Web Wizards, What Awaits You? Untold Riches or Jail?

Digital makes everything bigger. It can amplify an old college social introduction tradition into a world-changing social network, a taxi dispatcher into a multibillion-dollar Wall Street darling. It has the magic ability to transform geeky math-er-bators into pop-culture billionaires. But, as we learned a fortnight ago, its power to turn a cool, algorithmically inspired idea into an overnight Web phenomenon can also send you to jail for the rest of your life.

Here’s a prison trivia question: What do convicts Charles Manson, Sirhan Sirhan, and Mark David Chapman have in common that newly sentenced convict Ross Ulbricht does not? Answer: The killers of, respectively, Sharon Tate, Robert Kennedy, and John Lennon all are eligible for parole. But when Ross Ulbricht (above), the notorious “Dread Pirate Roberts” who founded the Silk Road marketplace, was sentenced on May 29 for drug trafficking, conspiracy, and operating a criminal enterprise, no parole was in the offing. The 29-year-old engineer got life with no chance of release—times two—plus sundry other decades behind bars. For creating a website. A Dark Web website that trafficked millions of dollars worth of heroin and methamphetamine, to be sure, but a website nonetheless.

Ulbricht amassed a true pirate’s treasure in Bitcoins, and knowingly created a conduit for dealers, but he never sold drugs himself. If I’m Jeff Bezos, I’m not feeling very comfortable with Manhattan Judge Katherine Forrest’s draconian dispatching of Ulbricht. Who handles more third-party transactions on the Web than Bezos? Who knows, 10 or 15 years from now, what will be considered contraband materials and illegal services by ours or any other government? What if some of the fine art Amazon brokers turns out to be something stolen by the Nazis? What if ISIS or Pat Robertson take control and Match.com is suddenly interpreted as a worldwide prostitution ring?

Digital makes things bigger, and makes them live on in cyber-perpetuity, too. Societal attitudes change, but the data remains forever and is, therefore, constantly subject to new interpretation.

One of the biggest crises that Internet retailers face is the issue of remote sales tax collection being debated by governments municipal, state, and federal. But could a harsher tax be lying in wait for them? In protesting his client’s sentence, Ulbricht’s attorney, Joshua Dratel, mentioned another Silk Road defendant, Peter Nash, who pled guilty and was released after 17 months in jail.

“I’m not suggesting Mr. Nash and Mr. Ulbricht’s sentences should be the same. But this is 17 months versus life,” Dratel said. “The only difference is that Mr. Nash pleaded guilty and Mr. Ulbricht exercised his constitutional right to trial. You could call it a trial tax.”

Digital make things bigger, and digital itself keeps getting bigger and bigger. How can one be sure that the wonderful idea she has for a retail website—an idea hatched to give her family a secure future—won’t somehow metastasize beyond her control and transform into something she’d never imagined?

In a pre-sentencing letter pleading for leniency, Ulbricht wrote, “I believed at the time [of founding Silk Road]  that people should have the right to buy and sell whatever they wanted so long as they weren’t hurting anyone else. I’ve learned since then that taking immediate actions on one’s beliefs, without taking the necessary time to really think them through, can have disastrous consequences…I learned from Silk Road that when you give people freedom, you don’t know what they’ll do with it.”

Oh, what a tangled web we weave when first we practice to receive contraband.

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