Security Boulevard Chats Podcast

Email the podcast: securityblvdpodcast@futurumgroup.com     In this episode of the Security Boulevard Podcast , Tom Hollingsworth , Fernando Montenegro , and Mitch Ashley break down modern offensive security strategies and why organizations must prepare for real adversaries, not theoretical ones.   The discussion focuses on red teaming, rules of engagement, and how understanding adversarial intent...

Cybersecurity roles are changing as AI becomes part of everyday business operations. In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Alan Shimel discuss how security teams must adapt to new technologies while staying aligned with business priorities. The conversation covers the challenges of scaling security alongside AI agents, the growing need to tr...

In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Alan Shimel, and Mitch Ashley examine how agentic AI is changing the cybersecurity landscape. The discussion focuses on the growing security risks introduced by autonomous AI agents, why stronger protections are required, and how observability is becoming critical for managing AI workloads at scale. The panel also looks at the r...

Cloud security keeps shifting under everyone’s feet, and organizations are scrambling to keep up. In Ep. 11 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley dig into what modern teams actually face: expanding attack surfaces, tangled interdependencies, regulatory pressure, and the constant need for better collaboration. The discussion highlights why vendo...

In Episode 10 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley break down the real impact of major service outages — including recent failures at Cloudflare — and what they reveal about modern cybersecurity challenges. The discussion covers why resilience matters, how economic pressures shape security decisions, and the growing complexity of today’s inter...

AI is reshaping cybersecurity faster than most organizations can adapt. In Ep. 9 of the Security Boulevard Podcast, Emanuela Zaccone and Eric Carter of Sysdig join Tech Field Day's Tom Hollingsworth and The Futurum Group's Fernando Montenegro to examine how AI is transforming cyber risk, decision-making, and business resilience. They discuss the rapid evolution of attackers, the need to secure AI-...

AI is reshaping cybersecurity on both sides of the fight. In Ep. 8 of the Security Boulevard Podcast, Tom Hollingsworth, Jack Poller, and Ed Weadon examine how AI strengthens defense while also creating new attack vectors. They break down recent failures, long-term gaps in AI security, and the growing responsibility on AI developers to build safer systems. As attackers weaponize AI, defenders must...

In Episode 7 of the Security Boulevard Podcast , Tom Hollingsworth of Tech Field Day , Fernando Montenegro of The Futurum Group , and networking and security expert Ed Weadon break down what it really takes to advance a cybersecurity career today. They discuss the demands of CISSP certification, the frustration of tracking continuing-education credits, and why lifelong learning is now essential fo...

In Ep. 6 of the Security Boulevard Podcast, Tom Hollingsworth, Mitch Ashley, and Alan Shimel discuss how ransomware tactics are shifting. Attackers are using AI-driven phishing to breach organizations while ransom payments decline as defenses improve. Malicious packages continue to exploit software vulnerabilities, and government hacking tools add new layers of risk. The panel highlights why cyber...

Will Agentic AI replace security teams? In this episode of the Security Boulevard Podcast, hosts Mitch Ashley, Tom Hollingsworth, and Fernando Montenegro explore how AI is reshaping cybersecurity — from large language models (LLMs) to autonomous agentic AI systems. Discover how professionals are integrating AI into modern security operations, why caution still dominates the industry, and what’s ne...

In Episode. 4 of the Security Boulevard Podcast , Mitch Ashley, Tom Hollingsworth, and Fernando Montenegro dig into the rising threat of nation state cyber attacks and the growing sophistication of global cyber warfare. They discuss: The evolution from small-scale hacks to state-backed intelligence operations Major breaches like F5 and what they reveal about attacker motives • How nation states fu...

In Ep. 3 of the Security Boulevard Podcast , Alan Shimel , Tom Hollingsworth , and Scott Robohn discuss MCP and its growing influence in cybersecurity. The panel unpacks: How MCP redefines traditional security models The importance of secure implementation and API security The rise of autonomous systems and agentic AI The challenge of building trust in intelligent systems Why innovation must be ba...

In Ep. 2 of the Security Boulevard Podcast, Tom Hollingsworth, Fernando Montenegro, and Kate Scarcella discuss how the rise of IoT devices is changing cybersecurity across both consumer and enterprise environments. They cover: Security and privacy risks from connected devices How consumer behavior influences enterprise protection Economic implications of large-scale IoT adoption The use of predict...

The Security Boulevard Podcast is back! 🎙️ In Ep. 1, hosts Tom Hollingsworth, Fernando Montenegro, and Mitch Ashley explore today’s most urgent cybersecurity challenges. They discuss: How AI is reshaping security practices The evolving complexity of ransomware Why user empowerment is critical Insights from Security Field Day Upcoming research on software supply chain security This relaunch sets th...

Mitch and Alan discuss plans for the free RSAC AI and AppSec event (4/28) with leaders from OpenAI, Anthropic, AWS, Google, and Meta, the increase in IT unemployment, and if Musk's DOGE is the largest security breach of our government? https://www.techstrongevents.com/ai-and-security/save-a-seat

Mitch and Alan discuss a recent security incident involving CrowdStrike, highlighting the challenges of software updates and the implications for the broader industry. They reflect on their experiences attending the Black Hat conference and the evolving intersection of software development and security. They also share personal anecdotes and insights into the importance of quality assurance in sec...

Mitchell and Alan talk about the ubiquitous collection of data including geolocation data by Apple, Google and other providers. The uses of this data can be relatively innocent for marketing purposes all the way to serious security issues of life and death. Alan & Mitch also talk about the current state of Cyber AI startups. Has the bloom come off the rose? Will Cyber AI become a big company g...

Mitch and Alan take a moment to catch their breath after a great week at RSAC, Broadcast Alley interviews and the DevSecOps and GenAI conference. They affirm that security is about community for them both. They also explore the emerging discussion of whether all this spending on security technologies is making us more secure or not. Links Referenced in Podcast: https://techstrong.tv/videos/rsa-con...

Mitch and Alan discuss rebranding the Security Creators Network; CISA brings a new focus to open source and Alan's interview with OpenSSF governing board member Brian Fox (Sonatype) from KubeCon + CloudNativeCon Europe 2024. References mentioned in this podcast: Security Creators Network: https://securityboulevard.com/2024/04/techstrong-group-announces-rebranding-of-security-bloggers-network-to-se...

Alan and Mitch discuss self-replicating AI malware, Cloudflare's announced firewall to protect generative AI LLMs and Alan's interview with Anna Pobletts, head of passwordless at 1Password, about how devs and DevOps teams can improve cybersecurity by eliminating passwords. https://securityboulevard.com/2024/03/compromptmized-ai-worm-malware-richixbw/ https://securityboulevard.com/2024/03/cloudflar...

Mitch and Alan discuss the State Department's intent to label fake content, expanding the Security Bloggers Network at RSAC 2024, and the government's focus on taking down LockBit and other large ransomware rings. Links Referenced in Podcast: https://securityboulevard.com/2024/02/us-russian-disinformation-richixbw/ https://securityboulevard.com/security-bloggers-network https://securityboulevard.c...

In this episode of Security Boulevard Chats, hosts Mitch and Alan delve into AI's profound impact on cybersecurity and the dual-edged nature it presents for attackers and security professionals. The conversation takes a deeper dive into the murky waters of deep fakes and AI-generated misinformation. Alan sits down with Chris Eng, Chief Research Officer at Veracode, for an insightful discussion on...

Alan and Mitch discuss data leaks and Bank of America' recent data loss and, Alan's interview with security marketing guru and colleague Jennifer Leggio, defending the expanding attack surface. Links referenced: https://www.bleepingcomputer.com/news/security/bank-of-america-warns-customers-of-data-breach-after-vendor-hack/ https://securityboulevard.com/2024/02/what-is-a-data-leak-causes-examples-a...

Return to the office mandates are on the rise, and Mitch and Alan discuss whether security concerns over working remote is a substantial driver. Mitch and Alan also explore the realization of deepfake fears covered in Richi Jennings' "CFO Deepfake Fools Staff — Fakers Steal $26M via Video" , should HR's role expand in "Why an HR-IT Partnership is Critical for Managing Cybersecurity Risk" by Guarav...

Mitch and Alan kick off 2024 by recalling the origins of Security Boulevard Chats, which started with their first security podcast in 2004. Twenty years ago!!! They discuss how security has gone from a niche job to today, where college grads emerge with security degrees and specializations. They discuss Marty Roesch's (snort creator and Sourcefire founder) article on the importance of holistically...