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#076: How Eileen Ormsby unpacked the Darkest Web

By Jordan Michaelides

Eileen Ormsby ( @EileenOrmsby ) is a writer, journalist and blogger of All Things Vice, as well as an author of two books – The Silk Road and The Darkest Web.

Every time I’ve sat down with professors and practitioners of sociology (Dr Monica Barratt), psychology (Dr Stephen Bright), or criminology (Dr James Martin) to talk about the Dark Web, one name kept recurring – Eileen Ormsby. She is undoubtedly the most sighted journalist in the field today, and we’re very lucky to have her living here in Australia.

The Dark Web is a fascinating place, mostly filled with scams, but also filled with people on the edge of the law and morality. The Gonzo style of journalism that Eileen embodies, challenges society on what should be right or wrong, showing the human side to every case and exploration.

This is a captivating discussion in which we cover:

  • Silk Road, The Dark Web and its marketplaces
  • Data privacy
  • Harm reduction and drug policy
  • Hitmen, hackers and scams
  • Cybercrime, and protecting yourself
  • Creative writing and true crime

Listen to the episode

Watch the episode: 


01:14 – Introduction
03:47 – “Come On, Eileen”
04:11 – The impact of the GFC on her
05:16 – Initial interest in the dark web
10:23 – Career background and writing
11:45 – Lessons learnt from her parents
13:55 – The importance of data privacy
17:45 – Reporting on dark net platforms
20:24 – Harm reduction and drug policy
28:04 – Living off-the-grid, introversion
29:57 – Dark net marketplaces
32:54 – Hitmen, hackers, and scams
36:00 – Cybercrime, protecting yourself
38:23 – The backdoor to Besa Mafia
42:17 – Casefile: Amy Allwine
44:13 – Assassination politics
46:30 – Dark web resources
48:22 – PGP encryption, Cicada 3301
50:30 – Chloe Ayling and kidnapping
53:17 – Creative writing and true crime
56:14 – Education over prohibition
58:29 – Trust, and the state of the dark web
59:47 – Daily routine
01:02:05 – What seems obvious to her, but not to others