WEBVTT

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JACK: I don’t know why, but I’m always amazed by a well-executed scam. There’s something especially

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elegant about the ones that are as simple as they are effective. Have you heard about

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the watermelon drop scam? Okay, so for a while in Japan, the prices of watermelons were really high,

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and so what con artists did is they got ahold of some bad watermelons, ones that were worthless,

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and they would carry it through a part of town where tourists visit, and they’d intentionally

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bump into a tourist and drop the watermelon at the same time which would burst open on the

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ground and make quite a mess. The con artists would then yell and scream at the tourists,

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saying don’t you know how much these are worth? I can’t believe you broke it.

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The tourist would feel bad and then pay for the broken watermelon. This con has been adapted.

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Sometimes you’ll see a con artist take a cheap vase and smash it up and put it into

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a box or a paper bag and then intentionally but accidentally bump into someone and drop

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the box. When they open it, the vase is all in pieces. The con artist shouts and gripes about

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this expensive vase of theirs and that this person just broke it and needs to

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pay them money. It’s common for con artists to collect as much as $100 for these broken vases.

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In this episode, we hear stories from a woman who breaks into places and

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steals for a living. She’s no con artist; she’s a social engineer.

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(INTRO): [INTRO MUSIC] These are true stories from the dark side of the internet. I’m

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Jack Rhysider. This is Darknet Diaries. [INTRO MUSIC ENDS]

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JACK: For this episode, we hear from a social engineer and physical penetration tester.

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JENNY: My name is Jenny Radcliffe. I’m known online as the People Hacker and I’m

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a social engineer and specialist in the psychology of security.

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JACK: [MUSIC] Jenny’s from Liverpool in the UK and she spent a lifetime learning

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social engineering skills and how to break into buildings but she’s not much for computer hacking.

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JENNY: So, I only deal with the humans. I’m hopeless technically.

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JACK: Jenny’s good at tricking people into doing what she needs but she’s

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no criminal. She’s a professional who legitimized her skills for a

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number of jobs. She’s worked as a negotiator working out business deals across the globe,

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and she’s done social engineering and physical infiltration, pen testing. She’s been at it for

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thirty years now but when she got started, no one used a term like social engineer.

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JENNY: No one used that term. I didn’t know that term.

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JACK: Yeah, they used the term con artist at the time.

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JENNY: Yeah, or burglar. I at no point thought it was gonna ever be something

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that was respectable or something that I could ever talk about. I couldn’t have told my family

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because they’d worry. My parents and everything would worry and I couldn’t have told my friends,

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really, because there – a lot of people I knew kind of had an idea about it,

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so I never really talked about it very much to anyone.

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JACK: [MUSIC] Jenny’s career as a social engineer and pen tester goes all the way

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back to her childhood. It all started when her neighbor kidnapped her. Jenny wasn’t even ten

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years old at the time. She wandered into the neighbor’s house but they just kinda

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closed the door and wouldn’t let her leave. Her parents couldn’t find her and began a frantic

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search. This was a very scary situation for her which kind of shaped who she would become.

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JENNY: I mean, I had made my mind up when I was being held captive that I would never be

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helpless again. I thought if I get out of this, I’m gonna be some kind of superhero.

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JACK: She was eventually found by her parents safe and sound, but being kidnapped gave her

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a whole different view on life. Yeah, she wanted to do something special after that,

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something like what a superhero would do, but she wanted to use brains over brawn. Coincidentally,

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her superhero training would start soon after when her parents set her up with her older cousins.

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JENNY: I think my folks decided that I needed to be more streetwise,

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and so they let me hang out with the older boys as opposed to just sort of play in the street.

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JACK: Her parents figured out the cousins could watch over her, show her how to protect herself

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and stay safe. But what they didn’t know is that the boys had a mischievous streak and they

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spent their nights breaking into abandoned buildings around the neighborhood. Now,

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young Jenny would be tagging along, picking up her superhero trade craft along the way.

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JENNY: As far as my parents were concerned, I was tucked up in bed with a story and a teddy bear

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at 8:00 at night and really, I was [00:05:00] out with the cousins helping them get into all

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these buildings. It was great fun. It starts off you get into the empty house in the neighborhood

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and then you go into the empty house at night and then you start to pick targets,

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you know? Like, do you think we could get into that place?

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Before I knew it, the places we were getting into weren’t empty anymore.

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JACK: [MUSIC] The cousins taught Jenny how to get past locks and alarms,

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things that could be crucial to her career later on as an adult. But in her youth,

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her greatest strength was her small size. This made her the ultimate physical penetration tester.

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JENNY: They used to throw me over fences and things and

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get me to kind of open gates or run around and check things out.

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JACK: After she had been with the cousins for a while, they let her pick the next target.

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JENNY: I asked if we could go to a local zoo and see if we could get into that at night.

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JACK: Jenny had been to the zoo before and she always wondered something.

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JENNY: I wanted to see if the lion got locked away.

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JACK: Yeah, what do the animals do at night? It’s a good enough question that

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the cousins were on board. They all grabbed their flashlights,

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or torches as they say in Liverpool, and headed to the zoo.

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JENNY: I had a little torch, had a little Sesame Street torch.

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JACK: This zoo had recently been shut down because of animal abuse issues,

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so it was even more mysterious to Jenny and her cousins to explore

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an abandoned zoo at night. They wanted to find out if the animals were still there.

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So, they head down there and they come to a fence which surrounded the zoo. The cousins

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boosted Jenny over the fence and then climbed over after her. Once inside, the boys just

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ran off for some reason, leaving Jenny all alone with her little yellow Sesame Street flashlight.

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JENNY: It was like, there was no alarms, there was no security guards. There was nothing.

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JACK: The Sesame Street flashlights are horribly dim and this was a very dark night,

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so she didn’t see which way the cousins ran off, but she did know which way the lion exhibit was,

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so she made her way over to that. But she could barely see, so she used her

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hands to sort of reach out in the dark to try to identify the exhibits by touch.

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JENNY: I kind of padded over to where I thought the lion’s cage was,

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and I shine this really dim torch into the cage of this lion. I couldn’t see it; it wasn’t there.

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JACK: She turns away to listen for her cousins who were laughing somewhere off in the distance.

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JENNY: Then I turned ‘round and I could smell a

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chicken soup breath and it was right in front of me.

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JACK: [MUSIC] All that separated her from the lion was a fence that suddenly seemed very flimsy.

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JENNY: It just went crazy; it threw itself at the fence and growled and it stalked me. I screamed,

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dropped the torch, started to run, and the cousins run after me. They were laughing.

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JACK: They scooped her up and retreated back over the zoo’s fence. They got

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out of there safely but that Sesame Street flashlight didn’t make it out.

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JENNY: That was my first ever kind of – that I really remember clearly. That was the first real

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unauthorized access that I ever really picked and kinda did and really remembered.

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JACK: Gosh, that could have left nightmares on you for life of…

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JENNY: Oh, it did.

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JACK: …falling asleep and having lions chasing you in the…in your dreams.

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JENNY: It did, and I still do dream that all the time. Really, seriously, I do. If I’m stressed

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at all, I’ll dream about lions. But it didn’t put me off breaking into buildings, though.

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JACK: Jenny was really starting to enjoy breaking into places. As the cousins grew up,

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they moved on from break-ins to working security at local bars. Jenny tagged along with this too,

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running deliveries between pubs. She also ran little side schemes

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like ripping off vending machines for change by entering a secret code.

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JENNY: So, I always had change, pockets full of money and things.

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All very – all terrible and I’ve made amends since; apologies to Coke and Pepsi.

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JACK: As Jenny went into her late teens, she went to college. The cousins figured

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out a way to turn their street skills into legitimate work. They started doing security

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audits for high-net-worth individuals like professional soccer players.

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JENNY: It was like, we used to break into houses. Do you want us to check

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out where you live and tell you how we’d get in?

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JACK: It was the same thing they did as kids, but now they were getting paid for

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it. But Jenny was grown up and was too big to just be thrown over a fence, so

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no more flying over walls. She adapted by using her people skills to get the cousins inside.

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JENNY: Often, the easiest way of getting in wasn’t to bust an alarm or get on the

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roof or anything dramatic. It was just have me knock and say can I come in?

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I want to talk to you about your curtains or something like that.

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JACK: Once she was inside, Jenny would just figure out a way to leave a door open or unlock a window

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so the cousins could just break in later. Some professional soccer players hired them to audit

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their businesses, too. This weird side business of theirs was actually getting some real work to do,

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but then something changed. [00:10:00] The cousins started meddling in heavier crime,

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stuff Jenny didn’t want to get involved in, and that’s about the time when she got offered her

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first solo gig as a professional security auditor. Still, at this time, social engineer and physical

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pen tester just weren’t terms yet and she was still going to college when she got this job.

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JENNY: [MUSIC] I got a phone call from this guy and he called the house. I was still living

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with my parents and he called the house. Mum answered and said there’s a guy on the phone,

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talking to – wants to talk to you about a job. I answered the phone and it was this

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guy and he said I’ve got – I want you to get into this office in Liverpool and I want you

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to steal an address book. It’s a security audit. I didn’t ask any questions except oh,

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well, I’ll – I need to ask the cousins. He said to me why do you need the boys?

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JACK: That’s when it dawned on her that she didn’t. She liked the idea of trying to break

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in without the cousins’ help this time. She knew all the tricks at this point. It would

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be less people involved, less work, so yeah, a solo mission. Let’s try it. But she did call

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her cousins to let them know that she was going to be going in on this job alone. Alright, step one.

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JENNY: So, reconnaissance stage.

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JACK: [MUSIC] The target was a politician in the British Labor Party. Jenny’s mission was

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to break into his office and steal his address book. His office was in a waterfront building

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in Liverpool. Jenny went over there one day to check this place out, to look for obstacles or

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weaknesses in the building. On the ground floor around the entrance there weren’t any barriers,

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no turnstiles that required her to badge through or anything like that. She looks

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at a directory on the wall and sees the office that she needs to go to is on the eighth floor,

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so she hops on the elevator. What she’s looking for is a POE, a point of entry.

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This is a public building; anyone can jump in the elevator and take it up to the eighth

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floor and then just look around the lobby. You can’t really get caught in this stage,

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but doing this can really be helpful for when you want to come back later and actually break in.

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JENNY: This is like, completely not how I would do it now. I guess I

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just thought I’m not doing anything at this point; I’m just looking around,

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so I’m not actually doing anything wrong. So, there’s no problem.

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JACK: Jenny steps off the elevator and sees some double doors with a big,

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open floor plan office on the other side. It’s bustling with workers.

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Jenny looks to the far end and sees the politician sitting at his desk.

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JENNY: I’m kinda thinking okay, so that’s where I need to go. Then one of the office

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workers comes out and just says oh hi, what do you need? Do you need to go in? I said no, no,

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no, I don’t need to go in. Actually, I’m looking for Mr. Whatever. I said,

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is that him in there? He said yes. I said oh, I need to speak to him but I’ll leave it;

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he looks busy. He said yeah, well, he won’t be there tomorrow; he’s at the conference. I said

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oh, oh right. I said, the conference? He said yeah, it’s the Labor Party Conference.

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JACK: Well, that accidentally worked really well. Jenny now knows that nobody’s gonna be

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in the office tomorrow. Again, her mission is to lift an address book off the guy’s

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desk. Jenny left the building and stopped at a cafe for a coffee. As she sipped her drink,

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it struck her how laid back security was at this office building.

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JENNY: I thought right, I’m just gonna go back. This is gonna be not as difficult.

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I’m gonna wait for the guy to go out of his office. [MUSIC] I’m gonna go and get it.

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JACK: She went back into the building,

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headed up to the eighth floor, looked through the office window. That politician, her target,

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was still at his desk where she presumed the address book was too, so she left.

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JENNY: I kind of…I guess I lost my nerve. Came out; right,

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I’m definitely waiting for the next day now.

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JACK: She does. She goes home, sleeps that night, and comes back the next day,

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but not straightaway. She waits until 5:00 PM to go back.

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JENNY: There was no one around. There was not even security at the front desk. It was wide open. I

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went up the stairs and I walked into this office – it wasn’t locked – went into the guy’s office,

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it wasn’t locked, and his address book was just in the drawer on his desk.

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JACK: Jenny grabbed it, stashed it in her bag, and was feeling good. The job was going well.

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JENNY: I kinda thought yes, this is great. Wait ‘til I tell my cousins and I’ve done this one on

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my own and I had deserved my fee. As I said it, I saw the doors open at the other side

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of the office and it was security. [MUSIC] Just panicked and I just ran out the office.

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JACK: Jenny dashed out of the office and ran to a stairwell.

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JENNY: I ran up to the roof, so went up the stairs rather than down the stairs,

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something that I’ve always done as a signature move now, I guess.

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JACK: It’s a little psychological trick that Jenny does sometimes. Her theory is that the security

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would see her go into the stairwell and assume she was going down to get out of the building, and

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so they’d go down to look for her. But instead, she went up. Jenny ran up the stairs and got to

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the top of the building and she came to a fire door which led to the roof. She could hear the

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security guards on the stairs, so somewhere below, and didn’t want to get caught with the book.

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JENNY: I just opened the door to the roof, threw the book onto the roof,

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let the door slam, ran down again, and just ran into them on the stairs.

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JACK: [00:15:00] She was caught but she didn’t have the book on her or any evidence on her,

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so her plan was to somehow talk her way out of the situation.

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JENNY: They were like, really nice, actually.

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They said what’s going on? I just said oh, I don’t want to say. I was really panicking.

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I was really young, really panicking, and I thought I don’t know what to say.

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JACK: She just kept saying she was supposed to be there but Jenny didn’t have a letter from

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her client, no Get Out of Jail Free card as they say, which explains that this is

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all a security audit and it’s on the level. She was unable to talk her way out of this, so the

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security guards escorted her to their office and sat her down and started questioning her.

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JENNY: They sat me in the security room. They were looking at me and they left me there.

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There’s only one door; they stood outside the door and I could hear them talking.

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They came back in and they said did you take anything? I said no.

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JACK: Jenny could only think to tell the guards that she was just looking around.

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JENNY: That was the best I could come up with and I just felt like if I just kind of – just said oh,

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I was looking for a politician, just was a bit dizzy, that they probably wouldn’t do anything.

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I don’t know what they thought and I don’t really remember exactly what I was thinking,

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but I don’t remember being particular concerned. I just thought they’ll let me go, and they did.

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Just sort of said don’t do that, don’t get into trouble.

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JACK: Jenny says her innocent demeanor helped her escape.

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JENNY: It was very strange at the time for a woman to do any of this. [MUSIC]

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You just – I got away with so much and there was so little scrutiny in my early

00:16:31.200 --> 00:16:37.680
years that it wasn’t even a legitimate thing. I mean, I still do get away with things just

00:16:37.680 --> 00:16:41.580
because I’m – not just because I’m female but more because I just look so innocent.

00:16:41.580 --> 00:16:45.300
It just doesn’t resonate with people that I’m a threat at all. It never did.

00:16:45.300 --> 00:16:48.480
JACK: She caught a bus home but she knew the job was only half-finished.

00:16:48.480 --> 00:16:52.140
She still needed to go back onto the roof and get that address book.

00:16:52.140 --> 00:16:56.460
JENNY: This would be an embarrassment if I didn’t get the book. All I need to do now

00:16:56.460 --> 00:17:02.040
is get back up to the roof, I’m laughing thinking about it now, grab the book, and it will be fine.

00:17:02.040 --> 00:17:08.160
JACK: So, she headed back that night because there was a sense of urgency to get the book before

00:17:08.160 --> 00:17:12.840
someone else found it. Even though she’s shown her face at this building three times now and has been

00:17:12.840 --> 00:17:17.880
caught once, she decided to go for it anyway and she tried to justify why it was safe to go back.

00:17:17.880 --> 00:17:21.120
JENNY: They didn’t call the police or do anything the first time,

00:17:21.120 --> 00:17:24.300
so they probably won’t do it the second time which is just the most stupid reasoning.

00:17:24.300 --> 00:17:27.180
JACK: She stood out in front of the building for a while,

00:17:27.180 --> 00:17:31.680
watching the front doors from a distance. It was late in the year, a couple weeks

00:17:31.680 --> 00:17:35.982
before Christmas. It was cold out and it was getting late. Like, it was after midnight now.

00:17:35.982 --> 00:17:39.600
JENNY: Waited and waited and it was completely quiet,

00:17:39.600 --> 00:17:44.280
and it started to rain, and it started to really rain. I’ve just thought I’ve got to move now;

00:17:44.280 --> 00:17:47.940
I’ve gotta go and get it or I’m gonna get wet, as if that’s the main thing to worry about.

00:17:47.940 --> 00:17:52.740
JACK: She didn’t see any movement in the building for a while, so she went in and

00:17:52.740 --> 00:17:56.880
then quickly ducked into one of the stairwells and made her way up the stairs to the roof.

00:17:56.880 --> 00:18:01.860
JENNY: As I got up to the roof, [MUSIC] the thunder and the lightning was just really

00:18:01.860 --> 00:18:06.180
loud and I just grabbed for this book and it was all soggy and wet, and I got the book,

00:18:06.180 --> 00:18:10.740
and then ran out. Didn’t get stopped, didn’t get any – there was nobody there.

00:18:10.740 --> 00:18:16.560
JACK: She successfully left the building with the address book in hand and made it to safety. Phew,

00:18:16.560 --> 00:18:20.580
she did it. She turned the address book over to her client and got paid.

00:18:20.580 --> 00:18:22.380
JENNY: But the thing is,

00:18:22.380 --> 00:18:27.480
that first one always reminds me that I was completely incompetent that first job.

00:18:27.480 --> 00:18:33.060
JACK: In the past, she’d had her cousins to lean on. They had experiences to share. They worked as

00:18:33.060 --> 00:18:37.980
a team and although she made some mistakes, the end result was that she did it all by herself.

00:18:37.980 --> 00:18:42.540
JENNY: It’s one of the reasons I kind of stayed in security, because it was so easy.

00:18:42.540 --> 00:18:47.520
I look back on that now and think that was ridiculous. There was no protocols. There

00:18:47.520 --> 00:18:51.840
was nothing keeping it safe, and that was a politician. God knows what was in that book.

00:18:51.840 --> 00:18:58.380
JACK: Security on that building improved a lot after this audit. The office was locked at night

00:18:58.380 --> 00:19:03.300
after that and the politician’s office door was locked at night, too. You can’t always rely on

00:19:03.300 --> 00:19:08.220
security guards catching everything. You have to make deterrents for thieves. After that, Jenny

00:19:08.220 --> 00:19:12.720
started to pick up more work and every job she did, she learned better techniques for breaking

00:19:12.720 --> 00:19:17.400
into buildings and manipulating people. Looking back at what she did, she sees how far she’s come.

00:19:17.400 --> 00:19:23.520
JENNY: I over-prepare now. I mean, we – I have Plan A, B, C. Our teams,

00:19:23.520 --> 00:19:27.000
we cover every eventuality. I have props, everything.

00:19:27.000 --> 00:19:30.780
JACK: As she grew her business over the years, the jobs got more complex and she

00:19:30.780 --> 00:19:35.400
started needing extra people to help her on certain jobs, and props. This one time,

00:19:35.400 --> 00:19:42.540
she had a job to con a business tycoon. For this story, we’ll just call him Mr. Big. [MUSIC] The

00:19:42.540 --> 00:19:48.180
job started when Mr. Big’s security team reached out to Jenny. Mr. Big thought his security was

00:19:48.180 --> 00:19:54.240
flawless but his security team thought otherwise. So, they reached out to Jenny to see if she could

00:19:54.240 --> 00:19:58.560
expose some security holes that would prove that Mr. Big would need to up the security budget.

00:19:58.560 --> 00:20:04.620
JENNY: They knew of me [00:20:00] and they asked him if he would allow them to hire a

00:20:04.620 --> 00:20:13.200
social engineer to get to him. He told them to knock themselves out. So, they came to me and

00:20:13.200 --> 00:20:18.080
said you can do whatever you like because he doesn’t believe that this is a thing.

00:20:18.080 --> 00:20:23.100
JACK: Mr. Big didn’t think anyone could gain access to his confidential data or

00:20:23.100 --> 00:20:26.940
con him. He thought he was too clever to be tricked by any social engineer.

00:20:26.940 --> 00:20:33.090
JENNY: He especially wouldn’t believe that some little woman from Liverpool will get past him.

00:20:33.090 --> 00:20:34.740
JACK: Challenge accepted.

00:20:34.740 --> 00:20:39.840
JENNY: They said do what you like, but he’ll be good about it in the end. I didn’t care if he

00:20:39.840 --> 00:20:45.240
was good about it in the end. I just thought silly sod; you’re gonna get hacked for real.

00:20:45.240 --> 00:20:51.420
JACK: [MUSIC] So, here’s the job; Mr. Big’s security team wanted to see if Jenny could

00:20:51.420 --> 00:20:55.980
get into his office and get access to his e-mail. If somebody could get into his e-mail,

00:20:55.980 --> 00:21:00.540
then they’d have access to future deals that are in the works, sensitive information about the

00:21:00.540 --> 00:21:05.220
business or other private information like his whereabouts. With that, they could track him,

00:21:05.220 --> 00:21:09.000
plot against him, and maybe figure out a way to con him out of a bunch of money. When

00:21:09.000 --> 00:21:13.320
starting the job or any social engineering job, her first step is always to do OSINT,

00:21:13.320 --> 00:21:17.640
open-source intelligence-gathering. So, Jenny starts looking on the internet to

00:21:17.640 --> 00:21:23.040
see what she can find about Mr. Big. By this point, places like Facebook and Twitter were

00:21:23.040 --> 00:21:26.820
pretty popular which became an important part of information-gathering on people.

00:21:26.820 --> 00:21:32.460
JENNY: I used to have to do proper surveillance. I used to have to sit outside offices and

00:21:32.460 --> 00:21:39.600
theatres and things and watch people to see what they – who they socialized with and everything.

00:21:39.600 --> 00:21:47.040
But when social media came in, I just couldn’t believe how easy they made my life.

00:21:47.040 --> 00:21:51.060
JACK: You can find out a lot about a person on social media because people

00:21:51.060 --> 00:21:55.260
post all kinds of private information there; name, location, job, high school,

00:21:55.260 --> 00:22:01.020
hobbies, friends, sexual orientation, trips. People post it all. There’s no reason to hack

00:22:01.020 --> 00:22:04.500
into someone’s phone to see their private photos when they’re posting these photos

00:22:04.500 --> 00:22:09.360
for anyone to see. For Jenny, social media was a game-changer for this type of work.

00:22:09.360 --> 00:22:12.840
JENNY: It was like someone being fed to the lions, you know? It was like,

00:22:12.840 --> 00:22:16.440
oh, this is gonna be so easy to get hold of this person.

00:22:16.440 --> 00:22:19.680
JACK: She has a specific goal in mind when she does OSINT,

00:22:19.680 --> 00:22:22.950
something she says that sets her apart from some of her other colleagues.

00:22:22.950 --> 00:22:27.600
JENNY: What I’m normally looking for is different, I think. I think when I speak to other people

00:22:27.600 --> 00:22:33.600
who do the job, they can collect the OSINT but the data’s nothing without the story, and I’m

00:22:33.600 --> 00:22:38.580
looking for what’s underneath it. I’m looking for the things that people fear or the things

00:22:38.580 --> 00:22:45.360
that people – the last thing someone would give up. What is it that really pushes this person’s

00:22:45.360 --> 00:22:52.800
buttons and how can I use that in a ethical way to simulate this attack? Obviously, I’d stop

00:22:52.800 --> 00:22:58.200
very short of anything criminal or anything very harmful, but we look at the art of the possible.

00:22:58.200 --> 00:23:02.505
JACK: So, she fires up her computer and starts searching for dirt on Mr. Big online.

00:23:02.505 --> 00:23:06.480
JENNY: [MUSIC] Normally it’s so easy. Normally you go to – you do some OSINT,

00:23:06.480 --> 00:23:11.040
right? So, I go over to the internet and I look at Facebook and he’s not on Facebook.

00:23:11.040 --> 00:23:18.960
JACK: He wasn’t active on Instagram or Twitter, either. Huh. Odd, but okay. Some

00:23:18.960 --> 00:23:24.120
people are just like that. She starts looking for the guy’s wife, but Jenny can’t find her,

00:23:24.120 --> 00:23:28.080
either. All this is becoming tricky. She might have to look him up on other

00:23:28.080 --> 00:23:32.640
databases or dig through public interviews with him or something. But as she looked more,

00:23:32.640 --> 00:23:39.060
she just wasn’t finding much on this guy. He was somehow staying off the internet pretty well.

00:23:39.060 --> 00:23:44.820
JENNY: In the end, in desperation, just as sweet, we found his secretary on Pinterest.

00:23:44.820 --> 00:23:49.980
JACK: Jenny took a hard look through Mr. Big’s secretary’s posts but didn’t find much.

00:23:49.980 --> 00:23:54.180
JENNY: She was in this extreme knitting group. She used to knit

00:23:54.180 --> 00:23:59.400
little cupcakes out of wool and that was all I had. It’s terrible; it’s not enough.

00:23:59.400 --> 00:24:06.300
JACK: Jenny kept pivoting her searches; LinkedIn, Reddit, nothing. Come on,

00:24:06.300 --> 00:24:11.580
this guy’s gotta be somewhere, so she just starts reading public articles about him and his company.

00:24:11.580 --> 00:24:13.980
JENNY: He and his wife were both in charge of

00:24:13.980 --> 00:24:18.420
a charity that was connected with an illness that had been in their family.

00:24:18.420 --> 00:24:26.640
JACK: Huh. Jenny is an ethical hacker but would she use a charity to exploit someone? That might

00:24:26.640 --> 00:24:32.040
not seem like an ethical approach, but then she thought you know what? The bad guys would do low

00:24:32.040 --> 00:24:38.640
blows if they had an opportunity, so Jenny decided yeah, let’s get to him through his charity. Even

00:24:38.640 --> 00:24:43.260
though this is an ethical grey area, Jenny doesn’t lose any sleep over something like that.

00:24:43.260 --> 00:24:49.020
JENNY: I sleep like a baby because I am showing you what the bad guys

00:24:49.020 --> 00:24:53.820
could do. I am not a bad person but I do know how criminals think.

00:24:53.820 --> 00:24:55.680
JACK: So, a charity or anything else,

00:24:55.680 --> 00:24:59.520
really, is fair game for her. The charity thing was a great lead.

00:24:59.520 --> 00:25:03.360
JENNY: I couldn’t [00:25:00] get to him through his business dealings because he

00:25:03.360 --> 00:25:06.780
just wasn’t public about it and he’s very guarded, but when it came to the

00:25:06.780 --> 00:25:10.860
charity and his wife, there’s your soft spot. There’s your chink in the armor,

00:25:10.860 --> 00:25:15.060
you see. I figured that the way to get to him was to get to his wife.

00:25:15.060 --> 00:25:21.720
JACK: Mr. Big’s name was on the charity but it was really his wife’s passion project. She was the

00:25:21.720 --> 00:25:27.720
way in, so Jenny hatched a plan. She bought two tickets to one of the charity’s dinners in London.

00:25:27.720 --> 00:25:33.420
She’d go posing as a journalist who was writing an article about Mr. and Mrs. Big and their charity,

00:25:33.420 --> 00:25:38.760
and this time Jenny brought a partner along, a confederate as she says, or an accomplice,

00:25:38.760 --> 00:25:44.460
to help her. The goal at this dinner was to somehow get the PIN from Mr. Big. She

00:25:44.460 --> 00:25:48.240
thought that would be a good first step in proving that Mr. Big’s security could use

00:25:48.240 --> 00:25:52.380
some work. [MUSIC] Yeah, if someone told me I wasn’t very secure and I told them oh yeah,

00:25:52.380 --> 00:25:58.080
prove it, and they said well, this is the PIN to unlock your phone, I’d be rightfully embarrassed.

00:25:58.080 --> 00:26:03.120
Jenny’s plan was to chat up Mr. Big at the dinner and somehow get him to take his phone out of his

00:26:03.120 --> 00:26:08.340
pocket and unlock it. She was thinking up ways she might be able to get him to do that. Maybe

00:26:08.340 --> 00:26:13.260
ask him to look something up on a website or maybe they’d trade e-mails and check his inbox

00:26:13.260 --> 00:26:18.720
while they were talking. If he did take his phone out while they were chatting and unlocked it,

00:26:18.720 --> 00:26:23.700
Jenny’s partner who would be hovering right nearby would look over his shoulder to see

00:26:23.700 --> 00:26:27.720
what PIN was entered when he unlocked the phone. On the night of the dinner,

00:26:27.720 --> 00:26:32.700
Jenny and her partner arrived. She saw Mr. and Mrs. Big and approached them.

00:26:32.700 --> 00:26:38.340
JENNY: I went up to them and I said look, I’m sorry, but I’m a journalist

00:26:38.340 --> 00:26:42.240
and I wanted just a few words for our online publication about the event.

00:26:42.240 --> 00:26:47.940
JACK: But she wasn’t just talking to both of them. She was really talking to the wife, Mrs. Big.

00:26:47.940 --> 00:26:54.600
JENNY: I went to her and said it and she was like oh, absolutely. She made him talk to me.

00:26:54.600 --> 00:26:59.340
JACK: Which was all part of the plan to get Mr. Big through his wife.

00:26:59.340 --> 00:27:01.320
She turned on her charm to build rapport.

00:27:01.320 --> 00:27:07.200
JENNY: I kind of assumed and surmised that people never told him no.

00:27:07.200 --> 00:27:12.300
I was very cheeky with him so I said well, I wanted to interview you but my glass is dry.

00:27:12.300 --> 00:27:16.500
I think you can afford a drink. He was like, right, and he got me a drink.

00:27:16.500 --> 00:27:21.420
JACK: [MUSIC] Jenny sunk her hook deeper. She recorded a short interview with them about this

00:27:21.420 --> 00:27:25.920
charity, told them that it’s gonna go into a magazine that she worked for. She said she’d

00:27:25.920 --> 00:27:29.400
send him a link to it and she kept chatting him up, trying to get him to pull out his phone.

00:27:29.400 --> 00:27:34.800
JENNY: I made sure that I spoke to him enough so that my confederate

00:27:34.800 --> 00:27:38.520
was watching him open his phone and put in his pass code.

00:27:38.520 --> 00:27:45.540
JACK: Her accomplice had a phone too and pulled it out and recorded Mr. Big entering in his pass

00:27:45.540 --> 00:27:51.900
code. This way, they could play it back later in slow motion to see what his PIN was. It worked;

00:27:51.900 --> 00:27:56.040
the confederate gave the signal that they got it and walked off. That was

00:27:56.040 --> 00:28:01.140
her cue to wind down the conversation and leave. They’d start Phase 2 the next day.

00:28:01.140 --> 00:28:05.400
JENNY: I called the next day and I called the secretary.

00:28:05.400 --> 00:28:12.360
I said it was great but unfortunately the recording just didn’t work. Now I’ve

00:28:12.360 --> 00:28:17.220
interviewed them, I really want a bigger piece. I want them to be on the cover, we want to take

00:28:17.220 --> 00:28:23.280
a few photographs, but the problem is I’m on a horrible deadline; this needs to be in by Friday.

00:28:23.280 --> 00:28:27.780
JACK: This sense of urgency was important to Jenny’s plan. It was a tactic she used regularly.

00:28:27.780 --> 00:28:32.400
JENNY: Because you never give a mark time to think. Got to rush people into doing something.

00:28:32.400 --> 00:28:36.840
We’re gonna flatter him, we’re gonna get the wife on board. They’ve got to sell it to me.

00:28:36.840 --> 00:28:42.780
JACK: Now, the Bigs were selling the interview to Jenny. Building rapport with Mrs. Big at the

00:28:42.780 --> 00:28:47.160
dinner paid off. She called Jenny back within a half an hour to let them know the interview

00:28:47.160 --> 00:28:52.260
was a go. Jenny worked out a plan to meet with Mr. Big in his corporate office so they could

00:28:52.260 --> 00:28:57.660
take some photos of him, but their real goal was to somehow gain access to sensitive information

00:28:57.660 --> 00:29:03.720
in the office; a computer, phone, anything that might lead to accessing his e-mail. On the day

00:29:03.720 --> 00:29:07.380
of the interview, Jenny and her partner showed up still posing as journalists.

00:29:07.380 --> 00:29:11.580
JENNY: We set up the camera and a little microphone, we took a few photographs,

00:29:11.580 --> 00:29:17.040
and we asked a few questions. Then he said oh, I’m sorry, I didn’t offer you a coffee.

00:29:17.040 --> 00:29:19.860
JACK: [MUSIC] Now, the thing that makes a good

00:29:19.860 --> 00:29:22.440
social engineer is someone who can think on their feet.

00:29:22.440 --> 00:29:27.180
JENNY: I said oh, I’d love a coffee. I said but I’m a pain; I like decaf.

00:29:27.180 --> 00:29:29.880
Have you got a decaf? He said I’ll go and find out.

00:29:29.880 --> 00:29:32.820
JACK: See, the thing is, Jenny hates decaf.

00:29:32.820 --> 00:29:36.900
JENNY: Death before decaf. What it was is I wanted him to have to go and really look

00:29:36.900 --> 00:29:40.500
for it and I thought maybe that was the better option, and he left us on our own in the office.

00:29:40.500 --> 00:29:45.840
JACK: Bingo; alone in his office as he hunts for decaf somewhere in the office,

00:29:45.840 --> 00:29:50.940
and he left his mobile phone on his desk. They weren’t really sure when this

00:29:50.940 --> 00:29:55.020
opportunity would present itself but when it does, Jenny says you have to be ready.

00:29:55.020 --> 00:29:59.460
JENNY: We weren’t banking on that happening. We had other things that we had in mind to get him

00:29:59.460 --> 00:30:03.360
out of there; [00:30:00] phone calls planned and all sorts of things but at the end of the

00:30:03.360 --> 00:30:08.400
day, if the opportunity presents – you need to know everything about the target so that

00:30:08.400 --> 00:30:12.960
you can tactically adapt if the opportunity arises. That takes enough bandwidth to have

00:30:12.960 --> 00:30:17.100
to adapt to a situation that you don’t need to be thinking of anything else. So,

00:30:17.100 --> 00:30:22.440
I need to know everything about the secretary, the building, who is in charge officially,

00:30:22.440 --> 00:30:28.380
but who do people rally to? Who do people like? Who really holds the power? There’s different

00:30:28.380 --> 00:30:33.600
types of power. Where do they celebrate? I always say a building’s like a person and it’s what’s

00:30:33.600 --> 00:30:38.760
the rhythm of the building? How does it breathe? When’s it alive? When does it sleep? The reason is

00:30:38.760 --> 00:30:43.560
is that once you have all those things in place, then when someone like the guy just pops out to

00:30:43.560 --> 00:30:48.360
get us a cup of coffee happens, we’re quick enough to act very quickly in the moment and leave.

00:30:48.360 --> 00:30:52.020
JACK: In this case, knowing that decaf coffee might be hard to find,

00:30:52.020 --> 00:30:56.880
that was the key to their success. With Mr. Big gone, Jenny quickly grabbed his phone,

00:30:56.880 --> 00:31:00.480
punched in the PIN that she had gotten the night before, and sent a text to the security team.

00:31:00.480 --> 00:31:04.800
Then she ran around his desk, sat in his chair, and sent an e-mail to the security team. This

00:31:04.800 --> 00:31:09.360
proved that she had gotten in and got access to his e-mails and phone. Once she finished,

00:31:09.360 --> 00:31:12.990
Mr. Big still wasn’t back, so Jenny and her partner vanished.

00:31:12.990 --> 00:31:14.460
JENNY: Yep, gone.

00:31:14.460 --> 00:31:21.360
JACK: [MUSIC] She says there’s no need to hang around after a successful con.

00:31:21.360 --> 00:31:25.380
There’s no point in exposing yourself to getting detained. The best move is just

00:31:25.380 --> 00:31:28.680
to get out. Once Jenny sent the code word to Mr. Big’s security,

00:31:28.680 --> 00:31:34.740
they quickly swooped in and debriefed Mr. Big. After the job, Mr. Big reached out to Jenny.

00:31:34.740 --> 00:31:38.520
JENNY: He was really good-natured about it. What he said to me was – he said I

00:31:38.520 --> 00:31:43.140
want to take you for dinner and I want you to tell me exactly how you caught me out.

00:31:43.140 --> 00:31:47.820
JACK: In the end, Mr. Big carved out more budget for his security team. For Jenny,

00:31:47.820 --> 00:31:50.400
the Mr. Big job was important because it showed

00:31:50.400 --> 00:31:53.820
that even if you’re not on social media, someone can still get to you.

00:31:53.820 --> 00:31:56.460
JENNY: A lot of the jobs we have, I can find out everything from social

00:31:56.460 --> 00:32:01.680
media. I don’t even have to go. We can just phish people or whatever.

00:32:01.680 --> 00:32:06.540
I’ll do a lot of my work over the phone. But everyone’s networked and someone in

00:32:06.540 --> 00:32:13.080
that network will be able to give you enough to just work out where the chinks are in the armor,

00:32:13.080 --> 00:32:19.140
where the psychology leads you. With him, it was always gonna be flattery. We always had

00:32:19.140 --> 00:32:23.460
to work with the ego but to get to his ego, we had to find out what they cared about.

00:32:23.460 --> 00:32:29.220
JACK: [MUSIC] Speaking of preying on ego, the next story from Jenny is about a time when a

00:32:29.220 --> 00:32:36.540
handsome sum of money helped lure her into a job. Stay with us. Jenny has another job;

00:32:36.540 --> 00:32:42.480
she’s also a professional negotiator. She’s really good at getting people to agree on certain things.

00:32:42.480 --> 00:32:45.360
JENNY: I was working for these big companies, big corporates,

00:32:45.360 --> 00:32:50.460
and they would send me on negotiation trips and supplier assessments all over the world.

00:32:50.460 --> 00:32:55.920
JACK: Some big companies need someone like Jenny to be on the ground, negotiating contracts.

00:32:55.920 --> 00:32:59.280
JENNY: I was good with people, right? So, I could negotiate well.

00:32:59.280 --> 00:33:02.640
JACK: Jenny realized over the years that yet another way she

00:33:02.640 --> 00:33:06.420
could legitimize her skills would be to teach others how to do this. So,

00:33:06.420 --> 00:33:11.805
she developed a negotiation course, but with her own little manipulation slant. Here’s how it goes.

00:33:11.805 --> 00:33:15.780
JENNY: [MUSIC] I will talk to them about all the usual things you’re learning in negotiation

00:33:15.780 --> 00:33:22.380
training; know your best alternatives to a negotiation’s outcome, your objectives,

00:33:22.380 --> 00:33:25.080
know what you’re willing to lose, all the stuff that you get in any other course.

00:33:25.080 --> 00:33:31.140
But then at like, half past three on day two, I’d say okay, now this is how you

00:33:31.140 --> 00:33:34.860
make someone do what you want them to do so you can manipulate someone to do anything you want.

00:33:34.860 --> 00:33:38.460
JACK: Jenny came up with nineteen identifiers that people could use

00:33:38.460 --> 00:33:41.820
for negotiating. It’s like a recipe for getting people to agree with you.

00:33:41.820 --> 00:33:45.720
JENNY: Normal, regular business people who are very legitimate and do very

00:33:45.720 --> 00:33:50.700
respectable jobs absolutely love the idea of being able to kind of input

00:33:50.700 --> 00:33:55.200
a formula and get that person to sort of bend to your will.

00:33:55.200 --> 00:33:57.960
JACK: She says her philosophy for all these negotiations and

00:33:57.960 --> 00:33:59.700
manipulations can feel a bit dark.

00:33:59.700 --> 00:34:06.540
JENNY: To change those peoples’ minds, I have to tune into the thing that they really fear,

00:34:06.540 --> 00:34:10.860
like the last thing they’d give under interrogation, the thing that wakes them

00:34:10.860 --> 00:34:15.540
up in the cold, dark night. I need to know what that is and I also need to know what

00:34:15.540 --> 00:34:19.980
they really care about. Like, not the first thing they tell you, not the second thing,

00:34:19.980 --> 00:34:25.740
but the why underneath all these things. It’s like a push and a pull, you know? What are they pushed

00:34:25.740 --> 00:34:32.100
towards? What do they run away from that pulls them back? Once we can sort of get inside that and

00:34:32.100 --> 00:34:37.620
know exactly where your heart beats, then we can persuade anyone of anything because you tune them

00:34:37.620 --> 00:34:46.200
into that. What I say to them on the negotiation training is it’s not football, right? It’s chess.

00:34:46.200 --> 00:34:52.620
You’ve got to think way ahead and what you’ve also got to do is understand the way people really are.

00:34:52.620 --> 00:34:59.760
It’s never just about money. In the corporate negotiations, they always fixate on the money.

00:34:59.760 --> 00:35:01.920
[00:35:00] I always say it’s never just about the money.

00:35:01.920 --> 00:35:07.560
It’s always about power or revenge or sometimes it’s about sex, but mostly it’s power and revenge

00:35:07.560 --> 00:35:14.640
in business. If it’s a power play, where are they pulling their source of power from? What is it

00:35:14.640 --> 00:35:23.100
that they’d hate the most to lose? That’s what we threaten and then back it up with a really easy

00:35:23.100 --> 00:35:29.820
decision. That sounds very dark but I’ve seen far darker. I still teach collaboration and I

00:35:29.820 --> 00:35:34.440
still teach actually being clever as opposed to threatening anyone is the best way to do

00:35:34.440 --> 00:35:40.800
the best negotiation. Like, apply your mind and get everybody what they want so nobody loses.

00:35:40.800 --> 00:35:46.740
But the principles involved in really reading and understand peoples’ psychology,

00:35:46.740 --> 00:35:52.200
particularly the darker side of that, is what everybody always wants to know.

00:35:52.200 --> 00:35:54.840
If you’re up against people who mean other people real harm,

00:35:54.840 --> 00:35:59.640
it’s very helpful to be able to tune into that and understand how that works.

00:35:59.640 --> 00:36:03.360
JACK: Yeah, Jenny goes all over the world helping companies negotiate contracts but

00:36:03.360 --> 00:36:07.080
also teaching people how to do it, too. One time she was in Hamburg,

00:36:07.080 --> 00:36:12.540
Germany teaching the art of negotiating and persuasion techniques. After she finished up

00:36:12.540 --> 00:36:16.860
her talk one night, she headed back to her hotel but someone approached her outside.

00:36:16.860 --> 00:36:24.180
JENNY: I’m stood outside and I hear this ‘Jenny, Jenny Radcliffe!’ Right? I’m like,

00:36:24.180 --> 00:36:30.300
shit. I look around and there’s this guy just sort of hiding in the shadows outside the hotel

00:36:30.300 --> 00:36:32.760
and he says we need your help.

00:36:32.760 --> 00:36:38.400
JACK: [MUSIC] This is strange but not completely unusual for Jenny.

00:36:38.400 --> 00:36:41.700
JENNY: I get jobs in lots of different ways and I always did.

00:36:41.700 --> 00:36:48.540
JACK: The guy had a big ask; he told Jenny he needed her help breaking into a bank in two days.

00:36:48.540 --> 00:36:53.400
JENNY: I said yeah, right. No. No. I said no because I didn’t know who it was. It could

00:36:53.400 --> 00:37:00.300
have been a real criminal. I didn’t speak German and this could be very dangerous so I said no and

00:37:00.300 --> 00:37:06.180
he said no, no, no, it’s all legit. We just need a social engineer. We need a woman in particular

00:37:06.180 --> 00:37:08.460
to get us past the security at this bank.

00:37:08.460 --> 00:37:12.960
JACK: The guy said he was with a security firm that was auditing this bank and they already

00:37:12.960 --> 00:37:18.060
did all the recon, but they needed Jenny’s help getting a USB thumb drive in the door,

00:37:18.060 --> 00:37:23.280
past security, and to be plugged into a computer somewhere. They didn’t think they could do this

00:37:23.280 --> 00:37:29.400
themselves. They all were huge, like great big Special Forces types with baldy heads

00:37:29.400 --> 00:37:34.200
and muscles and tattoos and they just would stand out a mile. I said look, I don’t know

00:37:34.200 --> 00:37:38.400
who you are and everything, and I don’t know if I can do it. He said well, we’ll pay you,

00:37:38.400 --> 00:37:42.960
and then he named this figure and it was more money than I’ve ever been paid – at that point,

00:37:42.960 --> 00:37:47.040
that I’ve ever been paid in my life for like, a day’s work. Like, thousands.

00:37:47.040 --> 00:37:52.080
JACK: Everyone’s got a price and this was Jenny’s price, so she thought it over and said…

00:37:52.080 --> 00:37:53.280
JENNY: Where do you want me?

00:37:53.280 --> 00:37:58.440
JACK: She agreed but she wanted to confirm all this was legit. Jenny got this mystery guy’s

00:37:58.440 --> 00:38:02.520
business card and went up to her hotel room and started researching this company that he

00:38:02.520 --> 00:38:07.920
worked for and yeah, it seemed legit. It was an above-board company doing actual security audits

00:38:07.920 --> 00:38:13.260
for big businesses. The security team of the bank was aware of this assessment. So, the job was

00:38:13.260 --> 00:38:17.640
this; they were going to give Jenny a USB thumb drive. She was to take it past lobby security

00:38:17.640 --> 00:38:22.380
and then go into a hallway where there were some offices and then she’d go into a specific office

00:38:22.380 --> 00:38:26.760
and plug the thumb drive into a computer, just plug it in for like a minute or so and then take

00:38:26.760 --> 00:38:31.920
it out and get out. Jenny didn’t ask what was on the thumb drive. She’s just not that interested in

00:38:31.920 --> 00:38:36.600
the tech side but I can guess that it was probably some kind of rubber ducky or something like that

00:38:36.600 --> 00:38:41.280
which is a device that acts like a keyboard when you plug it it. It just automatically starts

00:38:41.280 --> 00:38:45.660
typing commands and the computer then starts doing things. Like, it could create a reverse connection

00:38:45.660 --> 00:38:50.100
to a computer out in the world somewhere and now someone from the outside can access that computer

00:38:50.100 --> 00:38:55.680
that she plugged it into. So, she started thinking about a plan, her disguise, her back story…

00:38:55.680 --> 00:38:58.500
JENNY: My pretext was, I was going in to do some training

00:38:58.500 --> 00:39:03.660
on the inside of the bank. I was a sort of in-house trainer and that’s why I was there.

00:39:03.660 --> 00:39:09.240
JACK: Because she was training, she had some props with her that fit with this disguise.

00:39:09.240 --> 00:39:14.700
First was her handbag which she packed with minimal infiltration kit. She had a

00:39:14.700 --> 00:39:18.180
can of compressed air, like the kind you’d use to spray the dust off your computer,

00:39:18.180 --> 00:39:22.560
because it turns out you can use these to open certain kinds of doors.

00:39:22.560 --> 00:39:27.720
JENNY: You’ve got magnetic locks on fire doors that sense smoke and

00:39:27.720 --> 00:39:31.980
if you just get some – sometimes it even works with deodorant but if you just get

00:39:31.980 --> 00:39:37.320
that condensed oxygen can and spray through the little crack, it very often opens the door.

00:39:37.320 --> 00:39:40.200
JACK: She also packed one of her all-time favorite items to bring.

00:39:40.200 --> 00:39:43.140
JENNY: I always have smoke bombs with me to create my diversions.

00:39:43.140 --> 00:39:47.400
JACK: Why do you like smoke bombs so much? This is a new one. I haven’t heard people use this.

00:39:47.400 --> 00:39:53.040
JENNY: You know, it starts a diversion. It starts an evacuation. I was in a TV building once,

00:39:53.040 --> 00:39:59.220
TV studio, and there was this huge evacuation; not me that caused it but there was – someone

00:39:59.220 --> 00:40:03.540
had set fire to [00:40:00] toast or something in a kitchen. But the alarms go off, the whole

00:40:03.540 --> 00:40:08.640
building evacuates, but it’s when you go back in that you can go – you can tailgate, effectively;

00:40:08.640 --> 00:40:13.200
you can get in quicker. So, smoke bombs, it’s so helpful. You can draw people to an area,

00:40:13.200 --> 00:40:17.760
you can get a building to evacuate. The ones I use are like yellow wax and they

00:40:17.760 --> 00:40:21.000
really do draw a crowd. If you put – if you light one, there’s a tremendous amount

00:40:21.000 --> 00:40:25.920
of smoke that it gives off but briefly and safely. It’s just a really good diversion.

00:40:25.920 --> 00:40:31.680
JACK: [MUSIC] Jenny packs some more stuff for this job, too; a couple different IDs, a lighter, she

00:40:31.680 --> 00:40:37.080
likes taking little mints along with her because she can use them as chalk markings on things,

00:40:37.080 --> 00:40:42.900
a small hammer to smash locks with if she needs to, and something to lever a door with. These are

00:40:42.900 --> 00:40:47.400
things that are all helpful but Jenny would always rather talk someone into opening a door than

00:40:47.400 --> 00:40:52.980
forcing it open herself. She likes to keep her kit minimal and to keep things hidden. Like, if she

00:40:52.980 --> 00:40:58.260
needs a knife or a blade, hide it in something like a tampon. She says people rarely if ever

00:40:58.260 --> 00:41:04.560
search tampons. Finally, she packed the USB thumb drive with the security firm’s payload on it. She

00:41:04.560 --> 00:41:10.680
chose a thumb drive in the shape of a flip-flop because, well, it looks silly and it doesn’t

00:41:10.680 --> 00:41:15.960
look like a malicious USB drive. Jenny finished up her disguise with two other important props.

00:41:15.960 --> 00:41:20.880
JENNY: I bandaged up my arm so it looked like I had a broken wrist

00:41:20.880 --> 00:41:27.420
and then I put a load of box files under my left arm, and I had lots of loose-leaf paper

00:41:27.420 --> 00:41:33.360
so that if I dropped the file, the paper would sort of spill out like in a cascade.

00:41:33.360 --> 00:41:38.280
JACK: She had it in her mind that she could use a fake bandage to maybe get people to hold

00:41:38.280 --> 00:41:42.480
doors open for her or something. You never know what you might use these sort of things to do,

00:41:42.480 --> 00:41:47.220
but she’d be ready if there was an opportunity that presented itself. When the day came,

00:41:47.220 --> 00:41:50.520
Jenny headed down to the bank and walked up to the front door.

00:41:50.520 --> 00:41:56.220
JENNY: There’s a security guard that opens them but he’s just like the bellboy kind of thing,

00:41:56.220 --> 00:42:00.240
right? He’s got the big – the uniform and the

00:42:00.240 --> 00:42:03.300
hat and everything and it’s very sophisticated. He opens the doors.

00:42:03.300 --> 00:42:05.460
JACK: She walked in and scoped out the lobby.

00:42:05.460 --> 00:42:09.120
JENNY: It was a very expensive

00:42:09.120 --> 00:42:15.480
sort of financial institution with leather sofas and huge, wooden doors.

00:42:15.480 --> 00:42:19.320
JACK: The friend that hired Jenny had coached her up on where she

00:42:19.320 --> 00:42:24.120
needed to go. She saw the door to the staff offices over on the left side of the lobby.

00:42:24.120 --> 00:42:28.140
JENNY: The door wasn’t like a door. What it was like was – if you can imagine,

00:42:28.140 --> 00:42:35.160
the walls are just these huge oak panels, sort of – how high? Twelve,

00:42:35.160 --> 00:42:39.240
fifteen-foot high panels up to the ceiling. [MUSIC] This staff door,

00:42:39.240 --> 00:42:45.180
the only thing that gives away that it’s a door is that there’s this biotech pad on it.

00:42:45.180 --> 00:42:49.980
JACK: It’s a fingerprint scanner. Only people with valid fingerprints would be able to open

00:42:49.980 --> 00:42:56.760
the door. Jenny’s fingerprint obviously won’t open this door but hey, let’s try it anyway.

00:42:56.760 --> 00:42:58.740
JENNY: I didn’t make eye contact or do anything,

00:42:58.740 --> 00:43:02.820
just walked straight over. My arm’s bandaged up and I’m carrying all this stuff;

00:43:02.820 --> 00:43:09.180
my handbag’s over my shoulder and I put my thumb on the bio-lock. It just beeps.

00:43:09.180 --> 00:43:14.640
JACK: It didn’t work. She expected it wasn’t going to work but part of her job is to kind

00:43:14.640 --> 00:43:19.560
of test if things do work or don’t work. So, when that didn’t work, now what? I mean,

00:43:19.560 --> 00:43:22.740
the security guard probably heard the beep and is starting to look her way now.

00:43:22.740 --> 00:43:26.820
JENNY: So, what did was I swore really, really loudly.

00:43:26.820 --> 00:43:30.960
So, I’m trying to draw attention because I know I can’t get in without some help.

00:43:30.960 --> 00:43:37.020
JACK: Jenny calculated the situation and thought that she can either try to defeat this fingerprint

00:43:37.020 --> 00:43:42.360
lock or the security guard, and she decided to square off with a person and not the lock.

00:43:42.360 --> 00:43:45.420
JENNY: What I say is you don’t have to work on the lock. Work on the person

00:43:45.420 --> 00:43:50.640
behind the security. It doesn’t matter what they put in place; if someone’s got access,

00:43:50.640 --> 00:43:54.300
then I can access them, and then we’re down to me versus the person.

00:43:54.300 --> 00:43:57.060
JACK: Right on cue, a well-dressed security guard comes over.

00:43:57.060 --> 00:44:01.080
JENNY: He’s top security guard in the lobby. He’s got all the sort

00:44:01.080 --> 00:44:04.920
of – the earpiece and the radio and beautiful, immaculate suit.

00:44:04.920 --> 00:44:05.760
JACK: He says…

00:44:05.760 --> 00:44:06.480
JENNY: Madam?

00:44:06.480 --> 00:44:07.320
JACK: She says…

00:44:07.320 --> 00:44:11.460
JENNY: This isn’t working today and it wasn’t working yesterday.

00:44:11.460 --> 00:44:14.400
JACK: Which is a lie, of course. Jenny wasn’t there yesterday.

00:44:14.400 --> 00:44:16.020
JENNY: He said well, try again.

00:44:16.020 --> 00:44:18.840
JACK: She does begrudgingly because remember,

00:44:18.840 --> 00:44:24.720
she has her hand all bandaged up with a big box of papers under her arm and her purse on the other.

00:44:24.720 --> 00:44:30.000
JENNY: So, I made a huge job of it, right? I was like, ugh. It beeps again and I said okay.

00:44:30.000 --> 00:44:34.260
He said to me I think it’s because you’re not pushing your thumb down hard enough.

00:44:34.260 --> 00:44:36.240
JACK: He grabs her bandaged hand.

00:44:36.240 --> 00:44:40.980
JENNY: He got hold of my hand and pushed the thumb and I went ah, fuck,

00:44:40.980 --> 00:44:48.300
god, ah! He went right, and I just looked at him like this, like fury. He said try the other hand.

00:44:48.300 --> 00:44:52.140
JACK: I think at this point the guard was stalling. Yeah,

00:44:52.140 --> 00:44:57.120
maybe she scanned the wrong finger, but I bet he was just trying to get a better read on her,

00:44:57.120 --> 00:45:00.600
watch her closely and see what she does. She tells him they [00:45:00] didn’t

00:45:00.600 --> 00:45:04.560
scan the other finger; just this one. But she tries that other hand anyway.

00:45:04.560 --> 00:45:08.460
JENNY: As I did it, I made sure to – dropped all the files so now there’s

00:45:08.460 --> 00:45:13.080
files and paper everywhere and I’m swearing away.

00:45:13.080 --> 00:45:18.300
I just start to pick them up but really loudly and there’s people starting to look over. He just

00:45:18.300 --> 00:45:24.014
said for god’s sake, go in, and just beeped me in. I went like, thank you, danke schon.

00:45:24.014 --> 00:45:25.500
JACK: [MUSIC]

00:45:25.500 --> 00:45:30.840
Jenny was confident this plan would work. She says making a scene like this in Germany embarrasses

00:45:30.840 --> 00:45:36.360
people into action, but a similar tactic like that maybe wouldn’t work in a Mediterranean country

00:45:36.360 --> 00:45:40.980
where people are more laid back. You really have to know the territory to be most effective.

00:45:40.980 --> 00:45:44.220
JENNY: I just thought the last thing they’re gonna want is to be massively

00:45:44.220 --> 00:45:48.900
embarrassed in the middle of the working day, so he’s either gonna ring someone

00:45:48.900 --> 00:45:53.160
and I’m gonna have to kinda BS them or I think he’s gonna let me in, and he did let me in.

00:45:53.160 --> 00:45:56.700
JACK: Jenny stepped through the door and into a hallway where there’s offices.

00:45:56.700 --> 00:46:01.020
It was also high-end just like the lobby and there were wooden doors with frosted

00:46:01.020 --> 00:46:05.520
windows. The computer that Jenny was after was at an office at the end of the hall.

00:46:05.520 --> 00:46:08.100
JENNY: I just walked down the corridor and it was so quiet,

00:46:08.100 --> 00:46:12.840
and so it smelled of wood polish and money.

00:46:12.840 --> 00:46:15.840
JACK: She wasn’t alone; there were people working in this office.

00:46:15.840 --> 00:46:21.000
JENNY: A few people sort of looked up but didn’t do anything, so just looked up at me and then

00:46:21.000 --> 00:46:25.200
looked back down. I was just really quiet and respectful; didn’t make eye contact, didn’t smile.

00:46:25.200 --> 00:46:30.960
JACK: Along the way she discarded her file box and bandages. They served their purpose. She

00:46:30.960 --> 00:46:34.590
doesn’t need them anymore and the box fit well enough to just leave it on a bookshelf somewhere.

00:46:34.590 --> 00:46:40.440
JENNY: Got to the end of this office and walked past

00:46:40.440 --> 00:46:42.900
it once just to check no one was in there – it was empty – and just walked in the office and put this

00:46:42.900 --> 00:46:48.720
flip-flop USB into the guy’s desktop, huge, big, clunky desktop thing that was all switched on and

00:46:48.720 --> 00:46:53.340
wide open. I put it in and I didn’t – it whirred away and everything but I wasn’t looking at that.

00:46:53.340 --> 00:46:57.300
I trust – I have to trust that that will do what they tell me it’s gonna do. Meanwhile,

00:46:57.300 --> 00:47:01.740
I’m kind of just keeping an eye. But all I can hear in the background is just the quiet,

00:47:01.740 --> 00:47:05.040
polite calls in German. I couldn’t – nobody walking up and down or anything.

00:47:05.040 --> 00:47:09.360
JACK: She waits a minute or two with the USB drive in the computer and then pulls it out.

00:47:09.360 --> 00:47:11.760
JENNY: I just saw this line go across the screen,

00:47:11.760 --> 00:47:16.440
kind of like a lightning thing across the screen just once, and that was it.

00:47:16.440 --> 00:47:21.180
JACK: Instead of going out the way she came in, Jenny walked to the end of the corridor,

00:47:21.180 --> 00:47:24.480
through a door, and then out to the parking garage. She turned

00:47:24.480 --> 00:47:28.320
the thumb drive over to her contact and the security firm, and the job was over.

00:47:28.320 --> 00:47:33.240
JENNY: That was it. That was the most money I’d ever made ever. All legitimate;

00:47:33.240 --> 00:47:37.020
everything was fine, nobody was being robbed. I was being hired legitimately

00:47:37.020 --> 00:47:41.880
but I had no idea that people could make that much money just doing something this simple.

00:47:41.880 --> 00:47:47.520
JACK: The thing is, this job was really easy. She did it all in two days while on a trip already,

00:47:47.520 --> 00:47:52.380
without the need to do any write-up or do any reports or debriefs or anything like that.

00:47:52.380 --> 00:47:56.400
While she didn’t say what amount she got, you could still imagine that even if the job paid

00:47:56.400 --> 00:48:01.680
her just a few thousand pounds, making that kind of money in just two days is really nice.

00:48:01.680 --> 00:48:06.780
While breaking into a bank might sound hard, to Jenny, this is what she trained for. The Hamburg

00:48:06.780 --> 00:48:11.760
job was about jumping at certain opportunities and she said business really started to pick

00:48:11.760 --> 00:48:17.880
up after that. [MUSIC] Okay, so we have one more pen test story from Jenny, and this one is a doozy

00:48:17.880 --> 00:48:24.060
because this one went really bad. Alright, so to start, Jenny went to Asia to negotiate a contract

00:48:24.060 --> 00:48:28.680
for a large company and one of her old clients heard that she was in Asia and called her up.

00:48:28.680 --> 00:48:37.080
JENNY: Guy basically said are you traveling home business class? I said no.

00:48:37.080 --> 00:48:43.320
They’re sending me back coach. He said, do you want to travel back business class and

00:48:43.320 --> 00:48:49.140
have some spending money? I said yes. He said okay, I need you to do a little job for me.

00:48:49.140 --> 00:48:53.760
JACK: She had done work for this guy before, so why not take an extra job while abroad? She

00:48:53.760 --> 00:48:58.500
canceled her flight home and booked a new flight to this other country in Asia. This

00:48:58.500 --> 00:49:03.900
job was to see if she could get into someone’s house and find an address book in the office,

00:49:03.900 --> 00:49:08.820
then look through the address book, looking for a particular name and if she finds that name,

00:49:08.820 --> 00:49:12.840
then she’s supposed to leave a Post-it note on the desk with a secret message.

00:49:12.840 --> 00:49:18.000
If she doesn’t find the name, then she just leaves. Jenny accepted the gig and the client

00:49:18.000 --> 00:49:21.720
gave her half of the target’s address over the phone, and the other half would come when she

00:49:21.720 --> 00:49:25.980
checked into a hotel in this other city which all sounds a bit cloak and dagger.

00:49:25.980 --> 00:49:29.580
JENNY: I didn’t really question it although it was naive not to question it.

00:49:29.580 --> 00:49:33.540
JACK: She’s done some pretty interesting jobs before and it comes with the territory I guess,

00:49:33.540 --> 00:49:39.720
but she wasn’t robbing anyone; she was just planting a note and it didn’t seem that bad.

00:49:39.720 --> 00:49:45.360
She has done work for this guy before and she trusts him. Jenny checked into her hotel room in

00:49:45.360 --> 00:49:50.760
this new city. [MUSIC] She got the other half of the target address and moved forward with Step 1,

00:49:50.760 --> 00:49:56.880
recon. She caught a taxi over to the neighborhood where the house was, and got dropped off a little

00:49:56.880 --> 00:50:00.342
bit down the road and started walking the street to where the target house was.

00:50:00.342 --> 00:50:05.940
JENNY: [00:50:00] The neighborhood that I got out in was so rich and completely

00:50:05.940 --> 00:50:13.020
deserted. There wasn’t a sound of a dark barking, there were hardly any cars on this huge road.

00:50:13.020 --> 00:50:16.560
I could hear the water of this lake that ran beside the road

00:50:16.560 --> 00:50:20.820
but I could hear virtually nothing. It just – it seemed to be abandoned.

00:50:20.820 --> 00:50:25.440
JACK: Jenny looked for the house that she needed to gain access to. She didn’t have

00:50:25.440 --> 00:50:28.920
a smart phone at the time, just a map with the address written on it,

00:50:28.920 --> 00:50:30.870
and she strolled around the neighborhood, searching.

00:50:30.870 --> 00:50:34.980
JENNY: But then I saw it and it was the biggest house on the street. It

00:50:34.980 --> 00:50:37.560
was sort of set back a bit more from the road than the others.

00:50:37.560 --> 00:50:43.260
JACK: It was a big, colonial-style mansion with walls around the property and gardens

00:50:43.260 --> 00:50:46.860
and fountains and a fabulous driveway that looped around to the front door

00:50:46.860 --> 00:50:50.220
and back to the street. She saw the house number and confirmed

00:50:50.220 --> 00:50:53.910
it was the right one. Then she noticed the gate wasn’t locked.

00:50:53.910 --> 00:51:00.840
JENNY: It had the feeling that it was used as sort of a base camp but not really lived in,

00:51:00.840 --> 00:51:05.640
so it was kept nicely and everything, but I didn’t feel like it was a home.

00:51:05.640 --> 00:51:10.140
JACK: [MUSIC] She scoped the place out a bit more and noticed there were some

00:51:10.140 --> 00:51:16.140
exterior stairs that led up to some French doors on the second level. She figured out that might

00:51:16.140 --> 00:51:20.460
be a good way to break in, and that was it for recon. She thinks this place isn’t lived in,

00:51:20.460 --> 00:51:25.200
the street gate is unlocked, and the exterior stairs go up to the second story. With a house

00:51:25.200 --> 00:51:29.940
this big, there’s bound to be a door or window unlocked somewhere. The plan was to come back

00:51:29.940 --> 00:51:34.920
the following night for the job, so she headed back to the hotel. Her contact calls her and

00:51:34.920 --> 00:51:38.220
she tells him recon went well. I’m gonna go back tomorrow and finish up the job.

00:51:38.220 --> 00:51:44.880
JENNY: Get back to my hotel room, kind of – I was gonna run a bath, get a drink, get some dinner,

00:51:44.880 --> 00:51:51.000
have an early night, and I actually got undressed and put my robe on, ran the bath,

00:51:51.000 --> 00:51:54.180
and then just thought screw it, I’m gonna go back and do it now.

00:51:54.180 --> 00:51:57.900
JACK: Jenny’s recon had her convinced that this job would be easy,

00:51:57.900 --> 00:52:02.100
so why wait? Let’s get it over with now. The place looked deserted anyway.

00:52:02.100 --> 00:52:08.360
JENNY: I remember thinking that bathwater will probably still be warm by the time I get back.

00:52:08.360 --> 00:52:13.200
JACK: Jenny got dressed in all black. She wasn’t prepared for this job; after all,

00:52:13.200 --> 00:52:18.180
she traveled to Asia to go a negotiation, not some security assessment, so she has none of

00:52:18.180 --> 00:52:22.500
her equipment or props with her. She ties her hair back in a ponytail and looks around the

00:52:22.500 --> 00:52:26.640
room for anything useful to bring. She grabbed the Post-it note that she was going to plant

00:52:26.640 --> 00:52:31.380
on the desk. She stuffed some cash in her bra and went down to the hotel gift shop to

00:52:31.380 --> 00:52:36.720
look for any useful tools there. She buys a small flashlight and a bottle opener from the gift shop,

00:52:36.720 --> 00:52:41.310
which both have the hotel logo on them. She got a cab and went back to the neighborhood.

00:52:41.310 --> 00:52:45.960
JENNY: The reason this story is so significant – one of the reasons is that I broke my own rules,

00:52:45.960 --> 00:52:51.840
because by the time I get to this job in Asia, I’ve been doing this for a long, long time;

00:52:51.840 --> 00:52:59.040
eighteen years, maybe. I was first of all very superstitious about things. I have lots of little

00:52:59.040 --> 00:53:05.280
rituals and all sorts of bits and bobs that I kinda do before I go out and do a job, but

00:53:05.280 --> 00:53:10.560
there was also just sensible things like someone always knows when you’re on a job. You always

00:53:10.560 --> 00:53:18.000
check with the client right before you go; it’s still green to go or we’re gonna abort, all that.

00:53:18.000 --> 00:53:22.680
JACK: But in this job, she didn’t do that. She didn’t tell her client that she changed

00:53:22.680 --> 00:53:27.480
her mind and was going back that night. She didn’t tell any family or friends that she

00:53:27.480 --> 00:53:32.520
even took another job while in Asia. Right now, only her client knew where she was.

00:53:32.520 --> 00:53:37.020
JENNY: Moreover, he thinks that I’m tucked up in my hotel,

00:53:37.020 --> 00:53:41.100
good to go tomorrow, and I’m not. I’m a day early.

00:53:41.100 --> 00:53:46.560
JACK: She didn’t have a Get Out of Jail Free card on this job either, no little note to hand

00:53:46.560 --> 00:53:51.780
to some homeowner or to police saying that this is actually a security audit and call this number if

00:53:51.780 --> 00:53:56.160
you want to confirm everything is fine. With this particular client, she didn’t actually have his

00:53:56.160 --> 00:54:01.980
number. He always called her. These broke a few of her own rules but Jenny thought this job was

00:54:01.980 --> 00:54:07.080
so easy, it wouldn’t matter. Jenny got out of the taxi a few doors down from the house. It’s

00:54:07.080 --> 00:54:12.900
nighttime now. She made her way to the house and slipped through the unlocked gate. She headed for

00:54:12.900 --> 00:54:18.300
the exterior stairs to the French doors. Along the way, she realizes her little pen light is

00:54:18.300 --> 00:54:22.740
so ineffective that she just throws it on the ground and kicks some dirt over it at the front

00:54:22.740 --> 00:54:26.700
of the stairs. The moon was up anyway which was enough light to see without a flashlight.

00:54:26.700 --> 00:54:29.580
JENNY: Climbed up the stairs and as I got to the double doors,

00:54:29.580 --> 00:54:32.940
I heard a phone ring inside the house.

00:54:32.940 --> 00:54:38.520
So, just flattened myself against the wall and listened and listened. Nobody answered this phone.

00:54:38.520 --> 00:54:43.920
JACK: This was good luck, actually. A ringing phone can tell you a lot. How many rings until

00:54:43.920 --> 00:54:49.620
someone picks up? If someone answers, can you hear their voice? But the phone just

00:54:49.620 --> 00:54:56.580
kept ringing. Nobody picked up, not even an answering machine, so she looked in through

00:54:56.580 --> 00:55:01.020
the windows of the French door. Nothing in the house seemed to [00:55:00] be moving.

00:55:01.020 --> 00:55:05.520
JENNY: There’s this bedroom and it’s all sort of – there’s an unmade bed

00:55:05.520 --> 00:55:09.540
but no personal – no shoes on the floor or anything like that.

00:55:09.540 --> 00:55:13.380
JACK: Since no one answered the phone and the house seemed empty,

00:55:13.380 --> 00:55:17.580
Jenny got ready to force the French doors open with her bottle opener.

00:55:17.580 --> 00:55:19.500
JENNY: Then I remembered;

00:55:19.500 --> 00:55:24.240
something I’ve been told all my life was security only works if someone uses it.

00:55:24.240 --> 00:55:26.640
JACK: So, she grabbed the doorknob and twisted it.

00:55:26.640 --> 00:55:30.270
JENNY: It just swung open. They hadn’t even locked the French doors.

00:55:30.270 --> 00:55:33.240
JACK: She leaves the bottle opener outside. She just doesn’t need it

00:55:33.240 --> 00:55:37.140
anymore and didn’t have a good way to carry it. Those little things can be pokey sometimes. So,

00:55:37.140 --> 00:55:40.800
she just leaves it at the top of the stairs to get it on her way out. The

00:55:40.800 --> 00:55:45.900
house was dark and quiet. She didn’t want to turn any lights on to give away her presence.

00:55:45.900 --> 00:55:50.100
JENNY: Just padded into the bedroom; no one there, listening all the time. No lights,

00:55:50.100 --> 00:55:58.500
no alarms, nothing. I remember thinking what kind of person doesn’t even lock the windows? I mean,

00:55:58.500 --> 00:56:03.720
why would you not have alarms? What kind of person would do that?

00:56:03.720 --> 00:56:08.640
[MUSIC] The answer is someone who’s not frightened of being broken into is the answer.

00:56:08.640 --> 00:56:14.760
JACK: To Jenny, this could mean a lot of things, like are the people who live here dangerous? Are

00:56:14.760 --> 00:56:21.360
they looking for a fight? Are they some kind of criminal overlord? Was she walking into a trap?

00:56:21.360 --> 00:56:25.920
At this point though, she was in the house and felt invested in seeing the job through,

00:56:25.920 --> 00:56:32.760
so she pushed deeper and headed downstairs to where the office was supposed to be. Luckily it

00:56:32.760 --> 00:56:39.420
was the first door she tried. She went inside the office and saw the desk with an aquarium. She’d

00:56:39.420 --> 00:56:43.800
been super quiet up to this point but once she found this desk, she started to relax a little.

00:56:43.800 --> 00:56:47.580
JENNY: I kind of had a look around, sat in the chair, a great big chair that you

00:56:47.580 --> 00:56:52.020
swivel in. Swiveled on the chair a bit looking at the fish and smiling at the fish and stuff.

00:56:52.020 --> 00:56:57.420
JACK: Looking for the address book, she tried to open the desk drawer but it was locked. She

00:56:57.420 --> 00:57:03.420
looked around for the key. It was in a bowl on the desk. She grabbed the key and unlocked the

00:57:03.420 --> 00:57:08.760
drawer. In the drawer was the address book she was looking for. She opened it and looked inside.

00:57:08.760 --> 00:57:12.240
JENNY: Found the name almost immediately ‘cause there weren’t many names in English,

00:57:12.240 --> 00:57:15.780
put it back, and put the Post-it on the desk.

00:57:15.780 --> 00:57:20.640
JACK: Jenny can’t tell us what the message was that was on the Post-it. It was some kind of code

00:57:20.640 --> 00:57:25.800
word anyway, just to let them know that somebody was here. Now that the Post-it is on the desk,

00:57:25.800 --> 00:57:29.960
her job is done. That’s all she had to do, so now it’s time to go back home.

00:57:29.960 --> 00:57:36.600
JENNY: [MUSIC] I saw two car headlights of two massive cars pull up outside the front door.

00:57:36.600 --> 00:57:40.320
JACK: Oh no; two cars are whizzing up the driveway? Time to run.

00:57:40.320 --> 00:57:43.680
JENNY: I just padded all the way up the stairs, ran up the stairs,

00:57:43.680 --> 00:57:49.740
ran across the hall into the bedroom, and out through the windows which were still open.

00:57:49.740 --> 00:57:53.460
JACK: She was up on the balcony and she looked toward the driveway and saw two big

00:57:53.460 --> 00:57:57.300
guys looking around the place. They seemed like they could be security guards for the

00:57:57.300 --> 00:58:02.280
house. They had radios but they hadn’t seen her and started to move into the

00:58:02.280 --> 00:58:06.660
house. It didn’t look like they had any guns drawn but they were probably carrying them.

00:58:06.660 --> 00:58:13.080
JENNY: Just the type of people who would have no sense of humor at all and were definitely looking

00:58:13.080 --> 00:58:20.400
for me. I knew in that minute that this was not a legit job and that I was completely on my own.

00:58:20.400 --> 00:58:23.100
I knew that if they caught me, I was dead.

00:58:23.100 --> 00:58:28.920
JACK: [MUSIC] Jenny was spooked. She’d broken too many of her own rules on this job now and

00:58:28.920 --> 00:58:34.920
the situation just got very intense. She was here a day early. The client didn’t know she was even

00:58:34.920 --> 00:58:39.420
there. She hadn’t told any family or friends what she was doing. If security caught her, she would

00:58:39.420 --> 00:58:44.520
just look like a common burglar. Even worse, she was starting to doubt her client. Had they hired

00:58:44.520 --> 00:58:50.760
her to break into the house of some enemy? Was she some kind of pawn in a game? In moments like this,

00:58:50.760 --> 00:58:54.420
you start realizing your mistakes and she started regretting taking this job.

00:58:54.420 --> 00:59:00.600
JENNY: Every fibre of my being knew that they’d asked me to break into some massive

00:59:00.600 --> 00:59:05.760
criminal’s house. It made so much sense that they’d asked me to do it because

00:59:05.760 --> 00:59:10.860
if anything happened to me, it was just I’d gone missing in Asia, you know? Businesswoman

00:59:10.860 --> 00:59:14.400
goes missing in Asia. It wouldn’t have been – there would be no link to anything.

00:59:14.400 --> 00:59:17.220
JACK: But what would be the point of this whole thing?

00:59:17.220 --> 00:59:25.020
JENNY: What it is is it’s to show you that someone got in and didn’t take anything.

00:59:25.020 --> 00:59:30.240
That’s what it is. It’s to show you that you’re not invulnerable.

00:59:30.240 --> 00:59:37.740
JACK: Hm, I see. Perhaps her client wanted to do a security audit for whoever owned that house, but

00:59:37.740 --> 00:59:43.140
whoever owned that house didn’t think a security audit was valuable. By having Jenny break in and

00:59:43.140 --> 00:59:48.540
leave a note would be the perfect sales pitch. Like look, you obviously need better security

00:59:48.540 --> 00:59:55.920
and I can provide that for you. Or maybe this was just a bet between two friends or worse, a shot

00:59:55.920 --> 01:00:01.500
across the bow at some kind of rival. Jenny’s head was [01:00:00] racing in many directions.

01:00:01.500 --> 01:00:06.300
JENNY: It was like someone was proving a point that someone could get in and do that. I thought

01:00:06.300 --> 01:00:10.006
maybe it was more than that; maybe it was a warning or something to them. I don’t know.

01:00:10.006 --> 01:00:12.960
JACK: [MUSIC] But all that didn’t matter now. Jenny was trying to

01:00:12.960 --> 01:00:16.620
evade running into any of these security guards and she just didn’t want to get

01:00:16.620 --> 01:00:21.480
caught. She needed to get out of there. She tip-toed down the exterior stairs

01:00:21.480 --> 01:00:26.820
down to the ground level, and then snuck over a garden wall and laid down to hide.

01:00:26.820 --> 01:00:31.740
JENNY: I’m pressing myself up against the garden wall, so I’m sort of partially hidden by bushes

01:00:31.740 --> 01:00:36.960
and everything. I’m wearing completely black anyway, and I just hid my face towards the wall

01:00:36.960 --> 01:00:41.360
because my face would have been the only white thing against the shadows, you see.

01:00:41.360 --> 01:00:46.260
JACK: The guards were inside the house turning on lights and looking through the whole place,

01:00:46.260 --> 01:00:52.020
so Jenny started crawling along the wall, aiming for the gate to get out of there.

01:00:52.020 --> 01:00:59.220
But unfortunately she had to crawl past the guards’ cars to get there. She was freaking out.

01:00:59.220 --> 01:01:03.120
JENNY: I inch forward a little bit more and a little bit more

01:01:03.120 --> 01:01:10.620
and I felt like I would either laugh, throw up, or cough, was how I felt.

01:01:10.620 --> 01:01:15.900
JACK: Holding all that back, she kept crawling towards the gate. She wanted to stay low and out

01:01:15.900 --> 01:01:21.480
of sight but their cars were making it hard to get there, so she was pretty close to the cars now,

01:01:21.480 --> 01:01:27.420
inching along on the ground next to them. She stopped and listened for activity.

01:01:27.420 --> 01:01:32.640
JENNY: I thought if they stay in the house much longer, it might be that I make a move which is a

01:01:32.640 --> 01:01:37.920
stupid thing to do. You should just lie still and wait for it to go – it’s 50/50 now type of thing.

01:01:37.920 --> 01:01:42.660
JACK: As she turned her options over, she suddenly realized that she couldn’t move her

01:01:42.660 --> 01:01:49.020
head. Her ponytail was caught on something. She couldn’t see what it was hooked on. Maybe a bush,

01:01:49.020 --> 01:01:54.600
a wall, the car’s tires? After all, she was right next to the tires. She couldn’t move

01:01:54.600 --> 01:01:59.760
her head to look back at all. It was stuck. She tried to get her hair unstuck but she

01:01:59.760 --> 01:02:03.780
was having problems reaching back behind her head while staying low and motionless.

01:02:03.780 --> 01:02:07.140
JENNY: In that situation, every inch of you just wants to get up and leave

01:02:07.140 --> 01:02:10.320
and run. I’m fighting that and I’m gonna be sick and I’m gonna

01:02:10.320 --> 01:02:15.420
laugh. I felt like I was gonna laugh just nervous laughter. My mouth’s so, so dry.

01:02:15.420 --> 01:02:21.360
I taste soil. I could smell things and I could see bugs walking towards me on this wall. It was just

01:02:21.360 --> 01:02:27.240
sheer panic. I just remember thinking I’m gonna die. They’re gonna see me. I’m gonna get – I don’t

01:02:27.240 --> 01:02:30.360
know why I’m laughing now ‘cause it wasn’t funny at all but I kinda felt like I was gonna laugh.

01:02:30.360 --> 01:02:36.420
It was the ridiculousness of the whole thing just for the sake of a business class flight,

01:02:36.420 --> 01:02:42.540
you know? Nobody knows where I am. I just thought that’s it, my hair is caught and I can’t move.

01:02:42.540 --> 01:02:48.060
JACK: She laid there for a while trying to come up with a plan, any plan to get out of there.

01:02:48.060 --> 01:02:50.580
JENNY: [MUSIC] Then they came out, then suddenly

01:02:50.580 --> 01:02:56.100
they were both – started talking in this rapid language down the walkie-talkies.

01:02:56.100 --> 01:02:59.700
JACK: It was a tense moment. She was in danger,

01:02:59.700 --> 01:03:05.160
close to the cars, hair stuck, unable to move, hoping they didn’t see her.

01:03:05.160 --> 01:03:10.440
Then she heard them clear their guns and put them away. Then they climbed into their cars.

01:03:10.440 --> 01:03:16.980
JENNY: Guy gets into the car, slams the door, and then just raced off. [MUSIC] I was left

01:03:16.980 --> 01:03:22.740
there lying against this wall, and they’d just gone. As quick as they’d gone in, they left.

01:03:22.740 --> 01:03:25.260
JACK: For a minute, Jenny still couldn’t move.

01:03:25.260 --> 01:03:35.000
JENNY: Then I kinda got to me feet a bit wobbly and then just walked out.

01:03:35.000 --> 01:03:39.480
JACK: She caught a taxi back to the hotel and went straight to the bar.

01:03:39.480 --> 01:03:45.300
JENNY: I said to the barman, make me something very alcoholic but that a kid could drink.

01:03:45.300 --> 01:03:48.600
JACK: Jenny sat down with her sugary cocktail. It

01:03:48.600 --> 01:03:52.860
was early morning now. The sun was starting to come up. She was a mess.

01:03:52.860 --> 01:03:56.700
JENNY: I looked and I could see in the mirror behind the bar that my face was covered in

01:03:56.700 --> 01:04:01.320
muck and cuts, leaves in my hair, and my clothes are ripped and my shoe was ripped.

01:04:01.320 --> 01:04:03.870
JACK: Jenny downed the cocktail and the bartender asked…

01:04:03.870 --> 01:04:07.320
JENNY: Do you want a beer to chase that? As soon as he said it,

01:04:07.320 --> 01:04:09.660
I remembered I had left the bottle opener on the stairs.

01:04:09.660 --> 01:04:19.800
JACK: And the flashlight too, both of which had the hotel logo on them. But there was no

01:04:19.800 --> 01:04:27.300
going back to that place; not now, not ever. But what if they found these items and came to her

01:04:27.300 --> 01:04:33.540
hotel looking for her? Questions like this kept her up that night, worrying about every little

01:04:33.540 --> 01:04:41.880
sound she heard all night long. But fortunately for her, nobody came to her room that night.

01:04:41.880 --> 01:04:45.420
So, the next day, she booked it out of there and got on her business class

01:04:45.420 --> 01:04:50.520
plane ride home. Later, she had a phone debrief with her client.

01:04:50.520 --> 01:04:53.580
JENNY: Then he said but you said you were going in on the Saturday. I said I know,

01:04:53.580 --> 01:04:58.920
I changed my mind. Don’t give me a hard time about it. I know I made all kinds of stupid mistakes.

01:04:58.920 --> 01:05:04.800
He said well, there’s no harm done. [01:05:00] That’s fine. Then I just went,

01:05:04.800 --> 01:05:11.220
just one thing I need to know, I said, and then I’ll never want to talk about this one ever again;

01:05:11.220 --> 01:05:15.300
I said I was on me own, wasn’t I? He just said of course you were.

01:05:15.300 --> 01:05:20.220
JACK: [MUSIC]

01:05:20.220 --> 01:05:24.000
If Jenny had been caught, it would have been really bad for her. They would have thought

01:05:24.000 --> 01:05:28.620
she was a burglar. They looked mean, not a typical for-hire security guard but more

01:05:28.620 --> 01:05:32.640
like a security guard that an evil villain would hire, a villain that doesn’t care much

01:05:32.640 --> 01:05:36.780
about the law. To try to convince them that she was there on assignment probably would

01:05:36.780 --> 01:05:42.480
have made things worse. It could have turned into a dire situation and it left her shook.

01:05:42.480 --> 01:05:47.760
JENNY: Honestly, after that, I thought I’m hanging up me guns. I didn’t do another job then.

01:05:47.760 --> 01:05:55.200
JACK: That was it for Jenny. She was done. This was just way too dangerous and still at that time,

01:05:55.200 --> 01:06:01.260
her profession was just very uncommon. She just felt like she couldn’t talk about it. Who would

01:06:01.260 --> 01:06:06.300
believe you if you said you were a burglar for hire? If so, wouldn’t they immediately clutch

01:06:06.300 --> 01:06:10.980
their belongings, thinking you might steal their stuff? So, she just stopped answering the phone

01:06:10.980 --> 01:06:18.180
for calls to break into places and just stuck with the negotiation stuff. But then as time went on,

01:06:18.180 --> 01:06:23.640
there was a sea change; the security world started adopting this type of thing. It was

01:06:23.640 --> 01:06:27.750
becoming a normal part of a security audit and this really surprised Jenny.

01:06:27.750 --> 01:06:30.900
JENNY: There were people writing books called Social Engineering.

01:06:30.900 --> 01:06:37.860
There were people giving talks about physical infiltration and it was legit.

01:06:37.860 --> 01:06:42.000
JACK: She realized she didn’t have to hide this secret part of her life anymore and

01:06:42.000 --> 01:06:46.560
it was now more acceptable. There were all kinds of ways to do this safely and honestly,

01:06:46.560 --> 01:06:51.480
so she got back into the game and was able to call herself a physical penetration tester,

01:06:51.480 --> 01:06:56.520
and started doing jobs again. That kinda reminds me of this line from the movie Sneakers.

01:06:56.520 --> 01:07:01.020
SECRETARY: So, people hire you to break into their places

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to make sure no one can break into their places?

01:07:07.560 --> 01:07:08.083
MARTIN: It’s a living.

01:07:08.083 --> 01:07:08.580
SECRETARY: Not a very good one.

01:07:08.580 --> 01:07:13.980
JENNY: I couldn’t believe that at that point I could start to talk about it. I really had to look

01:07:13.980 --> 01:07:19.740
into it to work out that this was a thing and that I had really – the job I had done my whole life

01:07:19.740 --> 01:07:26.040
I could do legitimately, be paid for, speak about on stage,

01:07:26.040 --> 01:07:31.260
and it would be a legitimate business that everybody was interested in and

01:07:31.260 --> 01:07:35.520
you could even go on certain courses and train in it, for goodness sake.

01:07:35.520 --> 01:07:40.380
JACK: Even though this work was becoming more common, it took Jenny a long time to get back

01:07:40.380 --> 01:07:45.780
into it because she just couldn’t stop thinking about how terrified she was on her last job.

01:07:45.780 --> 01:07:53.880
JENNY: I just thought that was ridiculous. What for, really? ‘Cause they were – those

01:07:53.880 --> 01:08:02.340
guys would have just thought I was a burglar and shot me and they would have probably been right.

01:08:02.340 --> 01:08:10.380
(OUTRO): [OUTRO MUSIC] A big thank you to Jenny Radcliffe for sharing these stories

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with us. You can look her up online. Her Twitter is @Jenny_Radcliffe. That’s R-A-D-C-L-I-F-F-E. She

01:08:18.840 --> 01:08:23.580
goes by the name People Hacker. Her company is called Human Factor Security and their website

01:08:23.580 --> 01:08:30.900
is humanfactorsecurity.co.uk and she has her own podcast called The Human Factor, so

01:08:30.900 --> 01:08:35.940
definitely check out her podcast so you can hear her interview other social engineers. As always,

01:08:35.940 --> 01:08:40.620
if you want to help support this show, please consider donating to it through Patreon. Rain

01:08:40.620 --> 01:08:46.200
or shine, I bring this show to you every two weeks free of charge. You know why? Because I don’t want

01:08:46.200 --> 01:08:52.620
to leave you hanging, so don’t leave me hanging, okay? Visit patreon.com/darknetdiaries. Thanks.

01:08:52.620 --> 01:08:57.900
This show is created by me, the nightingale, Jack Rhysider. This episode was produced by battle-born

01:08:57.900 --> 01:09:02.880
Charles Bolte, sound design by Garrett Tiedemann Black-Briar, editing and mixing this episode from

01:09:02.880 --> 01:09:08.760
the snow-shod Proximity Sound, and theme music is by the shatter-shield Breakmaster Cylinder. Even

01:09:08.760 --> 01:09:14.220
though in the future everyone will have fifteen minutes of privacy, this is Darknet Diaries.