Episodes

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.

Monday Jan 20, 2025
68-Talking Cloud Podcast-with Marina Segal, Founder and CEO of Tamnoon
Monday Jan 20, 2025
Monday Jan 20, 2025
Episode 65 features Marina Segal, a friend, former colleague, and now co-founder and CEO of her VC-backed start-up, Tamnoon (www.tamnoon.io). I first met and worked with Marina Segal at Dome9 and, subsequently, Check Point Software. Marina is a shrewd and highly experienced executive with a strong background in Security Governance, Risk, and Compliance. In this age of AI, automation, and BOTs, she and her team have created an interesting value proposition with a human touch. I hope you enjoy the discussion.
*PLEASW NOTE*Correction* Midway through the broadcast I refer to CNAPP as a 'horizontal vertical' solution and I meant to say CSPM, not CNAPP. My bad. Thanks!

Monday Jan 06, 2025
67-Talking Cloud Podcast-Part 2 with Collin Graves, Founder of North Labs
Monday Jan 06, 2025
Monday Jan 06, 2025
Happy 2025! In this two-part episode, my guest is the founder of North Labs, Collin Graves. We discuss a variety of topics, including, of all things, the similarities between Higher Education and manufacturing! I'll never think of a 'bow-tie' in the same way again! Collin was an early pioneer in cloud computing and was one of the very first certified on AWS. Please comment and let us know what you think!

