Resilient Cyber

- Before we dive into the technical topics, you're a repeat Founder, including some acquisitions of firms you've founded. Can you tell us a bit about that Founders journey and what leads you to creating organizations?

- Something you've been focused on a lot lately is Software Supply Chain Security. Why is this such a complicated topic, and has it always been, or do you feel it is increasingly complex? 

- One of the challenges organizations have around OSS use is OSS Governance and software component inventory. Can you speak a bit about that challenge and how you are looking to solve it?

- A term thrown around a lot is "Dependency Hell" - which is the term developers use when it comes to managing their often large dependency footprints when it comes to updates, patches, versioning and so on. How are you seeing this problem addressed?

- There's a lot of hype around SBOM's and VEX. What are your thoughts on SBOM's and how they fit into the conversation around securing the software supply chain?

- One issue with the increased transparency is development teams drowning in hundreds or thousands vulnerabilities. As you know, this doesn't actually mean they are exploitable. How do we cut through that noise to drive down risk but also frustration?

- We talk a lot about CVE's and Vulnerabilities and so on but I know you recently shared research from Chinmayi Sharma who I've interviewed - and she points out CVE's are just one potential risk of OSS dependencies. Any thoughts on leading indicators of risk, as they're often called?

- Moving forward, what are some things you are focusing on at ENDoR Labs and where do we see us heading as an industry on this topic, in say 2-3 years? 

- You recently wrote an article about the SBOM Frenzy being Pre-Mature. For those not familiar with SBOM's, what is an SBOM and what has led to the frenzy as you call it?

- In your article you discuss challenges related to the build environments and hosts that can cause different outputs and SBOM's unless a build occurs on two identical machines. Can you explain why that is? 

- What role do you think emerging frameworks such as SLSA or SSDF and higher maturity requirements for things such as Reproducible Builds or Hermitic Builds play in alleviating some of these concerns?

- Given the challenges of dynamic ephemeral build environments and hosts, do you think this undermines the usefulness of SBOM's as an industry artifact related to software supply chain security?

- You also recently wrote a follow-up article about why Software Composition Analysis (SCA) is really hard. What are some of the reasons you think that is the case?

- You mentioned challenges with CVE's and their accuracy. As many know, CVE's are created via CNA's and as part of NVD. Do you think alternative vulnerability databases such as the Global Security Database (GSD) or OSV will alleviate any of the vulnerability issues in the industry? 

- You were involved in founding OWASP. I personally, and I suspect many others would love to hear about that a bit, given just how much of an industry staple OWASP is from Top 10 lists, CycloneDX and countless other widely used projects.

- You recently ran a campaign to be elected to the OWASP Board to try and modernize it and address many gaps you state lead to OWASP being on a path to irrelevance. Can you tell us what some of those issues are and your plan to address it to keep such a great organization a key part of our industry in the modern era of Cloud-native and DevSecOps?

Nikki: With your latest book, the Security Yearbook for 2022 ,this is the third iteration of the series right? It started in 2020 and has only grown since then. Can you talk a little bit about why you started this annual compilation of research? 

Nikki: For any other security practitioners or anyone in the field who's interested in writing a book or putting together a comprehensive manuscript or research, do you have any tips or advice for them to get started?

Chris: Can you tell us about your endeavors with IT-Harvest and your IT industry research, what is it and how did you get started?

Chris: I know you serve in various advisory roles. How does your industry research help inform your advisory perspective?

Chris: Based on your current IT industry research what are some of the most alarming or interesting trends around vendors, investors and M&A you see currently?

 Nikki: What is one of the most surprising statistics that you've uncovered year after year? I know one that continues to surprise me is just how prevalent and SUCCESSFUL phishing attacks are. What about you? 

Nikki: What are your top recommendations, based on your research, for security practitioners and business owners to be aware of and focus on when it comes to risk mitigation?

Chris: Looking at the current IT industry and trends, what is one prediction you have for some of the most significant changes we can expect in say 3-5 years?

- First off, tell us a bit about your background, you were a developer prior to focusing on Law. Why the change and do you feel that technical background helps you in your legal and academic career?

- Before we dive into the specifics of the paper and topics, what led you to focus on this issue for research and publication?

- You penned an article about how modern digital infrastructure is built on a "house of cards". Can you elaborate on that?

- Your paper is broken down into several sections, so let's step through those and dissect each area a bit.

- You touch on the unique aspects of OSS from proprietary code and discuss the benefits and also the risks. Can you discuss some of those?

- You claim that OSS should be designated critical infrastructure and arguably under areas such as the IT Sector. First off, why do you think it should be, and why do you think it already hasn't been?

- In part II of your paper you went into topics around the origins of OSS security issues and barriers to resolution. What are some of the major issues and barriers to resolving them?

- You touch on economic theory such as the least-cost avoider. What exactly is that, and why do you think software vendors in this case are best-suited to fix some of the core OSS security issues?

- In part III of the paper you discuss some of the current interventions and efforts. Can you touch on what some of those major efforts are?

- You discuss emerging things such as the Open Source Software Security Act as well as the OMB Memo requiring vendors to self-attest to NIST's SSDF and even provide SBOM's. What are your thoughts on these emerging requirements?

- How do you think we balance the need to keep the spirit of OSS, in terms of being open to everyone, cultivate a society of citizen developers and a thriving FOSS ecosystem while also pushing for more rigor and governance? 

Do we risk constraining the ecosystem and limiting the Federal government (and industry's) access to small innovative software projects and initiatives? 

- Looking at your background, you've held a lot of Identity-centric roles and positions in the industry. How do you think Identity and associated security is evolving with the continued adoption of Cloud?

- Identity is obviously at the core of the conversation around Zero Trust, what do you think some of the fundamental things organizations get wrong when it comes IAM at-scale?

- You recently made the pivot from roles with a strong Identity focus to API and API Security. What drove you to make that shift? 

- What do you think some of the most interesting challenges are in the current API Security landscape?

- I noticed you also have an Army background. It is very common to see veterans make their way into Cybersecurity. Why do you think that is, and there are any lessons from the Army you feel have benefited you in your Cyber career?

Chris: Before we dive into too many specific topics, one thing I wanted to ask is, you've been working in/around the topic of SBOM and Software Supply Chain for sometime via NTIA, CycloneDX, SCVS etc. How did you have the foresight or what drove you to focus on this topic well before many others in the industry?

Nikki: You mentioned recently about the SBOM Forum and their recommendation of the NVD adopt Package URL. I think the recommendations are great for NVD, because the NVD, CVE ID mechanisms, and CWE's weren't technically built for al ot of the updated vulnerabilities and concerns we see today, especially in the software supply chain. Can you talk a little bit about the challenges around vulnerability management when it comes to software supply chain?

Chris: I wanted to ask you about SaaSBOM which has been a topic of discussion in the CISA SBOM WG that I know you and I participate in. What is a SaaSBOM in your mind and where does it begin and end, given most of the Cloud, including Infrastructure is software-defined. 

 Nikki: I liked your article titled "SBOM should not exist! Long live the SBOM" - what really caught me was the idea that BOM's or Bill of Materials have been around for a while, and in other industries as well. I'm curious because there are a lot of potential implications for using BOM's outside of software. What are you thoughts on how we could potentially use the idea of BOMs in other cybersecurity or software development areas? 

Chris: I want to discuss some critiques of SBOM. VEX Is promising but of course requires information from software producers, and then of course trusting their assertions. 

VEX: Do you see a future where both SBOM and VEX and automated in terms of generation and ingestion to inform organizational vulnerability management and potentially procurement activities? 

Nikki: I would be re-missed if I didn't ask you about the human element in all of this. I fee like the complexity of the software supply chain, on top of infrastructure, operations, cloud deployments, etc, can get somewhat complex. How do you think the increased complexity around software supply chain is affecting the management and operations groups?

Chris: You have long been the lead on the wildly popular Dependency Track project. Can you tell us a bit about its origins, where it stands today and where it is headed?

Chris: There has been a lot of guidance lately on Software Supply Chain, such as NIST EO outputs from Section 4, NIST SSDF, guidance from CSA, CNCF et. al - how does SCVS fit into the mix and do you see organizations using all, or rallying around some of the guidance? 

Chris Follow Up: Some have claimed that these requirements are simply impractical for anyone except large enterprise organizations and software producers. Any thoughts on the practicality of the guidance for smaller organizations who still play a major role in the software ecosystem?

Chris: To start us off, why do you think OSS and the software supply chain are now beginning to get so much attention, despite being widely used for years now?

Chris: When it comes to OSS, any thoughts on how we balance security while also not stifling the innovative creative environment that is the OSS ecosystem?

Nikki: On one of your recent podcast episodes, you discussed how open source can be unfair, whether that's to users or to developers. Can you break that down a little bit for our audience?

Nikki: I think there are a lot of valuable lessons from the past that inform future trends. What would you say some of the top emerging trends are around open-source software - what should we be concerned about today versus a year from now?

Chris: What are your thoughts on the current state of Vulnerability Databases, we know you have some strong opinions and have been involved in an effort titled the Global Security Database with CSA - can you tell us a bit about that and why it is needed?

Chris: Do you think the emerging frameworks such as NIST 800 161 R1, SSDF, SLSA etc. are going in the right direction?

Chris: We couldn't let you go without discussing SBOM. What are your thoughts on the current state and direction of both SBOM and VEX. Do you think this increased level of transparency and granularity of vulnerabilities will be something most organizations can manage successfully?

Nikki: You have 341 episodes of your podcast - can you talk a little bit about why you wanted to get into podcasting? And also if you have any tips or advice for anyone who wants to start their own podcast?

Nikki: One of the major areas I don't hear being discussed around open source software is the 'human factor'. I see the integration of open source software as alleviating some of the mental workloads and information processing for developers and teams, but may also introduce other concerns. How do you feel about the human factor around OSS?

Chris: What do you think some of the fundamental changes of IAM are from on-prem to cloud?

Chris: What are some of the key tradeoffs and considerations for using IDaaS offerings?

Nikki: There are a lot of solutions out there that discuss zero trust as a product or a service that can be leveraged to 'bake in' zero trust into an environment. But I'm curious on your perspective - do you think we need additional tools to configure zero trust principles, or leverage the technology at hand to implement zero trust?

Nikki: There's this move towards passwordless solutions - I can see that being a big boost to zero trust architectures, but I think we're still missing the need for trusted identities, whether it's passwords, pins, or tokens. How do you feel about the passwordless movement and do you think more products will move in that direction?

Chris: You've been a part of the FICAM group and efforts in the CIO Council. Can you tell us a bit about that and where it is headed?

Chris: It is said Identity is the new perimeter in the age of Zero Trust, why do you think this is and how can organizations address it?

Nikki: There was an interesting research publication I read, titled "Beyond zero trust: Trust is a vulnerability" by M. Campbell in the IEEE Computer journal. I like the idea of considering zero trust principles, like least privilege, or limited permissions, as potential vulnerabilities instead of security controls. Do you think the language is important when discussing vulnerabilities versus security controls?

Chris: What role do you think NPE's play in the modern threat landscape?

Chris: If people want to learn more about the Federal FICAM/ZT Strategies, where do you recommend they begin?

- What do you think some of the primary factors are that contributed to GRC not coming along initially with the DevOps movement?

- Traditionally, what factors have plagued compliance when it comes to software delivery?

- How do some of those factors change in the era of DevOps and Cloud-native?

- Do you think regulation has a significant impact, and how can policy and regulation be improved?

- How important is it for the workforce aspect of GRC to be addressed when it comes to compliance innovation and new technologies and ways of work?

- Can incentives play a part, and if so, what can we do to improve that?

- Andres - What was the impetus of the book and can you tell us a bit about the writing experience?

- Where can people find out more about the book?