“Not everything works as configured. Not everyone behaves as trained.”

The reality of this statement makes it possible for us, the people in offensive security, to have a job. It also highlights how unpredictable our work can be and how never-ending our learning process is.

We work in a space where things are so complex that we need to combine big-picture, higher-level thinking with boost-on-the-ground practice.

And our guest today is brilliant at doing just that.

Pete Herzog has spent over two decades distilling the fundamental principles of security testing, turning them into a decade-defining manual - the Open Source Security Testing Methodology Manual (OSSTMM). Pete brings offensive and defensive security concepts together to break down important misconceptions.

Listen to this conversation to uncover:

• Why you can’t do security without understanding the process behind it [08:23]
• How automation can help but, at the same time, hurt the ones using it [11:00]
• Why you can’t rely only on automated security tools in your pentests [19:10]
• The importance of implementing security controls to change the environment [28:22]
• Pete’s perspective on "Zero Trust" and how they tackled this ion OSSTMM [35:18]
• Why he thinks there are “too many parrots, not enough pirates” in this space [43:42]
• The excitement of researching for OSSTMM v4 and exploring new technologies [51:40]

From the expert systems behind AI-driven tools and their blindspots to generalizations that hurt offensive security outcomes, we explore key elements that shape today’s problems - some of which you’re probably wrestling with as well.

Let’s explore them!

In this episode, we continue to ask the meaningful questions:

1. What makes a great pentester?
2. How can you balance the art of manual testing with the efficiency of automation?
3. What is the unique value that pentesters bring to offensive security?
4. And what can't be commoditized in this craft?

Gabrielle's mantra, “action for cyberpeace”, resonates through her work, and today, she shares her journey, experiences, and the lessons that shaped her career so far.

Key highlights from this conversation:

• What specific skills do you need to be a great penetration tester [02:45]
• How self-learning and consistency help you achieve your goals [07:55]
• Why she values team collaboration to deliver the best work you can do [13:57]
• How she got into cybersec and why she strives for cyberpeace [24:35]
• How to find balance between your personal life and your work [28:37]
• When automation is effective in pentesting and where that ends [32:02]
• How to set healthy boundaries to protect your personal life and health [41:11]
• Which hobbies juggle her curiosity and broaden her horizons [51:59]

Give this episode with Gabrielle a listen if you want to level up your ethical hacking skills and challenge your modus operandi.

With 20+ years of cybersecurity work, Tom unpacks the complexities of penetration testing, discussing the roles of vendors, practitioners, and technological advancements.

He also shares his perspective on what makes a good pentester, the value of mentorship, and the ethical challenges in this line of work.

Explore this conversation to learn:

• How pentesting changed over the years and who’s shaping it [03:02]
• How to avoid burnout and deal with imposter syndrome [09:13]
• Why he seeks and values mentorship for personal and professional growth [19:44]
• The importance of constant learning and networking with your peers [23:23]
• How compliance brings down the value of pentesting and what to do about it [30:04]
• How cultivating range can help you in your pentesting career [37:24]
• How to set healthy boundaries to protect your health [41:11]

This episode with Tom is a must-listen if you want to learn how to showcase your work and elevate your thinking and tactics.

• Tom’s personal website
• Tom on LinkedIn
• Tom on Twitter
• The Shared Security podcast
• The People Hacker book by Jenny Radcliffe
• Tom’s journey from offensive security to leadership at the Phillip Wylie Show
• Ethical hackers and the legacy of the hacker manifesto for Cyber Empathy
• Tib3rius
• Jason Haddix
• Dave Kennedy

Stay tuned as we explore how tools like Nmap and sqlmap have shaped penetration testing over the last two decades, and stick around to discover which aspects make pentesting predominantly a craft - and which parts have become standardized (and what that means for your work).

Unpack this conversation to discover:

• The depth of the work involved in crafting offensive security tools [04:45]
• What you can learn only by developing and maintaining tools [08:03]
• How Villain evolved and key learnings from building it [17:00]
• The challenges of finding balance in deep offensive security work [21:30]
• How Panagiotis uses automation to make his work smoother [25:35]
• How building his own tools shaped his thinking [32:00]
• What makes penetration testing a craft (with hands-on examples) [38:12]
• Why (and how) he finds the motivation to do meaningful work [48:16]
• What kind of projects keep him energized [50:55]

Venture with us into the evolution of hacking tools, as T3l3machus shares his journey from admiring early toolmakers to becoming a pioneer, creating tools like BabelStrike and Villain.

• Panagiotis on LinkedIn
• Panagiotis on GitHub
• His YouTube channel
• How to create your own GitHub projects
• John Hammond about hacking using Villain
• Villain
• Toxssin
• Hoaxshell
• BabelStrike
• Kerberos

Inti not only sheds light on what happens when expectations meet reality, but he also shares his unique approach to problem-solving with real-life examples you can add to your own process. 

With 12+ years of experience in this space, Inti De Ceukelaire is a Belgian ethical hacker and cybercrime investigator. He currently works as the Chief Hacker Officer at Europe’s largest vulnerability disclosure platform Intigriti and is also a founding member of the Hacker Policy Council.

Inti also excelled in various bug bounty competitions, where he’s been rewarded by companies like Google, Meta, Yahoo, The US Department of Defense, or Amazon for identifying critical vulnerabilities in their systems.

Dive deeper into this conversation to learn:

• Why the best hackers started their career by running scripts and trial and error [03:47]
• Why bug bounty hunters need to nurture their creativity when looking for particular vulns [07:37]
• What the main differences between bug bounty and pentesting are [09:46]
• How to impersonate developers as a bug bounty tactic [13:42]
• Why bug bounty often looks like a rabbit hole [25:24]
• Why it’s important to define your own success and appreciate your failures [30:33]
• How AI helps ethical hackers eliminate repetitive and boring tasks [34:19]
• How deep research can lead to unexpected wins in ethical hacking [43:55]

Join us as we explore the intricacies of bug bounties, the crucial role of mindset in hacking, and how to turn every failure into a stepping stone to success.

Today’s guest, Willa Riggins, talks about how “every small piece contributes to the larger picture” in pentesting and explains why “it's about understanding the intricacies and appreciating the craftsmanship."

From the mindset behind excellent pentesting work to the (difficult) things that are never going to change in this space, we glide through Willa’s experiences, hard-earned know-how, and thoughtful approach. 

Dive straight into the convo to learn:

• Why you need to get comfortable with trial and error to enjoy pentesting  [03:43]
• The key lesson Willa learned from working in app security [09:45]
• How to focus on your craft when reporting vulnerabilities [13:14] 
• The challenges pentest teams face in making their work count [19:07]
• The realistic, reasonable way to use automation in pentesting [24:28] 
• Two aspects of the hacker mindset worth cultivating [28:36] 
• Why (and how) having a hobby outside pentesting makes you more productive [33:33]
• How to set realistic expectations around developing a career in the field [36:42]
• What will be the key differentiating factor in penetration testing [42:40]

We believe you’ll get wisdom and inspiration from this kind and generous conversation. Willa will help you get a broader understanding of this field highlighting the fundamental role of people and teamwork. 

Just hit play! 

There’s a constant loop of learning, doing, and improving in offensive security. And one way to develop the “muscle” to tackle complex security challenges is through hands-on training. That’s what IppSec, our guest, does with kindness, passion, and in the community’s best interest.

IppSec helps us bust a couple of common myths which, if left unquestioned, may alter learning, distort results, and, ultimately, create big gaps in understanding, all of which can undermine your future success. 

Press play to listen to IppSec explain:

• Why recon requires constantly "reading between the lines" [03:20]
• Why AI can’t find business logic vulnerabilities [08:23]
• Why genuine communication with clients is essential [12:48]
• How rewarding and valuable it is to invest in the open-source community [17:35]
• How discipline makes a difference and how to develop it [24:00]
• How pentesting and bug bounty hunting complement each other [27:00]
• How you can build specific skills that differentiate you in the community [35:36]
• How to develop your own learning system [38:04] 
• Why it matters to make constant learning a positive experience [44:48]

IppSec’s generosity to share so many practical, valuable examples will help you get a better understanding of this discipline and enhance your knowledge. 

Ready to excel in offensive security this year? Delve into the mind of Vivek Ramachandran, a cybersecurity virtuoso who’s seen (and learned) a lot in this field. 

He's a force that fuels both his current company and the broader cybersecurity landscape with original thinking, educational and actionable insights.

And there's more to Vivek than just technical savvy. He's on a mission to revolutionize how we view ethical hackers and infosec pros, using his captivating comic books to challenge cliches and spark a new wave of enthusiasm in the next generation.

Tune in for this insightful episode with Vivek to find out:

• Why people mistakenly equate offensive security with functional testing [04:36]
• How (and why) the Hackers: Superheroes of the Digital Age comics came to be [07:13]
• Why first principles are essential in mastering and elevating security concepts [12:31]
• How to build your career on curiosity, gut feeling, generosity, and perseverance [19:33]
• Why we need human ingenuity as the nature of what we automate changes [29:10]
• What an entrepreneurial adventure will teach you about yourself - and others [43:45]
• How being part of the infosec community changes your work, thinking, and career [51:00]

Vivek’s vast career is a rich source of inspiration if you’re ready to practice extreme ownership, radical candor, and achieve the kind of alignment between your principles and actions that will propel your work and life to the next level.

Resources from this episode:

• Vivek on LinkedIn
• Vivek’s story in cybersecurity
• Comic books - Hackers: Superheroes of the digital age
• Vivek on the Philip Wylie Show
• Advanced Wi-Fi security with Vivek at DEF CON 23
• Training courses on Pentester Academy
• OSI model layers