Through his network he got wind of the target on his back and took drastic steps to protect himself-including ordering a hit on a former employee. He enlisted a loyal crew of allies in high and low places, all as addicted to the danger and thrill of running an illegal marketplace as their customers were to the heroin they sold. The Silk Road quickly ballooned into $1.2 billion enterprise, and Ross embraced his new role as kingpin. All the investigators knew was that whoever was running the site called himself the Dread Pirate Roberts. Spurred by a public outcry, the federal government launched an epic two-year manhunt for the site’s elusive proprietor, with no leads, no witnesses, and no clear jurisdiction.

It wasn’t long before the media got wind of the new Web site where anyone-not just teenagers and weed dealers but terrorists and black hat hackers-could buy and sell contraband detection-free. In 2011, a twenty-six-year-old libertarian programmer named Ross Ulbricht launched the ultimate free market: the Silk Road, a clandestine Web site hosted on the Dark Web where anyone could trade anything-drugs, hacking software, forged passports, counterfeit cash, poisons-free of the government’s watchful eye. Introducing Forbes Blockchain 50: Learn about the companies investing in the tech that will speed up business processes, increase transparency and potentially save billions of dollars.The unbelievable true story of the man who built a billion-dollar online drug empire from his bedroom-and almost got away with it. “That’s our burden to show this individual knew.” “You might have bitcoin on everything, but when you go to your accountant, you say, ‘Oh, I’ve never heard of bitcoin.’ Really? Every date you’ve ever been on, that’s all you talked about was bitcoin, but somehow when your accountant asks you, you forgot to talk about it?” Alford says. Ignorance of the law is not a good enough excuse, he says, especially if there are records that they kept a spreadsheet of their investments or discussed cryptocurrencies with their accountant.

The IRS is trying to get that number closer to reality by doing outreach events like EisnerAmper’s panel and urging voluntary compliance, but Alford warned that if the IRS can prove that a taxpayer willfully concealed cryptocurrency gains, they might be subject to prosecution. Alford cited an IRS summons to Coinbase in November 2017 that showed “more than 14,000 Coinbase users have either bought, sold, sent or received at least $20,000 worth of bitcoin in a given year,' but only about 800 taxpayers reported gains. Although the law requires cryptocurrency investors to report gains, not many comply.

Earlier this week, Bitwise global head of research Matt Hougan published an article about how cryptocurrency is similar and different to more traditional investments like gold, oil and good old-fashioned currency.

Silk road american kingpin