Security Boulevard: A Podcast about the Technologies and Developments Driving Modern Cybersecurity | The Futurum Group Podcast Network
Welcome to Security Boulevard, a podcast about the technologies and developments driving modern Cybersecurity and part of The Futurum Group Podcast Network.
Hosted by Tom Hollingsworth of Tech Field Day and Fernando Montenegro of The Futurum Group, each episode explores a variety of topics within development, artificial intelligence, and the technologies influencing the modern landscape of Cybersecurity in the Enterprise Technology industry. New episodes post every Tuesday.
The Security Boulevard Podcast is part of The Futurum Group Podcast Network.
Welcome to Security Boulevard, a podcast about the technologies and developments driving modern Cybersecurity and part of The Futurum Group Podcast Network.
Hosted by Tom Hollingsworth of Tech Field Day and Fernando Montenegro of The Futurum Group, each episode explores a variety of topics within development, artificial intelligence, and the technologies influencing the modern landscape of Cybersecurity in the Enterprise Technology industry. New episodes post every Tuesday.
The Security Boulevard Podcast is part of The Futurum Group Podcast Network.
Episodes

Feb 17, 2026
Feb 17, 2026
35 min
Cybersecurity failures increasingly originate inside the software supply chain.
In this episode, Tom Hollingsworth, Event Lead at Tech Field Day and Networking Industry Analyst, joins Mitch Ashley, Vice President and Practice Lead, Software Lifecycle Engineering at Techstrong Research, along with Steve Puluka, Network & Security Engineer and Network Architect, Tech Field Day Delegate.
They examine supply chain compromises, including incidents involving Notepad++ and software update distribution mechanisms. The conversation highlights why secure code distribution must be treated as an architectural control, not an operational afterthought.
As software ecosystems grow more interconnected, accountability now spans developers, hosting providers, infrastructure operators, and security teams. The traditional shared responsibility model must evolve to address increasingly complex dependency chains and third-party exposure.
The discussion also explores how artificial intelligence is reshaping networking operations, why observability has become foundational to modern security strategy, and how transparency and proactive incident response reduce systemic risk.
Security today is lifecycle discipline across the entire software delivery chain.
#Cybersecurity #SupplyChainSecurity #DevSecOps #AIinNetworking #Observability #SecurityLeadership
Feb 17, 2026
35 min

Feb 10, 2026
Feb 10, 2026
33 min
In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Mitch Ashley, and Zoe Rose, CSIRT SecOps Dev Manager at Canon EMEA, examine the growing challenges around data ownership, digital sovereignty, and privacy in modern cybersecurity.
The discussion breaks down the complexity of data privacy laws, particularly the differences between the United States and Europe, and what those regulatory gaps mean for organizations responsible for handling sensitive data. The panel also explores challenges around encryption, government access to data, and why transparency in privacy policies is critical to maintaining trust.
The conversation closes with a look at how AI is reshaping security and privacy practices, and why trust remains the foundation of any technology strategy in an increasingly regulated and data-driven world.
#Cybersecurity #DataPrivacy #DataOwnership #DigitalSovereignty #AISecurity #Trust #SecurityBoulevard #Podcast
Feb 10, 2026
33 min

Feb 3, 2026
Feb 3, 2026
39 min
Cybersecurity plays a critical role in disaster recovery planning, especially as threats and environments continue to change.
In this episode of the Security Boulevard Podcast, Mitch Ashley, Fernando Montenegro, and Tom Hollingsworth discuss why realistic threat models and regular testing are essential to uncovering hidden weaknesses. The conversation draws lessons from past weather-related disasters and cybersecurity near misses, showing how organizations can learn from incidents that almost went wrong.
The panel also explores how security practices must evolve to match modern environments, including the growing role of AI agents in security operations.
The episode closes with a reminder of the value of learning from history and staying engaged with the cybersecurity community through ongoing discussion, feedback, and shared experience.
#Cybersecurity #DisasterRecovery #ThreatModeling #IncidentResponse #BusinessResilience #AISecurity #SecurityTesting #SecurityBoulevard #Podcast
Feb 3, 2026
39 min

Jan 27, 2026
Jan 27, 2026
35 min
The appointment of Jen Easterly as CEO of the RSA Conference marks a pivotal moment for the cybersecurity industry.
In this episode of the Security Boulevard Podcast, Tom Hollingsworth, Alan Shimel, and Fernando Montenegro discuss what this leadership change signals for the broader security community.
The conversation examines the evolving role of CISA, the growing influence of venture capital on cybersecurity startups, and why public-private partnerships remain essential as threats grow more complex.
The panel also explores how AI is reshaping cybersecurity, what upcoming industry events reveal about market direction, and why practitioners must stay informed about funding, policy, and technology trends to remain effective.
#Cybersecurity #RSAC #JenEasterly #CISA #AISecurity #SecurityLeadership #SecurityBoulevard #Podcast
Jan 27, 2026
35 min

Jan 20, 2026
Jan 20, 2026
34 min
In this episode of the Security Boulevard Podcast, Mitch Ashley, Fernando Montenegro, and Tom Hollingsworth cover several of the most active conversations in cybersecurity and software development today.
The panel examines Palo Alto Networks’ SHIELD framework, the rise of vibe coding, and the security risks that emerge when non-programmers begin building software without embedded security practices.
The discussion also looks at how security is shifting earlier into development workflows, the evolution of data security platforms, and how AI is reshaping software development across the industry.
#Cybersecurity #DevSecOps #SecureDevelopment #AI #DataSecurity #SecurityBoulevard #Podcast
Jan 20, 2026
34 min

Jan 13, 2026
Red Teaming, Readiness, and Adversarial Reality
Jan 13, 2026
Jan 13, 2026
32 min
Email the podcast: [email protected]
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 changes defensive posture. The panel examines the balance between proactive and reactive security measures, ethical considerations in offensive testing, and how the evolving threat landscape is reshaping how teams plan, respond, and recover.
The episode also looks ahead to upcoming industry events and highlights why collaboration across teams and communities is essential to keeping pace with attackers.
Visit our website: https://securityboulevard.com/
#Cybersecurity #OffensiveSecurity #RedTeaming #AdversarialThreats #SecurityStrategy #SecurityBoulevard #Podcast
Jan 13, 2026
32 min

Jan 6, 2026
Jan 6, 2026
36 min
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 train and mentor junior professionals, and why community engagement remains critical as the industry evolves.
The panel also highlights upcoming cybersecurity events and emphasizes continuous learning as a core requirement for long-term success in security.
#Cybersecurity #AI #BusinessIntegration #SecurityTeams #AISecurity #Community #SecurityBoulevard #Podcast
Jan 6, 2026
36 min

Dec 16, 2025
Dec 16, 2025
32 min
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 responsibility shared by vendors, developers, and security teams to deliver safer AI systems, while reflecting on past security gaps and the industry’s path forward.
The episode closes with a look at upcoming events and an invitation for the community to stay engaged as AI security continues to evolve.
#Cybersecurity #AI #AgenticAI #AISecurity #Observability #SecurityBoulevard #Podcast
Dec 16, 2025
32 min

Dec 9, 2025
Dec 9, 2025
35 min
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 vendors must do more to educate customers, why system understanding matters as much as tooling, and how a holistic approach to cloud security keeps organizations ahead of emerging threats.
A straight, practical look at staying secure in a cloud landscape that refuses to stop changing. #
CloudSecurity #Cybersecurity #AttackSurface #CloudStrategy #SecurityBoulevard #Podcast
Dec 9, 2025
35 min

Dec 2, 2025
Dec 2, 2025
34 min
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 interconnected infrastructure. The panel also digs into the value of strong threat modeling, preparation for unexpected failures, and lessons learned from past outages that disrupted operations across industries.
A grounded look at keeping systems functional when everything feels like it’s built on hopes, dreams, and duct tape.
#Cybersecurity #Cloudflare #ServiceOutage #Infrastructure #Resilience #ThreatModeling #SecurityBoulevard #Podcast
Dec 2, 2025
34 min






