 So this is an interesting thought. Can an introvert actually convert himself to being one of the leading Essys in the industry, or herself? Both, right? Can it happen? Well, many people will disagree, but many people will agree. And what we have before us is a very good friend of mine, someone who I met four years ago. And he did just that exact journey. So I want you to join me in welcoming Ryan McDougal. He's the lead SE for my company, Social Engineer. And he did that very conversion. And he's going to share with you a very personal story about how that occurred. OK. So hello. My name is Ryan McDougal. I'm a senior social engineer-pantester for Social Engineer LLC. Please excuse my nervousness. I'm what many would consider a deep introvert by nature. Now I know what you're thinking. You're such an introvert, why are you standing on stage about to tell a large group of people your entire life story? And you would be right. Why am I doing this? First off, it's terrifying to be up here for me. But my reasoning will become very apparent through the course of this journey. I can only hope some of you will relate to some of my stories, maybe take something away that you can apply to your own life. Or at the very least, I hope you're mildly entertained. So my story begins at age 12, primarily because I don't really remember a whole lot about my life before age 12. So back in 1989, when I was 12, my family home caught fire one January morning when my parents and I were in the house. I was woken up by my mom screaming at me to get out of the house with no apparent reason why. So we made our way downstairs. And as we were about to exit the front door, we heard a giant explosion. And it was our sliding glass door in our house exploding into the house. So as my parents dealt with that situation, I was left in my neighbor's house across the street by myself, just kind of frantically watching my parents frantically assess the situation out front. My neighbors at the time weren't really interacting with me at that moment. So they were just so any emotions that I had or were basically internalized with no real outlet. But at that moment, I felt alone. And that was a moment that my mom told me later that she deeply regretted. But they were just really dealing with the situation any way that they really knew how. And their first priority was my safety. But in that moment, my main takeaway was that I was alone and all of my emotions were fully internalized without outlet. And that really shaped the next several developmental years. So we fast forward a few months, though. And my parents and I rebuilt our house on the same foundation. They included me in every part of that process. My dad and I actually architected the house together. And they treated me like an adult at all times. The construction crew was not entirely psyched to have a tween telling them where they were getting the design wrong. But my dad would usually come home later that night and back me up on all of the decisions that were being made. An example of that was that I put in a giant picture window in the back of the house. But they put it four feet from where it was supposed to be. And I came home from school and told them that it was wrong. And they just kind of brushed me off. And then my dad came home from work. And he told them the exact same thing. And they had to tear down the wall and they rebuilt it back up. But once we were all moved in, my parents bought me my first computer. Now, this was 1990. So it was expensive. It was about $3,000 for what amounted to basically a flip phone or the resources. But it was new at the time. And when it arrived, I literally tore it to pieces. Every piece that would come apart, I pulled apart on the living room carpeted floor. I knew nothing about static electricity, but I was just dying to know. I was dying to know how it all worked, right? So my mom was furious, to say the least. So I worked the entire next day putting it all back together. And miraculously, it actually worked. She was surprised, and frankly, so was I. So I got hooked on it right at that moment. And I spent far too much time on that computer, on the local BBS, and later in AOL, Prodigy Internet Connection. It left little time for social interactions. So anything that I did have were very awkward. Now I know that's not groundbreaking or new, but that's just what it was. I tried dating in middle school, and that was mildly successful. If you call dating late night phone calls with lots of silence, getting dumped for the cuter boy repeatedly. My first kiss was actually almost a forced experience. She knew exactly what was going on, and I had no idea. She dumped me later for a cuter boy. But due to that house fire, and that emotional suppression of that event, I started seeing my first therapist at age 13. I had issues I needed to deal with, and I really didn't know how to do that. My parents really didn't know how to deal with the way I was acting so strangely, but they were at least intelligent enough to seek help. So that was my first introduction to coping mechanisms, and how you recognize and employ them in the real world. The early exposure to professional therapy taught me that it can really be great. But the relationship between you and the professional needs to be good, or else you can really turn a bad situation worse. My first therapist was not a good fit at all, and my parents and I recognized that, and we ended that relationship very quickly. The next one was actually amazing. He was a great fit. I learned a lot about myself, and now that's where I was introduced to the concept of coping mechanisms in general in those sessions. Now for those of you that don't know what coping mechanisms are, it's basically, in simple terms, it's what we as complex animals use to deal with stress in stressful situations. So it can be positive or it can be negative, but my knowledge at that time mainly consisted of how to recognize when I was employing them naturally, and trying to determine if they were actually helpful or not. So as I grew up, I started recognizing the coping mechanisms that I used for my diagnosed depression and anxiety after a lot of failed attempts at drugs given by my first therapist. I didn't attend any of my own proms in high school, mainly because I really couldn't interact with girls in a way that was fitting for that situation. But I did attend one prom with an older girl that took a liking to me. But the way I dealt with social situations at the time, it was really a lot of just sitting in the corner, not really dancing, no after party invitations, nothing like that. I did take the opportunity to watch my peers though, and but I was really unable to mimic what they were doing to any real success. This would be an example of the identification coping mechanism where you try to copy the characteristics of others and employ them yourself. So my senior year was packed with decisions that everyone around me was telling me that was gonna affect the rest of my life. But I didn't really buy that story at the time. But I knew at least the sum had a few had to be made. I had no interest in college at the time, but I like to draw. So I thought art school might be a good option. After high school, I went to art school and I just barely got accepted. I actually had to take a summer course before the school to prove to them that I could actually do what they were gonna ask me to do. And I did convince them. I met a lot of different types of people there. And I started finding that there was a group of people that I could relate to and to make real lasting friendships. The artist type really fit my personality and it wasn't because I was an artist, but it was because I could talk to and be awkward around other artists without any judgment. It was refreshing, but after a year, the school was really starting to pressure me into picking a discipline. But I wasn't really interested in that path. The people and experiences were great. I just wasn't an artist. But my parents really wanted me to continue schooling. And I didn't, so we had to compromise. So I dropped out of art school to attend a seven month computer training course. I did well though. They gave me a task, I completed it, I repeated that for seven months. And during my electronics class, my teacher and I actually invented a circuit that we couldn't actually find a reference to in the MIT library that was down the street from where I was taking the course. I wish we had patented at the time, but we didn't, and I got a new teacher and the class changed and life went on. But at that school is where I met a wonderful woman named Dawn. She was also a student who saw something in me to give me a chance. And she arranged an interview with her company. And it was a financial company and I was interviewing for a desktop support position. All any and all dating stopped pretty much at that point. Gotta stay too far away from that. And I focused on my new job and I really excelled at it. My longtime love of computing really transferred into being successful at all the tasks they were asking me to do. After a year I was actually promoted to server support. And this was my coping mechanism at the time. Do work, think about work. No time for social interaction. This was an example of avoidance. My coworkers, who became some of my best friends even to this day, saw this and felt like they needed to intervene. So the day I turned 21 they decided to take me to a gentleman's club for my birthday. They thought it would help. Little did they know how I would actually approach that situation. It was so jarring of a situation that I went into full-on discovery mode just to see how and why these people were interacting with each other. I couldn't have a good time like my friends had intended. It had to be a social experiment to me. Now the women there were breaking the ice for me which was their job. But that's not how I saw it at the time. I wasn't falling in love with every girl that talked to me at the place. But it did give me an opportunity to have a social interaction with the opposite sex in a non-business setting. I was very respectful of the dancers. So much so that they were a little confused. It only took a few visits to that same club for them to realize that I was not the same type of patron that they were used to. I sat on my hands during all the dances that my friends were paying for. I asked them how they were doing that night. I told them they looked nice while they were dancing. After a while, they started coming over to our table just to sit down and have a regular, normal conversation with somebody. I actually liked that a lot. My friend and I used to, we went back to this club multiple times a week to see our new friends. They were always excited to see us. We weren't spending gobs of money. We were basically just spending enough money to keep the management off our backs. And we weren't getting drunk any sense. But within a year, so within a year of that social outing, we ended up driving these dancers to other clubs. We were going to their house to hang out as friends. I even took care of one girl's cats one weekend while she was out of town. And at no point did I ever have sex with any of them, which surprised one or two of them when the opportunity arose. I wasn't really interested in that. I just wanted to learn how to talk to other people and make friends. It provided a certain level of social acceptance that I just really couldn't find anywhere else. But not for lack of trying. I mean, the typical bar was kind of the prom situation. It was a lot of sitting alone, watching how others interacted, not really making any meaningful impressions on anyone. So up until this point, many of these experiences described in those situations were an attempt for me to interact with others. It was a driving force, but the how was really the lonely question. That early trauma took my reliance away from other people to the point where being alone felt much more comfortable. There was a driving force to connect with others, but it was just really easily suppressed. I never felt like I thought like everybody else. So most social interactions were just treated like experiments rather than just being a person. In my head, I stepped out and I passively observed an attempted mimicry instead of just being what I thought was a normal person. The early therapy sessions gave me tools to deal with my unexplored emotions, but it did very little for general interactivity. That wasn't really their goal. Although I didn't know it then, these experiments were actually disruptive to my natural development. I thought I was learning who I was, but I was just actually learning how other people were. It'd take a whole different perspective to start understanding myself. So a couple of years later, a coworker moved out of state to a new startup and built to me it was a way to get rich quick. He offered me a position at this new company with the promise that I'd be a millionaire in five years. Come to find out later that didn't really pan out as advertised. But I was young and I had no ties to my current location other than a couple of solid friendships. So I jumped at the chance. It took me thousands of miles away from everything I knew on a gamble. Once I got settled in this new location, I immediately went to the local gentleman's clubs to pick up from the social interaction that I had just left. But it was not that easy or the same in any way. It was different people, different situations, totally different results. It didn't take long for me to realize that no matter how hard I tried to push that narrative. So I stopped going to the clubs and I got back into full-on work mode. Not long into my new job, my boss was becoming friendly enough with me to start inquiring about my social life. His wife worked in the HR department at the same company and I happened to mention to him that I noticed one of her employees. But I didn't really feel like I matched up to the standards that she might have so I had really no intention of talking to her. He told his wife and they went into full-on matchmaker mode very quickly. So I started dating this young woman who was just a couple of years older than I was and we had a great time for a while. It was the first relationship I had had outside of high school, so it was new and different. We dated for almost a year and we even bought a house together. It was progressing to the point where marriage was likely discussed. Then things went sideways. We started disagreeing on very basic things and she suggested that I see a therapist. I agreed because the consensus was that the issues were probably my fault and since I had seen a therapist in the past I was clearly the broken one. So I started seeing a social worker who introduced me to the concept of an emotional toolbox. He was fantastic. I described my interactions with people in ways that I understood completely technically. TCP handshake, email flow, firewalls, all technical from my side and he translated that into human emotions and reactions. The tools that he was giving me were just new perspectives on situations so when I approached them in the future I could deal with them in a different way and not how I naturally would have. So after a couple months he determined based on my descriptions of events that my girlfriend was likely bipolar. He gave me a great book called Stop Walking on Egg Shows by Paul Mason and Randy Crager which is basically a book for people who live with someone who has bipolar disorder. The stories in this book felt like they were written directly from my life experiences with my girlfriend. We had word for word conversations that were depicted in this book. It was actually shocking to me. I took this new knowledge and I tried to apply it to my home life but she didn't really see it that way and started changing her interactions with me dramatically. We went from a seemingly happy relationship to a sour one to an abusive one. She punched and kicked me enough times that I moved out of the house we owned together and I slept in my car until I could find a new place to live. And once I moved out she stopped paying any bills at all and we sold the house as fast as we could and I paid way too much money to get out of that house. She paid nothing at all and I still think it was totally worth it. So at 24 I moved into a new place on my own and I focused on my job ahead. You might notice a trend happening. My comfort zone has always been my work. Interacting with computers was always easier to me than so it became my fallback. When the social world got me down I worked. When people started to really confuse me I worked harder. It drove my career very quickly and my employers noticed. After about five years at this one company I was offered a job in a new startup by my former matchmaker boss Steve. We're great friends now and it all started at this time where he appreciated my work ethic and knew where the line was from me on a personal level. I took a five year hiatus from dating and for any social interaction at all for that matter in my work life improved dramatically fast. But suddenly I felt that pull again for companionship. I learned from my past mistakes though and I did not date coworkers. I signed up on a popular dating site which was new in all the rage at the time. It took a little while to get going though. I was sending out messages to many women over the course of the year that I paid for and I was getting very little response. I did get some dates though. In fact, I got more in that one year than I did in the decade that preceded it. Talk about social research opportunities. I was experimenting with all different kinds of women and when I say experimenting all I mean is very awkward dinners. There was no sex at all from any of these experiences and I went on primarily first dates. In any that I did have a second date with it was clear there would not be a third. I did learn a lot about myself though for just trying too early. So my subscription was about to run out on the dating site and I started talking to a friend back home about all the dates I was going on and how nothing was really coming from it. I told her I was gonna send out one more email but I really didn't think anything was gonna result from it. I couldn't have been more wrong. My last email went to a lovely girl with a 77% match. We started talking over email for about a month before we decided to meet in person. Our first date was the day before my 30th birthday. We decided to meet at an Irish bar in town. I got there very early and scoped out the place. We had a couple, they had a couple of seats around the bar called the snug which is just basically two seats in an enclosed section kind of away from all the noise and the other goings on in the bar. So I texted my date, meet me in the snug. She arrived and my first words with her before even saying hi or wow, you're gorgeous. She smiled and sat down. For the next four hours we talked. I laid my whole history out to her and she seemed to take it pretty well. I metaphorically vomited my life at her and she stayed. We closed the bar, I walked her back to her car and she kissed me. I was not prepared for that. I was tense, my hands were clenched, kind of like right now. We scheduled the second date and then the third and then we lost count. Come to find out she was on a seven day trial of the same site I had just paid a year for. No figure. Both our subscriptions lapsed. My world changed and this was the relationship that I was searching for. We moved in together after about a year and I made it clear that if she was really in this for the long haul, we wouldn't talk about marriage until the five year anniversary. She agreed and we went on to develop a great relationship. Now this was not all puppies and rainbows but in a real adult relationship, it was a great challenge. A whole new experiment with emotions and compromise and love and care and kindness. We lasted the five years. We got married on her five year anniversary, the day before my birthday. This whole time my job was going well but I was really starting to feel that sysad and grind. With so much social and emotional input at this point, my love of the job really started to fall off. I needed to change. I needed to change and my boss, the matchmaker had just quit the company and I was about to take over his role. I wanted no part of it, so I quit with no plan. Steve's wife was a recruiter at a nearby security company for a very limited time. But she took my resume and she got me an opportunity for an interview. With no on paper security experience to be on the pen testing. Now at this point I had 15 years of sysad and experience but nothing as specific as pen testing. The hiring manager might gave me a chance and I'm forever grateful to him for that chance. I took a major pay cut to take that job but I knew I could do it and prove myself. And this is where I was introduced to social engineering. They told me what I needed to do and I knew I would try my best at it but I was not at all comfortable doing it. Sorry. All the anxiety from my past experiences flooded my brain at the thought of calling someone and actually asking for their password. I was given a chance to do that job so I had to do the job. I was a professional. I had my first vision experience was painful. I quaked on the phone. Everybody in the office knew how uncomfortable I was but I got the target's password. Maybe the target felt bad for me, I don't know. But that first success was gut wrenching. My co-worker Joe saw this struggle and decided to make a game out of it for the rest of the calls. Me versus him for points. It was a great way to redirect that anxiety to finish the task. Yeah, yeah, I got one more here. Thanks. I came prepared. I've read this before. Right? So, yeah, I actually felt bad afterwards after that call. I actually lost sleep thinking about having to do that again but it was my job and I had to do it. On-site impression was a very weird experience. Impersonation was a very weird experience. Let me start that again. On-site impersonation was a very weird experience but I started to get used to that feeling of being uncomfortable. It wasn't great, but I had to do it. I was given a chance and I had to prove myself. Here's where I employed compartmentalization and repression. By boxing out all of those negative feelings when I was uncomfortable. So within that first year, within my first year at that job I lost my dad. It was unexpected. He was far away and I was only told about his condition at the very end. I booked a flight to see him before he passed but I was too late. I talked to him on the phone before my flight. Well, I talked. He was on a ventilator at the time. But my sister told me that he could, he heard everything that I was saying. 20 minutes after I hung up from the call, I felt him leave. I texted my brother the moment I felt it and he confirmed it. I was heartbroken to put it mildly. I spent the next week with my family and then I came back to work. I was a professional and I had a job to do. He took every bit of every coping mechanism I had learned over the years to keep doing this job that was so uncomfortable. Instead of focusing on the negative of the situation though, I used that pain to push myself to get better. This is an example of post-traumatic growth where you use the energy of a trauma for good. I took a few classes over the next year related to network pentesting but the need to be a better social engineer was still looming. That's when I found Chris and took his APSE course. I was drawn to it because of a review I read on his site by a student who was amazed at the transformation of another student in that class. He witnessed a young man sitting alone in the back of the room not talking to anybody and by the end of the week was completing all the challenges and being successful. I thought that could be me. I convinced my boss to send me to the class and when I arrived that was me. I sat in the back, head down, totally unsure how I would get through it. I saw the need. That was the driving force of being there but I was not comfortable and then the music started. Chris has a habit of playing clutch at the start of every day of class. I thought there is no way he knew that was my favorite band. I relaxed a little bit. The first two days were rough but I was soaking up the information the best that I could. The homework is where I really struggled but I tried both because I had to do it for my job and I had just spent my company's money to be there so I felt obligated. I was adding these new techniques to my social toolbox and I was witnessing the more. Not only professionally but on a very personal level. By the last day I was doing the homework and asking strangers questions that would make any reasonable person blush. I got all the flags. I presented them to the class and I was not the only one in awe. Chris gave me the only challenge going through that class as most improved student. Upon returning the next week all my coworkers recognized how I had changed. They pointed it out to me numerous times. The tools I learned helped me in immeasurable ways and this is not a plug for Chris's great class. This is just a result of me learning new techniques to assess situations and understand why people act the way that they do. It was a piece of the puzzle I had never had. All my own research at this point was self-centered. Why am I this way? Why do I react this way? Now I had tools to help me understand why you react this way. I was suddenly empowered. By the end of that year I became a dad myself. Talk about world altering. I had to deal with situations I never could have thought of but now I had these tools to help me assess the situation and react appropriately, mostly. Not only, but it gave me a chance to get out of my head. It forced me to be silly, which is a state of mind I had never experienced at that point. Also I got to see how a new human learns basic aspects of the world. It was great for about a year. Then I was in a significant car accident. My poor wife, she was a new mom and suddenly almost a single mom. I was very close to dying on that accident. I fractured my pelvis in two places. My diaphragm ruptured into four flaps. My lower organs were all mingling with my upper organs, collapsing my left lung and breaking three ribs. Due to my injuries I was in the hospital for a solid miserable week and then moved to a rehab facility for another solid miserable week. Before I could actually go home. But even then I couldn't walk for four months. I'm almost through that stuff. This was perspective changing. I had to give up on my self-engrained, on my ingrained self-reliance through the entire recovery period. My primary motivator was my wife and son. I wanted to play with him as he grew up. So I had to get better as fast as I could. So I also had to embrace the notion of being uncomfortable. I experienced situations I would not wish on anyone. But I had to endure for them. I started to appreciate the feeling of being uncomfortable as a new normal. It allowed me to stop worrying about the things that felt weird and just accomplished one small goal after one small goal. I made a mostly full recovery in an unexpectedly short amount of time due to this drive and willingness to be uncomfortable just for the sake of progress. This is referred to as sublimation, where you turn unwanted feelings into something constructive. So at this point I learned so much on one slide. All right, so at this point, I learned so much about my emotions and interactions with other people that I felt like I had a good grasp on what it meant to be a functional adult. I went through so much change, I didn't even feel like the same person anymore. I wasn't the same person. I had grown through success and failure and heartbreak and love. Almost 20 years had passed and what might seem obvious to some people, I had significantly changed in ways I never could have predicted. I talked to various therapists and experts through that time and started answering the questions I posed to myself 20 years ago. I had a grasp on the how to interact and the ability to understand my own emotions and to read others more accurately. Most importantly though, I discovered that my comfort zone was holding me back. Once I stepped out of that and appreciated the real world is when most of the learning actually took place. It was in that moment of discovery when I decided to seek out those situations that make me uncomfortable because that's where my education actually comes from and that's how I better myself. So after almost four years at the security company and staying in touch with Chris through that time, I reached out, he reached out to me to fill some responsibilities for him at SEcom. My trainings and my assistance at the SE Village were basically my job interview without me knowing it. I joined his team with full knowledge that it would be difficult for me. The responsibilities he presented in my offer were terrifying. I jumped at the chance. At this point in my life, I learned if I'm not scared, it's not worth it. Through everything that I'd been through to get here, if I fall into my comfort zone, I'm doing just that, falling. I make it a point now to do the things that scare me that make me uncomfortable because I know I can do it. I know I'll be better on the other side than if I shy away. And yes, it's not easy. And every day I try to use positive hoping mechanisms to deal with whatever situation is presented. But I know I can do it. Even if I'm terrified, I know I can do it. So here I am on stage revealing parts of my life some of my closest friends have never known. To a room full of people I do not know. Primarily because it is terrifying. This moment scares the daylight. Seriously. But I know I can do it. And if you think you can't, I know you can. I don't even have to know you to say that. Because I'm not special or gifted in any way that I'm aware of. I just try to learn and grow in every opportunity I get. So it's okay to be scared of new experiences, but do them anyway. You'll appreciate the struggle and the reward is so much more. And you'll be better for having done it successful or not. So the purpose of telling you all of this was to tell you this part, the how. It took me 20 years to learn this. But it does not take anyone else that long that feels the way that I did. I'm gonna tell you three things that can get you from the first part of my story to the end in less than 20 years. And it's easy to say those things now, but it's a significant challenge to do it. One, you must force yourself out of your comfort zone and not once or twice, but repeatedly to embrace that challenge. This is the secret sauce. If you can be comfortable being uncomfortable, you will have so many more opportunities to grow. And to be a better you. Two, you have to change your perspective on failure. View it as a lesson and not a definition of who you are. It's hard to appreciate success without knowing how failure feels, but even better than that, with each failure, you learn something valuable to apply to the next attempt that you cannot get any other way. And three, real confidence is cultivated. There are many people that I've met that appeared confident, but it was a false front to protect themselves. Only through trial and error and effort can you achieve self-confidence that cannot be challenged. I'm still in that cultivation phase myself. As I've only had about three years where I feel like I have the tools and the knowledge to step up and be who I am and to take credit for it. And now that I can, I see so much more opportunity to grow. This journey I just described took me from a kid who was awkward and unable to talk to people to being a senior social engineer pen tester at the social engineer LLC. A destination I could never have imagined. And now I'm in a position to shape the company and its future. I can only hope that you feel better for having met me. I look forward to meeting you. Thank you so much for listening.