In this episode of Resilient Cyber I will be chatting with industry leaders Tyler Shields and James Berthoty on the topic of "Shift Left".

This includes the origins and early days of the shift left movement, as well as some of the current challenges, complaints and if the shift left movement is losing its shine.

We dive into a lot of topics such as:

• Tyler and Jame’s high-level thoughts on shift left and where it may have went wrong or run into challenges
• Tyler’s thoughts on the evolution of shift left over the last several decades from some of his early Pen Testing roles and working with early legacy applications before the age of Cloud, DevOps and Microservices
• James’ perspective, having started in Cyber in the age of Cloud and how his entire career has come at shift left from a bit of a different perspective
• The role that Vendors, VC’s and products play and why the industry only seems to come at this from the tool perspective
• Where we think the industry is headed with similar efforts such as Secure-by-Design/Default and its potential as well as possible challenges

In this episode we sit down Shyam Sankar, Chief Technology Officer (CTO) of Palantir Technologies. We will dive into a wide range of topics, from cyber regulation, software liability, navigating Federal/Defense cyber compliance and the need for digital defense of the modern national security ecosystem.

- First off, for those unfamiliar with you and your background, can you tell us a bit about yourself, as well as Palantir?

You're a big proponent on the role that software plays now, and will play in the future when it comes the fifth domain of warfare, cybersecurity, so let's give into some of those topics.

- I know you've voiced some strong opinions on the role of cyber insurance and also compliance when it comes to its static nature, compared to the dynamic activity of malicious actors and the threat landscape. Can you expand on that?

- You and I also chatted about the fact that most cyber issues tie back to hygiene, and that there are no silver bullets. Do you feel like this gets lost among the marketing hype of cyber?

- I know you've talked about externalizing some of Palantir's software infrastructure to enable more companies with security infrastructure and toolchains. Can you tell us about some of those capabilities?

- The enablement of more companies is key, as you know the DIB has seen massive consolidation in the past decade or more, largely with the small handful of players dominating the lions share of the work in the DoD. This arguably poses systemic concentrated risks, as well as doesn't give access for the DoD to commercial innovation.

You called the DoD's most powerful ally America's commerical tech sector in a recent piece. We know that times have changed, and unlike eras of the past, most digital innovation comes from the commercial space, but DoD tends to have a not built here syndrome, no doubt driven by incumbents, incentives, fiefdom building and more. What do you think the national security risks of this are?

- Given you've been around DoD for some time, you've no doubt been exposed to processes like ATO's and RMF and more. What are your thoughts on the current state of compliance in the DoD and how it could potentially hinder access to commercial innovation?

In this episode we sit down with Mark Simos to dive into his RSA Conference talk "You're Doing It Wrong - Common Security AntiPatterns" to dig into several painfully true anti-patterns in cybersecurity and how we often are our own worst enemy.

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- First off, for those not familiar with you or your background, can you tell us a bit about that.

- So you delivered this talk at RSA, focused on Cybersecurity "Anti-Patterns". How did the talk come about and how was it received by the audience?

We won't be able to name them all, but I would love to discuss some of them.

- You talk about the technology-centric thinking, and how folks believe security is about technology instead of business assets. Can you explain this one?

- The silver bullet mindset was another that jumped out to me. This is thinking a single solution can 100% solve complex and continuous problems. What ways have you seen this one play out?

- The paradox of blame is one that made me laugh because I have seen this play out a lot. You talk about the CYA mentality, how security warns about issues, they are skipped and then security is blamed. This one really stings because I have seen it happen, and in fact, I feel like we're seeing it play out with some of the CISO liability cases and regulations that are emerging.

- Perhaps one of the most well known anti-patterns of security being the office of no or resisting trends. I feel like we saw this with Cloud, Mobile, SaaS and now AI. Why do we keep repeating these mistakes?

- First off, for folks not familiar with your background, can you tell us a bit about that and how you got to the role you're in now?

- We see rapid adoption of AI and security inevitably trying to keep up, where should folks start?

- There are some really interesting intersections when it comes to AI and supply chain, what are some of them?

- We see a thriving OSS ecosystem around AI, including communities and platforms like Hugging Face. What are some key things to keep in mind here?

- AI BOM's - what are they, how do they differ from SBOM's, and what are some notable efforts underway right now around them?

- First off, for those who don't know you, can you tell us a bit about your background?

- You've been providing a deep dive talk into how to become a CISO. I'm curious, what made you put together the presentation, and how has it been received so far when you've had a chance to deliver it?

- You have broken down what you call "four stages of the journey" that encompasses skills in areas such as Technical, Management, Leadership and Political. This to me comes across as CISO's need to be multidisciplinary professionals with a variety of skillsets. What do you think makes this so important for CISO's to be successful?

- Let's walk through the four stages a bit. You start off with Technical skills. This seems to the foundation many CISO's start with, coming from roles in areas such as engineering, architecture and so on. What makes this foundation so key?

- How do CISO's maintain a strong technical foundation and depth, as they get further away from the tactical work and more into the leadership and strategic role?

- CISO's of course have to be able to manage the teams they build and/or oversee. What are some of the key management leadership skills you think CISO's must have?

- Leading is a fundamental part of what CISO's do. Whether it is direct reports, or the broader security org. What are some of these leadership skills and how can they have a positive or negative impact?

- Last but not least is the political side of things. CISO's of course operate among other C Suite peers, the board and within complex organizations with competing interests, personalities and incentives. This could arguably be the most important skill to hone in terms of ensuring you're effective in your role, and have a lasting impact on organizational risks. What are your thoughts on the political skills front?

- I'm curious as someone who's been a multiple time CISO and is now advising others on how to obtain the role - where do you see the role of the CISO headed in the future? We see new aspects such as litigation, SEC rules, determining materiality, CISO's needing to speak the language of the business and more - all while needing to manage risks with the ever changing technological landscape, with AI being the latest example. Where is it all headed?

In this episode we sit down with Amir Kessler and Aviram Shmueli of AppSec innovator Jit to dive into the complexities of the modern AppSec landscape and explore the emerging Application Security Posture Management (ASPM) ecosystem.

- First off, for folks not familiar with your backgrounds, can you tell us a bit about both of your backgrounds and how you got to the roles you're in now?

- We're seeing a ton of interest in the topic of ASPM in the AppSec space. What do you think has led to this emerging category and what key problems is it looking to solve?

- I know your team puts a big emphasis on not just the tech but also the DexEx and UX. Why is this so critical to address AppSec risks and securing organizations and their code?

- While there is value in ASPM platforms, many Dev teams and engineers are opinionated about their tools, how important is this flexibility and extensibility in the platform that the Jit team has built?

- A key challenge includes vulnerability overload. Teams drowning in massive vulnerability backlogs and trying to add vulnerability context and focus on the most relevant risks for developers. How does Jit approach this?

- Not all ASPM platforms are the same, but we see many vendors rallying around the category. What do you think makes Jit unique and differentiates what the team has built?

- For those that don't know you, can you tell us a bit about your background and your current role?

- I know you help lead the ATLAS project for MITRE, what exactly is ATLAS and how did it come about?

- The AI threat landscape is evolving quickly, as organizations are rapidly adopting GenAI, LLM's and AI more broadly. We are still flushing out some fundamental risks, threats and vulnerabilities to consider. Why is it so important to have a way to characterize it all?

- When it comes to AI Security, there is also a lot of hype, buzz and dare I say FUD out there. Why are you so adamant that we take a data-driven and actionable approach?

- I know you recently helped participate in the first big AI security incident focused TTX, including with CISA and other Government and Industry partners, can you speak a bit about the experience and why exercises like this are important for organizations to do when it comes to AI security?

- As someone close to the AI domain, when it comes to security, what are your thoughts on both where we're headed for security of AI, and AI to bolster security?

- For folks wanting to learn more about ATLAS, and the work MITRE is doing around AI security, where should folks get started?

- What are some key open questions and opportunities for the community to help shape the future of AI security and assurance?


https://atlas.mitre.org/ ← Check out MITRE ATLAS!

In this episode we sit down with GenAI and Security Leader Steve Wilson to discuss securing the explosive adoption of GenAI and LLM's. Steve is the leader of the OWASP Top 10 for LLM's and the upcoming book The Developer's Playbook for LLM Security: Building Secure AI Applications

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- First off, for those not familiar with your background, can you tell us a bit about yourself and what brought you to focusing on AI Security as you have currently?

- Many may not be familiar with the OWASP LLM Top 10, can you tell us how the project came about, and some of the value it provides the community?

- I don't want to talk through the list item by item, but I wanted to ask, what are some of the key similarities and key differences when it comes to securing AI systems and applications compared to broader historical AppSec?

- Where do you think organizations should look to get started to try and keep pace with the businesses adoption of GenAI and LLM's?

- You've also been working on publishing the Developers Playbook to LLM Security which I've been working my way through an early preview edition of and it is great. What are some of the core topics you cover in the book?

- One hot topic in GenAI and LLM is the two large paths of either closed and open source models, services and platforms. What are some key considerations from your perspective for those adopting one or the other?

- I know software supply chain security is a key part of LLM and GenAI security, why is that, and what should folks keep in mind?

- For those wanting to learn more, where can they find more resources, such as the LLM Top 10, your book, any upcoming talks etc?