Relating to DevSecOps
A Podcast dedicated to forging iron clad relationships between developers, engineers, operations, and security practitioners by discussing hot topics in the world of DevSecOps. This podcast aims to air out some of the common gripes, misconceptions, and hardships that these teams face in the real world every day.
Episodes
AI is changing the economics of cyberattacks by making them faster, cheaper, and easier to scale. In this episode of Relating to DevSecOps, Ken is joined by Conor Sherman, Chief Security Officer at Sysdig and host of the Zero Signal podcast, to explore what the rise of agentic threat actors means for defenders.
Using the Jade Puffer ransomware attack as a real-world example, they discuss how autonomous attack...
Ken and Mike are back in the AI trenches, this time unpacking the hype, fear, and practical security implications surrounding Anthropic’s Mythos preview. As the industry reacts to claims around AI-driven vulnerability discovery and exploit generation, the hosts ask a more important question: are we actually ready to fix what we already know is broken?
The conversation cuts through the zero-day panic and focuses...
Ken and Mike are back from the grave to kick off 2026 with a timely debate on the AI panic cycle hitting software and security. They dig into the biggest questions flying around the industry right now: Is AI taking developer and security jobs? Is SaaS dying? Is software engineering being replaced by vibe coding and agents? From maker-checker workflows and token costs to AI-generated bugs, false positives, and attack...
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. Wheth...
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 p...
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...
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 fr...
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 fa...
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 ...
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...
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...
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 ...
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 alo...
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.
Ken and Mike discuss supply chain security, including software composition analysis (SCA) and software bill of materials (SBOM). They highlight the importance of understanding the components that make up your software and the risks associated with using third-party libraries. They also discuss recent supply chain failures, such as the XZ library hack and the SolarWinds attack. The hosts emphasize the need for organi...
In this episode Mike and Ken dive into the wild world of SaaS products in DevSecOps. From vendors to security tooling hygiene they cover an often overlooked ecosystem of cloud and software services that may be rotting in the sky of your workloads. Join up for a listen on SaaS Security!
With pep and full youtube energy Ken and Mike discuss the findings of the IBM "Cost of a Data Breach" report and its implications for DevSecOps. They highlight the importance of integrating security into every phase of the software development life cycle and the positive impact it can have on reducing the cost of a data breach.
Ken and Mike discuss their new year's resolutions related to application security. They also reflect on the impact of AI and its adoption in the industry. The hosts share their experiences attending conferences and highlight interesting talks on topics such as zero-day vulnerabilities and fuzzing LLM models. They discuss the OWASP LLM Top 10 and the evolving perception of AI in the industry. The conversation conclud...
We are joined by incredible guests Mikhail Chechik and Marcus Hallberg as they help us define DevSecOps and emphasize the importance of a security mindset throughout the development process. These two incredible folks explore common misconceptions about shifting left and discuss the challenges of triaging and validating vulnerabilities early in the development lifecycle. We enter in the wild world of this wonderful ...
On this episode of R2DSO Mike and Ken dive into their takeaways and experiences from LASCON 2023 in Austin, TX where AI was both a problem child and praised bringer of salvation in security. Vendors and companies alike are embracing AI with wide eyes and there was no shortage of talks, presentations, and hallway conversations about the topic. Beyond that security is fast accepting that they can't be the department o...
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