Episodes

Monday May 26, 2025
Monday May 26, 2025
In this engaging conversation, Vikram Phatak and I explore the rapid evolution of AI and cloud technology, discussing its profound impact on daily life and the cybersecurity industry. We delve into the significance of trust in technology leadership and the challenges of maintaining integrity in a market filled with hype and misinformation. Our discussion also highlights the transformative role of AI technologies like transformers and the importance of data-driven assessments in cybersecurity. In this conversation, we delve into the complexities of product development, particularly in the cybersecurity sector. We discuss the challenges faced by engineers and developers in understanding the context of their work, the importance of testing and assurance in cybersecurity, and the dynamics of leadership in tech companies. The conversation also touches on the monetization strategies of cybersecurity testing organizations and the integrity of their testing processes. We also discuss the critical aspects of network visibility, the dynamics between market leaders and challengers in cybersecurity, the implications of cloud testing, and the importance of integrity in cyber ratings. Finally, we explore the future of cybersecurity, emphasizing the role of AI and human resources, and the challenges posed by rapidly evolving technologies such as quantum computing.

Monday May 19, 2025
Monday May 19, 2025
In this episode of Talking Cloud, I engage with Craig Calder to explore the evolving landscape of AI and its implications for business and society. We discuss the importance of curiosity in tech, the shift towards outcome-based pricing models, and the challenges of implementing AI in organizations. The conversation also touches on the future of identity security and the rapid evolution of technology, emphasizing the need for education and adaptation in this fast-paced environment. I hope you enjoy it!

Sunday May 11, 2025
76-Talking Cloud Podcast-with Kirsten Bay, CEO and Co-Founder, Cysurance
Sunday May 11, 2025
Sunday May 11, 2025
In this episode of Talking Cloud, I interview Kirsten Bay, CEO and co-founder of Cysurance, discussing her journey from supply chain operations to the world of cybersecurity and insurance. We explore the evolution of data valuation, the complexities of cyber insurance, and the importance of understanding risk management in today's digital landscape. Kirsten shares insights on how businesses can better navigate cybersecurity challenges and the innovative approaches being taken in the insurance sector to address these issues. In this conversation, Kirsten and Grant delve into the complexities of cyber insurance, discussing the evolving landscape of risk management in the face of increasing cyber threats. We explore the integration of security products with insurance solutions, the impact of AI on cybersecurity risks, and the importance of managing severity in cyber incidents. Our discussion highlights the need for organizations to adapt to new technologies while maintaining robust security measures, and the future implications of data security and privacy.

Monday Apr 28, 2025
Monday Apr 28, 2025
In this episode of Talking Cloud, Grant Asplund interviews Paul Chang, CEO of Brand Engagement Network (BEN), discussing the evolution of AI technologies, particularly large language models, and their applications in business. Paul shares insights from his extensive experience at IBM and how BEN is leveraging AI to create tailored solutions for various industries. The conversation explores the importance of customer engagement through AI avatars, the integration of middleware and backend systems, and the scalability of AI solutions in enhancing customer service. In this conversation, Grant Asplund and Paul discuss the transformative role of AI in customer service, healthcare, and various industries. They explore the evolution of Ben, an AI platform, and its applications in enhancing user engagement through customizable avatars and personalized interactions. The discussion highlights real-world use cases, including healthcare awareness campaigns and automotive sales, emphasizing the importance of tailored solutions and the future of AI technology.

Monday Apr 14, 2025
Monday Apr 14, 2025
Episode #74 features a great discussion with Steve Winterfeld, Advisor, and Fractional CISO with Cyber Vigilance Advice (CVA) LLC. Steve is passionate about cybersecurity. He served as CISO for Nordstrom Bank, Director of Cybersecurity for Nordstrom, and Director of Incident Response and Threat Intelligence at Charles Schwab. Steve also published a book on Cyber Warfare and holds CISSP, ITIL, and PMP certifications. We discussed a variety of topics, and during our conversation, Steve offered these resources:
On finding job: Lessons Learned on Finding a Cybersecurity Job After a Layoff - Security Boulevard

Monday Mar 31, 2025
Monday Mar 31, 2025
This week, my guest is Matt Stamper, CEO | CISO & Executive Advisor. Matt is a multi-time CISO with extensive experience in cybersecurity, information security, cloud security, IT audit, risk management, privacy, AI security, and governance. Matt is a former research director and security analyst at Gartner (NYSE: IT) and has extensive experience in cloud services and IT service management, including international experience in Latin America and China. Throughout his career, Matt has spoken to 1000s of CISOs, CIOs, and other corporate leaders and boards of directors. Matt’s experience includes early-stage startups and large, multinational public companies spanning multiple industries, including managed services, managed security services, global telecom, and advisory. Matt excels at conveying complex cybersecurity and technology concepts to boards of directors, executive management, professional service providers, cybersecurity personnel, and vendors in the cybersecurity industry.

Monday Mar 17, 2025
72-Talking Cloud Podcast-with Paul Nguyen, Co-Founder and Co-CEO at Permiso
Monday Mar 17, 2025
Monday Mar 17, 2025
I was so excited to post this episode, I forgot to write an introduction!! In this program I sit down with Paul Nguyen, Co-Founder and Co-CEO at Permiso. Paul has a long history of success in the cybersecurity. He's an invovator and entrepreneur and a fantastic guest! I hope you enjoy it!!!

Monday Mar 03, 2025
71-Talking Cloud Podcast-with Chris Risley, CEO at Bastille
Monday Mar 03, 2025
Monday Mar 03, 2025
I first met my episode 68 guest in 2002. I recently completed the reacquisition of MetaInfo from Check Point. While Check Point retained 20%, my employees and I owned 80%. Chris, the CEO of Nominum, reached out to me to discuss a possible merger between our companies.
The short story is we never merged. Chris led Nominum until they were acquired by Akamai Technologies in 2017.
Today, Chris is the CEO of Bastille, a unique wireless security vendor disrupting the industry. We have a wonderful, wide-ranging discussion. I hope you enjoy this episode!

Monday Feb 17, 2025
Monday Feb 17, 2025
In this episode, I sit with the Head of Cloud Security Engineering at Check Point Software. Brian McHenry joined Check Point after over a decade and a half at F5 focused on WAF. Brian has been a practitioner, a Sales Engineer, and a Product Manager. Hear why Brian left F5 and joined Check Point and what he started in NY in 2016.

Monday Feb 03, 2025
Monday Feb 03, 2025
All the way from Northern Ireland, my episode 66 guest is Chris Cooney, Director of Advocacy at Coralogix. Chris explains the differences between 'visibility' and 'observability' and discusses the benefits of their support for open systems.

