Hacker Conversations: Rob Juncker, a Knock at the Door and a Moral Compass

Rob Juncker is chief product and technology officer at Mimecast. Is he a hacker? “Unequivocally yes,” he says. “And I think every security leader should be able to answer ‘yes’ to that question, for so many reasons.”

He started early, when his parents brought home an Apple IIc. He was 10. They wanted to use it for word processing; but within two days of it arriving he had the lid off, trying to figure out how it worked. He had a driving curiosity to understand it. This curiosity, which he describes more as a thirst for knowledge, started before the arrival of the Apple – but with hands-on access, it rapidly focused on technology.

Back then, especially for a 10-year-old, there were few books and little training available. But it was obvious that what made the Apple do things was software. So, he taught himself Basic programming by looking at the code on the screen and working out what words caused which actions.

“Pretty soon I found myself sitting there with the command prompt and starting to program in Basic. I think that was my first experience of the beauty of computers and electronics in general. Suddenly I was unlocking a world where I could write something and create it. It was like an artist being given a paintbrush for the first time and then realizing that you don’t need to stick within the confines of what’s on the paper in front of you – rather, you create your own canvas and what you can do with it.”

Then came modems. They were just 300 baud in those days but still magic to a new teenager with an Apple. His parents got one; but that wasn’t enough for him – especially after he discovered wardialers. To get the full benefit, he needed his own dedicated phone line for the modem, but his parents refused.

“So, I did what any hacker would do,” he explains – but remember that this was a hacker barely into his teens. “I called the phone company and ordered a phone line to be installed at my house. But the best part of this story,” he added, “is before the scheduled appointment, I was in the basement running laps around my house to get my body temperature high enough to tell my parents that I was sick and couldn’t go to school the next day. When the engineer arrived to do the installation, I was home alone with a forged letter from my dad.”

The forgery would not have been difficult. The family already had a computer being used as a word processor, and the engineer had nothing to verify the signature against. The letter explained that the family wanted a dedicated low-noise line for a modem – and it worked. The youngster expanded his hacking repertoire into successful social engineering – and all because he couldn’t afford the games he wanted and needed to find a different way to access them.

Think about this for a moment. He started when only ten years old. In the space of a year of access to an Apple IIc, he taught himself rudimentary hacking and the ability to code in Basic; and a few years later, he designed, delivered and succeeded with a complex example of social engineering. “I effectively did the first ‘deepfake’: a kid faking his father and ordering a phone line. I had no legal right to do this, but I succeeded in doing it.”

With the modem, he began more serious hacking. “I’ll admit it. I downloaded early samples of pirated software; and that eventually got me into trouble – which I’m completely free of now, by the way!”

By the time he was in his teens he had become more adventurous. He gave an example. “In the early days, SimCity asked you for the population of a city provided on a red sheet (red, so it couldn’t be photocopied) every time you played the game. I was working alongside another hacker to find a way to bypass such controls; so, we’d be working in code and especially assembly. To be honest, I wasn’t the one who solved the problem – it was another member of the group. But it’s an example of the sort of stuff I was trying to do.”

The trouble arrived with the proverbial knock on the door in his early teens.

“One day a certain US legal organization came to the house and the doorbell rang. My mother answered it, and I overheard the words, ‘We need to have a conversation with you all. We understand that there has potentially been some activity here relative to tapping into phone lines or trying to gain access to certain services.’ Well, that was true. I had been trying to. I hadn’t been successful, but I had been trying to.”

His mother replied, “No. That’s not possible.” And then he saw the lightbulb go on as it dawned on her. He heard, “Rob!” They sat down and had that conversation.

“Long story short, I lost my second phone line and had to rein back on my activities. I received a warning. And I’m grateful that I got a warning at that point, because had I continued along the path I was on, I think I would have ended up with more than just a warning. It was a turning point for me.”

The threat of jail time caused an immediate bit flip in his attitude. It was the moment he realized he should probably change what he was doing. 

But that’s only half his story. When he later went to college, he wanted to continue learning about technology and computers, but he added economics. “If you mix Computer Science and Economics, you actually get the most boring geek on the face of the earth,” he mused.

On the one hand, he had been warned off using computer skills for negative purposes, while on the other hand, the new study of economics pointed toward an alternative use of computer skills. It made him realize he could have a legitimate and well-paid career in protecting computers rather than attacking them.

“What I learned through economics is you can make really good money in software and do great things with computing. I’ll go back to that artist analogy. I believe that hackers and their curiosity are no different than artists. The artist in the hacker doesn’t simply wish to paint a new picture; he wishes to create a new canvas on which to paint.”

He excelled at painting on his brand new ‘canvas of potential’, where computers could drive and push the boundaries through curiosity. “I think that’s something that I’ve brought to the industry; that maybe the way that we’re doing things isn’t necessarily the way we should be doing things, but rather just the way that we’ve always done them in the past. I love that quote from Grace Hopper: ‘The most dangerous phrase in the language is, ‘We’ve always done it this way’.”

It was the combination of legal threat and understanding the economics of business computing that led to a complete 180-degree about-turn from his early life. He fell in love with technology, taught himself to program in Basic and started hacking when he was 10. He studied computer science and economics at college – and the latter showed him negative hacking was not the only way to use his skills. 

In his early twenties, a third factor emerged. Health issues made him question what he wanted in life. “As I went through those health problems, I asked myself, ‘What defines me; what is the legacy I want to leave in this world?’” The answer is simple to say, but hard to do: “I really want to leave the world a better place.” 

Kick-started by health, a moral compass had appeared. He probably always had one (he thinks its subtle presence is what kept him just on the right side of prison when he was younger), but he only now became aware of it. It is the almost innate understanding that most of us possess: a natural understanding of right and wrong with a preference to do what is right. On his moral compass, morality became his true North Star.

“That North Star brought me to a place where I can use everything I’ve learned and the skills I’ve acquired to defend organizations – to make the world a little safer.” His knowledge of how to attack systems had given him an understanding of how to defend them; and that is where he has spent his professional career.

After senior R&D and engineering roles at VMware, LANDesk and Ivanti, he joined Code42 in 2017. He became Code42’s CTO in 2020, and moved to Mimecast when it acquired the company in July 2024.

Everything he began learning when he was 10 (software, technology and security) is now combined into his current position: chief product and technology officer at Mimecast. 

Related: Hacker Conversations: Joey Melo on Hacking AI

Related: Hacker Conversations: Alex Hall, One-Time Fraudster

Related: Hacker Conversations: Kunal Agarwal and the DNA of a Hacker

Related: Hacker Conversations: Rachel Tobac and the Art of Social Engineering