Hacking the Novel: A Journey From Tech Support to Published Author with Ryan Rutan, Senior Director of Community at Synack

Episode Summary

Ryan Rutan has worked in tech support, as a computer repairman, application developer, software engineer, entrepreneur, and head of community…and most recently, fiction writer. Listen to this episode to hear what inspired Fork This Life, a novel that follows the life of a teenager growing up with the early internet of the 90s who eventually gets into hacking, and how it relates to today’s cybersecurity challenges.

Episode Notes

Ryan Rutan has worked in tech support, as a computer repairman, application developer, software engineer, entrepreneur, and head of community…and most recently, fiction writer. Listen to this episode to hear what inspired Fork This Life, a novel that follows the life of a teenager growing up with the early internet of the 90s who eventually gets into hacking, and how it relates to today’s cybersecurity challenges.


Why You Should Listen:

Hear about Ryan’s approach to hacking the fiction writing process.

* Get the inside story of how working in tech support informed Ryan’s career in cybersecurity. 

* Nerd out on nostalgia about the nineties tech scene.

* Pick up tips for developing your creative voice.  

* Get tips for how you can help spread a culture of good security hygiene. 


Key Quotes:

* “I’m a technical person, therefore I create.” 

* “I need a computer but why? I want to get online, but why? Everyone knew they needed it and wanted it but they didn’t know why.”

* “The people who know and understand what it means to keep things secure... It’s incumbent upon them to pay if forward as much as possible.” 

* “Security back in the 90s.. your death was going to come from a swift sledgehammer to the head...now it’s death by a thousand cuts from a million different websites.” 


Related Links:

* Synack.com

* https://www.synack.com/lp/enterprise-security-testing-101/

* Forkthislife.com

* https://twitter.com/ryanrutan

Episode Transcription

Bella DeShantz: [00:00:00] Hey, Jeremiah. Jeremiah Roe: [00:00:40] Hey, what's up, Ryan really appreciate it. Thanks so much for your time. Uh, as Bella said, we're super excited to have you here.We're excited to talk a little bit more about your book, which that's super cool to say Ryan's book, but we're also excited to learn a little bit more about you. Uh, you know, I understand you've been in this industry for a bit.

You've got a lot of experience. You wrote a book, tell us in your words, who is Ryan?


Ryan Rutan: [00:01:49] I would say, you know, to almost quote Jonathan Moxon from varsity blues, I would say I'm just one, man. No, um, there is a, I like movies. Um, I think the biggest thing for me is I'm [00:02:00] just all about technology. Uh, I started with computers around eight years old. Um, started building my first one around 11, started programming at 13.

By 15. I had kind of earned a reputation in a small town as being one of a handful of teenagers who knew what these computers could do and what they, you know, how to fix them and whatnot. Um, you know, as a result of that, I got a job as a software manager in town. So again, it was kind of weird being 15 years old, but also.

Being kind of at the heartstrings of where all software was bought in town at the time. So it was kind of an interesting thing. Um, from there I pivoted to like a BBS ESOP role, a local BBS, which ended up turning into an ISP, which I ended up being tech support, web admin network support. Um, we just being thrown in at 16, 17, helping grow that business.

You know, from there, uh, I went to college where I was my, I was with a roommate. We were fortunate enough to find someone in our same apartment who actually ran a similar startup ISP in the town that we were moving to and they needed some help. So we [00:03:00] jumped in and did the exact same thing there. Um, picked up more sales, more front end stuff, learned some more languages.

Did you know, Nat firewall, custom internets network. Cidery I mean, all these things that I had never really been taught how to do, I just kind of picked it up and ran with it, given instruction manuals and go do itJeremiah Roe: [00:05:49] So you didn't want to be a chef. Ryan Rutan: [00:05:52] I did not. Uh, you know, I, I'm actually a pretty decent chef. If you put me in an instant pot, in a room, there's some good magic that comes from that. Bella DeShantz: [00:06:02] I work in tech.

I consider myself pretty technical and not very creative. And I think that's something that I've been exploring myself as well. And one thing that I'm trying to reconcile is like, how do our creative brains and our tech brains, uh, where do they meet? And it seems like you might know a little bit about that.

Ryan Rutan: [00:06:41] the biggest thing for me was leveraging my strengths, which is in, in the modern, I don't think if I, if I was born 20 years earlier, I would probably have written a book because the, the ability to write a book, the barriers to entry into that. was, was substantial.

But given the way the marketplace was, you know, in 2015, I actually wrote a children's book back then as a, kind of like a pilot proof of concept, just to see if it, you know, if it made sense and the technologies were there. And I knew that if five years later they would be a little bit better. And I was like, well, if I'm going to do this and might as well do it Now you need to tap into the, you know, the creativity is a by-product of who I am as a technical person, because most of the technical, or actually I would say the reciprocal I create because I I'm a technical person, therefore I create and I create, you know, they just [00:08:00] go hand in hand.

Bella DeShantz: [00:08:01] how did you go from, you know, computer repairment IOT, inventor, software engineer, and now head of community to writing a children's book and a novel.

Ryan Rutan: [00:08:28] I think it was something around the element is I really wanted an outlet for my creativity that I wasn't getting. From a technical side, you know, when you're in a, when you're in a theater production or, you know, you're in a cast or whatever, you have a lot of scheduling conflicts. There's a lot of things where you, um, you have to work with other people's schedules.

And my schedule just wasn't very flexible. Um, so I was seeking an outlet that would allow me to be creative, but also kind of work in the way that I could. And so for me, the book was a very easy thing. I was the sole author, the sole ideation person for it. And I was like, I can [00:09:00] control when it goes out.

If it ever goes out. So it was just one of those things that started out as a, Hey, wouldn't this be funny if you know, but ultimately when it, when it con it all came down to it, I think it kind of was a result of this last one was a result of a midlife crisis. I, I was turning 40 and I kind of always thought as a kid, there were some things that I thought I would always do in my life.

One of them was to become a published author. At the time when I made those high-level goals, you know, as a joke, I kind of thought, Oh, that's gonna be a technical manual. That's going to be an O'Reilly book or, or whatever. And it never dawned on me that it would ever be something creative like this in high school, I was not a fan of English.

It was not something I would ever consider myself doing as a recreation activity. But to be honest, I was coming up on the 40, 40 Mark. And it was passively in the back of my mind that I wanted to write something bigger, something that a little bit more [00:10:00] substantial.

And I actually just read ready player one from Ernest Klein. Who's an Austin author and. It was a book that was really interesting. The tone of the book was written in a way that I thought was very approachable. It resonated with how my mind like, to like, to, you know, articulate out thoughts and I just really liked it. and so after I read it, I got really excited because I didn't, I don't read a whole lot. I read technical manuals more than I read for pleasure for the most part. And so I thought I would write about this really pivotal time in my life, where, because of what I was able to capture and what I was able to understand, and just the opportunities of where I was at time and happened to slip into, Oh, Hey, here's this cool ISP that needed someone with exactly my skill sets and was willing to pay me a decent rate and, you know, And they were able to benefit and I was able to benefit those things happen still.

But at that time, that was really, really difficult. So yeah, I liked romantic. I like romantic comedies. And So that was, I wanted something that was a technology book. Part romantic comedy. I worked at like a radio, uh, video music software store. So I kind of always did that. Empire records, high fidelity theme always kind of resonated with me.

So I really wanted to write a techie book that was a montage to that era that highlighted the ISP tech support people who, if you've ever been in ISP tech support back in the nineties, there's. Bad. There's like, you, know, medals of honor that needed to be given out to some people because it, it was not a [00:13:00] great time and a, not a great profession.

And so I figured this would be a really fun topic that, you know, nerds would really get, and those who lived it would appreciate the detail that I was willing to put into it.

Bella DeShantz: [00:13:10] So you, you keep referencing, you know, the nineties. He's your childhood. And, and you mentioned earlier that you got into tech at a very young age, and I think, you know, the nineties is the nineties tech scene is definitely centered in this book. Can you tell us a little bit more about what the tech environment was like in the nineties?

Ryan Rutan: [00:13:28] I was a member of it and I didn't know it at the time. I was kind of just doing my thing. And then I found out I kind of backed into realizing, Oh, I'm a technology professional, but I would say fast paced, I would say even more fast-paced than today.

Only from the fact that. You know today, like if a new technology is released, you can always learn lean on the older technology. Right. Cause it's out for awhile back then one point it was 1.0 1.1, two point. Like they were rolling out so fast. There was no mechanism to get the information out. I mean, most of us [00:14:00] were, you know, I was on IRC or use net following, you know, finding the people that I followed all the time.

And they were the ones that they had the pulse on the finger, on the pulse, on what was interesting and what was good. And so you listen for them or, you know, slash dot was, you know, amazing. Um, at the time, but there was in terms of like all the mechanisms we have today to get information out and make people aware.

No one really knew. I w I would argue that most people back then who said they were experts were just faking it till they made it, because at the end of the day, they just had to be good enough to not have people realize or call them on it that they didn't know. =

Jeremiah Roe: [00:15:39] I totally, I totally remember the nineties and then it's bringing back all these memories for me. Yeah. As well in the process. So you talking about it.

Ryan Rutan: [00:15:54] No, it was just great. I mean, again, like I really, again, if I was born a couple of years earlier, it [00:16:00] was older, a little bit sooner. I probably would have had a different trajectory because. It would, it would have been so easy to get caught up and, you know, making, making, you know, interestingly, uh, odd mistakes, right.

That you would dig, Oh, wow, this is hilarious. This is fun. Technology was evolving at such a fast pace. You know, people were trying to sell it. People were trying to build it and sell it in and there was no. Consumer expectation for it.

It was just like, I need a computer, but why I want to get online, but why? And no one, everyone knew they needed it. They knew they wanted it, but they didn't know why it was just because the other person had it. And when you mix all that together, you just get a bunch of, a bunch of people running around, pinning each other online and, and they it's.

It's, it's really interesting. 

Bella DeShantz: [00:16:44 how much of [00:17:00] you and like your memories and your experience is reflected in the characters and the story of your novel. 

Ryan Rutan: [00:17:05] there's no one character in a book that is any one person I've taken stories and experiences and traits of people and I've mixed and matched them to make compelling characters and to make characters that I feel have a good amount of depth.

And so trying to provide those, those oddities in a way that helps me tell the better story. But most of the details, if you look at some of the rants that I go on in the book where, you know, that are just odd things that you would imagine, why is there, why is there six paragraphs on some subtle detail around the 1990 song that came like, there's a story back there.

And there's a reason why I'm going to death because there was a nuance element that really made that just imbue itself in my memory. Bella DeShantz: [00:18:06] But of nostalgia in this book. What'd you say? 

Ryan Rutan: [00:18:08] I would say this book is 99.9% installed with a couple of adverbs. So. 

Bella DeShantz: [00:18:15] Jeremiah Roe: [00:18:33] So as I was listening to you discuss, you know, a lot of the background around fork, this life. How it transpired and some of the processes behind, you know, how you hacked the process of writing the book inside of your blog posts, you discussed, you know, your voice and how you, how you really focused on your voice.

I was wondering if you could maybe touch on a little bit of that.

Ryan Rutan: [00:18:56] telling a coherent story that this long was going to be a big, a big detail, a big endeavor, but I think. To do it successfully in a way that I felt was authentic to the way that I, I experienced the nineties was to be in a way that really had, you know, embraced time jumping, embraced, like sub narrative thought.

And overall just, it didn't create a linear, like I didn't want to start the book linearly and just kind of go, I wanted it to jump around because to be honest, like at no point in the nineties, did I ever feel that I was on any one path? I was simultaneously running down six, seven, eight different things at any given time.

Whether it was a creative focus in theater, whether it was, you know, ISP support, whether it was trying to start a business, whether it was trying to, you know, work at a software, like all these different aspects of my persona were being ripped apart. And I was trying to hold [00:20:00] on and just seeing which one of them would went out.

You know, for me, it was, it ended up being the tech pioneer in entrepreneurial type spirit that kind of led out. And over the years, I kind of. Assembled the pieces of that persona back. And so for me, I wanted to make sure all of those were represented in the book. Jeremiah Roe: [00:30:29] 

Jeremiah Roe: what's one of your favorite, uh, sort of technical challenges that you've highlighted inside the book.

Ryan Rutan: [00:31:19]I mean, all of the ISP support stuff, the two that come to mind right away, there's a scene in there, or there's a segment in there where I talk about a tech support person. Calling someone calling tech support and trying to get online, being on the phone for hours with this person, trying to get them connected.

They think they're on a computer the entire time. And in fact, they're on a web TV and it was something that was brand new to the time. Uh, you know, regardless of how many times I, and this one actually is, I can say was me. Every time I ask the person, are you sure you want a computer? Are you sure that you see the click, the start button?

Are you sure you this like this? And it was just one of those things where like I could not [00:32:00] believe. And I was so frustrated. My, my, the guys that were in the room with me, they were just laughing at me. And what was really cool about that story was, you know, it is true that everything about that interaction, you know, uh, she, she signed up, she prepaid for.

Three months. We tried to get her set up. I spend three or so hours on the phone. Couldn't get it to work. And we finally figured out why and respectfully said, okay, thank you. Here's your refund. And then ushered her off to a web TV compliant provider. And I think about four months later, This woman walks in.

I had never seen her before, but she walks in and I mean, her voice just sent chills in my brain. I was like, Oh my God, this is a triggered moment. It was like, Oh my gosh. And I knew exactly who she was. And she came in and said she wanted to buy a year's account. And she went and bought a brand new computer and she had gone to try this other ISP and they just weren't as patient.

They weren't as nice. And she came in and she said a really nice things about me to my boss. [00:33:00] And it really made me feel good and be honest. It's one of the, you know, I've had a couple of experiences similar to this, but this is one that stands out to me is I always try to have as much empathy and patience as possible.

Um, I like to move fast. I like to get going really, really, really fast, but you never know whatever someone else is going through. You don't know their story and. For, But that was a moment to me as a kid, I was, you know, 17 or 18 at the time. I did not have a very deep empathy. Well to pull from, I was very much like, Oh my gosh, you know, you're either, uh, you know, or you don't know.

And those were the worlds that existed. when I started using the internet, the things that I was exposed to, I didn't have to tinker with and try to understand they were made for me. They were made to be used by like the average person. And it's, it's been, it's, it's really interesting to sort of compare those experiences. 

Ryan Rutan: [00:35:44] Yeah, I would, I would agree like the internet, when I remember my first, I can still run. I went to shakespeare.com. That was my first website I ever visited my friends and I were trying to figure out how to do . CPIP set up for our ISP. We just gotten all the board set up. We were dialed in and we were trying [00:36:00] to get them going.

And I had a popular mechanics magazine next to me, and that was advertising that website. And you go there and it was just all the works of Shakespeare and. And at the time I was like, Oh, this is cool, but it really didn't do much. It was, and it was information and that was as good if it was there. Wasn't e-commerce there, wasn't all this stuff.

So it was the, the e-commerce and all the things that we have today came in drips in waves. Um, whether it was good or bad, it came. And so there was a lot of people having to adapt themselves to what the internet could provide as the internet providing what they needed. So it was very, very different frame of mind. 

Bella DeShantz: [00:36:35] 

You ha you have [00:37:00] seen such a broad range of technology over, you know, this, this time period. What is it now that tech is, is like, like we've said at our fingertips everywhere, ingrained in every part of our lives. Uh, what are the implications for, for, for the people that work on securing technology? 

Ryan Rutan: [00:37:20] it's getting harder every day in terms of. For me at least, uh, it's very, it's becoming more and more difficult to try to keep pace. So, uh, I think for me, the biggest importance that we have today is that the people who know and understand what it means to keep things secure, to keep things protected.

It's an incumbent upon them to kind of pay it forward as much as possible. Like, I'm a big fan of like, you know, secure your inner circle, find your people, find the people that you know, that you have influence over. That will jump when you say jump and make sure that they are doing the, you know, the best practices that are available, you know, the, the simple ones, here's a password, use a password manager, you know, use double check links before you [00:38:00] click on like don't open, you know, answer calls to crazy, crazy numbers that you don't know.

So like there's some basic things that you can do. And I think if everyone did that, I think it would, the world would be a lot better. I think, unfortunately like we're in a world right now where security back in the nineties was much more like, you know, your, your death was going to come from a Swift sledgehammer to the head.

And now it's just a, you know, it's a death of a thousand cuts from a million different websites that you'd never know that you, you never knew that that was going to be the wink link that took down your identity or that, you know, ruined your credit score or whatever. So, and my mind, like I said, it's.

Yeah. I don't think it's anything necessarily super nuanced. I think that it's just incumbent upon everyone to make sure that they have, you know, have that experience. I think the, I always joke, but Madai, Moody's constant vigilance is the thing that I always think about, you know, it's common sense in getting that to proliferate out to everybody.

Bella DeShantz: [00:38:49] I just finished that book a few weeks ago. Um, so it's, and it's interesting that you talked, you talked a little bit about like, you know, the, what did you say death by a thousand cuts [00:39:00] from a bunch of different websites? Uh, I like that a lot, and I think that really is the kind of world where we're in.

There's so many, maybe minor threats, but all over the place. And, you know, you talked a little bit about getting kind of the average people, citizens to understand how to secure themselves. Uh, With all of that in mind. What do you think is the future of cyber security? You know, as this continues and, and as technology changes. 

Ryan Rutan: [00:39:27] I think the future is really going to be interesting. I would say that where we are as an industry and technology is we're in a, we're in a precipice, in a transition where security is now is being acted on as a bolt-on. It's like we're going to build software. Oh, wait. Oh, we did. To make it secure. Okay.

Let's do that. And I think that there are, you know, the leading, leading technology innovators out there who have already switched, but it's not going to be a solution until majority of them, like, we're not going to have herd immunity from insecure software in development until most people will bring in build secure software [00:40:00] from the beginning.

Uh, you know, making sure that. You know, they make that they don't capture PII if they don't need to, that they secure end points and encryption at rest. And they do all the basic things that are now available, like off the shelf. Like, it's not like you have to, you know, I hate to go back tonight. The nineties, you had to build almost everything, right.

Everything. There was no shirt libraries out there. If there were, they were very, you know, they were only in certain languages, whatever. But now, like every library has a suite of, of libraries that are out there. Uh, every program program language has a suite of libraries that are out there. That you can pull from or standards that have been involved in baked into the OSS.

So just you guys got to use them and then mind your supply chain attack. And I don't don't know where your dependencies come from. I think that's the big thing that needs to happen is that we need to, we need a title shift. In the industry for people to take seriously what it means to build secure software from the, from the go and making sure that that is part of the, the origination of this new tech.

Bella DeShantz: [00:41:27] While we're on this super big topic that the three of us probably can't solve in this one episode. Any ideas on how we, you know, push for that shift because, you know, you said there are solutions in place. There are libraries, secure libraries, um, How do we make, you know, developers use them? 

Ryan Rutan: [00:41:45] I'm a big fan of accountability. if someone [00:42:00] willingly is introduced to a security problem and they actively do not.

Solve it, and it becomes a problem that needs to be an accountable offense. You can't just say, oops, sorry. I didn't know. Here's your LifeLock annual, you know, whatever, something like that, that can't be the go-to. Right. I think that there needs to be a, an accountability aspect for if you're going to participate in this space where, you know, where you hold consumers information.

And are kind of being trusted and trusted with it. You need to be able to be held accountable so that when those things happen, that there's a precedent right now, there's the precedent is very, very weak. Um, and it's only on the massive scales of things. And again, I think part of this is investing in these, these solutions and services that can be proliferated out to the small, medium business owners that are the millions of cuts of places where, you know, someone's information gets squirreled away and make it easier for them to uptake it, you know, uh, whether it's incentives or, you know, Tax benefits or whatever, finding ways to bring them up.

And again, as we kind of raised the, the lowest common denominator, I think that's kind of how [00:43:00] we start, you know, moving the sh moving and raising the tide. 

Bella DeShantz: [00:43:03] I like that. 

Jeremiah Roe: [00:43:17] So, obviously we want to give you an opportunity to, to, uh, to plug the book and to detail some information where we can hear more about you. Maybe hear more from you what's next in the future. What does Ryan have happening?

Ryan Rutan: [00:43:31] if you want to check out stuff at the book, fork, this life.com for me, That's pretty much the, uh, the start and stop. I curate all the things there. Um, I don't update the site that much, uh, mainly because of time to work on it. But in terms of what's next. Um, I do have a second, second version of the book that is our second volume to the book that I'm working on, or that I've kind of got a story arc laid out for how soon I write it will be a [00:44:00] function of time and interest.

So. Um, I've hidden an Easter egg in the first book for anyone who finds it, that will kind of give you a hint of what that second book will be. And the more people who find it, the more interest will, you know, more priority at that we'll get. But, um, but for this life, there's a, there's a potential. I may actually turn it into a podcast.

Uh, of some sorts where, um, just as a monitor, a brand to talk about random things about technology, um, educate people on various topics. Again, it's to be yet another podcast possibly, but again, just share my thoughts and kind of like see where it goes. If anything takes off from there.

Jeremiah Roe: [00:47:17] thank you so much for your time. Um, I know I've enjoyed reading the book and everyone else needs to go out and buy, you know, five copies like today. But that being said 

Ryan Rutan: [00:47:32] And find the Easter egg. So 

Jeremiah Roe: [00:47:34] and find the Easter egg there's there's, that's, that's pretty fun to do.

Um, if looking, looking at your profile on LinkedIn, right? What's, what's something that. We don't, don't something that makes Ryan who Ryan is without us looking at your LinkedIn and it's, and it's not on there. We would never guess it. We have no idea what, yeah,

Ryan Rutan: [00:47:55] Uh, I, I would, I mean, to be honest, I mean, so I have a lot, a little, little factoid squirreled away. [00:48:00] Um, I remember in 2000 I actually registered to become the Reverend Ryan Rutan. So I have a certificate of that. So that's something I, at one point I, I almost officiated a wedding, um, in the, in the early two thousands, I think the big one that the big ones is my theater background.

I don't really tout it that much. On LinkedIn. I don't have the professional accolades, but I, I did over eight years of theater in high school and middle school and community theater afterwards it's was a source of great joy for me in terms of having comradery, like, you know, telling stories and really, you know, playing, finding ways to explore life through another person's experience or through a story that someone else wrote.

And so those were some things that I thought were, I think I take with me and, um, I would say probably most of the benefits that I have. Today, around public speaking, you know, being comfortable, like, you know, confident in talking and telling my story and, uh, and just being open and authentic come from the vulnerability that comes from doing stage performance.

And again, [00:49:00] there's, I'm not saying by any means that I was the world's best person. I was definitely, I had a lot of fun. I had a lot of great friends. Um, it was something that we did did really well together, but it was definitely an experience that opened my, I think, opened the doors for me from being just a closet nerd.

Jeremiah Roe: [00:49:29] Well, Ryan, again, thank you so much for your time. Bella DeShantz: [00:49:34] thank you again for your time.