Reimagining Cyber - real world perspectives on cybersecurity

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223

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Oct 2026

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About the show

Explore the critical intersection of cybersecurity and business impact while gaining insights into CISO priorities with "Reimagining Cyber." Stay informed on the latest cybersecurity news, trends, and solutions tailored for today's CISOs and CIOs. This podcast is your go-to resource for staying updated on cybersecurity developments and addressing common challenges in the rapidly evolving digital landscape. As featured on MillionPodcasts' Best 100 Cybersecurity Podcasts https://www.millionpodcasts.com/cyber-security-podcasts/ Top 50 Chief Information Security Officer CISO Podcasts https://www.millionpodcasts.com/ciso-podcasts/ Top 70 Security Hacking Podcasts https://www.millionpodcasts.com/security-hacking-podcasts/

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October 14, 2026Episode 22332 min

Think Like an Attacker - #223

Think your security tools are keeping you safe? Think again. Ryan Basden, Head of Offensive Security at Xora, has spent more than a decade thinking like an attacker. And what he finds inside organisations often has little to do with the tools they’ve bought — and everything to do with the gaps they’ve overlooked. In this episode of Reimagining Cyber , Ryan shares what red-team exercises reveal about real-world security, from supposedly segmented networks and default passwords to exposed developer credentials and cloud environments where everyone has admin access. He explains why understanding your network traffic and actually reading your logs can be more valuable than buying another security product, where AI can help defenders (and where it still needs human guidance), and why he’s concerned that cutting-edge cybersecurity capabilities could become accessible only to those who can afford them. Plus, hear the surprising story of how a guest Wi-Fi network gave Ryan access to an industrial mainframe — and why the organisation struggled to accept what he’d found. As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

October 7, 2026Episode 22230 min

Inside the Mind of a Hacker - #222

What really goes through a hacker’s mind? Samy Kamkar, creator of the infamous MySpace worm, takes us inside the hacker mindset — from curiosity and experimentation to the human weaknesses that still leave businesses exposed. We explore how hackers see technology, why people remain the easiest way in, how AI is changing the game, and what defenders can learn by thinking like an attacker. As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

September 30, 2026Episode 22127 min

Application Security in the AI Era - #221

AI is changing application security at breakneck speed — and it’s not just about generating code faster. In this episode, Keelin Conant's guest is Diogo Rispoli, an application security leader, architect, and longtime industry expert. They explore what happens when AI agents start writing, testing and fixing code, and even talking to each other. The episode also digs into rogue agents, exploitability, AI-powered testing, the limits of auto-remediation, and why security teams need to look beyond the code itself. Plus, Diogo looks ahead to 2030 and asks a big question: will finding vulnerabilities even be the job of AppSec anymore? As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

September 23, 2026Episode 22018 min

Inside a Ransomware Negotiation - #220

In this episode of Reimagining Cyber, Keelin Conant welcomes Kurtis Minder, author of Cyber Recon, former founder of GroupSense, and one of the industry's most experienced ransomware negotiators. Together they discuss the evolution of ransomware, what organizations get wrong about cyber risk, how AI is changing the threat landscape, and the critical actions leaders can take today to protect their businesses. Plus, Kurtis shares insights from years spent communicating directly with the people behind some of the world's most damaging cyberattacks. Relevant links: https://www.kurtisminder.com/ Cyber Recon: https://a.co/d/8R4ewib As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

September 16, 2026Episode 21927 min

Your Scam Message Was From a Human Trafficking Victim- #219

In this powerful episode of Reimagining Cyber , Keelin Conant speaks with Dr. Kelsey Morgan of EverFree about the growing connection between human trafficking and cybercrime. Learn how victims are being forced into scam operations, what recovery looks like for survivors, and how the cybersecurity community can play a role in creating change. It's a conversation that will forever change how you view cybercrime. Links mentioned in this episode: Fight of my Life podcast - https://fightofmylifepodcast.com/escaping-scam-city-roll Forbes - How Romance Fraud Links The U.S. To East Africa And Southeast Asia Forbes - Pay Attention To The Victims Behind Scams, Various Groups Urge World News Group - Trapped inside a cyberscam center As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

September 2, 2026Episode 21823 min

From Ransomware to AI: 15 Years of Cybersecurity - #218

In this special episode of Reimagining Cyber , Tyler Moffitt hosts the podcast for the final time — looking back on 15 years in cybersecurity, the lessons he’s learned from speaking with security practitioners, researchers, MSPs and incident responders, and how dramatically the threat landscape has evolved. Tyler and incoming host Keelin Conant explore the shift from early malware and ransomware to double extortion, data theft and increasingly sophisticated nation-state activity. They also discuss how AI is accelerating the speed at which new exploits and attacks move from proof of concept into the wild. The conversation covers why organizations should report cybercrime to law enforcement, the role cryptocurrency trails can play in investigations, and the increasingly blurred line between financially motivated ransomware groups and nation-state operations. Looking ahead, Tyler shares some practical advice for defenders: treat identity as part of the security perimeter, limit privileges, protect administrative accounts, prepare for AI agents with excessive permissions, test backups, run tabletop exercises and focus on the fundamentals. But this episode is ultimately about more than technology. Tyler and Keelin discuss the importance of people, curiosity and human experience in cybersecurity — and why, despite changing technology and evolving attackers, there will always be a need to understand what is really happening and what defenders should do about it. As Tyler hands over the hosting role to Keelin, the next chapter of Reimagining Cyber begins. In this episode: 15 years of cybersecurity lessons How ransomware has evolved AI and the acceleration of cyber threats Why organizations should report cybercrime Nation-state attacks and ransomware-for-hire Identity as the new security perimeter AI agents, permissions and OAuth tokens Incident response and tabletop exercises Why cybersecurity fundamentals still matter The human side of cybersecurity Tyler’s final episode and Keelin’s new chapter as host As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

September 2, 2026Episode 21714 min

The Boardroom Edition - #217

What does cyber resilience really mean when the stakes extend far beyond the security team? In this special Reimagining Cyber: The Boardroom Edition , we bring together perspectives from three 2026 conversations to explore how cybersecurity is becoming a board-level business and operational issue. Theresa Lanowitz, Cybersecurity Analyst at Omdia and former Gartner analyst explains why resilience can't be treated as simply another cybersecurity initiative — and why the whole organization, from the board and C-suite to frontline teams, needs to take responsibility. We then look at the first year of the Digital Operational Resilience Act (DORA) with tech leader Dominic Brown (founder, Graves Light Consulting) , exploring what the regulation means for financial services, why implementation has proved challenging, and why governance, testing and accountability are becoming increasingly important. Finally, Doug Merritt, CEO of Aviatrix and former CEO of Splunk, argues that cybersecurity is entering a new “containment era.” If organizations have to assume that breaches will happen, how do they prevent those breaches from becoming catastrophic? His answer: measure the blast radius . Across all three conversations, one message stands out: cyber leadership is no longer simply about protecting technology. It's about preserving operations, protecting customers, sustaining trust and ensuring the business can continue when disruption occurs. This is cybersecurity from the boardroom perspective. As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

August 26, 2026Episode 21622 min

Hackers Are Already Inside - Now What? -#216

In this episode of Reimagining Cyber , Tyler Moffitt talks with Robert Salzwedell about what happens when attackers get past the firewall — and why keeping them out is no longer enough. With cloud services, remote workers, SaaS applications and compromised credentials blurring the boundaries of the traditional network, organisations can no longer assume that someone is safe simply because they are already inside. Robert explains why organisations need to look beyond the perimeter, understand where their sensitive data lives, rethink how they trust identities, and use behaviour to spot suspicious activity. They also discuss Zero Trust, AI agents, continuous security validation and how organisations can limit the damage when an account or device is compromised. In this episode: Why the traditional network perimeter is no longer enough What happens when attackers use legitimate identities Why understanding your data is critical to security How Zero Trust can help limit access and reduce risk The growing security challenge around AI and AI agents Why security needs to be continuously assessed and improved Practical steps organisations can take to reduce their exposure A conversation about moving from simply trying to keep attackers out to making sure that, when they do get in, they can't get very far. As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

August 19, 2026Episode 21516 min

Return of Cl0p and Their 'One to Many' Tactics - #215

Cl0p is back — and once again, the ransomware group is showing why attacking the technology that connects organisations can be far more powerful than attacking them one at a time. This episode examines Cl0p’s latest campaign targeting vulnerabilities in PTC Windchill and Flex PLM, enterprise software used across engineering, manufacturing and other industries. The conversation explores Cl0p’s “one-to-many” approach: find a widely deployed piece of enterprise software, exploit a vulnerability, and use it as a gateway into potentially hundreds of organisations. It’s a strategy the group has used before, most notably in the MOVEit campaign, which ultimately affected thousands of organisations. The episode looks at why data theft and extortion can now be more valuable than traditional ransomware encryption, why attackers are increasingly targeting the “multiplier” in an organisation’s technology ecosystem, and why simply patching a vulnerability may not be enough if an attacker has already gained access. It also explores the risks posed by MSPs, remote management platforms and trusted third parties — and what security teams should be doing to identify their own potential multipliers. The key lesson? Don’t just ask what happens if this system is compromised. Ask: if this system is compromised, what else does the attacker get? As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com

August 12, 2026Episode 21424 min

The Attack Is Over. Now Comes the Hard Part - #214

Ransomware recovery doesn’t end when the malware is removed and the servers come back online. In this episode of Reimagining Cyber , Tyler Moffitt is joined by Keelin Conant, a cybersecurity professional with firsthand experience of ransomware restoration, to explore what happens after the immediate crisis is over. They look beyond restoring systems to the human and business consequences that can linger for weeks, months and even years. Keelin shares stories of exhausted IT teams, leadership pressure, employee trauma, reputational damage and the danger of falling back into old habits once the immediate crisis has passed. The conversation also examines why organizations can be more vulnerable to another attack after the first one, the importance of fixing the vulnerabilities that allowed attackers in, and why backups and incident response plans aren't enough if they aren't regularly tested. From ransomware-as-a-service and repeat attacks to communication, leadership and the psychological impact on the people involved, this episode asks a fundamental question: when has an organization really recovered from a cyberattack? The answer may have less to do with getting the technology running again—and much more to do with whether the business and its people can genuinely move forward. As featured on Million Podcasts' Best 100 Cybersecurity Podcasts Top 50 Chief Information Security Officer CISO Podcasts Top 70 Security Hacking Podcasts This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best! Follow or subscribe to the show on your preferred podcast platform. Share the show with others in the cybersecurity world. Get in touch via reimaginingcyber@gmail.com