice, a firm that offers specialized tax-lowering service for American companies. Twitter International's "secretary," for example, is a corporate trust called "Matsack," a subsidiary of Matheson that also serves as secretary for over one thousand other companies.

A presentation prepared by Matheson, and obtained by Valleywag, touts Ireland's "favourable tax regime" as first among the country's perks for American corporations—the "flexible business and company law regime" is number two on the list. Diagrams like this one demonstrate how a shell game of holding companies and trusts lets a company like Twitter conduct business far, far away from Silicon Valley, while avoiding taxes:

This is an industry unto itself. Matheson is in the business of obfuscation, the creation of elaborate—and legal—money mazes. Twitter is its customer.

Three other subsidiaries disclosed alongside Twitter's S-1 make the maneuvering more clear: T.I. Sparrow I, T.I. Sparrow II, and Twitter Netherlands B.V.—the ingredients you need to make a "Double Irish With a Dutch Sandwich," which is an actual term that actual tax attorneys use to describe a convoluted tax-avoidance scheme. The sandwich is a classic play, the shotgun formation of money-shirking. All it takes is two Irish shells and one in the Netherlands: intellectual property and revenues can be offloaded to one of the Irish firms, bounced through the Netherlands, and then thrown to the second Irish firm (technically headquartered in the Cayman Islands or Bermuda, where tax is infinitesimal). Twitter's got all the pieces it needs—and should it ever need to bring a significant amount of cash back to the US, Apple has already petitioned Congress favorably for a repatriation tax holiday.

Unlike Twitter International Company, which is tied to an actual place of business, T.I. Sparrow I & II don't ostensibly do anything. Their only registered physical existence is the Dublin law offices of Matheson, and its directors all reside either in California or the Cayman Islands—again, aping the globe-trotting gimmicks of Google, Apple, Facebook, LinkedIn, and others. These subsidiaries don't appear to employ anyone, though they are "administered" at the notorious Ugland House of the Caymans—a property that hosts almost 20,000 companies looking to evade taxes, once described by Barack Obama as "either the biggest building in the world or the biggest tax scam in the world."

Twitter Netherlands is tied to Intertrust, a Dutch wealth management firm. It's unclear which part of Twitter Netherlands is working to make the company's advertising efforts profitable.

Twitter declined to comment on its offshore structure, citing "the SEC's quiet period restrictions" before its IPO. And, to its credit, Twitter isn't enjoying the benefits of its structural labyrinth, given that it doesn't actually make any money. But it's shrewd planning, says a corporate tax attorney we talked to: "The key to these structures is that you have to set them up when you are creating the [intellectual property]. It is almost impossible to move the IP offshore after it has been created, so it makes sense that [Twitter has] the structure in place up front." With the expectation that Twitter should, somehow, some way, turn a profit, it could funnel dollars across the ocean, from island to island, just like the big kids. Better to get it over with before Ireland cracks down. And besides—why should Twitter suddenly start paying its taxes in full now?



Read Twitter's Irish documentation below.