In the first half of the program, George Knapp was joined by author and media researcher Jamie Bartlett for a discussion on the Dark Net, an online underworld which exists in the most secretive corners of the web. "We have, alongside the Internet that we all know, a separate, encrypted part of the Internet," he said, describing the Dark Net. This realm of cyberspace, Bartlett explained, cannot be found via search engines nor explored using traditional browsers such as Firefox or Chrome. Those who wish to access the Dark Net must use a special browser known as 'Tor,' which shrouds the identity of the user and allows them to visit up to 60,000 clandestine websites. "Because of the way it is all hidden and secret," he mused, "more or less anything goes."

To that end, Bartlett detailed one of the most notorious sites on the Dark Net known as 'Silk Road.' He likened the site, which was shut down by the FBI in 2013, to a black market version of eBay that allowed users to buy and sell drugs, counterfeit paperwork, and other illicit items. The site proved so popular that, over the course of its brief existence, Silk Road is believed to have facilitated transactions totaling over a billion dollars and spawned twenty to thirty similar illegal exchange sites. Bartlett also detailed how there are sites which feature alleged hit men brazenly advertising their 'skills' for prospective clients. While these assassins' sites have been verified by many visitors to the Dark Net, the actual veracity of the would-be killers remains a mystery. During his appearance, Bartlett also discussed his research into the allure of anonymity in cyberspace and the subculture of Internet trolls.

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In the latter half, researcher Heidi Hollis talked about a supernatural being known for wearing a hat and peering into people's homes and lives. She traced her original awareness of this entity back to when her college roommate had an encounter with a man that appeared to emerge from the shadows of her bedroom and cornered her. When she heard her roommate's screams of terror, Hollis ran into the room and seemingly caused the entity to disappear. Later, the woman drew a picture of what she saw and sketched a man sporting a three-piece suit, a trench coat, and a gaucho hat, which led to the entity being christened the 'Hat Man.' Much to Hollis' surprise, when she posted the picture on her website, she began receiving emails from people claiming to have had similar encounters with the entity.

While Hollis originally thought the 'Hat Man' was another form of the infamous 'shadow person' phenomenon, further insights from witnesses has led her to conclude that the entity is an entirely separate enigma. Moreover, she suggested that the distinct outfit donned by the 'Hat Man' is an intentional tactic aimed at ensuring recognition from witnesses. "He wants people to know that he is showing up everywhere," she surmised, "it's a disturbing pattern." Chillingly, Hollis also observed that the 'Hat Man' appears to have a sense of awareness and that he will make his presence felt when people discuss him. Although Hollis refrained from speculating on what the true nature of the 'Hat Man' might be, she noted that witnesses consistently report feeling a sense of dread from their encounter and warned that "whatever he is, it doesn't matter, just know that you don't want him in your life."