Luckily not everyone in cryptocurrency gets to see the inside of a prison cell – and not everyone who does is lucky enough to survive and make a comeback. Early Bitcoin evangelist and entrepreneur Charlie Shrem can say both about himself.
In today’s profile piece, DisruptionBanking looks at the life of a self-confessed “cowboy” who ended up an outlaw and still believes passionately in Bitcoin – even though he went to jail for it.
This Cowboy Had One Hell of a Ride…
Before we delve into Shrem’s chequered past, let’s get one thing straight: as at the time of writing, his story does not appear to be an unhappy one by any means. Worth an estimated $40 million (how much of which is denominated in Bitcoin, who can say?) and a celebrated podcast host with his fingers in (legal) pies aplenty, the crypto pioneer, 35, is doing all right.
So let’s not feel too sorry for him. Having said that, Shrem did spend two years in prison after he pleaded guilty in 2014 at a federal court in Manhattan to using his business to transmit Bitcoin to “facilitate drug trafficking,” as the U.S. Department of Justice put it.
Said business was BitInstant, a Bitcoin exchange Shrem cofounded in 2011 with Gareth Nelson that fell foul of anti-money laundering regulations. The presiding Judge Jed Rakoff found that Shrem had been “knowingly, willfully, and to some extent excitedly” involved in Silk Road, a dark web market for illegal drugs.
Guilty As Charged – But Was It Fair?
Shrem entered a guilty plea and served his time, but was it truly a fair cop? Well, that depends on whom you ask.
Technically, the law had him bang to rights. Shrem ran into trouble when he facilitated around $1 million in Bitcoin transactions for Robert Faiella, aka the “BTCKing,” who supplied the cryptocurrency to people seeking to purchase illegal drugs on Silk Road – the digital coin was at that time the only tender accepted by the site’s illicit dealers.
Faiella too received a sentence – at four years, double Shrem’s tariff – for money laundering. Both men also forfeited nearly $1 million each. If guilt by association is enough to get you banged up, Shrem unfortunately qualified.
However, it has since been noised around the crypto space that the young idealist from Brooklyn was simply victim of a far larger game, the game of money – who owns and controls it, the why and the how.
Crypto Cowboy Fell Foul of Big State
Shrem himself, while admitting to the Wall Street Journal that he “was a cowboy […] moving too fast,” has also said: “A lot of people say that I took the first shot for Bitcoin. The first person to walk through the [Wild West saloon] door always gets shot, and then everyone else can come through.”
Summarizing Shrem’s early rise and fall as a Bitcoin pioneer, Bitcoin Magazine says his story serves “as a cautionary tale about the potential dangers posed by government intervention and regulatory overreach.”
Playing the by-now-familiar theme tune of crypto-bro heroes against statist baddies, it adds: “It highlights the need for the Bitcoin community to protect the industry from policymakers who may seek to impose restrictive measures.”
Book Smarts Can Get You Through Sing-Sing
Whatever your take on that, most can agree that Shrem’s fall was a case of down but not out. He says he read 140 books while inside – assuming he served his full term, that’s an average of one every five days – and tutored fellow inmates.
Having a valuable and rare skill to share in the joint appears to have worked well for him – despite U.S. federal prisons being notoriously bad places for white-collar criminals to end up in, there are no reports that Shrem was attacked inside.
Crypto Cowboy Back in the Saddle
After getting out in 2016, Shrem picked up where he left off – less the legal imbroglios, of course. In 2019 he launched the Untold Stories podcast – if you’re wondering how successful that has been, try this for an indicator. It’s ranked in the top 1% of podcasts by Listen Notes and in 2023 rebranded as The Charlie Shrem Show.
When you get a podcast named after you, it’s usually a sign that things are going pretty well. As we said earlier, federal time or no federal time, let’s not feel too sorry for Shrem.
The Show Goes On…
His show, which has aired more than 400 times, may have brought him fame, but Druid Ventures and numerous other businesses have brought Shrem fortune. Founded in 2021, the $13 million venture capital fund is invested in more than twenty Web3 projects, focusing on infrastructure, privacy, scalability and interoperability.
Shrem remains a passionate advocate for Bitcoin and the perceived freedom from the money-controlling establishment it promises.
“We weren’t perfect,” he says of the Bitcoin Foundation he helped set up in 2012. “But we were there first. And we set the tone for everything that followed. Bitcoin gave us, for the first time, a way for one internet user to transfer a unique piece of digital property to another internet user… and nobody can challenge the legitimacy of that transfer.”
Still in Crypto!
Other cryptocurrency business ventures on the Shrem portfolio include CryptoIQ, which he founded in 2017, Crypto Investor Network, which attracted a 75,000-strong subscriber base between 2020 and 2024, and Bitcoin ATM network ByteFederal, in which he is a principal investor.
And speaking of portfolios, Shrem is also founder of Amalgamated Suncoast Portfolio, a family concern that managed crypto and other forms of equity and employs more than twenty people.
From Crypto to Hollywood
He’s also turned his hand to film-making, collaborating with Hollywood stars like Cuba Gooding Jr. Not content with appearing as himself in documentaries The Rise and Rise of Bitcoin (2014) and Banking on Bitcoin (2016), Shrem also worked as a film producer on Dark Night of the Soul and McVeigh in 2024. Another film he produced, Whiskey Run, is in post production, as is Break The Cycle, which Gooding Jr appears in.
His personal life, which he keeps private, seems to be in good working order too. Married to actress and crypto advocate Courtney Shrem, he resides in Sarasota, Florida.
All in all, not bad for a Brooklyn boy with a criminal record. And one has to wonder, compared with the real cowboys in traditional finance who tanked the global economy back in 2007, was what Shrem did really so terrible? If there is such a thing as good karma, it appears to have spoken its verdict on that question quite loudly.
#cryptocurrency #blockchain #digitalassets #Bitcoin
Author: Damien Black
The editorial team at #DisruptionBanking has taken all precautions to ensure that no persons or organizations have been adversely affected or offered any sort of financial advice in this article. This article is most definitely not financial advice.
