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In this candid and cathartic episode, Ken and Mike unpack the chaos that is Q4 for security professionals. From budget burnouts to end-of-year pentesting sprints, they explore why the final months of the year feel like a perfect storm for stress. Tune in as they share hard-earned lessons, practical advice for maintaining your sanity, and some gentle reminders that not everything needs to ship before Christmas. Whether you’re a tired vendor, an overwhelmed engineer, or just trying to make it to PTO, this episode is for you.

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In this no-punches-pulled return from hiatus, Ken and Mike dig deep into the messy middle of vulnerability management, SLA fatigue, and the illusion of compliance. Are we building secure systems or just passing audits? From legacy cruft to exploitable CVEs, this episode unpacks the real-world pressures of SOC 2, the auditor dance, and whether fixing every “critical” is even feasible.

Perfect for practitioners trying to balance the checkbox culture with actual risk reduction, this one’s got stories, strategies, and spicy takes. Bonus: tips on managing auditors without losing your mind—or your security posture.

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In this episode of Relating to DevSecOps, Ken and Mike discuss the challenges faced by CISOs in today's security landscape, particularly the struggle to balance immediate security needs with long-term preventative strategies. They explore the disconnect between security leadership and practitioners, the urgency of addressing security issues, and the importance of understanding the root causes of vulnerabilities. The conversation emphasizes the need for CISOs to engage more deeply with their teams and to focus on effective, context-driven security solutions rather than simply reacting to the latest threats.

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In this must-listen episode of Relating to DevSecOps, Ken welcomes the ever-inspiring Tanya Janca, aka SheHacksPurple—author, AppSec expert, and champion of making security usable. Together, they dig into why so many application security policies fail, why developers ignore them, and how to make them actually work. Tanya shares real-world experiences from both dev and security perspectives, plus her journey from being ignored to lobbying governments for change.

From communication failures and TL;DR policy pages to leveraging wikis and code reuse, this episode is a practical masterclass in creating impactful, developer-friendly security standards.

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In this episode of Relating to DevSecOps, Ken Toler and Mike McCabe dive deep into Google's blockbuster acquisition of Wiz.io for a reported $32 billion. They explore the implications for cloud security, the consolidation of the DevSecOps tooling landscape, and how this move compares to Google’s previous acquisitions like Mandiant and Chronicle. The duo debates the future of multi-cloud strategies, platform fatigue, and whether Wiz will remain the darling of the security community—or get lost in the labyrinth of Google Cloud products. With sharp insights and a dash of hot takes, they paint a picture of a cloud security ecosystem at a pivotal turning point

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Welcome to 2025! Ken and Mike kick off the new year with their security resolutions (or lack thereof) before diving into the bittersweet farewell to ShmooCon, one of the most beloved hacker conferences. Ken shares his experiences from the final event, including insights on hardware hacking, radio security, and the unique hacker culture that made ShmooCon special.

They also unpack one of the most practical talks from the conference: a deep dive into open source security tools versus enterprise solutions, highlighting ways security teams can cut costs without sacrificing effectiveness. Speaking of open source, the hosts discuss the controversy surrounding Semgrep’s licensing changes and the rise of OpenGrep, the latest community-driven fork in response to closed-source shifts—drawing parallels to the Terraform/OpenTofu saga.

Finally, the duo explores cyber risk from an insurance perspective, breaking down how breaches translate into real-world financial costs (hint: mailing breach notifications alone could bankrupt you). Whether you're a security pro, an open source advocate, or just here for the ShmooBall nostalgia, this episode has something for you!

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In this special holiday-themed episode of Relating to DevSecOps, hosts Ken and Mike channel their inner Dickens with a retrospective journey through the "Ghosts of DevSecOps Past, Present, and Future." From lessons learned about security awareness and collaboration challenges of the past, to the growing pains and contradictions of today’s implementation of security basics, they explore it all. Wrapping up with a hopeful look at future innovations like policy-as-code and preemptive security measures, the hosts outline their visions for a more integrated and automated security future. Packed with insights, humor, and holiday spirit, this is a must-listen for those charting the path forward in DevSecOps.

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In this episode of Relating to DevSecOps, hosts Ken and Mike tackle the complex challenges of managing security budgets in organizations of all sizes. From small, scrappy teams to sprawling enterprises, they explore how security leaders can navigate tight financial constraints while maintaining strong security postures. They share insights on integrating security into IT operations, leveraging open-source tools, and rethinking traditional budget allocations. Whether you’re a CISO grappling with scaling or a developer looking to improve security outcomes, this discussion is packed with actionable strategies and thought-provoking debates on the future of security spending

https://www.youtube.com/watch?v=8U3QzJBCNZ0 

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In this episode, Ken and Mike discuss the pressing issue of staffing security in the DevSecOps field. They explore the challenges of finding qualified application security professionals, the importance of diverse backgrounds in security roles, and the paradox of understaffed security teams despite a high demand for cybersecurity jobs. 

The conversation also delves into strategies for mitigating staffing issues, such as empowering security champions within organizations, leveraging automation and tooling, and avoiding bottlenecks in security processes. Throughout the discussion, they emphasize the need for a balanced approach to security that considers both technical and human factors.

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Ken and Mike dive deep into the world of metrics and measurement in the context of security and DevSecOps. They explore the critical role metrics play in driving security improvements, from tracking vulnerabilities to gauging the effectiveness of incident response. The hosts discuss what makes a good metric, the importance of aligning metrics with business goals, and the dangers of relying too heavily on numbers alone. They also tackle the challenges of quantifying "squishy" aspects like culture and training effectiveness. Whether you're a seasoned security professional or just getting started, this episode offers valuable insights into the art and science of measurement in security

Reference talk:

https://www.youtube.com/watch?v=GXTvlQXVCOs&t=0s

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Ken and Mike discuss the importance of postmortems in incident response and security incidents. They explore the definition of postmortems, the value of reflection, the challenges of blame, and the significance of actionable outcomes. They also touch on the transparency of postmortems and the need for root cause analysis. The conversation concludes with a brief announcement about an upcoming conference series.