• Cyrus

Interview - Chris (InfoSec Enthusiast)

"As for learning... I'm always learning something. That's not going to change, no matter what job I take." - Chris

This has been my longest interview thus far, however I believe that this is a very good one. We haven't really focused much on the more personal aspects yet in this little series. Chris is one of my many good friends in a community I am active in, and he's probably among the most knowledgeable people I've ever met. In this interview he talks about how he defied societal norms, became happy with himself, and is striving towards his goals of becoming a penetration tester. I believe that most people have a lot to learn from him, and it is rather inspirational. You can follow him on twitter here, and check out his website here.


Cyrus: So I'm going to ask you some basic questions and branch off if your replies permit it. Before we get started is there anything you want to ask me?


Chris: I'm curious what topics we'll cover, but honestly, I am cool with waiting until the question gets asked. So fire away!


Cyrus: That's the spirit. Let's start off with the basics again - what's your interests within the tech sphere?


Chris: I'm interested primarily in software design, development and deployment, cryptography and privacy, and hacking and security. The internet and various networking technologies are central to a lot of my interests.


Cyrus: Around what age did you get interested in these things? Was there any sort of experience you had that made you think "hmm yeah I wanna learn more about this"?


Chris: I started programming when I was 9 years old. I'd been playing games on my parents' old Apple IIe computer. Zork and other text-based adventure games. And I thought "I'd really love to learn how to make games like this!" I've always been the kind of person who sees something and says "I wonder if I could create something like that."


Originally released in 1983, The Apple IIe is the third model in the Apple II series. Initial price was US $1,395 ($3,509 adjusted for inflation)


One day I was reading 3-2-1 Contact magazine, and discovered the "BASIC Training" articles, which featured source code to simple programs for kids to learn how to code. It got me interested, and I started learning BASIC. I then discovered that my family had a giant book with accompanying casette tapes called "Step By Step" that taught BASIC programming from the ground up. So my first language was BASIC on the Apple IIe. I was hooked.


After that I learned C, C++, Perl, Java, Javascript, HTML, CSS, and all kinds of other stuff.


In high school I learned about the Cult of the Dead Cow from a PBS documentary, and discovered the world of hacking. From that point forward, hacking and coding were life-long passions.


Cyrus: That's pretty interesting. How old are you now? What has been your main method of learning? If you've taken "official" classes in school or whatnot, what have you taken?


Chris: I'm 33. Primarily I've learned by reading books and practicing the things I've read. Recently I've turned to the internet and websites like w3schools.com to learn new skills, but I still prefer a good paper book over staring at a screen. When I was in high school, my first computer science class was in my Junior year. We picked up the textbooks a week before school started, and I read through the entire C++ textbook before the first day of class. As a result, I wound up already knowing everything the teacher was going to teach, so he let me loose to work on my own coding projects. I got up to a bit of mischief and gave him some grief with a few pranks, but on the whole he was glad I was there. I acted as a teacher's assistant of sorts, helping my fellow students when he was busy helping someone else.


I did the same thing the following year. We shifted from C++ to Java, and again I read the whole textbook prior to the first day of class. I wasn't as fond of Java, though. The cross-platform compatibility was nice, but it was such an ugly language.


After high school, I attended college to pursue a Computer Science degree. But I was young and irresponsible, and had an ego the size of a planet. I attended my first computer science class, the teacher asked "What's the #1 biggest security flaw on computers today?" and I said "Microsoft Windows." That got a few laughs. But I never went back to class after that. Instead, I stayed in my dorm room, writing software and playing video games. I made some decent money that year, writing scripts for Linden Labs' virtual world called Second Life. But after a year of zero attendance, I dropped out of college entirely.


Since then, I've had no formal training in programming. It's all been self-taught. On one hand, I regret dropping out and not attending classes. I could have started my career much sooner. But on the other hand... If I hadn't dropped out, I would have had a very different life, and I wouldn't have met my wife or had any of the amazing experiences I had since then. I'm looking forward to going back to college though.


Cyrus: What's some sorts of things that you've struggled with? Over 20 odd years i'd imagine that your goals and aspirations would have shifted a bit. If they did, how so? Based on what you've said about your past and knowing you now, it seems as if you have grown a fair bit. Is there anything you wish you knew earlier in your life, or anything you wish you did sooner?


Chris: My path to maturity and success has been a very difficult one. From a very young age I struggled with depression, low self-esteem, lack of motivation, and a number of other psychological issues. As a result, I barely graduated high school, dropped out of college, took on one job after another, getting fired or laid off from each one, racking up the credit card debt and making poor decisions. My passions never changed, but my "goals and aspirations" changed regularly, as I failed at one thing after another, until finally I had no goals and felt utterly rudderless. The goal became "find a way out of this mess I've created." And the only way out seemed to be to find a job that couldn't easily fire me, and one I couldn't easily quit. A job that would force me to get off my ass and go to work every day, that wouldn't tolerate lateness or laziness. Basically, I needed a job that would force me to become the person I'd failed to become on my own. So I joined the military.


They got me into shape, taught me to wake up and get to work on time, trained me to be an aviation electrician, gave me the confidence to succeed, and pushed me to always be improving myself. I still struggled with mental health issues, but my confidence was growing. I spent my days working in the shop, and my nights writing software or reading books about philosophy.


At one point though, I had a bit of a breakdown. Pressure at work was high, and I was in a relationship with a girl back home. She and I were engaged, but then she called it off. We got back together again, were engaged again, and again she called it off. It was all too much to handle at once, and I started seeing a therapist.


Around that time I came to the conclusion that I'd been too busy judging myself based on what others saw in me, which was a bit of a downward spiral. I'd go to work depressed and lethargic, and people would see me as lazy. Then I'd get more depressed because I'd been so lazy. It was self-defeating. Instead, I needed to stop letting the world define me and start living according to my own terms.


I began to evaluate all the rules by which I lived my life. My religious upbringing had caused me more harm than good. Society's norms had caused me more harm than good. My own assumptions about life had caused me more harm than good. So I decided to start over, look at myself objectively, appreciate my good qualities and recognize my flaws, and devote myself to self-improvement. Not so that I could change how the world saw me, but so that I could be happy with myself. That was the tipping point. It wasn't easy changing my habits and my thought patterns, and I still struggle sometimes. But making that first decision to live on my own terms was the key to my future happiness and satisfaction.


So I decided to start over, look at myself objectively, appreciate my good qualities and recognize my flaws, and devote myself to self-improvement.

I wish I'd had that kind of self-respect earlier in life... But at the same time, if it weren't for my struggle, that moment of realization wouldn't have been so powerful, and my appreciation for the simple joys in my life wouldn't be so deep.


So again, I have to say I wouldn't change anything. But if I were to give advice to young people, I'd say to find out what matters to them, and live life on their own terms, pursuing their own truth, instead of trying to cowtow to society's expectations. It's not an easy path, but it's better than letting the world tell you who to be.


I would say, I wish I'd paid my debts off sooner. Debt sucks.


Cyrus: You have quite the story to tell. That's part of the reason why I asked you if you'd be interested in an interview. Maybe someone reading this is struggling and this is the wake up call they need to get their life in check.

What's your current goals? You say you want to go back to college, so i'd assume that is part of it. What is your current employment like and how do you fit learning into your time?


Chris: After the military, I went back to college for Creative Writing. I have always been passionate about writing and good stories, and about being able to communicate with people. I met my wife in college. We graduated with honors, moved to Texas, and started our lives together. But money was tight, and after she lost a job I realized that each of us individually needed to make enough to support both of us together, that way if one of us was injured or lost a job, the other could keep us afloat. It was then that we decided to try out trucking. I had considered going back to college for computer science, or trying to get a job in IT, but I didn't know how to get started, and we didn't have enough money to support us while I went back to school. Trucking was an easy choice. One month of school, and I could get a job right away.


So for the past two years I've been driving trucks for a living, with my wife as my co-driver. While we haven't had a lot of down-time, the job made us enough money that we could build a nice nest egg, and when we did have down-time, I spent it writing code and studying programming and information security.

I've listened to a ton of infosec podcasts and programming tutorials, and read a ton about the subjects while I wasn't behind the wheel.


Recently, my wife decided that she was ready to leave the trucking industry behind, which meant that both of us would have to leave our company (because the company only worked with teams). As a result, I'd have to search for new employment as a solo driver -- a prospect that I wasn't too thrilled about. After two years of spending every day with my wife (who is my best friend), the prospect of being on the road without her for a month at a time, seeing her for a total of maybe two months out of the year, just felt terrible to me.

So I decided that I wanted to take a chance and try to get a job in IT/programming/infosec.


We've got enough money in the bank that we can survive without jobs for a while, which means that I can pursue training and certification in order to seek a job opportunity. And if I should fail to get a job this time around, I know that with two years' experience in truck driving, I can get hired just about anywhere.

So I have trucking as my back-up plan, but my current goal is to pursue some certifications and seek a career in tech. From there, I'll use some of my income to pay for online courses or night school at a nearby college so I can perhaps gain my Bachelor's in Computer Science. As for learning... I'm always learning something. That's not going to change, no matter what job I take.


Cyrus: I personally believe that every day I haven't learned something new is a day I've spent wasted. I realize how cheesy that statement is, but I have basically the entirety of humanity's knowledge at my fingertips right now and it would be such a waste to not utilize that.


Are there any particularly good podcasts or books that you can recommend? Do you have any sort of advice to people looking to learn about IT/Infosec topics? Any pitfalls to avoid or things to be aware of? What's personally helped you the most on your learning journey and what has given you the most struggle? Additionally, is there anyone you look up to that has influenced or helped you become the person you are today?


Chris: Nothing cheezy about it. I feel the same. Hmm... Good podcasts. Where do I begin? :)


I'm going to list these in no particular order: Purple Squad Security, Black Hills Information Security, Risky Business, Smashing Security, The Many Hats Club, Security Now, SANS Internet Stormcenter


The SANS Internet Stormcenter is a great daily podcast that is typically less than 20 minutes long, good for catching up on the latest news on the drive to work. Security Now has some great hosts who (though VERY nerdy) are able to break down some of the latest news and explain what's going on behind the scenes. They're good for learning how stuff works, and why stuff breaks. Black Hills Information Security is a good podcast for learning about new techniques and new technologies, and for generally interesting lectures about various information security topics. Smashing Security is a fun and funny podcast where the reporters take a light-hearted look at the latest security news. Purple Squad, Risky Business, and The Many Hats Club often have good interviews and interesting commentary.


As for advice for people getting into InfoSec... I can't tell you how to get a job (still working on that one). But I can say that the field is broad and ripe for exploration. I'd say find something you're passionate about and dig into it. No matter where you look, there's always more to learn. If you're interested in networking, you could dig into routers and firewalls and the protocols used by systems to communicate with each other. Or you might dig into IoT, which is exploding in popularity (but lacking in security). Or if you're into cryptography, you might check out cryptocurrencies, cryptomining attacks, ransomware, etc. Or you could get into forensics, packet analysis, web exploitation... there are too many avenues to count. Find your passion, dig in deep, and always ask yourself "How can I break this?" and "How can I prevent others from breaking this?"

"Find your passion, dig in deep, and always ask yourself 'How can I break this?'"

As for pitfalls or things to avoid... Don't be a black-hat. I know, I know, everyone's seen Mr. Robot and wants to become the next amazing hacker who takes down Wall Street and liberates the world from their capitalist blah blah blah... But honestly, listen to the news, and you'll hear story after story of criminal hackers going to jail or failing at their attempts to get rich quick. For every malicious hacker that makes it rich, there are thousands who live in poverty. In fact, that's the primary reason why many illegal hackers choose the illegal route: in many countries, there is no infosec industry, so people with their skills can't get hired. So they employ them in illegal ways, because that's the only way they know to make money with their skillsets. If you're someone who lives in a developed country with companies that hire infosec professionals, you would do well to stick to the legal, ethical side of things. You'll make a better paycheck, you'll stay on the good side of the law, and you'll be able to do all the same stuff that the unethical hackers do, but you'll be able to make the world a safer, more secure place in the process.


What's helped me the most is, like you said, the fact that the whole wealth of human knowledge is at our fingertips, free for the taking. Anything you want to learn can be learned for free, or for very cheap. Sure, most of my skills I learned from books that cost $50+ USD each... But all of that information is available online and free. I could have learned everything I know without paying a dime. (And a great deal of what I've learned was thanks to free online sources.) Google or DuckDuckGo are your best friend. Never stop learning.


"Never stop learning."

What's hindered me the most has been my bad habits. When I get frustrated with a project, I tend to put it aside for a long time, and often never return to it. But that's not the best way to handle that frustration.


When you get frustrated with a project, or when you're stressed and overworked, it's good to set it aside for a little while and go do something else. Play a video game for a little while, or read a book, or better yet, go for a walk in the park. But when you're done, come back to the project, consider what was frustrating you, and see if you can find a way to break down the problem and find a solution. Don't give up!


I've lately been kicking myself for not keeping all those old projects I've worked on over the years. I have written so much code that has been lost to time, and I wish I could find all that code. I'd add it to my GitHub, revamp it, and use it for my portfolio.


That's the thing about art -- and rest assured, coding is an art -- it's never completed, only abandoned. There's always a way to improve, and it's up to the artist to decide when improving the product is no longer worth the time they're spending on it.

That's the thing about art -- and rest assured, coding is an art -- it's never completed, only abandoned.

Finally... Role models. That's a tough one.

There are a lot of people I look up to. Most of them have nothing to do with coding/infosec. Many of them are dead. But I'll give you some of the living ones.


JK Rowling began writing the Harry Potter series on the backs of napkins when she was living in poverty. She dedicated herself to her passion, and turned it into a beloved work of art that is still appreciated by new generations to this day. She didn't give up on her dreams, despite her adversity, and she's become a living legend.


Amanda Palmer started off (if I recall correctly) as a street performer with her music, pursuing the thing she loved despite struggling to make ends meet. She learned that it's OK to ask for help and to be humble. She went on to form The Dresden Dolls and later to become a solo musician, and then she married my all-time favorite novelist, Neil Gaiman. She was once urged by her record label to lose some weight because they didn't think that she fit the image they wanted to present. She told them they could either accept her for who she was, and recognize that her fans love her for who she is, or they could shove their record contract where the sun doesn't shine. She's a brilliant bad-ass.


There's also those people who inspire me due to their tragedies. Sylvia Plath was an incredible writer, creating some of the greatest poetry and fiction I've ever read. Yet she always lived in the shadow of her husband (also a writer, if i remember correctly) because he was a man, and society showed him more regard than they showed her. She was a genius, and an amazing talent, but because of the strict and oppressive rules of society, and the terrible state of mental healthcare at the time, she wound up killing herself. Tragic story, but it reminds me to stay true to myself, respect myself, and not care too much what society thinks.


A lot of my role models and inspiration come from people who struggled with poverty and/or mental illness to achieve greatness. The running theme there seems to be self-sufficiency and individualism.


I guess I could also list my dad. He's lived a tough life and dealt with addiction and a lot of personal struggles. But from a very young age, he taught me to question everything, learn all I can, and form my own opinions, rather than let the world tell me what to believe.


He wasn't too pleased when I questioned everything, learned all I could, and then decided to abandon his religion and social norms in order to live as an agnostic, polyamorous, left-leaning liberal arts major... But it was because of his advice that I finally found happiness in life. We're still on good terms.


Cyrus: You've been through a lot. You might not have made the best choices and you have had your struggles, but is there really anyone out there who has made perfect choices and has no problems they've needed to overcome? I think everyone's fighting their own battles, whether we realize it or not. It's good that you've come to terms with who you are. I'd argue that most people have yet to even admit that there are things about them that they don't like. You keep doing you, and don't let anyone get you down.


I'd like to continue asking more questions as i'm sure you have more interesting stories to tell and some more insight to glean, but this is by far the longest interview I've done so far. I'm glad that you've allocated some time to participate in this. This might help someone somewhere.


Are there any closing statements you'd like to make, or anything you personally would like to talk about? I believe I have asked you all the questions I wanted to ask.


Chris: I don't really have any major closing statements. Mainly, it boils down to "find your own truth." You've got to find out what "success" means to you. Don't let society dictate whether you're successful or not. Oh, and... You are under no obligation to be the person you were five minutes ago. It's never too late to try something new. That's all.





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