The Silk Road and other dark destinations with Eileen Ormsby

EILEEN ORMSBY

Obviously anyone could go on the Dark Web – and my handle on there is Aus Freelancer – anyone can go on there and say I’m Aus Freelancer. The only way that they can check that I really – they’re really talking to me is by having me sign a note with PGP encryption.

MATT ASHBURN

Welcome to NeedleStack, the podcast for professional online research. I’m your host Matt Ashburn and personally I like my dark web to have at least 70% cacao.

JEFF PHILLIPS

And I’m Jeff Phillips, tech industry veteran and curious to a fault. Today we’re continuing the dark web conversation as we’ve done in some prior podcasts. Now in this episode, we’ll hear from someone who has lived and breathed, and written, about the dark web for many years. So, we’re joined by true crime writer and investigative journalist Eileen Ormsby. Eileen, welcome to the show.

EILEEN ORMSBY

Thanks for having me, looking forward to talking about it.

JEFF PHILLIPS

We’re super excited. You know, I was on your website and I had read, she has shopped on darknet markets, contributed to forums, waited in red rooms and been threatened by hitmen on murder for hire sites, so I can imagine you’ve seen some pretty interesting things and some things people couldn’t even imagine. So how did you get into this topic from a journalist and from an author perspective, the dark web? And did you know what you were getting into once you got started?

EILEEN ORMSBY

Well, it sort of started for me around 2011, 2012 when I first heard about something called the Silk Road, which was the first major point-and-click dark web drugs market. I’d heard about it and I logged on to have a look at it, and it was absolutely fascinating because it was simply like an eBay for drugs. It was like any other e-commerce platform, it had little pictures of the things that you could buy and pop into your basket and take home, and the only thing was that these things were cocaine, heroin, ecstasy, marijuana, all that were ready to be delivered directly to your door by the postman. And it was a pretty fascinating story and it was still very much in its infancy at the time, so I pitched that to – as a freelance journalist, I pitched that to a newspaper, major newspaper, here in Melbourne and they took up that story, and so that was a pretty big story in, I think, April 2012, it finally went to print, and from there my editor just kept on asking for more and more dark web stories. So I started hanging around on the dark web very much every single day, but especially in that Silk Road because that was the most interesting place to be at the time, and it also had these really engaged forums where everybody that was using it was getting very, very involved and talking about not only buying and selling drugs, which you could expect, but also philosophy, they had a book club, they had a movie club, they had a lot of harm reduction stories in there. And it was, as I said at the time, a lot of people said, I came for the drugs, I stayed for the revolution; and it’s almost what it felt like at the time because it was so audacious, so different from anything you’d ever seen. The very fact that this was a place that’s on the dark web doesn’t want to be hidden, it’s not trying to be hidden. It’s actually advertising to get as many people to go there as possible. It’s not some secret place, they’re actually trying to get as many customers as possible, just like any other e-commerce platform. So that made it fascinating, considering, you know, what they were doing was very, very illegal.

MATT ASHBURN

I’m curious, Eileen, so as a lawyer turned author turned journalist, what’s your process for beginning a story? Are you out there looking for things on the dark web? Are you following leads that you found previously? Are you getting tips? What’s the process like for you?

EILEEN ORMSBY

Well, certainly in the early days, most of the time was spent on the Silk Road, and my process there was to let them all know, this is me. I’ve written this story, I’m writing more stories. If you want to tell me your story, I’d really love to hear it. And surprisingly, not surprisingly, a few people had some very choice words to say about a journalist being in their forum, but more than that, the people that ran the Silk Road – so that the staff of the Silk Road and most of the major vendors on the Silk Road – were actually very, very keen to tell their side of things, you know? A lot of them were very much into ending the war on drugs, drug reform – a lot of people, especially the buyers that were on Silk Road, their only crime was taking drugs, which in and of itself should not be a crime. And so a lot of people were very, very keen to talk to somebody who is not tabloid, who they could trust was going to give the story fairly from the side of the criminals. Plenty of people do it from the law enforcement narrative. I was doing it from the inside.

MATT ASHBURN

And some of the work you’ve done seems inherently risky. As Jeff noted, you’ve been, in some cases, even threatened by purported hitmen that are out there. When you were starting this out, did you have an idea of some of the precautions that you needed to take, did you have an idea of the risk? And are there any best practices that you’ve developed over the years?

EILEEN ORMSBY

In a lot of ways, I take a lot less precautions because the main precautions that you take when you’re on the dark web are to prevent yourself from being doxxed. And I decided very, very early in the days that the best way to prevent myself from being doxxed was just to tell everybody who I was, and then they have a choice of whether they’re going to speak to me or not, so I was always very open and honest about who I was. Obviously, I did learn all those things. I learned how to boot from Tails and get onto Tor and do all the things that most security-conscious people do, but all those things really are just to prevent people from finding out who you are, and if you’re going around and telling them who you are anyway, doesn’t matter so much. The things that I really needed to make sure that I had a handle on were things like PGP encryption, because most of the people that you’re talking to will not speak to you without PGP encryption, and that’s also the way that you make sure that you are talking to the person that you’re talking to. Obviously, anyone can go on the Dark Web – and my handle on there is Aus Freelancer – anyone can go on there and say, “I’m Aus Freelancer.” The only way that they can check that I really – they’re really talking to me is by having me sign a note with PGP encryption. So that’s very, very important for trust on the dark web, same with me. Anyone could say, “Hey, I am the Dread Pirate Roberts, I own Silk Road.” But I can only be sure that I’m speaking to the Dread Pirate Roberts if he signed a PGP note to me, so they’re the sort of things that I really needed to learn as a journalist.

JEFF PHILLIPS

Super interesting, you know, honesty is the best policy there in that, if you want to tell your story, tell it. If not – and you’ve not had any problems, I take it, since then from a doxxing perspective.

EILEEN ORMSBY

Well, other than the hitman wanting to kill me, but that was okay because what happened there was there’s always been hitman sites on the dark web, and I’ve always been 100% certain that they are fake, and there’s a very basic reason for this: the only things that it’s really viable to sell on the dark web are things that are easily transferable and things that have repeat customers. So hiring a hitman is not an easily transferable thing, it is a personal service – someone has to go out and carry out the murder. And not only that, you’re more likely than not only to want one hit, you know? There’s not many people that want hit after hit after hit, so it’s not a repeat service thing. So once you’ve paid a hitman in cryptocurrency, who you don’t know, you don’t know who this person is or where they are, what possible incentive do they have to carry out the hit? There is no incentive to do that. You’re not going to come back and be a repeat customer like the drug buyers. And so, I was 100% certain that they were all fake, including this one that bounced out onto the dark web in about 2016 called Besa Mafia. But Besa Mafia was a bit different in that they were advertising all over the clear web, especially Reddit, places like that. They had testimonials from people that had had successful hits carried out on them. But I was still 100% sure that they were not real. And the owner of Besa Mafia started writing to me and saying, look, stop saying we’re not real, we are real, we are real. But unfortunately for him, around that same time, someone alerted me to a hacked database of the back door of the Besa Mafia. And so what I had then was hundreds and hundreds of pages of all the communications between Besa Mafia and people who had paid with Bitcoin to have hits taken out, and what those communications showed me was that the owner of Besa Mafia, and at that time it was just one person, was really what we would traditionally call a Nigerian scammer, as in, not that he came from Nigeria, but he was the sort of person that would take some money and then keep on having issues why the hitman didn’t turn up, he needs more money and more money and more money and keep on dragging more money out of his victims until they finally realize they’ve been scammed and stop paying. But from that hack, I had all these email messages to and from these people, and I also had Bitcoin addresses so that you could actually see that these Bitcoin had been paid by people who genuinely wanted a hit carried out. So that’s where the danger was, was in those people – the danger was not in the owner of Besa Mafia because he very much did not want anyone to be hurt – well, he didn’t care that much, but he certainly went out of his way to make sure that people weren’t getting hurt, and I knew that. So when he came to me and he said, “look, I know who you are, you don’t know who I am, I’m going to send people around, my operatives around, to beat you up and kill you,” I knew that he didn’t have any operatives. I knew that they were very much empty threats. So I let him know that I knew that after a while. I didn’t tell him right away that I had the hack of his site, so he didn’t know. And I also was working with a cyber security researcher who was able to get into the back door and watch things happen live – and yes, we did go to law enforcement about it all, that’s another very long story, getting law enforcement to believe anything you say about an online hitman. Yeah, so by the time he was threatening me, I knew that they were empty threats, so I wasn’t too worried about it, and then I engaged with him because I really wanted to write a story with him about how, you know, he was fooling all these people, and he eventually sort of came around and we almost had a friendly relationship. We started not just talking over his encrypted messaging service, but through Google Hangouts and everything, just in real time, and he even sent me a couple of hits that were being ordered in Australia so that I could follow them up with law enforcement here. He told me what was going on in his business, told me about his family, things like that. So, yeah, it became quite surreal, I have to say. I never got to meet him, but it became quite surreal.

JEFF PHILLIPS

That is surreal. Wow. That’s what I’ve got on that as well. Now, you started with Silk Road – what did you say, that was probably in 2012 when you wrote that first article – we’re ten years later, you’ve got many books and articles related to the dark web. Anything you can say, have the people changed or the sites you’ve encountered changed, or your perception of the dark web and who’s on it, has that evolved over the last ten years?

EILEEN ORMSBY

Oh, I might say devolved. The people that are on it are different. The markets are very different. In a lot of ways, I don’t think the darknet markets would have become what they are if the first darknet market hadn’t been run by the Dread Pirate Roberts, Ross Ulbricht, the person it was run by, because it was very much run as a philosophical thing, as well as being to buy and sell drugs. And it was run very, we could say honestly on his side in that he was very much trying to make sure that everybody had a good customer, user experience, and so it ran very smoothly for a couple of years. And also he got this almost cult-like following, the people that were involved in the early days, they weren’t just there to buy and sell drugs and that’s it. And now, there are new markets. I would suspect a lot of them are being run by organized crime and they are very much just about buying and selling drugs and nothing else. No one’s there for the discussions, no one’s there for the book nights, the movie nights, anything like that. They are there to buy and sell drugs and it’s purely commercial. So, yeah, it’s definitely changed in that way, and that also obviously makes it a lot less interesting to hang around on a daily basis because there aren’t all these really interesting discussions going on. There’s other places in the dark web where you still have that, especially amongst the psychedelic community, but, yeah, as far as being an interesting place to hang out, it’s just not that anymore. But there’s more people than ever before. A lot of people think, oh, Silk Road was the biggest – it’s been dwarfed by the markets that have come after it when it comes to how much money is going through them. And one of the big changes now is very few markets will accept Bitcoin anymore, it has to be Monero because Bitcoin has that open blockchain, which means that you can trace absolutely – once you know one transaction that’s taking place and you know who’s on the side of that transaction, there’s a lot of things that you can trace, and there’s places like Chainalysis and that now that are going historically and being able to trace Bitcoin through tumblers, through all sorts of ways of trying to obfuscate what they are, the transactions are, so people are moving over to Monero now that they realize that Bitcoin is anything but anonymous.

MATT ASHBURN

Eileen, you authored a book called Silk Road, and that gave pretty amazing insight into the rise and fall of the dark web marketplace of the same name. How did you begin your research there? What brought about the interest?

EILEEN ORMSBY

Well, I’d already spoken to a lot of people, I’d interviewed a lot of people because of my articles that I was doing, and then I mentioned to the Dread Pirate Roberts, “I want to write a book about Silk Road, will you help me out?” And he said, “look, show me a first draft once you’ve done it, and I’ll see how much input I’ll have into it.” So it was just a matter of gathering all the stories that I’d come up with over the years, or the year and a half or so at that time, when I pitched it to my publisher, it wasn’t the rise and fall of Silk Road, it was the rise and rise of Silk Road because it was still going strong, we all thought it was going to last forever. So it was only just as I was putting the finishing touches to that first draft that Ross Ulbricht got caught, Silk Road got shut down, and it became – I had to quickly change it with my publisher to a rise and fall situation. So I never got as much input from the Dread Pirate Roberts as I would have liked, but I certainly had a lot of input from a lot of other people that were involved, including all of the staff members other than Ross Ulbricht. All his staff members were certainly very helpful in coming forward with stories, and I got to meet all of his main deputies and his mentor afterwards after they all got arrested in various – sometimes in prison, sometimes at home. For my second book, I got to meet them all in real life.

JEFF PHILLIPS

So you met him, but he didn’t give input on that first one?

EILEEN ORMSBY

No, not in the first book, because at that time, no one had gone to prison yet. People had been arrested, but, you know, no one had been tried yet. So that book is actually very much before Ross Ulbricht’s trial, and at that trial, a lot of things came out that we didn’t know about – I certainly didn’t know about – before then. So that’s why I had to write the second book, The Darkest Web, because there was a lot of information that I hadn’t known previously, and also a lot of the gloss of what I thought Silk Road was, was this peaceful, utopian sort of place where people could buy and sell drugs willingly. A lot of that was not quite as truthful behind the scenes as I definitely thought.

MATT ASHBURN

Yeah, as you mentioned before, it wasn’t just Ross that was involved in operating Silk Road, right? It was a number of other deputies and other people. And earlier we were speaking some about those persons that were otherwise involved, and I thought it was interesting that a lot of those people were not motivated by necessarily financial gain, but were really working on the project because they believed in its philosophy, the – sort of the open marketplace, free market economy, libertarian ideals, that type of thing. Can you talk a little about some of the other motivations that people had in working on that project?

EILEEN ORMSBY

Oh, yeah, well, definitely there was a lot of philosophical reasons for it. He was constantly having people offer to work for free for him. And originally, the doctor, Dr. Fernando Cordova, who is a Spanish physician, he offered to work for free with the harm reduction advice that he was providing, but then he was eventually put on the payroll because Dread Pirate Roberts had a lot of money on his payroll and could afford to do that. But yeah, there were always – and he always chose people that had the same sort of ideals that he had. So that’s how he chose his staff rather than necessarily technical ability. Obviously, there were some backend people that had technical ability, but the customer-facing staff, the moderators of the forums and those sorts of people were all people that shared his ideals.

MATT ASHBURN

As we start to wrap up here in the next couple of minutes, what are some of the go-to resources that you recommend that folks know about and research on the dark web?

EILEEN ORMSBY

Well, the Darknet Market Bible is probably the number one; now that is actually aimed at people who want to buy drugs on the dark web, but it’s also a very, very good primer for anyone who wants to first get onto the dark web and start exploring. It’s – I mean, it’s really dangerous just to get on there to go and find – you know, you can find wikis and starting points on the dark web, we can just start clicking on different links. That can be really dangerous because the thing that the dark web harbors a lot of, besides drugs, is child exploitation material. So if you don’t know what you’re doing and you just start clicking on links, you’re almost bound to come across this child exploitation material, so one thing I’m going to warn anybody that just does go there and starts looking around is beware of the word uncensored. Uncensored is just – that just means that this will link you to child exploitation material and you don’t want to see that. It’s illegal just to look at it in most of our jurisdictions anyway, and it’s also stuff that you just can’t get out of your head so you do have to be very, very careful if you’re doing that sort of research. Anyway, learn PGP. PGP encryption is the only way you’re going to be able to speak to – if the reason that you’re going onto the dark web is to speak to people that are using it, then you need to learn PGP so that you can encrypt all your messages and also that you can know that you’re speaking to the people that you think you’re speaking to. Other than that, it’s really just a matter of good old-fashioned journalism work. It’s the same sort of work that you do off the dark web is what you do on the dark web to get people to talk to you and to really tease out the stories that are there.

JEFF PHILLIPS

Well, I was going to ask you about some of that advice for listeners, but you hit on that really well. One of the things you mentioned there, I’ve been asked a number of times, is it illegal to get on the dark web? Which, by the way, listeners, I’m not a lawyer, I’m playing one today. But that’s a different scenario than what you just said with child exploitation, right? That if you do come across that and it does show up on your screen, then you have issues. But in general, accessing the dark web like you were doing and hanging out in those marketplaces, if you’re not buying the drugs and you’re just in the forums or watching what’s going on, then that’s generally not typically illegal to access the dark web. It has legitimate uses for it, as we’ve heard from some of our other guests, right? There are legitimate reasons people are on the dark web.

EILEEN ORMSBY

Oh, absolutely. Most newspapers have got a dark web presence so that whistleblowers can upload documents to them without any worries about it getting back to them. Even the CIA does, so that you can upload information about threats to national security. So the dark web itself is not illegal, but some things on the dark web are doing some things on the dark web are illegal, and just visiting those child exploitation sites could get you into a lot of trouble. They can be illegal, just say, by visiting them, even if you do it accidentally.

MATT ASHBURN

And Eileen, I wanted to also plug for you, you have an extensive library of books and articles and everything else that you’ve written, podcasts, blogs, and a lot of other material on your website, so I’ll make sure listeners have that readily available, and that’s eileenormsby.com. Is there anything else you’d like to plug for our audience to check out?

EILEEN ORMSBY

No, that’s fine. Everything’s there, I think.

MATT ASHBURN

Yeah. Well, thanks very much to our special guest today, Eileen Ormsby. And thank you to everyone who tuned in to today’s show. If you liked what you heard, you can subscribe to our show wherever you get your podcasts. You can also watch episodes on YouTube and view transcripts and other episode info on our website at authentic8.com/needlestack. That’s authentic with the number 8 dot com slash needlestack. We’ll be back next week with more on the dark web with another guest who is used to looking into the dark. We’ll be joined by Darknet Diaries podcast host Jack Rhysider. See you there.

EILEEN ORMSBY

I love Jack!

MATT ASHBURN

Yeah, Jack’s a good guy.