Hacker in the Loop (formerly Simply Offensive)

In this episode, Aaron Colclough shares his unique journey from military service to cybersecurity, emphasizing the importance of hands-on experience, continuous learning, and leveraging AI responsibly in pen testing. Discover insights on career pivots, training tips, and the future of AI in security.

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Connect with Aaron Colcough:

LinkedIn: https://www.linkedin.com/in/aaronjcolclough/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, host Phillip Wylie sits down with Denis Calderone, Co-Founder and Principal at Suzu Labs, to discuss his journey from early curiosity about how technology works to building a long career in cybersecurity consulting and penetration testing.Denis shares stories from the early days of security when breaches often went unnoticed, how compliance shaped the industry, and how today’s AI-driven development is creating both opportunity and risk. The conversation explores the evolution of pentesting, the importance of community in hiring, the growing role of AI in offensive security, and why human expertise still matters despite increasing automation.The discussion also highlights dark web monitoring, talent development, and how relationships—not transactions—drive long-term cybersecurity success.

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Connect with Denis Calderone

LinkedIn: https://www.linkedin.com/in/deniscalderone/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

/ suzu-labs

Chapters00:00 Introduction to Cybersecurity Journeys03:17 From Network Technician to Cybersecurity Professional05:52 The Importance of Experience in Cybersecurity09:04 Adopting a Purple Team Mindset11:45 The Role of Tabletop Exercises in Security Training14:24 Understanding Learning Styles in Cybersecurity Training17:03 The Impact of AI on Cybersecurity Operations19:47 Challenges in Corporate Security Mindsets22:34 The Future of Cybersecurity Training25:09 Connecting with the Cybersecurity Community29:03 Simply Offensive Outro

In this episode of Simply Offensive, host Phillip Wylie sits down with cybersecurity leader Christopher Marks to discuss his journey from networking into security leadership, the importance of offensive security knowledge for defenders, and how AI is changing security operations.

Christopher shares how community involvement, mentorship, and hands-on offensive security training helped shape his career and leadership philosophy. The conversation explores why security teams benefit from understanding attacker techniques and how organizations can improve resilience through purple team exercises and realistic simulations.

Connect with Christopher Marks:

LinkedIn: https://www.linkedin.com/in/christopher-m-7357441b/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabshttps://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

Chapters

00:00 Introduction to Cybersecurity Journeys

03:17 From Network Technician to Cybersecurity Professional

05:52 The Importance of Experience in Cybersecurity

09:04 Adopting a Purple Team Mindset

11:45 The Role of Tabletop Exercises in Security Training

14:24 Understanding Learning Styles in Cybersecurity Training

17:03 The Impact of AI on Cybersecurity Operations

19:47 Challenges in Corporate Security Mindsets

22:34 The Future of Cybersecurity Training

25:09 Connecting with the Cybersecurity Community

29:03 Simply Offensive Outro

In this episode of Simply Offensive, Phillip Wylie interviews Dan DeCloss, founder of PlexTrack, discussing the evolution of cybersecurity, the importance of report writing in pen testing, and the impact of AI on the industry. Dan shares his unique origin story, insights on the challenges of report writing, and how PlexTrack aims to streamline the process. The conversation also explores the future of AI in cybersecurity and its implications for the job market.Connect with Dan DeCloss:LinkedIn: https://www.linkedin.com/in/ddecloss/PlexTrac Website: https://plextrac.com=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/Chapters00:00 Introduction and Background of PlexTrack03:15 The Importance of Report Writing in Pen Testing06:09 Dan DeCloss's Origin Story08:45 The Evolution of Cybersecurity and AI11:32 AI's Impact on the Job Market14:14 Future of AI in Cybersecurity16:44 Closing Thoughts and Future Directions28:51 Simply Offensive Outro

In this episode, Phillip Wylie and Jacob Krell discuss the integration of AI in Capture The Flag (CTF) competitions and its implications for cybersecurity. Jacob shares his experiences with AI in penetration testing, highlighting how it enhances efficiency and changes the competitive landscape. They explore the future of certifications, the importance of human skills, and the ethical considerations surrounding AI in cybersecurity.

Connect with Jacob:⁠

https://www.linkedin.com/in/jacob-krell/⁠⁠

https://x.com/hackerfren⁠

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Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabshttps://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

In this episode, Darius Houle joins the conversation to explore the real-world limitations of AI in problem-solving and why context matters more than most people realize. The discussion covers how AI systems struggle with nuanced tasks, why developers must understand the boundaries of these tools, and how clearer prompts can dramatically improve outcomes.

Darius shares insights from his experience in application security, tool building, and community leadership. The conversation also highlights the growing role of AI in cybersecurity testing and the responsibility developers have when integrating AI into their workflows.

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Connect with Darius Houle

LinkedIn: https://www.linkedin.com/in/dariushoule/

Trail of Bits Skills Marketplace: https://github.com/trailofbits/skills

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

00:00 Introduction to Darius Houle and Trillobits
03:18 Darius Houle’s Origin Story in Cybersecurity
05:41 The Importance of Foundational Knowledge in AppSec
08:33 The Role of AI in Cybersecurity
10:52 AI Tools and Their Impact on Security Testing
13:36 Getting Started with AI in Cybersecurity
16:30 Building Tools in the Security Community
18:55 Darius’s Recent Talk at DistrictCon
21:25 Vulnerabilities in the Electron Framework
23:57 Highlights from DistrictCon
26:28 Conclusion and Resources
28:54 Simply Offensive Outro

In this episode, Phillip Wylie interviews Matt Brown, a hardware hacker and content creator, discussing his journey in technology, the fundamentals of hardware hacking, and the importance of affordable training. They explore the impact of content creation on career opportunities, the significance of community and conferences in the field, and provide advice for aspiring content creators. Matt shares insights on his recent milestone of reaching 200,000 subscribers on YouTube and emphasizes the value of sharing knowledge and learning in the hardware hacking space.

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Connect with Matt Brown

YouTube Channel: https://www.youtube.com/@mattbrwn

LinkedIn: https://www.linkedin.com/in/mattbrwn/

Website: https://brownfinesecurity.com/

Training: https://training.brownfinesecurity.com/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

Chapters

00:00 Introduction to Hardware Hacking and Content Creation

01:58 Matt Brown's Journey in Technology

03:58 Understanding Hardware Hacking Basics

06:37 Fundamentals of IoT Security

08:12 Learning Hardware Hacking

10:57 The Landscape of Training and Education

15:07 Conferences and Community Engagement

21:09 The Impact of Content Creation on Career

24:05 Advice for Aspiring Content Creators

26:26 Celebrating Milestones in Content Creation

In this episode of Simply Offensive, Phillip Wylie interviews Dahvid Schloss, a cybersecurity expert and the emulated mob boss of emulated criminals. They discuss Dahvid's background in the military and cybersecurity, the differences between red teaming and pen testing, the importance of red teaming in understanding real risks, and the role of purple teaming in improving security practices. They also delve into the significance of tooling in adversarial emulation, the planning involved in red team operations, and the impact of AI on red teaming. The conversation concludes with Dahvid sharing insights on how to get started in adversarial emulation and the future of cybersecurity.

Connect with Dahvid:

https://www.linkedin.com/in/dahvidschloss/⁠

https://emulatedcriminals.com/

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Connect with your host, Phillip Wylie:

LinkedIn: ⁠https://linkedin.com/in/phillipwylie⁠

YouTube: ⁠https://youtube.com/@PhillipWylie

=========================

Presented by Suzu Labs

=========================

All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

Chapters

00:00 Introduction to David Schloss

02:02 David's Background and Career Path

03:44 Understanding Red Teaming vs. Pen Testing

07:40 Time Requirements for Testing

10:31 The Importance of Undetected Operations

12:19 Practicing Incident Response

15:52 The Role of Purple Teaming

18:12 Tooling in Adversarial Emulation

22:03 Planning Red Team Operations

24:20 Getting Started in Adversarial Emulation

26:03 AI's Impact on Red Teaming

31:07 Closing Thoughts and Future Projects

32:49 Outro