Getting Into Infosec

By Ayman Elsawah (@coffeewithayman)

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Interviews with people who have transitioned and got jobs in #infosec and #cybersecurity so you can learn and be inspired from their experience. There is no linear path into the field of Information Security, so the hope is that you will resonate with at least one of the guests. Some of my guests were teachers, paralegals, librarians, military vets, developers, and IT help desk techs (to name a few) before transitioning. Also featuring "spoof" ads poking fun at the industry.

Episode Date
Nick Vissari - Engineering Dropout to Math Tutor to Security Architect/Engineer

Nick Vissari went from being an engineering dropout (he didn't like creative writing) to tech consultant to math tutor. His penchant for fixing things homed him back into tech where he is now responsible for security at a large school district. He recently went back to school and received his cybersecurity degree as well.


  • At 10 yro Dad had problems putting computer together, so he helped his dad with it
  • Family never stifled any inquisitiveness he had
  • Started at a Math Tutor at the school system
  • Nick talks about how he had the wrong attitude in security [11:38]


  • "Once you get into a position somewhere, do whatever you can to make yourself invaluable. Find the things people don't want to do and do them. The hard problems are the ones most rewarding." [8:55]
  • "If you're not automating right now, it's probably because you have more resources than you know what to do with." [18:54]
  • "There are a lot of people that are security professionals but they really don’t know about how a system works." [25:22]
  • "Just got to have that passion to want to learn and you can definitely jump into security."[22:50]
  • "My grandmother always said: 'Those who don't make mistakes, don't do much.' So get out there a make a bunch of mistakes." [25:35] Tweet This!
  • "Don't be that guy that says 'No' to everything. You have to be somebody that says 'Yes… and'." [26:06]


Getting Into Infosec:

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Feb 04, 2020
Page Glave - Professor of Kinesiology to Cybersecurity Analyst!

Recast An Audiogram on Social Media

Page Glave was a tenured Associate Professor of Kinesiology with a focus in exercise science and was successful in her field. However she came to the realization that she can't see herself doing this for the rest of her life. This is her story. She offers lots of great advice on resume tips when switching, homelabs, certifications, and how she was able to break into the field.


I am an analyst, project manager, ethical hacker, and tech consultant with more than 10 years’ experience with research and project management. I spent awhile in higher education – long enough to get tenure and decide it was time to do something else. I have eJPT (eLearnSecurity Junior Penetration Tester), Security+ and Splunk User certifications. I love learning and tech, so digging into all of this stuff just makes me happy.


  • 5 Months in to her first security job!
  • Being in a small environment, she gets to do everything from governance to pentesting.
  • Previous to this she was a tenured associate professor in kinesiology with a focus on biomechanics and obesity.


  • "Pretty big adventure on a daily basis because no day is the same."
  • "Really is an environment where security is everyone's job."
  • "I think I'll always be in-house tech support for as long as I live." [7:08]
  • "I kinda got bored… I didn't want to keep doing something that wasn't challenging." [7:28]
  • "Do I really want to do this for the next 30 years?" [7:58]
  • "…going through the headers, that should have been a clue that maybe tech would have been a good fit for me."
  • "You'd be hard pressed to find anyone in Information Security who was just thrilled with their budgets."
  • "Being able to translate that self-directed learning to something on my resume."


Page's Twitter: (Thank her via Twitter)

Brakeing Down Security Podcast:

Pacific Hacker's Conference:

Sam Bowne's Class:

Skadi VM: (by Alan Orlikoski

Marco Palacios:

Keirsten Brager:

Intro Music:

Outro Music:

Getting Into Infosec:

Follow Me on Twitter:

Subscribe To YouTube:

Checkout My Book: Breaking IN: A Practical Guide to Starting a Career in Information Security

Sign up for updates and commentary:



Nov 16, 2019
Nick Jeswald - Confessions of a Cybersecurity Recruiter (Part 2)

RECAST any part of this episode:

Part 2 of 2 - Nick Jeswald has been an external and internal recruiter in security. He shares with us what he looks for in a candidate, common mistakes made by candidates, and the nuances of hackers he's learned over the years.


Show Notes:


Getting Into Infosec:

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Nov 02, 2019
Nick Jeswald - Confessions of a Cybersecurity Recruiter (Part 1)

RECAST Any part of this episode:

Part 1 of 2 - Nick Jeswald has been an external and internal recruiter in security. He shares with us what he looks for in a candidate, common mistakes made by candidates, and the nuances of hackers he's learned over the years.


I've been in infosec for 8 years, and in various IT roles since 1996. Developer -> Sales Engineer -> BD Specialist -> Security BD -> Security Recruiting -> Dir. Corp Dev. However, whatever role I've had, I've also been one of the top recruiters for each company I worked at.

Show Notes:

  • Internal recruiters != external recruiters
    • Backgrounds are different
      • External recruiters come from varied backgrounds, virtually zero from infosec
        • Much like BD people
      • Internal recruiters are more likely to have a greater understanding of infosec or at least IT
      • A recruiter that doesn't understand security is more likely to make bad placements with higher turnover
    • Motivations are far different
      • I want to choose people to spend a career with
      • They want to make a commission and meet SLAs
    • Attention to detail is very different
      • A tiny detail that could betray a hidden skill set or flaw would likely be overlooked by a 3rd party
      • I have an interest in understating the person, not just the resume
        • What is their desired career/life trajectory?
        • How will our company enrich/hinder that life?
  • You are in competition with an army of low-skilled counterfeits
    • You need to be able to demonstrate raw skills, not just list your certs
    • Have a body of work available for review on GitHub, your own site, etc.
    • Internships are a nice touch, but they cut both ways
      • You interned with unnamed-big-4-biz-consulting firm? Don't drag that culture in here. I fear for what you learned.
    • Can't talk about where you interned because it was a non-DOD three letter agency? Communicate that point to me in your way. If that is the truth, I'll trace you back and verify.
  • Always be client facing
    • I have seen many recruits passed over for poor hygiene, arrogant treatment of interviewers, disclosure of illegal activity, and just generally obnoxious behavior
      • You couldn't act like this on a client site and not get sent home; don't do it on the interview
      • Yes, you are talented...there's always someone cooler than you
  • Interview your interviewers
    • You should have a standing list of questions for interviewers
      • Why do you stay with them?
      • What is the intended growth path? Organic? IPO? Channel?
      • Is there any merger/acquisition activity going on? Planned? Intended impact?
      • Is there any rebranding activity going on? Planned? Intended impact?
      • What conditions are driving this open role? Turnover? Internal restructuring? Organizational growth?
      • Will I be supported in my security research? How?
      • Does your company have a defined mentoring path? Why not?
      • How does the company support continuing infosec education?
  • Meet your team
    • Watch the team interaction closely
    • Can you see cohesion? Are they supportive or adversarial? Are they authentically happy with their jobs?
  • Understand the org chart you are stepping into
    • To whom does security answer? CXX? IT Director? General Counsel?
      • Understanding this will help mitigate surprises later
  • Understand the company culture
    • Big corp? Big corp problems.
    • Boutique? Founder problems.
    • Is there a "tree house" mentality among the senior employees?
  • Never forget who you are
    • I know you want a job, but don't take a job that is sure to kill you slowly from the inside
      • Like doing offensive security? Don't start in the SOC.
    • Did you walk away from the interview(s) thinking that this company understands the care & feeding of hackers?
    • If you can already see the point at which you will outgrow the company, is it the right place to start?
      • Maybe! If you have a goal of entrepreneurship, or of working for a specific team, this first step just needs to support that eventual goal. This may be detected by an astute interviewer, though.
  • Resume tips
    • One page.
      • My dad started at the bottom, and worked up to EVP of a Fortune 50 corp. One page.
    • Focus on your relevant work experiences and extracurricular infosec work
    • I'd rather read about 0days and CVEs than certs
    • I want to know about your community involvement
      • 2600, local DCs, TOOOL, OWASP, etc.
      • Presentations at cons matter to me, especially if I can watch you deliver information to an audience
        • Like a free audition, and believe me I watch every one people link in resumes
    • I don't care about your GPA, fraternity/sorority, who we know in common, what sports you enjoy, or what you look like. At all.
      • Seriously, don't add a photo.
  • General tips
    • Code. Know it. In several languages.
      • Despite semantic differences, you should have a pretty good working knowledge of the most widespread VMs, coding languages, and compilers
    • Web apps are your paycheck
      • Knowing the OWASP Top 10 is like knowing your middle name...not impressive in and of itself, but if you don't know them, there's something wrong.
      • Many composite "red team" projects will involve some Web app hacking, and even the most specialized consultancies will agree to a Web app assessment for an established client
  • Think holistically, and make yourself more valuable
    • If you can't write a report, of what value are your assessment activities?
    • Seem to always have interpersonal conflict? Time to read up on Empathy and EQ. Be the go-to on your squad.
    • Get comfortable with an audience. Toastmasters is there for you.
  • Learn the value of "the Halloween Mask" as Henry Rollins called it
    • Sure, you're a young security professional. We all expect eccentricity from you. We're all also trying to make money and be taken seriously
      • Don't forget: in boardrooms of white haired old men across the nation, we're still the same guys who lost them millions of dollars on ERPs and useless Y2K preparations
      • I'm not kidding about this.
    • Don't wield your difference like a blunt object. A little bit goes a long way when you're also scaring the hell out of everyone with pen test reports.
    • My life is far more complex and wacky than my coworkers know, and I talk a lot. I just know how much to let through the mask.

Getting Into Infosec:

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Oct 25, 2019
September 2019 Update

Summer was crazy, my day job is keeping me super busy, and I've been really mentally occupied lately dealing with kids, family, and school. I miss producing shows, and will be getting back into it, have some really good shows queued up. I've still active on Twitter when possible, so we can stay in touch there in between shows.

Oh and by the way, it's been a year since I started podcasting! Pretty cool. So many things I want to do with the show like animating my spoof ads and transcribing the shows.

Anyway, just wanted to update you and let you know I didn't forget about you. I can't wait to release some of these amazing shows.

As we depart, here is a preview of draft a spoof ad I put together real quick. It talk about my love of the word "cyber". See you next time.


Getting Into Infosec:

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Checkout My Book - Breaking IN: A Practical Guide To Starting A Career In Infosec -


Sep 23, 2019
Fareedah Shaheed - From Tech Curious to Information Security

Fareedah, a lifelong learner, was always interested in technology and grew up reading her father's Cisco books. His influence led her to the field of information security where she stepped up and is always tackling new challenges.


Fareedah Shaheed was born in Maryland but spent most of her childhood outside of the US. She returned to the States in 2013 and attended the Community College of Baltimore County (CCBC), where she majored in Cybersecurity.

Her experiences with different cultures and the tech field led her to combine her interest in psychology with cybersecurity and thus, her passion for security awareness was born.

In 2018, she founded Sekuva with the mission to educate and support small business owners and families with understanding how to secure their sensitive information.

She currently works as a Security Control Analyst at a financial firm in Maryland.


Currently works with Security Awareness and Threat Intelligence.

Must break down concepts for both executives and associates.

Saw that there was a lack of cyber-security awareness for "regular" people, especially with parents.

Got thrown into leading "lunch & learn" events and experienced imposter syndrome due to her lack of her experience.

Her lack of experience became a benefit to the audience as they were able to relate!

Father was in tech. Changed her major in college based on his advice.

Wanted to teach but didn't want to be a teacher.

Read 2000 books since childhood.

Fareedah had really good role models growing up.


"I vowed never to have anything to do with math whatsoever."

"I was a broker, I did an internship, I did teaching... and through all of that I realized I didn't really want anything but tech."

"Whatever your parents' field is that kind of is in the back of your head, whether it's a yes or no."

"Let me do it. Let me try this out."

"Cybersecurity is new, it's upcoming. I really believe that your skills would be good for cyber. There's not a lot of women there. Especially not a lot Muslim women there, who look like you."

"I remember just lying awake at night just thinking about how does WiFi work."

" Instead of guards we have guides." [21:12]

"You have to do it afraid, you can't wait for the perfect moment." [25:35]


Fareedah on Twitter:

Fareedah's Company- Sekuva:

Year Up:

Getting Into Infosec:

Follow Me on Twitter:

Subscribe To YouTube:

Checkout My Book:

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Jul 31, 2019
BONUS - Updates, Defcon, More


Hey everyone!

It's been awhile, I know! Life has been busy. Lots of transitions, so schedule has taken time to get used to.

Feedback has been amazing, so a big thank you to every one of you.

I've been busy trying to get ready for Defcon as well. Super excited about being there! Look for me in the Getting Into Infosec t-shirt and please say hi. I'll be attending Bsides, The Diana Initiative, and Defcon.

I'm actually planning on having a meetup for listeners on Friday August 9th, at Defcon, with many of the guests from the show. Details still being worked out.

I also plan on bringing stickers! I ordered 1000 stickers (not cheap by the way) and will be going to the unofficial Defcon sticker swap!

Also working on some other schwag as well like T-Shirts and Mugs. Feel free to send in any ideas you may have.

If you missed it, checkout a recent Darknet Diaries episode were both the GUEST and HOST were on this show. That's kind of exciting! It's Episode 42, mini stories Vol2. Link in the notes.

Make sure to check my twitter feed (@coffeewithayman) for updates.

Lastly, checkout the Security Sandbox podcast by Sean Sun ( I had the pleasure of meeting him in person, and he's an all around cool person. He also runs Hacker Culture FM ( as well, so I'd keep an eye on that.

Your support and energy has been awesome. Please continue telling your friends about the show and showing your love like you have been. It's really appreciated.

Ok! That's all I have. Back to editing episode 25 and getting ready for Defcon. If you've never been, I highly encourage you to go. See you next time.


Security Sandpox Podcast:

Sean Sun:

Hacker Culture FM:

Defcon Sticker Swap:

Outro Music:

Getting Into Infosec:

  • Follow Me on Twitter:

  • Subscribe To YouTube:

  • Checkout My Book:

  • Sign up for updates and commentary:

  • Website:

Jul 26, 2019
Keya Horiuchi - From Teacher, Filmmaker, and Website Design to Security Engineer!

Keya was a public school teacher who stood out of the crowd. She loves problem solving and challenging environments. Keya was also a filmmaker and web designer. She's currently a detection security engineer who get knee deep in malware on a daily basis.


Knew she didn't want to be a teacher her whole life

Was the only one in the rational thinking group at her school.

Enjoys rational thinking and the problem solving process.

Prototyped a mock medical device with a Raspberry Pi and won a national competition!


"Easy to get in to what you're comfortable with... and I didn't want to have a job like that."

"It was something that I enjoyed but I definitely feel more at home with the cohort that I work with currently and with what I do."

"... for me it was an amazing process because I hadn't ever SSH’d into a device and I had to figure out how to get like ports scan."

"I read so much documentation on all the little things that we connected to it. I watched a bunch of YouTube videos I looked at a lot of GitHub accounts trying to figure out like I've got to make this move." [14:24]

"It was incredibly challenging. A lot of times I was trying to figure out... where sometimes the information that you get from the client is essentially just a hint of what's going on in the network." [17:07]

" You just have to be creative and keep going at it until you can do what needs to be done." [18:08]

"Yeah. It's amazing, and especially coming from public school teaching where I had seen almost physical fights altercations happen over like reams of paper because there's just not that much allocated towards schools to where snacks are brought in. Like it's a very different environment…" [21:22]

"You did great on the test, but I want to watch you take the test." [23:06]


Keya Online


NSF Project:

Intro Music: Cascadia by Trash80 - (Released under Creative Commons)

Outro: Cosmetic Cosmos by Verified Picasso

Getting Into Infosec:

Website, Show Notes, Transcripts:

Follow Me on Twitter:

Subscribe To YouTube:

Checkout My Book:

Jun 15, 2019
BONUS - Audiobook Sample!

Listen to the retail audio sample of my book: Breaking IN - A Practical Guide to Starting a Career In Information Security

The book is narrated with a female voice, Kati Fredlund. She did an amazing job!

You can read a sample or purchase the whole book here:

Full Audiobook to be released soon!

Jun 04, 2019
Hossam Mohamed - Young Hacker to "Not A Security Researcher"

A 19 year old "not a security researcher". Facing limitations because of his age and not having the right "prerequisites" Hossam has had to make his own path. He also dreams in code and is one of the youngest OSCE's in the world!


Hossam Mohamed is one of the youngest OSCE in the world and currently working in cyber security domain for a financial company in Istanbul. His area of interest includes exploit development, offensive security, secure web development, malware analysis and he is a big python lover


On the organizing team of BSides Istanbul

Best friend is a computer.

Just finished high school last year!

Was doing freelance web design and security projects for clients.

Taught himself assembly.

Developing offensive security labs.

Hacked his way to getting a job. :)


"Because I love code."

"I wanted to understand how these games work." [5:56]

"I developed a project for my school. They liked it, but no one cared actually."

"No one in infosec doesn't play a little bit (hacking)." [8:04]

"Technical interview was great... didn't work because of my age and my education. I was only 18." [10:22]

Do you ever dream in code? "Actually... how did you know that?" [12:35]

"People think when it's about assembly and reverse engineering, omg it's untouchable.... No I'm telling you there is much more lower level than that."

"I feel bad when I get sick because I don't go to work... I don't (get to) open my laptop and looking to code."

"When I'm far from my computer for two or three days... I'll be depressed."

"You can make it part of your day." [22:52]

"I wanted to send them the new domain controller password with the report. " [25:23]


Hosam on Twitter:

Hosam's Website:

BSides Istanbul:

Upcoming talk "Hunting For Windows Remote Zero-days":

Intro Music: Cascadia by Trash80 - (Released under Creative Commons)

Outro: Weak Knight by Devon Church -

Getting Into Infosec:

Website, Show Notes, Transcripts:

Follow Me on Twitter:

Subscribe To YouTube:

Checkout My Book:

May 26, 2019
BONUS - Consuming VS Producing

My thoughts on consuming vs production and how it relates to Getting Into Infosec. Sometimes we get stuck learning, consuming security news, trends and etc... but we forget to produce something. Whether it be testing a new exploit we heard about, trying something new in our lab, or applying something we learned the day before. Finding the write balance is important. If we're stuck, take little steps - better than no steps.




Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

May 21, 2019
Izzy - Random and Unplanned: From Annuities to ISO!

Ismaelle Vixsama (aka Izzy) has a knack for finding strategic flaws and speaking up about them. Doing so helped her get her first full-time job as well as have repercussions for defensive egos. Her whole career is a war story.


Izzy is an ISMS manager with 7 years of experience. She has worked in FinTech, Government, and Security R&D. Her work has allowed her to work on several mainstream products and services with some of the most well recognized brands.


ISMS - Information Systems Security Manager

  • Creates a security program around a company's information systems.

Played the CISO role initially, very CISO like role

First role in security was in Risk

Izzy comes from a very traditional Haitian back

Izzy came up benefits at her job for an opportunity to learn something new and be in a non-toxic environment.

First heard/learned about hacking at 15 from an AOL chat with a "hacker".

At 23 decided to speak up in a meeting a provide feedback, which led to her being hired Full-Time.


"At the time I was 22 years old, the pay wasn't that great but for me it was amazing because I was doing something I hated, I had benefits at my previous job but this company was giving me an opportunity to learn something new. To me that was so exciting."

"He looked at my resume and he said 'I realize you have no cybersecurity experience.' By starting the conversation like that it took some pressure off of my shoulders." 10:00

"I was so nervous that he was going to drill into me about all these topics I had no clue about."

"I didn't even [know] I had sisters."

"Everyone just kinda wrote me off." 16:20

"Who is the audience, what do we want to say here?" 21:13

Worst comment ever... "We have to really train you on your critical thinking skills." 22:45

"A good idea is a good idea, regardless of who it came from."

"My whole career is a war story." 32:05


Izzy on Twitter:

Izzy's BUsiness, VixCyber:

NIST Cybersecurity Framework:

Intro Music: Cascadia by Trash80 - (Released under Creative Commons)

Outro Music: "Feather Duster" by Geographer:

Getting Into Infosec:




May 12, 2019
David Scrobonia - Lifelong builder, Appsec Engineer, Creator of ZAP Heads Up Display

From Zero to One, David is a lifelong builder. Wherever he goes he just builds things. From an electric car to adhoc android apps to ZAP HUD, an awesome heads up display for ZAP Proxy, a game changer imho. We discuss the lack of UX in the security tooling community, how contributing to Open Source got him his job, and even about imposter syndrome.


David Scrobonia is part of the Security Engineering team at Segment working to secure modern web apps and AWS infrastructure. He contributes to open source in his spare time and leads development for the OWASP ZAP Heads Up Display project.


Mostly interested in architecture and mechanical engineering when younger.

Built his own electric car with his dad, out of a Porsche 914!!

David explains XSS and why certain languages are better than others, such as react.

David gets lost in El Segundo. Yes.


"It's just a program that listens on these silly protocols."

"Playing with my hands I wanted to do more hands on stuff, quickly fell in love with the coding side as a lot of people do."

"I was like... what's GET? what's POST? What do you mean?"

"Before you know it right it seems so daunting."

"Still plenty of opportunities out there. Will be a long time before the world is perfect and secure."

"With all those things, I've been working in the security industry, but I didn't really feel part of any security community."

"I have nothing but good things to say about the open source community."

"...they're (security tools) just not built with user experience first."

"I think people underestimate what they are able to contribute."


David on Twitter:

Rube Goldberg Machine:

Dan Boneh's Cryptography Course:

OWASP Appsensor Project:

Zap Proxy Heads Up Display (HUD):

Article by David on Zap HUD:

Brakeman Pro:

My talk at Sam's class:

Intro: Cascadia by Trash80 ( Licensed Under Creative Commons

Outro: Cancun by Topher Mohr and Alex Elena

Getting Into Infosec:




May 03, 2019
BONUS - Cliff's Notes To The First 20 Episodes!

Having completed 20 episodes, I decided to take a moment to go over each episode briefly.

Thanks to call my guests!

Ep01 - Dan Borges:

Ep02 - 0daySimpson:

Ep03 - Christina Hanson

Ep04 - Matt Toth:

Ep05 - Rob Carson:

Ep06 - Robin Stuart:

Ep07 - Clay Wells:

Ep08 - Elvis Chan:

Ep09 - Virtual Kyle Kennedy:

Ep10 - InfoSteph:

Ep11 - Yaron Levi:

Ep12 - Jack Rhysider:

Ep13 - Marcus Carey:

Ep14 - Nipun Gupta:

Ep15 - Adrian Kaylor:

Ep16 - InfosecSherpa:

Ep17 - InfosecJon:

Ep18 - Masha Sedova:

Ep19 - Jared Folkins:

Ep20 - Leron Gray:

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Apr 27, 2019
BONUS - MCOHMI New Song, Trap Music, and Domain Song Background

MC OHM-I (Leron Gray) talks about his next project about tabs in the browser, trap music, and some background on his awesome song Domain.

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Apr 17, 2019
Leron Gray - From Navy E6 to Pentester, SANS Mentor and Nerdcore Rapper!

Leron Gray is a man of many talents. Not getting really into computers until much later in life, but always having a creative side, he now finds himself as a pentester working from home and nerdcore rapper producing amazing beats!


Leron is currently a penetration tester and a ten year Navy veteran with four years experience as a Cryptologic Technician (Networks), focusing primarily in offensive cyber operations. He holds a Bachelor's degree from Dakota State University in Cyber Operations. With a passion for Python, he loves automating tedious daily routine tasks for efficiency and considers himself to always be in a position to learn more and pass on knowledge. He always enjoys competing in as many Capture-the-Flag events as possible and also often performs as a nerdcore rapper.

Leron currently holds eCPPT, eWPT, GPYC, GPEN, GAWN, GCFE, and GICSP certifications. He also maintains a blog and maintains an active Twitter discussing music, information security and wrestling.


  • Went to a high school that made you choose majors.

  • Grew up poor, was not allowed to go out much.

  • Technological learning came from school.

  • Didn't really get into computers until he was 25.

  • Has been in music sister Jr. High School. Marching band, jazz band, and concert band... all the bands.

  • Networking is the biggest thing that Leron says would help.

  • Leron offers his passionate opinion on "aptitude". It's a pet peeve of his.


  • "I learned a lot... I made sure not to waste any opportunity for learning..."

  • "Job searching in general is a pain."

  • "I don't think I would be where I am right now if I hadn't gone out and made that effort."

  • "One of the big deals that people had were degrees, I wasn't really sure why; I have 10 years of IT/Cyber experience."

  • "It turned out the company no longer owned that server. Their DNS was still pointing to it though."

  • "I took Java in high school and was really bad at it and I found out everyone is bad at Java so it doesn't really matter."

  • "It's so much easier to learn when you have a problem to fix."

  • "It's not even just information security that learning pyt hon could help... it could be anything you do.. .often enough to warrant not to do it manual."

  • "Nobody does a CTF and expects not to learn something by the time they leave ."

  • "Job searches shouldn't be like that. They should be based on you merit. But..."

  • "Maybe the person can't get OSCP, but maybe they have the skills or knowledge..."

  • "The idea of aptitude... raises too many borders."


  • Leron on Twitter:

  • Leron's Blog:

  • Leron's GitHub:

  • Class that Leron Is Mentoring:

  • Visual Studio Code:

  • PyCharm:

  • IPython Notebook:

  • San Antonio's Hackers Association:

  • MC OHM-I:

Intro Music: Cascadia by Trash80 - (Released under Creative Commons)

Outro Music:

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Apr 12, 2019
Jared Folkins - 18 YRO Manager To Education Security To Human Hero

Jared Folkins understands people, technology, and the world around him. He can smell a toxic environment from a mile away and has used that EIQ spider sense for good. Jared shares with us some VERY personal stories (tear jerker warning!) in integrity and life decisions as well a bunch of on the job war stories including a famous one featured in the news! This is probably my most dramatic episode yet.


  • At 18 got promoted to manage a team of 50, because he wasn't lazy.

  • In hindsight was able to see indicators of the dot com crash, but didn't realize that.

  • Had a fork in the road where he had a major decision to make.

  • Jared shares with us a VERY personal story and the life lesson from that which he applies in his professional life.

  • Having low tolerance for toxic relationships, Jared has been able sense toxicity and it's been a driving force for good for him.


  • "I believe in the power of admitting when you're wrong."

  • "I carry my guilt between my shoulder blades."

  • "When I make that mistake; When you have a team that you can trust or a team that honors you, you have the freedom to say stuff like that."

  • "You can only control you."

  • "Constraints can be healthy."

  • "Stepping outside of your comfort zone... super healthy too."

  • "If someone tells me this person... is not a good person, I'll actually go meet that person. I want to asses it for myself."

  • "You get rejected, don't get super emotional... just work with what you have and move on."


Jared's Blog:

Jared's Twitter:

Jared's GitHub:

Opsec Edu:

KayPro Computer:

Donkey Kong Clone:

Grand Mal Seizure:

Project Dir Fu:


Getting Into Infosec:




Apr 03, 2019
Masha Sedova - From Generations of CS to Behavioral Science and Entrepreneurship

Masha Sedova comes from a history of computer scientists! Her grandmother was in the first Computer Science graduating class in 1954 under Stalin in the Soviet Union!! She loves challenges and is now utilizing what she thought was a waste of time in Liberal Arts to conquer challenges in Information Security using behavioral science, emotional intelligence, and other human factors.


Masha Sedova is an industry-recognized people-security expert, speaker and trainer focused on engaging people to be key elements of secure organizations. She is the co-founder of Elevate Security delivering the first people-centric security platform that leverages behavioral-science to transform employees into security superhumans. Before Elevate, Masha Sedova was a security executive at Salesforce where she built and led the security engagement team focused on improving the security mindset of employees, partners and customers. In addition, Masha has been a member of the Board of Directors for the National Cyber Security Alliance and regular presenter at conferences such as Black-hat, RSA, ISSA, Enigma and SANS.


  • Grandmother was in the first Computer Science graduating class in 1954 under Stalin in the Soviet Union!!

  • Her Grandma taught her dad and her dad taught her programming around the 6th grade.

  • Had access to a computer only through the local University.

  • Masha began her search into 3 disciplines

    • Game Theory
    • Positive Psychology
    • Behavioral Science
  • Leaderboards are better for only a small subset


  • "You can't patch a human being."

  • "We've taken a technology solution to a human problem, and I think that's totally wrong way of going about it."

  • "Without the human interaction we would not have been able to get that alert."

  • "Focus on failure as an eventual outcome."

  • "I like picking hard challenges and very tall mountains to climb and computer science seemed like a tall mountain."

  • "If you give people the correct amount of challenge, that is a state of happiness."

  • "I found that leaderboards are effective for a small subset of people."

  • "The reasons people don't do things is not because they don't know."


  • 6:1 Positive Feedback Ratio for Performance:

  • Dr Gottman:

  • Reality is broken by Jane McGonigal:

  • Flow by Mihaly Csikszentmihalyi:

  • BJ Fogg:

  • Opower Report:

  • Predictably Irrational by Dan Ariely:

  • Intro Music (Cascadia by Trash80):

  • Outro Music (Quincas Moreira - Entire):

Getting Into Infosec:




Mar 22, 2019
BONUS - InfosecJon Learns Trust But Verify The HARD way

InfosecJon expands on some CRAZY follies he experienced during his times in the Navy. He learns through trial by fire, literally, trust but verify!


  • Jon almost gets crushed inside the engine of Naval Ship

  • A boiler explodes and Jon, a Jr Engineer, was left in charge of the situation and had to give orders

  • Jon got soaked with engine Oil on a running ship resulting in the loss of pitch control

  • Luckily Jon was wearing a PEP suit

  • Tag-out manual:

Getting Into Infosec:




Mar 20, 2019
InfosecJon - From Rudderless Youth to Navy Engineer to Security Professional

InfosecJon runs a website cataloging his learning and dedicated to helping others get in the field. He shares his personal story from a directionless youth to enlisting in the Navy (and it's follies) and his tribulations getting into the field. He also shares some interesting Navy stories. Lookout for the bonus episode.


Jon is a father, husband and a veteran. He went from aimless youth to enlisting into a career path he never liked. After 7 years as an electrical engineer, he got the chance to pursue his dream of working in information security. Now, he runs a website devoted to helping others.


By almost getting crushed in a two story engine, Jon learned to be adaptable to the situation.

Got exposure to computers by working with dad at his computer store.

Was an engineer at heart who fell in love with the inner workings of things and how they work.

Became the go to person for technology in his department.

Always had a knack for helping others, even before the military.


"Biggest skill I got was to be able to figure things out quickly and troubleshooting."

"You can't troubleshoot something until you know how it works."

"I just wanted to learn as much as I could."

"I want to work with technology, I want to help people."

"Going to a traditional school, being more mature, was a negative."

"Everybody doesn't know everything. That's why most security teams are... teams!"

"I want to help people, I want to protect people."

"The networking knowledge, the sysad knowledge, and then the drive to learn new stuff... is what they were attracted to."

"Nobody wanted to do it. I volunteered and stepped up."

"One thing that attracted me to the school 100% was they advertised hands-on labs.":


InfosecJon (Twitter):

InfosecJon (Website):

Navy C-School:

Jon on the different types of hackers:

Intro: Cascadia by Trash80:

Outro: White Smoke by Endless -


SEED Labs by Syracuse University :

David's CTF Post:

Getting Into Infosec:




Mar 16, 2019
InfosecSherpa - From Travel Agent to Law Librarian to Security Analyst!

Tracy Maleeff (@InfosecSherpa) was a professional law Librarian and at the top of her game. Looking for change and meaning, she searched until she found the field of Information Security. This is her journey.


Tracy Z. Maleeff (/may-leaf/), @InfoSecSherpa, is an independent information professional providing research and social media consulting, with a focus on information security. She is a frequent presenter about best practices of data mining from social media, professional networking, and introduction to information security topics. Tracy has 15 years of experience as a librarian in academia, corporate, and law firm industries and earned a Master of Library and Information Science from the University of Pittsburgh. She is the Principal of Sherpa Intelligence LLC – your guide up a mountain of information.


  • There is a condition called "Librarian Face"

  • Librarians, who Master's Degree in Library Science, are taught to be approachable

  • Was never a public librarian, worked in "special" libraries. This made her really good at finding and accessing data.

  • Tracy shares some social engineering tricks she did earlier in her life.

  • Didn't grow up with computers around her.

  • Advice: "Know yourself"


  • "If you are out in public… people are likely to come ask you questions because you look like you know things."

  • "I did fail, but I did not fail as badly as I thought I would!"

  • "I don't regret the path that I took."

  • "For someone like me who does come from a technical background... having the certifications is what people want to see."

  • "They need to see some receipt!"

  • "Even if it turned out to be nothing, don't be afraid to speak up."

  • "I don't think I realized it was social engineering, I just knew it was something that I wanted."

  • "Managed to talk my way not only on the plane, but also into business first."

  • "They had me at port scanning."


  • Infosecsherpa:

  • Women’s Society of Cyberjutsu (WSC):

  • Intro Music: Cascadia by Trash80 -

  • Outro Music: JR Tundra - Natty Roadster


  • Art of Improvement:

Getting Into Infosec:




Mar 01, 2019
Adrian Kaylor - From Network Admin to Trainer to Sales Engineer for Life

Adrian is a Sr Sales Engineer with Splunk who focuses on security. He has worked for various security startups in the bay area for the past 15 years from vulnerability management, to endpoint investigation, to ML based threat hunting.


  • Had an interest in security early on, starting with opening binaries on Sierra's King's Quest games and looking for hints.

  • Took any opportunity he got to get exposed to security

  • His job as an instructor was very useful during support and later as a sales engineer

  • Keeps a Trello board for his lab!!

  • Adrian expenses (deducts) what he spends on his lab from his taxes. (Consult a tax attorney)

  • He mentions an awesome hack for installing Kali on a chromebook (~22 mins)


  • "I remember the first time I found Phrack, my mind exploded a little bit."

  • "Experience is experience, everything that you use [skills] will get used later on."

  • "...figure out what pieces their missing, so you can fill them in."

  • "Go through the CIS top 20 critical controls"

  • "Be less focused on the whizbang fun stuff, and more focused to get you the most return."


Please thank my guests for sharing their time with us and let them know if this episode helped you.

Adrian Kaylor on Twitter:

Adrian Kaylor on LinkedIN:

Phrack Magazine:

Lack Rack:


Splunk Dev License:

CIS 20 Controls:



Netsec Reddit:

SANS Holiday Hack Challenge:

Garage Door Hack by Samy Kamkar:

Sam Bowne's Class:

Adrian's Presentation on YouTube: (Picture of lab at 24:05)

Intro Music by Trash80:

Outro Music (Liberation Theology - Exploitation is Sin):

Learning Resource Mentioned: based on:

Getting Into Infosec:




Feb 22, 2019
Nipun Gupta - From Security Consultant to Security Innovator

Nipun graduated during the recession, but found a job as a consultant which helped him gain experience quickly. He was in fact discouraged to pursue a career in information security due to his immigrant status. Nipun is now a Cyber Security Executive focused on innovation.


Nipun Gupta is a Cyber Security Executive at a large global financial institution focusing on innovation. Armed with many years of experience helping Fortune 500 companies solve cyber risk challenges, Nipun is tasked to help his employer discover, asses & adopt new cybersecurity solutions protecting against emerging threats.

In the past two years, Nipun co-founded and ran the global Cyber Innovation Ecosystem strategy at global consulting company, with a specific focus on US and Israeli startups. He offers a strong network of security executives, startup founders, and the Venture Capital community in the West Coast and abroad. Technically proficient in network and application security, Nipun is a trusted advisor for many financial service institutions, technology, and telecom companies contributing, to solutions worth tens of millions of dollars. Nipun completed his Masters of Information Technology and Information Security from Carnegie Mellon University, and has been collecting industry certifications like CISSP and SABSA ever since.


  • Was discouraged to go into cyber security due to his immigrant status

  • Graduated in a tough time during the 2008 recession

  • Discusses burnout and having to work odd hours for 6 months of the year

  • The show "24" was an influence in sparking the interest in information security

  • Shares an interesting war story where he accessed tons of files

  • Discusses the personality traits needed to be a consultant


"The biggest problem security professionals will continue to face is how to bridge that gap between technical conversation and business conversation."

"You have to be technical to understand the depth of the issue, but at the same time you need to be able to express it in business language so non-technical people can make those decisions."

"I think you have to talk in terms of risk. Every business professional [in a] large or small company understands risk, because risk can put them out of business."

"While I'm an introvert when it comes to working, I'm an extrovert when it comes to expressing my work related conversations or expressing my work related issues."


Nipun on Twitter:

Nipun on LinkedIN:





Intro Music - "Cascadia" by Trash80:

Outro Music - "Put This Rap Together
" by Bobby Cole:

Feb 09, 2019
BONUS - My Book is OUT: Breaking IN: A Step-by-Step Guide to Starting a Career in Information Security

My book is out!

Breaking IN: A Step-by-Step Guide to Starting a Career in Information Security

Jan 25, 2019
Marcus Carey - Childhood Builder/Breaker to Navy Cryptologist to Founder and Mentor

Marcus Carey has been hacking since we was five. A true MacGuyver he had to make due with little resources available to him. He later enrolled for the Navy, worked for 3 letter agencies including the NSA, and now has his own security startup. Marcus shares a TON with us in this episode.


Marcus is renowned in the cybersecurity industry and has spent his more than 20-year career working in penetration testing, incident response, and digital forensics with federal agencies such as NSA, DC3, DIA, and DARPA. He started his career in cryptography in the U.S. Navy and holds a Master’s degree in Network Security from Capitol College. Marcus regularly speaks at security conferences across the country. He is passionate about giving back to the community through things like mentorship, hackathons, and speaking engagements, and is a voracious reader in his spare time.


  • Marcus had an opportunity to play college basketball, but couldn't since it was only a partial scholarship

  • After taking the ASVAB test had the choice of nuclear engineering or cryptography. He chose cryptography.

  • Marcus made a olympic sized track pit, up to spec as a child.

  • Marcus like many other security professionals, had a strong artistic side. Achieved first chair in just a few weeks in Jr. High.

  • Marcus teaches us "How to Learn".

  • Marcus achieved over 115 college credits, on his own, without attending college!

  • Open source tools Marcus created ended up being used be used to save people's lives in other parts of the world.


  • "[I] Told them all I wanted to do was work with computers."

  • "I've always been a tinkerer. I built stuff, I was a science fair geek... the whole nine."

  • "I was the poorest person growing up... so anything I did was a hack. I made my own hackey sack. I used to make my own toys."

  • "You can't learn how Marcus learns, because everyone is different.... Nobody can tell you how to learn as good as yourself."

  • "So now, I'm like a finely tuned weapon when it comes to learning... cause I know exactly how to learn."

  • "Never be surprised how your work turns out to be used for good... it actually blew my mind that my stuff was being used to do that [saving people's lives]. "

  • "Show externally that you've mastered those concepts in some way."

  • "Sometimes your employees are going to go rouge, and hopefully you can detect when they do."

  • "If you're focusing on a specific set of skills that are evergreen, and if you work that long enough, it doesn't matter your aptitude, you can become an expert at that."

  • "There's people out here that are celebrities and they act like they know everything. Don't be one of those people."

  • "Aptitude allows people to learn stuff faster. I think the military requires you to learn stuff fast."


Resources Mentioned:

The Paradox of Choice by Azeria Labs

Cyberseek Pathways

Jan 11, 2019
Jack Rhysider - From Odd-jobs to Network Analyst to SOC Architect to... Darknet Diaries!

Jack Rhysider's origin story. With an engineering background Jack found himself doing odd jobs at first. Looking to get back into tech he "certed" up and got a job in the NOC (Network Operation Center) and eventually became a SOC architect building a SOC from scratch. Looking to do something different, he started Dark Net Diaries and it's been an adventure since!


Jack Rhysider started his professional career in a NOC and then became a network security engineer. Doing a lot of work around hardening the network and detecting threats in the network. He became a security architect and successful built a SOC for an MSSP. Currently he's the host of the podcast Darknet Diaries where he interviews hackers or those who've suffered a major attack. The podcast has experienced phenomenal growth so Jack now works on it full time.


  • A glimpse into the life of a security analyst and a Managed SOC

  • Takes about 3-6 months for an analyst to baseline and come up to speed

  • First hack was hacking the Sim City savegame file. Dad was thrilled!

  • Several years of blogging his journey in Infosec helped Jack with his communication skills and explaining difficult concepts to people.


  • "As a Security Engineer, I need to know a little bit about everything."

  • "I would do things like remove (rm -f /) the whole root directory, just to see how many files I could delete before the whole operating system would crash!"

  • "Be fearless grandma!"

  • "I think there is a lot of shaming that goes on of people that do security wrong... that kind of makes things stressful."

  • "I think what us as security people lack sometimes is good communication."

  • "Taking on tasks when nobody asked them to take it on... in the eyes of ... wherever you work... this is amazing!"

  • "...I would keep corrupting files over and over but eventually I figured out which byte in the file was for the amount of money and I was able to give myself a Billion Dollars!"


Darknet Diaries Podcast


CFP Time

Intro Music by Trash80

Outro Music by Mid-Air Machine

Jan 01, 2019
Yaron Levi - Entrepreneur to Security Architect to CISO and Security Champion

Yaron Levi is the CISO for Blue Cross and Blue Shield of Kansas City. We talk about what he looks for in people when hiring in Infosec and a time when he took a chance on someone (against the opinion of his peers) and his chance was a big success. We also discuss a breach he had to deal with only 3 months into his job!


Yaron Levi is the CISO for Blue Cross and Blue Shield of Kansas City (Blue KC). In this role he manages a team responsible for information risk management, cyber defense, regulatory and compliance, architecture and engineering, and identity and access management for an organization that provides health insurance for about 1 million members and over $2B in annual revenue.

Prior to joining Blue KC, Yaron was a Director of Information Security for Cerner Corporation; an Information Security Business Partner for Intuit; an Information Security Architect and Product Manager for eBay; and a Director of Cloud Security for ANX.

Yaron is a Research Fellow for the Cloud Security Alliance (CSA). The Research Fellow designation is the highest honor and distinction that can be given to a CSA research volunteer who has demonstrated significant contributions to CSA research. Yaron is a co-chair and lead architect of the Cloud Enterprise Architecture. Contributor to the Consensus Assessments Initiative Questionnaire (CAIQ), Cloud Controls Matrix and Promoted the CSA as best practice in various cloud projects with various Fortune 500 companies.

Yaron is the co-founder of the Kansas City CISO forum, B-Sides Kansas City, and is a frequent speaker on Cyber Security Architecture, DevSecOps and Cyber Defense.

Yaron holds a B.A in Social Sciences and Management and is a graduate from the FBI CISO Academy.


  • Created his own IT company to pay his way through college

  • A SOX Compliance project was his first exp

  • First computer was a Sinclair ZX81

  • Had to save up to by his own Commodore 64!

  • Yaron's discussion with youth whether a laptop is more dangerous than a gun? What about 2nd Amendment?

  • 3 Months into his job, he experienced a breach!


  • "Security is one of those areas that you can be part of something that is bigger than yourself."

  • "Having a real calling for something ... that can make a difference."

  • "It's one of those communities that people really want to help each other."

  • "I think for many people, there isn't a prescription, if you will, of how and where to start."

  • "Are you the type of person who likes to crack codes and puzzles and bang your head against the wall for 16 hours...that may lead you to a dead end or nothing? Oh no, I like to talk to people."

  • "...First and foremost, we are educators."

  • "Sometimes when we look for people, we tend to look for people based on a very specific mold or template [unfortunately]"

  • "Usually I hire for character first, then skill."

  • "At the end of that record is a person... a human being."

  • "I think people need to realize that it can be a very thankless job, not just hoodies and hackers all day long. If you google a "Hacker" today... it's kind of depressing to everyone with hoodies like that... that's not the reality."

  • "It's all about defense... protection... enablement of the business securely. When everything goes well, nobody really think of you, nobody thank you for that. But when something bad happens, everybody looks for a head to chop."

  • "It's in my opinion one of the more rewarding careers one could have and being part of something bigger than just themselves."


Yaron Levi on Linked IN

Yaron on Twitter

Women in Security KC

BSides KC

Sec KC

Intro Music: Cascadia by Trash80

Outro: A Rising Wave - Jeremy Blake

Dec 25, 2018
InfoSteph - From Journalism to IT Support to Security Analyst

Steph is brand new to the infosec field! We go over her interesting and eventful path into Information Security, reflections on her role today, and some really interesting war stories!


Steph is a Security Analyst for a retail company as a team of one. She has a background in journalism and web hosting. She is the creator and editor of, a blog focused on technology, inclusion and lifetime learning. It is Stephanie's life work to encourage and fight for more diversity and inclusion in tech spaces for more innovative and original collaboration. She spends her time mentoring high school students, hosting virtual labs via Women In Tech-a-thons, and learning as much as she can about any and everything. Stephanie believes that giving back to the community at every stage is very important. In addition to technology, Stephanie has a secondary passion in Psychology, so don't be frightened if you hear her discuss cognitive distortions or attachment styles. Her hope is to develop research that explores the dichotomy between human beings and technology. She is currently on a mission to speak at three events in 2019 and has already been booked for one event.


  • Dreams of Creative Writing, but chose Journalism for practicality

  • Encouraged to Computer Science by mom

  • Had her eye on Security, through IT or Web Hosting... eventually.

  • A story of being so close, yet so far

  • Was very close to giving up on the whole industry due to the difficulty and lack of encouragement... but was NOT comfortable with quitting.


  • "You have to talk to strangers about their story... you want me to walk up to a complete stranger as an introvert? Uh.. what?"

  • "The type of person I am I can't fully commit to something without getting my hands dirty." 12:57

  • "The way that I learn is situational."

  • "We had a vulnerability scan tool and so I just tried to work with that." 17:45

  • "It's kind of like what doctor's have to do before they have to become a doctor." 18:24

  • "So many people are trying to get into the industry and facing the same issue. I've done all these things people have told me to and it hasn't gotten me anywhere."

  • "Just do a bunch of stuff until it sticks!"

  • "Twitter was one of the best... decision I made."

  • "Get a champion that is more senior than you." 23:30

  • "Don't count yourself out, before someone else has counted you out."

  • "The lessons that are best learned are the ones that resulted in catastrophic failure."

  • "When you want to be a lawyer, you go to law school, you sit for the bar. There ya go! There's a plan." 24:43


  • Steph's Website:

  • Speaking engagement next year:

  • Steph's Tech a Thon's:

  • WISP - Women in Security and Privacy:

  • Intro - Cascadia by Trash 80:

  • Outro - That Night In Your Car - Spazz Cardigan:


  • HackEDU:

  • Open Bug

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Dec 18, 2018
Virtual Kyle Kennedy - Stories, not resumes: Breaking educational and other barriers in cybersecurity

Today's episode is a reading of an amazing written by Kyle Kennedy, president of The reading is performed by Allison, an IBM Watson personality. I also go through some recent resources discovered to help you on your journey to a Career in Infosec.


Kyle F. Kennedy is a social cybersecurity expert and president of His organization provides foundational soft-skills training for a small fee (supported by corporation donations) and plans to launch soft-skill Masterclasses in 2019.They helped organize an event called Day of Shecurity, for women of diverse backgrounds to have one day of learning: tech/ hard skills, soft skills. They had opportunities for mentorship and guidance. Day of Shecurity was FREE to attendees!


Article: Stories, not resumes: Breaking educational and other barriers in cybersecurity

Google Image Search for "cybersecurity"

Associate of (ISC)²

Adrian Kaylor's talk "Sales Engineering and getting into infosec"


City College of SF Cybersecurity Program

CCSF Information Security (Cybersecurity) Analyst Apprenticeship

Sam Bowne's Classes

Article in IBM Watson's Expressive SSML used on the show

Intro/Outro Music: Cascadia by Trash80

Full Text of Article:

When you search for images under the key word “cybersecurity,” a familiar shot always turns up: a guy wearing a hoodie, operating in a dark room, fingers on a keyboard.

I’d like to replace that image with…anything. To be a cybersecurity professional, you can be anything. And anyone.

We’ve heard the statistics. There is currently a human capital crisis, with 1.5 million cybersecurity jobs available and no takers. The number is projected to balloon to 3.2 million by 2021.

But who exactly are these cybersecurity professionals we are looking for?

For so long, we have had our own definition of who can fit that talent. A good cybersecurity professional has to have a computer science degree. They must have solid professional background. They have to be male. This pattern of defining success has led us to the shortage we are experiencing today. It’s kind of like insanity, really: Doing the same thing over and over and expecting different results.

What really makes up a good professional? Every human being brings a different experience. You need critical thinking and creative thinking, both. A variety of educational, ethnic, geographical, backgrounds.

For example, cybersecurity is not the obvious career path for someone with a biology degree; however, a biology major might help throw a new perspective on cybersecurity given that advancements of technology will eventually interface with the human body organically creating a scary threat landscape.

Often too we talk about cybersecurity in the context of oil and gas, or transport, or finance. Cybersecurity today and going forward, is a horizontal across every industry, as opposed to just being by itself.

Every industry needs cybersecurity professionals. People from other disciplines could provide their own perspectives and add value to how the job is done. For example, some of the best cybersecurity communicators otherwise known as “Social Engineers”, I know are drama majors, communication majors and liberal arts majors.

Why are soft skills critical? The risks here are complex. If these risks are not articulated in a business language, such that executives are not able to grasp their importance, then what you will have as a result are cyber policies, created from the ivory tower, which everyone must follow, and which would inhibit the business instead of enabling it.

If cybersecurity becomes more inclusive instead of exclusive, then we will be all the more superior to the attackers. As it is, it’s the enemy who are inclusive. They don’t have any requirement that hackers should have this or that degree or should have attended an Ivy League school. Most hackers are self-taught, and when something sparks their interest, they go online. They read. Nobody tells them they could not do it because they are not a good fit.

Initial strides

Foremost, before anything can be done, there must be an acknowledgment of the current situation and the need to be more welcoming. Business leaders and decision-makers must recognize the unconscious bias that they have. They have to understand that creating positive disruption and changing patterns are a business differentiator.

My organization is active in our advocacy for inclusion in cybersecurity, specifically for women. We have been speaking to organizations on positive disruption. A good way to create action is through regional events and grassroots involvement. We bring the community together, and it is these communities that conduct classes and organize meet-ups and training courses.

We did this in reaction to the more established cybersecurity conferences that present numerous barriers to entry, and which are more for senior professionals. Women may not have the luxury of being able to spring for the travel, or leave their homes for days at a time, and perhaps find childcare for the time they are away.

ISC2 also now has an associate certification, where an individual can take the certification examination without the work experience; providing an opportunity for employers to recognize & support candidates entering or transitioning to the cybersecurity industry.

Personal reasons

My passion for diversity in cybersecurity is driven by several things.

First, given my degree in sociology, I must have had a hundred interviews before landing on a job in technology, even though I knew a lot about it – it had been a hobby for years — and it was clear I was keenly interested and willing to learn. They said I was not the right fit because I did not have a technology degree; specifically, a computer science degree. Didn’t matter that I could code in Assembler, BASIC, C, Cobol, Comal, Forth, Fortran, Logo, Pascal, PL/1 or Algol.

And I thought, if this could happen to me, a white male, think of all the others who could not break the barriers!

I ended up leading the engineering department of the first company that hired me.

And then I met my wife, who herself had to break barriers in IT because she was a woman. For example, during meetings, she was seen as more of an assistant rather than a peer, even though she was very technical.

My male colleagues initially said I was just on the bandwagon with my advocacy for women in cybersecurity. I said no. Men have to recognize that we have to be part of the solution, since many of the positions of senior leadership are occupied by men.

‘This is not my coffee’

I have a good analogy for all this. Suppose you went to a Starbucks, and when your coffee is given to you, you see that it was not what you asked for.

For a moment you might think you might as well take it, because the barista probably knows what is good for you, more than you do.

But no – you renegotiate. The barista does not know any better. You then look for the manager to explain the mistake and to get the drink you want.

Empathy is what can truly enable us to understand that we need to change the status quo. Yes, I am male, I am white, but I know that my background is a lot different from that of my peers. Because of this, I am very empathetic in that I know there are institutionalized barriers. I should know – I have spent the past 25 years in security.

What should really matter is that there are many talented individuals capable of both critical and creative thinking. They may not come in the shape and size we have traditionally expected them to be, but they are interested. They are intelligent.

In the end, only three questions should matter to organizations when they decide on investing in somebody for a cybersecurity role: Do you have the brain? Are you passionate? Can you learn?

Kyle F. Kennedy is a social cybersecurity expert and president of His organization provides foundational soft-skills training for a small fee (supported by corporation donations) and plans to launch soft-skill Masterclasses in 2019.They helped organize an event called Day of Shecurity, for women of diverse backgrounds to have one day of learning: tech/ hard skills, soft skills. They had opportunities for mentorship and guidance. Day of Shecurity was FREE to attendees!

Dec 11, 2018
Elvis Chan - From Making Computer Chips to FBI Supervisory Special Agent!

Elvis Chan is a Supervisory Special Agent Elvis Chan, who works cyber security matters for the FBI San Francisco Division. We discuss how we got into the FBI, Life in the FBI CyberSecurity Division, and how to get involved.

The FBI is always looking for qualified applications for Special Agent and professional staff positions. Please see for more details.


  • There are three main roles in CyberSecurity at the FBI:

    • Special Agent (Gun Carrying Badge)
    • Intelligence Analyst
    • Computer Scientist
  • It may be quiet on the outside, but you can bet the FBI is hard at work on the inside.

  • Protection of the recent elections was discussed. The sheer number of people involved in protecting the elections from foreign actors couldn't be enumerated. Both the public sector and private sector involved.

  • In an incident response, there is often coordination with FBI headquarters and sometimes other 3 letter agencies.

  • FBI San Francisco was the squad of record for investigating the 2014 Yahoo hack.

  • Elvis goes into detail explaining more about Russian Hacking and how the FSB culture works.

  • Placement in the FBI is based on a ranking system.


"There are a LOT of things behind the scenes I can't talk about."

"If you see in the news that there is a hack, you can be sure that there is at least one maybe two, maybe several, office mobilized to figure out what the heck happened."

"On a regular day, I would love to just go through my email and have the scheduled meetings I'm gonna have."

"Why are the Russains coming after us..."

"Whatever happens to you... 'The Need of the Bureau'"

"My current job, despite all the paperwork and meeting I don't want to go to is a 10 out of 10!"

"People would not believe some of the stuff that we've seen or that we've gone through. They would make the worst movie plot because they would be so unbelievable!"


FBI Jobs

2014 Yahoo Hack



FBI Field Offices

Dec 04, 2018
Clay Wells - From SysAdmin to Security Architect to Con Organizer!

Clay Wells ... Security Architect, Musician, Defcon Blue Team Village Co-Organizer, and organizer of the first annual WOPR Summit. Clay shares some really insightful tips on making it Information Security, as well as a really interesting war story from recently.

WOPR Summit is March 1st, 2019 in Atlantic City!

Living in kernel/userland since Red Hat 4.0 Colgate. Work life has primarily been in Academia and has included programming, system administration, and information security. He's a point of contact for the DC215 group and one of the coordinators for the Blue Team Village at DEF CON. He also creates unofficial CTF challenges for local hacker cons and is organizer for the first annual WOPR Summit this March 2019 in Atlantic City.


  • "My heart was racing... that was a huge rush and that's when I was like yea... Blue side F*** rocks!!"

  • "Take a holistic approach to InfoSec, dive into the culture, different cons, music, people...volunteer, get out, get involved... learn a little about everything, then find what really interests you... and go for it!"

  • "It's great to apt-get stuff... but try compiling a custom linux kernel."

  • "I'm a strong believer in embracing that creative side."

  • "It [Blue Team] certainly hasn't been the sexiest infosec job to have... yes defense is what people want... there's a lot defense work out there."


Clay Wells on Twitter:

Clay Wells on LinkedIN:

Clay Wells Blog:

WOPR Summit 2019

WOPR Summit Sponsorhip Prospectus

DEF CON Blue Team Village

Opensoc by Recon Infosec




H.O.P.E Conference

No Starch Press

Outro Music by Clay

Nov 27, 2018
BONUS: Robin Stuart - Road to Becoming a Cyber Crime Author

Robin Stuart is a debut author in cyber crime fiction with a short story called "SegFault" in the Sisters in Crime NorCal anthology Fault Lines , which is due out in early 2019!!!


  • Wrote her first full length mystery in the mid-90's!
  • Pitching is basically a job interview
  • Honing your pitch
  • You only get one shot at that first impression
  • She has a backlog of stories to tell... Stay Tuned!!! (So Excited!)


The New York Pitch Fest

Mystery Writers

Sister in Crime Northern California Chapter

Paula Munier, Robin's Literary Agent

Robin Stuart Full Interview:

Nov 18, 2018
Robin Stuart - From Paralegal to Malware Researcher (and Cyber Crime Author!)

Robin Stuart started off as a paralegal until she was challenged one day to get her boss's password. (Hint: Do not challenge Robin). Fast forward she switched careers to Technology but kept a lookout for a career in security.

Speaker Bio

Veteran cyber crime investigator and contributing author to the Handbook for Information Security by Wiley.

She is also debut author in cyber crime fiction with a short story in the Sisters in Crime NorCal anthology Fault Lines, which is due out in early 2019.

She consults on all things cyber security for Fortune 100 companies, television shows, and media outlets, including BBC and NowThis News.

She was a significant contributor to the Tech Museum of Innovation's acclaimed Cyber Detectives interactive installation, one of the museum's most popular permanent exhibits, which earned praise from the Obama Administration.


"Years of being a paralegal, I think like a lawyer and that's helped me very well"

"My Google works a little better than other people's Google"

Someone said to Robin once: "I've got an hour... can you teach me everything you know?"

"Taught myself Assembly by writing a program all in assembly, just to prove to myself that I understood it."


  • Combination of Enthusiasm and Perseverance
  • Creativity matters a lot!
  • Setting up a home lab to train
  • Robin's First "Hack"! EPIC!
  • There isn't a linear path into information security, no need for a degree necessarily


Robin Stuart on Twitter

Robin's Upcoming CyberCrime Short Story

Robin's Twitter

Year Up Program

Lexis Nexus DB

Shellcoder's Handbook

Information Security Handbook by Wiley


Practical Malware Analysis

Outro Music

Nov 13, 2018
Rob Carson - From USMC Infantry Officer to Information Security Officer

Speaker Bio

Rob Carson founder of Semper Sec. Rob knows how to simplify the problem and deliver solutions.

His clients base includes:

  • Fortune 200 Companies
  • US Government Contractors
  • State and Local Governments
  • Fuel Retailers
  • Software and hardware manufacturers

His distinguished career includes service as a Marine Corps Infantry Officer, as well as leading roles in IT and Security. Before devoting his work fulltime to facilitating his client's success, He built highly successful information security programs for ISO 27001:2005/2013, PCI, HIPAA, NIST 800-171, GDPR. He also volunteers his time as the Chief Security Officer for BSIDES Las Vegas, a non-profit educational organization designed to advance the body of Information Security.

Episode Highlights

  • Matt reveals how much he made when he got out of the Marines
  • Matt hilariously talks about the nuances he had to deal with when going to the private sector:
  • Not saying "Sir" and "Madamn"
  • Figuring out what to wear
  • How being early is too early


"I wasn't getting shot at... I was working in climate control, you know, so people be all stressed out and I was like 'Well no one's going to die'."

"I like to call myself a lessons learned enthusiast."

"The hardest job you'll ever get in infosec is that first step in."

"A first sergeant told me your hobbies should reflect part of your career."

"You can be outside the box, but you need to stay inside the room."



Rob Carson's LinkedIN Profile:

Nov 06, 2018
Matt Toth - From Slinky Network Support Engineer to Security Sales Engineer

Matt Toth is a Senior Security and Veteran Sales Engineer. Matt has two decades of experience in IT with a focus on cybersecurity, having collaborated with the Department of Defense on War Games and advised senior leaders on possible cyberthreats. With a passion for security, Matt is deeply engaged with the community to educate and prepare the next generation of Cyber Professional.

On top of that, he’s a good friend of mine in the industry with solid advice for those looking for a career in Information Security.

In our chat, Matt breaks down a Sales Engineer’s role, explains his love of conference badges, and gets philosophical on issues related to those trying to make it in the field.

Episode Highlights:

  • The jack-of-all-trades nature of Sales Engineer work.
  • Matt describes one company’s dishonest approach to “AI.”
  • How a luxury car and stylish threads can make the wrong impression on your client.
  • Con culture and breaking through the shyness barrier.
  • Matt delves into #BadgeLife.
  • The surprising accuracy of Hackers and Mr. Robot.
  • How Matt’s art school’s aspirations shifted to IT.
  • InfoSec wargames and the “Russian nesting doll” scenario Matt encountered working with a client.
  • Why some companies prefer to live with a security problem rather than attempt to fix it.
  • Lastly: Have you been keeping an ear out for my Easter eggs? Listen closely.


“I’m here, the customer trusts me to be here, and I’m gonna make sure that when they’re done, they’re happy with the situation so that they never come back and say ‘Hey dude, you screwed me over’.”

“You have to understand that you’re responsible for your own success. You can’t hide because you do have a quota.”

“If you really don’t like the technology you’re dealing with you’re not going to sell it well.”

“It’s awesome.. It’s iconic… that soundtrack is still incredible! On the way out to BlackHat this year I watched Hackers on the airplane and it was freaking me out… all of the attacks… are real world attacks we’re dealing with today still!”

“When you’re meeting with your audience, understand who they are and understand what they expect.”

“‘Hi, I’m Matt and I’m an InfoSec addict!’ ‘Hi Matt!’”

“If you’re just getting into the industry, recognize that all of us have our skill gaps. There is no one who knows everything.”

“My thoughts on certs are, do you like to get paid?”

“Most insider threats aren't malicious, they're just people trying to do their job and oftentimes working around the system to try to be more efficient.”


Matt’s LinkedIn

Matt’s Twitter - @willhackforfood

Matt’s blog


William Gibson and Neuromancer

Grifter and #trevorforget


Oct 30, 2018
Christina Hanson - From HOA Manager to Headfirst Into InfoSec!

Christina Hanson is a security analyst working for Truvantis Cyber Security Consulting and one of my former boot camp students. She has extensive technical experience and a deep understanding of the collaborative nature of InfoSec, not to mention how women and other underrepresented groups in the community have a more difficult time navigating this industry due to institutional barriers.

In our discussion, Christina touches on the wide variety of resources and events that helped her enter information security, why teamwork is just as important as technical work, and why InfoSec's responsibilities will continue to grow in the near future.

Episode Highlights:

  • How Christina's aptitude for IT led her down the path to InfoSec.
  • The "elective" course Christina took that turned out to be career-changing.
  • Why cooperation and group work are so important in InfoSec.
  • The "soft skills" needed to work in security.
  • Infosec was not her 1st or 2nd career!
  • An overview of Christina's day at Truvantis and how she works with clients.
  • Christina's experience at a SANS women's academy and the Day of Shecurity conference.
  • Why the InfoSec industry needs contributions from people from all backgrounds and how it benefits from diversity in general.
  • The increasing accessibility of conferences and other tech events for those who can't attend.
  • InfoSec's important role as companies have more and more access to users' data.


"I found that just the general atmosphere of security and the overall focus of what you're trying to accomplish was really helpful."

"Anything you're gonna do in security, you're gonna do as a team."

"Being open to learning new things is really important with this particular field."

"Even if I don't understand everything they're talking about, it gives me at least a start and a basic understanding that I can then research later."

"Being a professional in this field, it's so important that we are able to make other people safe."


Christina's LinkedIn:

Day of Shecurity:

SANS Women's Academy:

Merritt College:

Dr. Johannes Ullrich:

SANS Daily Podcast:

The Cyberwire Podcasts:


Amanda Rousseau (@malwareunicorn):

Dead Drop SF:

Oct 22, 2018
0day - From "Geek Squad" tech to DevSecOps

0day (“Zero Day”) is a security researcher who specializes in distributed systems security.

In his career journey through a "Geek Squad" like service at Circuit City ("Firedog") to trading floors and corporate information security, he’s amassed significant experience in the industry and is an example of how security consciousness is important even before you're an official security "pro".

In our conversation, 0day discusses getting into computers as an inner city kid, acknowledging how our hangups can affect the growth of InfoSec, the benefits of older technology, and much more.

Episode Highlights:

  • 0day defines distributed systems and how he and his team ensure they remain secure.

  • How his first hacking experience arose out of necessity.

  • The inner-city program that fostered 0day’s early interest in computer systems.

  • How the less-advanced technology of the Modem Age gave him a clearer understanding of how computers and the Internet worked.

  • How did Circuit City allow 0day to take his first step into the professional tech world?

  • His first taste of information security dealing with his company’s most dissatisfied clients.

  • 0day tracking down a security vulnerability through a coworker’s NSFW browsing habits.

  • What are 0day’s thoughts on the modern security industry and how it could be improved?

  • The importance of getting over our own prejudices and mentoring those coming into InfoSec.

  • 0day recommends books and conferences for those starting out or interested in the industry.

  • What’s 0day’s average routine at his current job?

  • Why computer science alone isn’t a solid enough background to get into InfoSec.

  • His advice for overcoming shyness at your first security conference.


  • “The malware I came across in those days, I still don’t see anything as unique.”

  • “We should really reach out to a wider swath of society to give them an interest in information security.”

  • “We as a community need to be less exclusionary by default, and be willing to look at some of these candidates who we are ignoring just for the sake of our feelings toward a particular certification or particular path.”

  • “We as people who are more seasoned in the industry now have the responsibility to also make ourselves available to those who are coming into the industry.”

  • “When you take away some of the complexity it makes it more difficult for someone to understand the underlying constructs, but at the same time it makes it easier for them to access, so there has to be a balance.”

  • “As you start to get really familiar with anything, you can see both the dark side and the light side of it.”

  • “We as professionals have some responsibility to disseminate correct, accurate knowledge.”


  • 0day’s Twitter account:

  • Youtube talk about Twitter:

  • Outro: "Cyber Sunset"

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Oct 15, 2018
Dan Borges - From Infosec ITAdmin to Red Teamer to CTF Organizer

Permalink and Transcript:

In this first episode, I chat with Dan Borges, a professional red teamer, blogger, and security tool developer.

Dan discusses his early experiences using and exploiting computer systems, how InfoSec experts work with companies, and a new tools he and other created and released this year!

Episode Highlights:

  • Dan explains how he became involved in information security,
    including his introduction to programming through a Lego robotics

  • His early experiences as a pen-tester—i.e. a penetration tester, who
    looks for system security weaknesses—and why it’s difficult to get
    hands-on experience in that field.

  • The benefits of becoming an Offensive Security Certified Professional

  • What does a red team do in an organization, and how is it different
    from pen-testing?

  • Dan describes the day-to-day life of a pen-tester and the kind of
    conflicts they can run into.

  • A few war stories from the trenches of InfoSec, as well as some of
    the tools pen-testers use.

  • How being grounded led to Dan’s earliest hacking experiences, and the
    ways his parents fostered his interests and mentality.

  • What conferences should InfoSec beginners check out?

  • Fun and beneficial ways you can “hack” reading.

  • Dan’s tips for those starting off or looking to transition into

  • An in-depth look at one of the newer tools Dan uses for his work.

  • The rules and intricacies of InfoSec competitions.


  • “It’s such a catch-22 to get practical, hands-on experience to go to these jobs because, y’know, hacking’s illegal, right?”

  • “We don’t just go in and blow the brakes off people, we’re trying to measurably improve security.”

  • “It was a constant escalation war, cat-and-mouse like that. They’d take something away and I’d figure out how to use the computer with that limitation.”


  • Dan Borges’ personal blog:

  • Dan’s LinkedIn:

  • Dan on Twitter:

  • Dan and Alex's DEFCON Talk on Gscript:

  • Gscript: Genesis Scripting Engine:

  • NationalCPTC (Collegiate Penetration Testing Competition):

  • Outro Music: Missing You by Trash80:

Getting Into Infosec:

  • Twitter:

  • YouTube:

  • Book:

Oct 08, 2018

Hi there! I am Ayman Elsawah, the host of a new podcast focused on helping you learn more about the information security field and how to be successful in it. We will walk through the shoes of seasoned information security experts as well as those new to the field, learn from their experiences, and find out how they got started. Join me on this wonderful journey!

Music: "Modem" by @Skilldrick

Sep 05, 2018