<![CDATA[Automate or Die Trying]]>ef0ccd45-473f-55bb-9bc2-e22a5a671a5eThu, 19 Mar 2026 16:00:20 +0000Captivate.fmWil Ramoshttps://artwork.captivate.fm/0c0d03b1-d449-437a-8ffd-bf1b98573d5e/Automate-Or-Die-Trying-Podcast-Cover.jpgAutomate or Die TryingWil RamosWil RamosA show exploring how today’s tech leaders secure innovation through automation and trust. Hosted by Wil Ramos, each episode shares real stories and lessons in DevSecOps, AI security, and building resilient modern organizations.https://automateordietrying.comfalseserialnopodcast“How John Shende Is Redefining AI Security, Agentic Governance, and the New Insider Threat”“How John Shende Is Redefining AI Security, Agentic Governance, and the New Insider Threat”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Jon G Shende, CTO of Data Security & AI and Global VP of SecOps at Sutherland, to explore what it really takes to secure AI at enterprise scale.

Jon shares how he helped rebuild a modern AI-driven security stack in partnership with Google Security, retiring legacy systems and standing up a new, machine-learning-powered operation from the ground up. He also reflects on his early work coining “cloud forensics as a service,” a concept that anticipated many of today’s cloud security challenges.

The conversation examines the rise of agentic AI and why traditional governance models are no longer sufficient. Jon explains how AI is becoming the new insider threat, not because it’s malicious, but because of the level of access, autonomy, and trust organizations are giving it.

They also unpack real-world lessons from large-scale security transformations, including the challenges of aligning stakeholders, managing risk, and ensuring data integrity across complex systems. Jon emphasizes that while automation and AI create massive opportunities, they also require strong fundamentals in access control, policy enforcement, and auditability.

For leaders building in today’s AI-driven world, Jon highlights the importance of collaboration, practical security design, and responsible adoption of emerging technologies.

Key Takeaways:

  • AI is becoming the new insider threat due to its trusted access and speed at scale
  • Governance must evolve to operate at the workflow level, not just static control points
  • Overprivileged AI agents increase the risk of data exposure and misuse
  • Automation without strong fundamentals can amplify security failures
  • The ROI of security lies in preventing incidents, not generating revenue
  • Large-scale transformations require alignment across technical and business stakeholders
  • Great leadership is about enabling teams, not taking the spotlight

Connect with Jon G Shende:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Jon G Shende, CTO of Data Security & AI and Global VP of SecOps at Sutherland, to explore what it really takes to secure AI at enterprise scale.

Jon shares how he helped rebuild a modern AI-driven security stack in partnership with Google Security, retiring legacy systems and standing up a new, machine-learning-powered operation from the ground up. He also reflects on his early work coining “cloud forensics as a service,” a concept that anticipated many of today’s cloud security challenges.

The conversation examines the rise of agentic AI and why traditional governance models are no longer sufficient. Jon explains how AI is becoming the new insider threat, not because it’s malicious, but because of the level of access, autonomy, and trust organizations are giving it.

They also unpack real-world lessons from large-scale security transformations, including the challenges of aligning stakeholders, managing risk, and ensuring data integrity across complex systems. Jon emphasizes that while automation and AI create massive opportunities, they also require strong fundamentals in access control, policy enforcement, and auditability.

For leaders building in today’s AI-driven world, Jon highlights the importance of collaboration, practical security design, and responsible adoption of emerging technologies.

Key Takeaways:

  • AI is becoming the new insider threat due to its trusted access and speed at scale
  • Governance must evolve to operate at the workflow level, not just static control points
  • Overprivileged AI agents increase the risk of data exposure and misuse
  • Automation without strong fundamentals can amplify security failures
  • The ROI of security lies in preventing incidents, not generating revenue
  • Large-scale transformations require alignment across technical and business stakeholders
  • Great leadership is about enabling teams, not taking the spotlight

Connect with Jon G Shende:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>c747cb3a-c5ee-472d-9921-6aec40be699cThu, 19 Mar 2026 09:00:00 -070044:56falsefull“How Ryan Donahue Secures Millions of Devices and Billions of Transactions at Comcast”“How Ryan Donahue Secures Millions of Devices and Billions of Transactions at Comcast”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Ryan Donahue, Senior Director of Cybersecurity at Comcast. Ryan leads vulnerability management, asset inventory, compliance, and fraud detection across one of the largest and most complex networks in the world, supporting millions of internal assets and more than 100 million customer devices.

Ryan shares how his background as a software engineer shaped his approach to security leadership. Instead of relying solely on vendor tools, he often builds internal systems to solve security challenges at massive scale, including credential management platforms handling billions of transactions per day and automation frameworks designed to protect telecom infrastructure.

The conversation explores the realities of securing large-scale telecom systems, where pushing updates or configuration changes can impact millions of devices simultaneously. Ryan discusses the challenge of maintaining visibility across massive infrastructure and how his team works to identify unknown assets and reduce operational risk.

Ryan also explains why automation must be implemented carefully in security environments. While automation enables scale, poorly designed systems can amplify vulnerabilities. His approach focuses on building secure defaults into platforms so engineering teams can move quickly while maintaining strong security standards.

For security leaders and engineers, Ryan emphasizes the importance of strong debugging skills, clear security metrics, and designing platforms that make security scalable across large engineering organizations.

Key Takeaways:

  1. Security at telecom scale requires deep engineering and custom tooling
  2. Asset visibility is the foundation of an effective security program
  3. Automation must be designed carefully to avoid amplifying risk
  4. Security platforms should simplify protection for developers
  5. Security reporting should focus on patterns rather than raw vulnerability counts
  6. Strong debugging and system-level thinking remain essential skills

Connect with Ryan Donahue:

  1. LinkedIn: https://www.linkedin.com/in/ryan-donahue-28324a5
  2. Website: https://rydonahue.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Ryan Donahue, Senior Director of Cybersecurity at Comcast. Ryan leads vulnerability management, asset inventory, compliance, and fraud detection across one of the largest and most complex networks in the world, supporting millions of internal assets and more than 100 million customer devices.

Ryan shares how his background as a software engineer shaped his approach to security leadership. Instead of relying solely on vendor tools, he often builds internal systems to solve security challenges at massive scale, including credential management platforms handling billions of transactions per day and automation frameworks designed to protect telecom infrastructure.

The conversation explores the realities of securing large-scale telecom systems, where pushing updates or configuration changes can impact millions of devices simultaneously. Ryan discusses the challenge of maintaining visibility across massive infrastructure and how his team works to identify unknown assets and reduce operational risk.

Ryan also explains why automation must be implemented carefully in security environments. While automation enables scale, poorly designed systems can amplify vulnerabilities. His approach focuses on building secure defaults into platforms so engineering teams can move quickly while maintaining strong security standards.

For security leaders and engineers, Ryan emphasizes the importance of strong debugging skills, clear security metrics, and designing platforms that make security scalable across large engineering organizations.

Key Takeaways:

  1. Security at telecom scale requires deep engineering and custom tooling
  2. Asset visibility is the foundation of an effective security program
  3. Automation must be designed carefully to avoid amplifying risk
  4. Security platforms should simplify protection for developers
  5. Security reporting should focus on patterns rather than raw vulnerability counts
  6. Strong debugging and system-level thinking remain essential skills

Connect with Ryan Donahue:

  1. LinkedIn: https://www.linkedin.com/in/ryan-donahue-28324a5
  2. Website: https://rydonahue.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>a6d14518-741d-43d4-8050-7b40f10c7559Mon, 16 Mar 2026 09:00:00 -070030:05falsefull“How Art Pugach Turns AI and Co-Pilot into Practical Business Automation”“How Art Pugach Turns AI and Co-Pilot into Practical Business Automation”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Art Pugach, CTO of Key Associates and Microsoft MVP, recognized for his work with M365 Co-Pilot. Art shares insights from his 27-year career building ERP, CRM, AI, and automation solutions, and discusses how organizations can move beyond hype to apply AI practically.

The conversation explores the importance of understanding human workflows before deploying automation, practical examples of AI creating knowledge bases and streamlining order processing, and the role of AI as an assistant rather than a replacement. Art also highlights lessons learned from early ERP implementations, managing AI credit limits, and showing employees how to effectively use AI tools.

For business leaders, IT professionals, and tech enthusiasts, Art emphasizes starting with use cases, combining human oversight with AI agents, and leveraging automation to free up resources for higher-value work.

Key Takeaways:

  • AI and automation succeed when human workflows are well-defined
  • Co-Pilot and AI agents can dramatically reduce repetitive tasks
  • Knowledge bases and help desk automation save months of work in days
  • Human oversight is critical; AI cannot read minds
  • Understand AI licensing and credit limits to avoid hidden costs
  • Focus on practical use cases to demonstrate value

Connect with Art Pugach:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Art Pugach, CTO of Key Associates and Microsoft MVP, recognized for his work with M365 Co-Pilot. Art shares insights from his 27-year career building ERP, CRM, AI, and automation solutions, and discusses how organizations can move beyond hype to apply AI practically.

The conversation explores the importance of understanding human workflows before deploying automation, practical examples of AI creating knowledge bases and streamlining order processing, and the role of AI as an assistant rather than a replacement. Art also highlights lessons learned from early ERP implementations, managing AI credit limits, and showing employees how to effectively use AI tools.

For business leaders, IT professionals, and tech enthusiasts, Art emphasizes starting with use cases, combining human oversight with AI agents, and leveraging automation to free up resources for higher-value work.

Key Takeaways:

  • AI and automation succeed when human workflows are well-defined
  • Co-Pilot and AI agents can dramatically reduce repetitive tasks
  • Knowledge bases and help desk automation save months of work in days
  • Human oversight is critical; AI cannot read minds
  • Understand AI licensing and credit limits to avoid hidden costs
  • Focus on practical use cases to demonstrate value

Connect with Art Pugach:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>ff38f598-30e3-41e7-9256-e774e40728aeTue, 10 Mar 2026 09:00:00 -070033:56falsefull“How David VonThenen Designs Production-Ready AI Systems and Agent Architectures”“How David VonThenen Designs Production-Ready AI Systems and Agent Architectures”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with David VonThenen, an AI/ML engineer and systems architect focused on building reliable AI systems that move beyond demos into real-world production.

David shares insights from his background in infrastructure and distributed systems, explaining why strong architecture, observability, and governance are critical when deploying AI at scale. The conversation explores hybrid retrieval approaches beyond simple vector search, the rise of multi-agent AI systems, and the growing need for monitoring and safeguards as AI tools become more autonomous.

For founders, engineers, and technical leaders, David emphasizes a practical approach: design systems carefully, prioritize reliability, and continuously validate AI models in production environments.

Key Takeaways:

  • Start with solid system architecture before scaling AI models
  • Hybrid retrieval strategies often outperform pure vector search
  • Multi-agent architectures allow modular, scalable AI workflows
  • Observability and governance are critical for production AI systems
  • Adversarial prompts highlight the need for strong safeguards
  • Infrastructure design still matters as much as model quality

Connect with David VonThenen:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with David VonThenen, an AI/ML engineer and systems architect focused on building reliable AI systems that move beyond demos into real-world production.

David shares insights from his background in infrastructure and distributed systems, explaining why strong architecture, observability, and governance are critical when deploying AI at scale. The conversation explores hybrid retrieval approaches beyond simple vector search, the rise of multi-agent AI systems, and the growing need for monitoring and safeguards as AI tools become more autonomous.

For founders, engineers, and technical leaders, David emphasizes a practical approach: design systems carefully, prioritize reliability, and continuously validate AI models in production environments.

Key Takeaways:

  • Start with solid system architecture before scaling AI models
  • Hybrid retrieval strategies often outperform pure vector search
  • Multi-agent architectures allow modular, scalable AI workflows
  • Observability and governance are critical for production AI systems
  • Adversarial prompts highlight the need for strong safeguards
  • Infrastructure design still matters as much as model quality

Connect with David VonThenen:


Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>21435c7e-5027-4437-9d2a-eca2bd547e7eMon, 09 Mar 2026 09:00:00 -070037:25falsefull“How Oleg Danyliuk Builds Real-Time AI for Sales and Automation Across Continents”“How Oleg Danyliuk Builds Real-Time AI for Sales and Automation Across Continents”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Oleg Danyliuk, CEO of Duanex and CTO of Insyghtful.ai. Oleg combines nearly two decades of enterprise software experience with a deep focus on AI-driven automation and real-time insights, helping businesses scale efficiently while keeping human judgment in the loop.

Oleg shares his journey from a Java developer in Ukraine to leading distributed engineering teams across continents, building high-load banking systems, ticketing platforms, and enterprise service buses. He discusses founding Duanex in 2016 to provide clients with high-value automation solutions, emphasizing transparency, delivering real outcomes, and prioritizing client relationships over short-term revenue.

The conversation explores how Oleg applies enterprise-grade rigor to AI agent development. He walks through his work deploying AI for lead validation at Duanex and developing Insyghtful.ai, a platform that reads the emotional temperature of sales calls in real-time, providing actionable guidance to reps while balancing speed, latency, and usability. Oleg explains the challenges of working with incomplete or messy data, handling human-AI collaboration, and managing distributed teams under extreme conditions, including operating with developers in active war zones in Ukraine.

Oleg also shares insights on scaling AI responsibly: start small, focus on meaningful impact, avoid automating everything, and use external APIs like OpenAI’s Gemini to test quickly before committing to full custom models. He emphasizes that AI should augment human intelligence rather than replace it, highlighting the ongoing need for maintenance, monitoring, and cultural context when interpreting emotional signals in conversations.

For founders, technical leaders, and AI enthusiasts, Oleg’s advice is clear: focus on solving high-value problems incrementally, maintain transparency with clients, and continuously validate your models in production to ensure real-world efficacy.

Key Takeaways:

  1. Start small with AI automation—test single steps before scaling
  2. Use APIs for low-cost experimentation before building custom models
  3. Real-time AI requires low latency (sub-second) for actionable insights
  4. AI augments humans; it does not replace nuanced human judgment
  5. Distributed engineering teams can maintain high performance even under extreme conditions with proper infrastructure and human connection
  6. Data quality is an ongoing effort, not a one-time cleanup
  7. Transparency with clients builds long-term trust and drives referrals

Connect with Oleg Danyliuk:

  1. LinkedIn: https://www.linkedin.com/in/oleg-danyliuk
  2. Company: https://duanex.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Oleg Danyliuk, CEO of Duanex and CTO of Insyghtful.ai. Oleg combines nearly two decades of enterprise software experience with a deep focus on AI-driven automation and real-time insights, helping businesses scale efficiently while keeping human judgment in the loop.

Oleg shares his journey from a Java developer in Ukraine to leading distributed engineering teams across continents, building high-load banking systems, ticketing platforms, and enterprise service buses. He discusses founding Duanex in 2016 to provide clients with high-value automation solutions, emphasizing transparency, delivering real outcomes, and prioritizing client relationships over short-term revenue.

The conversation explores how Oleg applies enterprise-grade rigor to AI agent development. He walks through his work deploying AI for lead validation at Duanex and developing Insyghtful.ai, a platform that reads the emotional temperature of sales calls in real-time, providing actionable guidance to reps while balancing speed, latency, and usability. Oleg explains the challenges of working with incomplete or messy data, handling human-AI collaboration, and managing distributed teams under extreme conditions, including operating with developers in active war zones in Ukraine.

Oleg also shares insights on scaling AI responsibly: start small, focus on meaningful impact, avoid automating everything, and use external APIs like OpenAI’s Gemini to test quickly before committing to full custom models. He emphasizes that AI should augment human intelligence rather than replace it, highlighting the ongoing need for maintenance, monitoring, and cultural context when interpreting emotional signals in conversations.

For founders, technical leaders, and AI enthusiasts, Oleg’s advice is clear: focus on solving high-value problems incrementally, maintain transparency with clients, and continuously validate your models in production to ensure real-world efficacy.

Key Takeaways:

  1. Start small with AI automation—test single steps before scaling
  2. Use APIs for low-cost experimentation before building custom models
  3. Real-time AI requires low latency (sub-second) for actionable insights
  4. AI augments humans; it does not replace nuanced human judgment
  5. Distributed engineering teams can maintain high performance even under extreme conditions with proper infrastructure and human connection
  6. Data quality is an ongoing effort, not a one-time cleanup
  7. Transparency with clients builds long-term trust and drives referrals

Connect with Oleg Danyliuk:

  1. LinkedIn: https://www.linkedin.com/in/oleg-danyliuk
  2. Company: https://duanex.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>c6f5b193-731a-44cd-85dd-c25b8113c62fFri, 20 Feb 2026 09:00:00 -070025:41falsefull“How Alessandro Pireno Leverages Full-Stack Experience to Scale AI & Technical Products”“How Alessandro Pireno Leverages Full-Stack Experience to Scale AI & Technical Products”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Alessandro Pireno, a fractional CTO and CPO, board advisor, and AI, data, and go-to-market leader who helps early-stage startups scale. Alessandro has led product engineering and sales engineering teams at Snowflake and Surreal DB. His unique path spans applied physics, engineering, product leadership, and sales, giving him a 360-degree perspective on building, selling, and scaling technology.

Alessandro shares insights from his experience helping startups navigate technical product commercialization, particularly in the AI infrastructure space. He explains common pitfalls, including products that technically excel but fail to align with customer value or economic impact. He highlights how startups can distinguish between “nice-to-have” features versus core value drivers, emphasizing the importance of translating technical capabilities into measurable outcomes for customers.

The discussion explores the critical role of sales engineers in driving adoption, not just demos, and how cross-functional collaboration between sales and engineering teams accelerates success. Alessandro also dives into key differences between CIO and CISO perspectives, how AI has reshaped executive priorities, and why understanding the true customer pain is more valuable than superficial feature adoption.

He shares real-world examples of when beautiful UX or “pretty packaging” can mislead buyers, stressing that delivering the right solution—even if it looks less polished—creates real value and long-term trust. He also emphasizes the importance of leveraging proprietary data effectively as a competitive advantage in AI product development.

For technical leaders—CTOs, VPs of engineering, and founders building AI or data-driven products—Alessandro’s principle is clear: stress-test assumptions, focus on delivering measurable impact, and use cross-functional experience to bridge the gap between engineering, product, and sales.

Key Takeaways:

  1. AI adoption alone does not guarantee differentiation; understand real customer impact
  2. Translate technical features into measurable business value, not just performance metrics
  3. Strong collaboration between sales engineers and sales teams accelerates adoption
  4. CIOs often focus on cost optimization, while CISOs prioritize risk management
  5. Proprietary data is the “crude oil” that makes AI-powered products unique
  6. Avoid prioritizing aesthetics over function when delivering solutions
  7. Early-stage startups benefit from fractional leadership with a cross-functional lens

Connect with Alessandro Pireno:

  1. LinkedIn: https://www.linkedin.com/in/apireno
  2. Website: https://pireno.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Alessandro Pireno, a fractional CTO and CPO, board advisor, and AI, data, and go-to-market leader who helps early-stage startups scale. Alessandro has led product engineering and sales engineering teams at Snowflake and Surreal DB. His unique path spans applied physics, engineering, product leadership, and sales, giving him a 360-degree perspective on building, selling, and scaling technology.

Alessandro shares insights from his experience helping startups navigate technical product commercialization, particularly in the AI infrastructure space. He explains common pitfalls, including products that technically excel but fail to align with customer value or economic impact. He highlights how startups can distinguish between “nice-to-have” features versus core value drivers, emphasizing the importance of translating technical capabilities into measurable outcomes for customers.

The discussion explores the critical role of sales engineers in driving adoption, not just demos, and how cross-functional collaboration between sales and engineering teams accelerates success. Alessandro also dives into key differences between CIO and CISO perspectives, how AI has reshaped executive priorities, and why understanding the true customer pain is more valuable than superficial feature adoption.

He shares real-world examples of when beautiful UX or “pretty packaging” can mislead buyers, stressing that delivering the right solution—even if it looks less polished—creates real value and long-term trust. He also emphasizes the importance of leveraging proprietary data effectively as a competitive advantage in AI product development.

For technical leaders—CTOs, VPs of engineering, and founders building AI or data-driven products—Alessandro’s principle is clear: stress-test assumptions, focus on delivering measurable impact, and use cross-functional experience to bridge the gap between engineering, product, and sales.

Key Takeaways:

  1. AI adoption alone does not guarantee differentiation; understand real customer impact
  2. Translate technical features into measurable business value, not just performance metrics
  3. Strong collaboration between sales engineers and sales teams accelerates adoption
  4. CIOs often focus on cost optimization, while CISOs prioritize risk management
  5. Proprietary data is the “crude oil” that makes AI-powered products unique
  6. Avoid prioritizing aesthetics over function when delivering solutions
  7. Early-stage startups benefit from fractional leadership with a cross-functional lens

Connect with Alessandro Pireno:

  1. LinkedIn: https://www.linkedin.com/in/apireno
  2. Website: https://pireno.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>47e116a5-1772-477e-9bf4-b4d0d3ef3034Thu, 19 Feb 2026 09:00:00 -070033:25falsefull“How Abukari Einus Went from Healthcare and Robotics to Building AI-Powered Food Tech in Ghana”“How Abukari Einus Went from Healthcare and Robotics to Building AI-Powered Food Tech in Ghana”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Abukari Einus, Co-Founder & CEO of FoodQwik. Abukari has built across multiple domains, from healthcare systems at First Line 24, decentralized finance at NorthStar, to robotics at Three Farm State Farming.

The conversation explores Abukari’s journey shipping full-stack systems, smart contracts, automated deployments, and managing Linux servers while solving real-world problems in emerging markets. They discuss how FoodQwik uses AI to personalize food recommendations for dietary and allergy needs, creating a more mindful and health-conscious food ordering experience in Ghana.

Abukari shares lessons learned from building in highly regulated and technical domains like healthcare and DeFi, emphasizing accountability, automation, and iterative user feedback. He also highlights the operational and logistical challenges of running a food tech platform in Northern Ghana and how his team overcomes them to ensure timely delivery.

The discussion touches on AI-driven personalization, the importance of conversational interfaces in food tech, and how FoodQwik differentiates itself from general ordering platforms by focusing on users with niche dietary needs. Finally, Abukari offers advice for builders in emerging markets: keep shipping, iterate with users, and embrace automation to scale effectively.

Key Takeaways:

  1. Building technology in emerging markets requires iterative user feedback and adaptability
  2. AI can tailor food ordering to dietary, allergy, and health needs
  3. Accountability and security lessons from DeFi and healthcare transfer to consumer tech
  4. Automation is critical for small teams with limited margins for error
  5. Operational logistics are a key challenge in scaling food delivery in Africa
  6. Differentiation comes from focusing on niche needs and user experience

Connect with Abukari Einus:

  1. LinkedIn: https://linkedin.com/in/abukari-einus-913721177
  2. GitHub: https://github.com/blackdante101

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Abukari Einus, Co-Founder & CEO of FoodQwik. Abukari has built across multiple domains, from healthcare systems at First Line 24, decentralized finance at NorthStar, to robotics at Three Farm State Farming.

The conversation explores Abukari’s journey shipping full-stack systems, smart contracts, automated deployments, and managing Linux servers while solving real-world problems in emerging markets. They discuss how FoodQwik uses AI to personalize food recommendations for dietary and allergy needs, creating a more mindful and health-conscious food ordering experience in Ghana.

Abukari shares lessons learned from building in highly regulated and technical domains like healthcare and DeFi, emphasizing accountability, automation, and iterative user feedback. He also highlights the operational and logistical challenges of running a food tech platform in Northern Ghana and how his team overcomes them to ensure timely delivery.

The discussion touches on AI-driven personalization, the importance of conversational interfaces in food tech, and how FoodQwik differentiates itself from general ordering platforms by focusing on users with niche dietary needs. Finally, Abukari offers advice for builders in emerging markets: keep shipping, iterate with users, and embrace automation to scale effectively.

Key Takeaways:

  1. Building technology in emerging markets requires iterative user feedback and adaptability
  2. AI can tailor food ordering to dietary, allergy, and health needs
  3. Accountability and security lessons from DeFi and healthcare transfer to consumer tech
  4. Automation is critical for small teams with limited margins for error
  5. Operational logistics are a key challenge in scaling food delivery in Africa
  6. Differentiation comes from focusing on niche needs and user experience

Connect with Abukari Einus:

  1. LinkedIn: https://linkedin.com/in/abukari-einus-913721177
  2. GitHub: https://github.com/blackdante101

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>a58ebef6-5753-40df-a4fe-9fa6601184f6Wed, 18 Feb 2026 09:00:00 -070016:07falsefull“How Terry O’Daniel Went from Engineering to Redefining DevSecOps and Building Trust Across Tech Giants”“How Terry O’Daniel Went from Engineering to Redefining DevSecOps and Building Trust Across Tech Giants”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Terry O’Daniel, CISO, advisor, and investor with experience at Amplitude, Instacart, Netflix, Salesforce, and Yahoo!.

The conversation explores Terry’s journey from hands-on engineering to executive security leadership, emphasizing how security can enable business rather than act as a blocker. Terry shares how automation and embedding security directly into development pipelines have transformed the way teams operate, allowing them to focus on meaningful outcomes instead of repetitive tasks.

They dive into DevSecOps, continuous threat exposure management (CTEM), and the evolution of enterprise security practices. Terry explains why traditional compliance-driven approaches are insufficient for modern software delivery and how organizations can prioritize threats, reduce noise, and adopt continuous, operationalized security practices.

The discussion also covers the role of AI in security, from simulating attack scenarios to intelligent vulnerability prioritization, and how these innovations are helping companies maintain resilience while scaling operations.

Finally, Terry reframes security as a driver of customer trust and business growth, showing how strong security practices can accelerate adoption, meet enterprise expectations, and become a competitive advantage.

Key Takeaways:

  1. Security as a business enabler, not a blocker
  2. Automating repetitive tasks to focus on high-impact work
  3. Embedding security early in development pipelines
  4. Continuous Threat Exposure Management (CTEM) in practice
  5. Using AI for threat simulation and vulnerability prioritization
  6. Prioritization strategies for large volumes of security alerts
  7. Building customer trust through security excellence

Connect with Terry O’Daniel:

  1. LinkedIn: linkedin.com/in/terryodaniel
  2. Website: terryodaniel.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Terry O’Daniel, CISO, advisor, and investor with experience at Amplitude, Instacart, Netflix, Salesforce, and Yahoo!.

The conversation explores Terry’s journey from hands-on engineering to executive security leadership, emphasizing how security can enable business rather than act as a blocker. Terry shares how automation and embedding security directly into development pipelines have transformed the way teams operate, allowing them to focus on meaningful outcomes instead of repetitive tasks.

They dive into DevSecOps, continuous threat exposure management (CTEM), and the evolution of enterprise security practices. Terry explains why traditional compliance-driven approaches are insufficient for modern software delivery and how organizations can prioritize threats, reduce noise, and adopt continuous, operationalized security practices.

The discussion also covers the role of AI in security, from simulating attack scenarios to intelligent vulnerability prioritization, and how these innovations are helping companies maintain resilience while scaling operations.

Finally, Terry reframes security as a driver of customer trust and business growth, showing how strong security practices can accelerate adoption, meet enterprise expectations, and become a competitive advantage.

Key Takeaways:

  1. Security as a business enabler, not a blocker
  2. Automating repetitive tasks to focus on high-impact work
  3. Embedding security early in development pipelines
  4. Continuous Threat Exposure Management (CTEM) in practice
  5. Using AI for threat simulation and vulnerability prioritization
  6. Prioritization strategies for large volumes of security alerts
  7. Building customer trust through security excellence

Connect with Terry O’Daniel:

  1. LinkedIn: linkedin.com/in/terryodaniel
  2. Website: terryodaniel.com

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>59266243-83ad-4a7e-a8f4-6efd49c17008Tue, 17 Feb 2026 09:00:00 -070035:30falsefull“How Thomas Stiehm Went from Y2K to AI-Driven DevSecOps Innovation”“How Thomas Stiehm Went from Y2K to AI-Driven DevSecOps Innovation”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Thomas Stiehm, a seasoned technology leader and former CTO at Covaras, with nearly two decades of experience driving DevOps, DevSecOps, and large-scale cloud transformation initiatives.

The conversation explores how Thomas’s early experience during Y2K shaped his perspective on software longevity, risk, and the hidden assumptions in system design. He shares insights from leading global engineering teams, scaling agile practices across distributed organizations, and building high-performance systems that support millions of users.

They discuss DevOps culture, the evolution into DevSecOps, and how organizations can integrate security into fast-moving pipelines without slowing down innovation. Thomas also breaks down how AI and large language models are transforming software development, particularly in automating test creation and improving developer productivity.

The episode closes with Thomas’s perspective on the future of AI in engineering, emphasizing the importance of test automation, security-first thinking, and building confidence to move fast without breaking critical systems.

Key Takeaways:

  1. How Y2K shaped modern thinking around system risk and longevity
  2. Scaling DevOps and agile across global, distributed teams
  3. Integrating security into DevSecOps without slowing delivery
  4. Using AI and LLMs to accelerate testing and development
  5. Why test automation is critical for speed and reliability

Connect with Thomas Stiehm:

  1. LinkedIn: https://linkedin.com/in/stiehm

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Thomas Stiehm, a seasoned technology leader and former CTO at Covaras, with nearly two decades of experience driving DevOps, DevSecOps, and large-scale cloud transformation initiatives.

The conversation explores how Thomas’s early experience during Y2K shaped his perspective on software longevity, risk, and the hidden assumptions in system design. He shares insights from leading global engineering teams, scaling agile practices across distributed organizations, and building high-performance systems that support millions of users.

They discuss DevOps culture, the evolution into DevSecOps, and how organizations can integrate security into fast-moving pipelines without slowing down innovation. Thomas also breaks down how AI and large language models are transforming software development, particularly in automating test creation and improving developer productivity.

The episode closes with Thomas’s perspective on the future of AI in engineering, emphasizing the importance of test automation, security-first thinking, and building confidence to move fast without breaking critical systems.

Key Takeaways:

  1. How Y2K shaped modern thinking around system risk and longevity
  2. Scaling DevOps and agile across global, distributed teams
  3. Integrating security into DevSecOps without slowing delivery
  4. Using AI and LLMs to accelerate testing and development
  5. Why test automation is critical for speed and reliability

Connect with Thomas Stiehm:

  1. LinkedIn: https://linkedin.com/in/stiehm

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>ba97493e-a8d1-4f8d-800f-bf877ffad2aaMon, 16 Feb 2026 09:00:00 -070026:25falsefull“How Lin Sun Went from IBM Master Inventor to Building AI Agents in Kubernetes and Leading Open Source Infrastructure”“How Lin Sun Went from IBM Master Inventor to Building AI Agents in Kubernetes and Leading Open Source Infrastructure”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Lin Sun, a leader in cloud-native open source and AI infrastructure. Lin is part of Open Source at solo.io, a core maintainer of Istio, kgateway, and kagent, a member of the Istio TOC and Steering Committee, a CNCF TOC member and Ambassador, and an international speaker.

The conversation explores the rise of AI agents running on Kubernetes and how open source infrastructure is evolving to support agentic workloads in production. Lin shares lessons from her journey as an IBM Master Inventor to shaping some of the most widely adopted cloud-native projects in the ecosystem.

They discuss Istio, service meshes, AI agent security, and why running agents is fundamentally different from running traditional microservices. Lin also breaks down the importance of open standards, community governance, and sustainability as AI adoption accelerates across enterprises.

The episode closes with insights on leadership in open source, contributing at scale, and what builders need to understand to prepare infrastructure for the next generation of AI systems.

Key Takeaways:

  1. How AI agents change Kubernetes and cloud-native design
  2. Securing and operating AI agents in production
  3. The role of open source governance in AI infrastructure
  4. Lessons from leading Istio and CNCF communities

Connect with Lin Sun:

  1. LinkedIn: https://linkedin.com/in/lin-sun-a9b7a81

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Lin Sun, a leader in cloud-native open source and AI infrastructure. Lin is part of Open Source at solo.io, a core maintainer of Istio, kgateway, and kagent, a member of the Istio TOC and Steering Committee, a CNCF TOC member and Ambassador, and an international speaker.

The conversation explores the rise of AI agents running on Kubernetes and how open source infrastructure is evolving to support agentic workloads in production. Lin shares lessons from her journey as an IBM Master Inventor to shaping some of the most widely adopted cloud-native projects in the ecosystem.

They discuss Istio, service meshes, AI agent security, and why running agents is fundamentally different from running traditional microservices. Lin also breaks down the importance of open standards, community governance, and sustainability as AI adoption accelerates across enterprises.

The episode closes with insights on leadership in open source, contributing at scale, and what builders need to understand to prepare infrastructure for the next generation of AI systems.

Key Takeaways:

  1. How AI agents change Kubernetes and cloud-native design
  2. Securing and operating AI agents in production
  3. The role of open source governance in AI infrastructure
  4. Lessons from leading Istio and CNCF communities

Connect with Lin Sun:

  1. LinkedIn: https://linkedin.com/in/lin-sun-a9b7a81

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>08c0f3e5-8abf-4460-bae8-dbe417274ac3Fri, 30 Jan 2026 09:00:00 -070030:45falsefull“How Kisa Brostrom Went from Weather Data to Leading Generative AI at Boodle”“How Kisa Brostrom Went from Weather Data to Leading Generative AI at Boodle”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Kisa Brostrom, Chief Technology Officer at Boodle AI. Kisa’s career spans analyzing weather data in Oklahoma, predicting gas turbine failures at Rolls-Royce, building healthcare AI models, and now leading Boodle Box, a generative AI platform for higher education.

Kisa shares her journey from self-teaching programming and machine learning to executive leadership, emphasizing building high-performing teams and balancing strategic vision with hands-on problem-solving. She discusses challenges in automation, model reliability, and human-in-the-loop AI, as well as how Boodle Box equips students to use generative AI responsibly while democratizing access to cutting-edge technology.

The episode also explores team culture, adoption, and leadership perspective, highlighting how to maintain trust, ethical practices, and innovation in high-velocity tech environments.

Key Takeaways:

  1. Building AI teams that deliver results
  2. Human-in-the-loop AI for ethical, trustworthy systems
  3. Staying connected to ground-level operations as a tech leader
  4. Educating the next generation on responsible AI use

Connect with Kisa Brostrom:

  1. linkedin.com/in/kisabrostrom

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Kisa Brostrom, Chief Technology Officer at Boodle AI. Kisa’s career spans analyzing weather data in Oklahoma, predicting gas turbine failures at Rolls-Royce, building healthcare AI models, and now leading Boodle Box, a generative AI platform for higher education.

Kisa shares her journey from self-teaching programming and machine learning to executive leadership, emphasizing building high-performing teams and balancing strategic vision with hands-on problem-solving. She discusses challenges in automation, model reliability, and human-in-the-loop AI, as well as how Boodle Box equips students to use generative AI responsibly while democratizing access to cutting-edge technology.

The episode also explores team culture, adoption, and leadership perspective, highlighting how to maintain trust, ethical practices, and innovation in high-velocity tech environments.

Key Takeaways:

  1. Building AI teams that deliver results
  2. Human-in-the-loop AI for ethical, trustworthy systems
  3. Staying connected to ground-level operations as a tech leader
  4. Educating the next generation on responsible AI use

Connect with Kisa Brostrom:

  1. linkedin.com/in/kisabrostrom

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>e1a4ca40-c60d-4f53-bce2-ff3f6536e16fWed, 28 Jan 2026 09:00:00 -070028:13falsefull"How Abhinav Agarwal Went from Non-Invasive CGMs to Governing AI in Women’s Health""How Abhinav Agarwal Went from Non-Invasive CGMs to Governing AI in Women’s Health"Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Abhinav Agarwal, founder of a stealth startup, AI researcher at the Stanford Center for AI in Medicine and Imaging, and former CTO at KOS. Abhinav is the creator of Argus, the world’s first truly non-invasive continuous glucose monitor, and a leader in responsible healthcare AI.

They discuss his latest venture, Clear Health, which develops wearable technology to continuously track 100+ biomarkers for women’s health—completely non-invasive, without blood draws or needles. Abhinav explains why most existing solutions still fall short, and how Clear Health uses optical sensors, edge AI, and multimodal data fusion for personalized hormone tracking.

The conversation covers fertility planning, IVF, perimenopause, menopause, and athletic performance, highlighting how inaccurate period tracking apps fail most women. Abhinav also shares lessons from high-stakes healthcare AI projects, emphasizing trust, transparency, and human-in-the-loop decision-making.

Key Takeaways:

  1. What “non-invasive” really means in healthcare technology
  2. How personalized hormone tracking transforms women’s health
  3. Balancing AI automation with human oversight
  4. Ethical and trust-focused AI design principles

Connect with Abhinav Agarwal:

  1. linkedin.com/in/agarwalaabhinav
  2. wearclair.com
  3. instagram.com/hereandabhi

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Abhinav Agarwal, founder of a stealth startup, AI researcher at the Stanford Center for AI in Medicine and Imaging, and former CTO at KOS. Abhinav is the creator of Argus, the world’s first truly non-invasive continuous glucose monitor, and a leader in responsible healthcare AI.

They discuss his latest venture, Clear Health, which develops wearable technology to continuously track 100+ biomarkers for women’s health—completely non-invasive, without blood draws or needles. Abhinav explains why most existing solutions still fall short, and how Clear Health uses optical sensors, edge AI, and multimodal data fusion for personalized hormone tracking.

The conversation covers fertility planning, IVF, perimenopause, menopause, and athletic performance, highlighting how inaccurate period tracking apps fail most women. Abhinav also shares lessons from high-stakes healthcare AI projects, emphasizing trust, transparency, and human-in-the-loop decision-making.

Key Takeaways:

  1. What “non-invasive” really means in healthcare technology
  2. How personalized hormone tracking transforms women’s health
  3. Balancing AI automation with human oversight
  4. Ethical and trust-focused AI design principles

Connect with Abhinav Agarwal:

  1. linkedin.com/in/agarwalaabhinav
  2. wearclair.com
  3. instagram.com/hereandabhi

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>d9066b6d-55b6-4f70-b0e0-1d05c44293c0Mon, 26 Jan 2026 09:00:00 -070033:44falsefull“How Aby Rao Went from Identity Security to Governing Generative AI”“How Aby Rao Went from Identity Security to Governing Generative AI”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Aby Rao, Deputy CISO and cybersecurity leader with over two decades of experience across identity security, cloud and enterprise security, GRC, and AI risk management.

Aby shares how his background in identity and cloud security shaped his approach to responsible AI adoption. The conversation focuses on AI governance, model risk management, and the secure adoption of generative and agentic AI, including why enterprise-wide ownership and human-in-the-loop controls are critical as automation accelerates.

He also offers practical advice on translating AI risk into business language, aligning security with product and engineering teams, and building future-ready security programs that enable innovation without sacrificing trust.

Key Takeaways:

  1. Why identity remains central to AI security
  2. What effective AI governance looks like in practice
  3. Securing generative and agentic AI without slowing the business
  4. Communicating AI risk to executives and boards

Golden Nugget:

“You can’t secure what you don’t understand. Start with the technology, then build the guardrails.”

Connect with Aby Rao:

  1. LinkedIn: linkedin.com/in/abyrao

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Aby Rao, Deputy CISO and cybersecurity leader with over two decades of experience across identity security, cloud and enterprise security, GRC, and AI risk management.

Aby shares how his background in identity and cloud security shaped his approach to responsible AI adoption. The conversation focuses on AI governance, model risk management, and the secure adoption of generative and agentic AI, including why enterprise-wide ownership and human-in-the-loop controls are critical as automation accelerates.

He also offers practical advice on translating AI risk into business language, aligning security with product and engineering teams, and building future-ready security programs that enable innovation without sacrificing trust.

Key Takeaways:

  1. Why identity remains central to AI security
  2. What effective AI governance looks like in practice
  3. Securing generative and agentic AI without slowing the business
  4. Communicating AI risk to executives and boards

Golden Nugget:

“You can’t secure what you don’t understand. Start with the technology, then build the guardrails.”

Connect with Aby Rao:

  1. LinkedIn: linkedin.com/in/abyrao

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>7877792b-dbbd-4534-8ba2-ceebdce72cddWed, 21 Jan 2026 16:34:00 -070031:34falsefull“How Joshua Copeland Went from Military Cyber Operations to Burning Down Broken Security Models”“How Joshua Copeland Went from Military Cyber Operations to Burning Down Broken Security Models”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Joshua Copeland, CISO, Professor, Best-Selling Author, Speaker, Startup Advisor, and Board Member, also widely known as the #UnpopularOpinionGuy in cybersecurity.

Joshua shares his 25-year journey across military, federal, state, and commercial cybersecurity environments, from Air Force communications and nuclear cybersecurity missions to leading enterprise security programs and advising startups and boards. He explains how operating in zero-fail military systems shaped his philosophy around resilience, accountability, and building fearless teams.

The conversation dives into what actually makes security programs effective, why many organizations confuse compliance with security, and how automation and AI should be used to eliminate noise, not judgment. Joshua challenges industry norms around certifications, vanity metrics, and tool sprawl, arguing that resilient systems are built on strong foundations, clear ownership, and empowered people.

Finally, Joshua offers practical advice for CISOs and technology leaders navigating rapid change, emphasizing business alignment, human-centered security, and leadership courage over checkbox security theater.

Key Takeaways:

  1. Why compliance is a baseline, not a cybersecurity strategy
  2. What resilient systems actually look like in real organizations
  3. How automation and AI should reduce burnout, not replace thinking
  4. The danger of security theater and metric-driven decision-making
  5. How to build fearless, accountable security teams

Golden Nugget:

“The next tool won’t save you. Resilient systems are built by people who understand risk, own outcomes, and aren’t afraid to challenge bad assumptions.”

Connect with Joshua Copeland:

  1. LinkedIn: linkedin.com/in/joshuacopeland

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Joshua Copeland, CISO, Professor, Best-Selling Author, Speaker, Startup Advisor, and Board Member, also widely known as the #UnpopularOpinionGuy in cybersecurity.

Joshua shares his 25-year journey across military, federal, state, and commercial cybersecurity environments, from Air Force communications and nuclear cybersecurity missions to leading enterprise security programs and advising startups and boards. He explains how operating in zero-fail military systems shaped his philosophy around resilience, accountability, and building fearless teams.

The conversation dives into what actually makes security programs effective, why many organizations confuse compliance with security, and how automation and AI should be used to eliminate noise, not judgment. Joshua challenges industry norms around certifications, vanity metrics, and tool sprawl, arguing that resilient systems are built on strong foundations, clear ownership, and empowered people.

Finally, Joshua offers practical advice for CISOs and technology leaders navigating rapid change, emphasizing business alignment, human-centered security, and leadership courage over checkbox security theater.

Key Takeaways:

  1. Why compliance is a baseline, not a cybersecurity strategy
  2. What resilient systems actually look like in real organizations
  3. How automation and AI should reduce burnout, not replace thinking
  4. The danger of security theater and metric-driven decision-making
  5. How to build fearless, accountable security teams

Golden Nugget:

“The next tool won’t save you. Resilient systems are built by people who understand risk, own outcomes, and aren’t afraid to challenge bad assumptions.”

Connect with Joshua Copeland:

  1. LinkedIn: linkedin.com/in/joshuacopeland

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>a979f469-f4ab-458a-8560-3ffdb2750e54Mon, 19 Jan 2026 09:00:00 -070033:38falsefull“How Dr. Glen Vickers Went from Help Desk to Rebuilding Mission-Critical Systems Without Breaking Uptime”“How Dr. Glen Vickers Went from Help Desk to Rebuilding Mission-Critical Systems Without Breaking Uptime”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Dr. Glen Vickers, a technology and cybersecurity leader with global impact across cloud, SaaS, DevOps, and enterprise security. Dr. Vickers shares his decades-long journey from early help desk roles to leading complex, mission-critical technology environments under extreme operational constraints.

Dr. Vickers explains how hands-on experience across infrastructure, cybersecurity, and enterprise platforms shaped his disciplined approach to reliability, governance, and secure-by-design systems. He discusses rebuilding fragmented technology organizations, stabilizing legacy platforms, and delivering measurable improvements in uptime, security posture, and operational efficiency.

The conversation explores cybersecurity and AI in production environments, emphasizing identity-first security, data classification, and the importance of human judgment in high-stakes systems. Dr. Vickers outlines why integrity, governance, and people-first leadership are essential when scaling technology responsibly.

Finally, he shares practical advice for technology leaders navigating modernization, AI adoption, and cybersecurity risk—without sacrificing trust, resilience, or business continuity.

Key Takeaways:

  1. How to rebuild and stabilize mission-critical systems without downtime
  2. Why identity and data governance are foundational to cybersecurity and AI
  3. Balancing modernization with legacy system realities
  4. The role of human judgment in secure, AI-enabled environments
  5. Why secure-by-design thinking must start at the leadership level

Golden Nugget:

“Security isn’t something you add later. If systems and teams aren’t built with integrity from the start, speed will eventually work against you.”

Connect with Dr. Glen Vickers:

  1. LinkedIn: linkedin.com/in/drglenvickers

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Dr. Glen Vickers, a technology and cybersecurity leader with global impact across cloud, SaaS, DevOps, and enterprise security. Dr. Vickers shares his decades-long journey from early help desk roles to leading complex, mission-critical technology environments under extreme operational constraints.

Dr. Vickers explains how hands-on experience across infrastructure, cybersecurity, and enterprise platforms shaped his disciplined approach to reliability, governance, and secure-by-design systems. He discusses rebuilding fragmented technology organizations, stabilizing legacy platforms, and delivering measurable improvements in uptime, security posture, and operational efficiency.

The conversation explores cybersecurity and AI in production environments, emphasizing identity-first security, data classification, and the importance of human judgment in high-stakes systems. Dr. Vickers outlines why integrity, governance, and people-first leadership are essential when scaling technology responsibly.

Finally, he shares practical advice for technology leaders navigating modernization, AI adoption, and cybersecurity risk—without sacrificing trust, resilience, or business continuity.

Key Takeaways:

  1. How to rebuild and stabilize mission-critical systems without downtime
  2. Why identity and data governance are foundational to cybersecurity and AI
  3. Balancing modernization with legacy system realities
  4. The role of human judgment in secure, AI-enabled environments
  5. Why secure-by-design thinking must start at the leadership level

Golden Nugget:

“Security isn’t something you add later. If systems and teams aren’t built with integrity from the start, speed will eventually work against you.”

Connect with Dr. Glen Vickers:

  1. LinkedIn: linkedin.com/in/drglenvickers

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>44b931f1-a971-4bf2-acfa-ea3ed0191fd9Wed, 14 Jan 2026 09:00:00 -070029:36falsefull“How Sara Fuerst Went from CTO to CEO While Automating Security and Scaling BeHerVillage”“How Sara Fuerst Went from CTO to CEO While Automating Security and Scaling BeHerVillage”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Sara Fuerst, CTO and Co-Founder of BeHerVillage, founder of TIBSar Software, and a technical leader navigating the transition from CTO to CEO while scaling a mission-driven startup.

Sara shares her journey building BeHerVillage, a baby registry focused on supporting moms rather than just babies, and growing it to nearly $500,000 in gifted funds. She explains how her diverse technical and entrepreneurial background shaped her approach to automation, efficiency, and security.

The conversation explores how Sara leverages AI and automation across content workflows, social media, and technical monitoring, while ensuring the human element remains central. She discusses implementing secure systems, handling cyber threats, integrating third-party services like Cloudflare and DigitalOcean, and the lessons she’s learned prioritizing what to automate in a resource-constrained startup.

Finally, Sara shares her philosophy on AI, balancing human customer service with intelligent automation, and her vision for guiding first-time parents through personalized support and education using technology.

Key Takeaways:

  1. How Sara uses automation to reclaim time and scale operations
  2. Prioritizing automation based on value and human oversight
  3. Approaches to secure AI implementation in small, growing startups
  4. Maintaining human-centered customer service even as AI adoption grows
  5. Lessons learned transitioning from CTO to CEO while building a mission-driven business
  6. Avoiding automation pitfalls, like runaway email loops
  7. Leveraging AI for content creation, brainstorming, and parent guidance

Golden Nugget:

“Perfection is the enemy of progress. Focus on solving your customers’ problems first, automate what frees you to lead, and never let AI replace genuine human connection.”

Connect with Sara Fuerst:

  1. LinkedIn: linkedin.com/in/sarafuerst
  2. Company Website: tibsarsoftware.com
  3. BeHerVillage Instagram: @BeHerVillage
  4. BeHerVillage Website: behervillage.com
  5. Birth Worker Partner Listing: behervillage.com/partners

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Sara Fuerst, CTO and Co-Founder of BeHerVillage, founder of TIBSar Software, and a technical leader navigating the transition from CTO to CEO while scaling a mission-driven startup.

Sara shares her journey building BeHerVillage, a baby registry focused on supporting moms rather than just babies, and growing it to nearly $500,000 in gifted funds. She explains how her diverse technical and entrepreneurial background shaped her approach to automation, efficiency, and security.

The conversation explores how Sara leverages AI and automation across content workflows, social media, and technical monitoring, while ensuring the human element remains central. She discusses implementing secure systems, handling cyber threats, integrating third-party services like Cloudflare and DigitalOcean, and the lessons she’s learned prioritizing what to automate in a resource-constrained startup.

Finally, Sara shares her philosophy on AI, balancing human customer service with intelligent automation, and her vision for guiding first-time parents through personalized support and education using technology.

Key Takeaways:

  1. How Sara uses automation to reclaim time and scale operations
  2. Prioritizing automation based on value and human oversight
  3. Approaches to secure AI implementation in small, growing startups
  4. Maintaining human-centered customer service even as AI adoption grows
  5. Lessons learned transitioning from CTO to CEO while building a mission-driven business
  6. Avoiding automation pitfalls, like runaway email loops
  7. Leveraging AI for content creation, brainstorming, and parent guidance

Golden Nugget:

“Perfection is the enemy of progress. Focus on solving your customers’ problems first, automate what frees you to lead, and never let AI replace genuine human connection.”

Connect with Sara Fuerst:

  1. LinkedIn: linkedin.com/in/sarafuerst
  2. Company Website: tibsarsoftware.com
  3. BeHerVillage Instagram: @BeHerVillage
  4. BeHerVillage Website: behervillage.com
  5. Birth Worker Partner Listing: behervillage.com/partners

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>6d58dccd-e7a5-469f-b814-ff6c179214f4Mon, 12 Jan 2026 09:00:00 -070026:50falsefull“How Mex Emini Went from Scaling iGaming Data Engines to Redefining Decision Intelligence”“How Mex Emini Went from Scaling iGaming Data Engines to Redefining Decision Intelligence”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Mex Emini, Co-Founder of DataFlair.ai and former CTO of Sigma, the world’s largest iGaming festival network. Mex shares how his 16 years in data-driven industries have shaped his belief that insights alone aren’t enough; what matters is what happens after the data.

The conversation explores why most companies stall at dashboards, how broken processes undermine automation, and why decision intelligence must be contextual, outcome-focused, and action-oriented. Mex breaks down how DataFlair.ai turns fragmented data into trusted recommendations, helping businesses move faster, pivot earlier, and make smarter decisions at scale.

Mex also reflects on scaling global teams, deciding when humans stay in the loop, and how AI should amplify talent rather than replace it. He closes with practical guidance for leaders navigating automation, AI adoption, and high-stakes decision-making.

Key Takeaways:

  1. Why dashboards fail to drive real business action
  2. The difference between output and outcome in automation
  3. How contextualized AI recommendations build trust
  4. When to automate and when humans must stay involved
  5. Scaling decision intelligence without automating broken processes

Golden Nugget:

“You can’t automate a broken process. Measure what matters, focus on outcomes, and let AI amplify human judgment.”

Connect with Mex Emini:

  1. Mex’s Profile linkedin.com/in/mexiter
  2. Website about.dataflair.aI

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Mex Emini, Co-Founder of DataFlair.ai and former CTO of Sigma, the world’s largest iGaming festival network. Mex shares how his 16 years in data-driven industries have shaped his belief that insights alone aren’t enough; what matters is what happens after the data.

The conversation explores why most companies stall at dashboards, how broken processes undermine automation, and why decision intelligence must be contextual, outcome-focused, and action-oriented. Mex breaks down how DataFlair.ai turns fragmented data into trusted recommendations, helping businesses move faster, pivot earlier, and make smarter decisions at scale.

Mex also reflects on scaling global teams, deciding when humans stay in the loop, and how AI should amplify talent rather than replace it. He closes with practical guidance for leaders navigating automation, AI adoption, and high-stakes decision-making.

Key Takeaways:

  1. Why dashboards fail to drive real business action
  2. The difference between output and outcome in automation
  3. How contextualized AI recommendations build trust
  4. When to automate and when humans must stay involved
  5. Scaling decision intelligence without automating broken processes

Golden Nugget:

“You can’t automate a broken process. Measure what matters, focus on outcomes, and let AI amplify human judgment.”

Connect with Mex Emini:

  1. Mex’s Profile linkedin.com/in/mexiter
  2. Website about.dataflair.aI

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>376fdfb4-b849-4581-bc73-879613503d91Tue, 06 Jan 2026 00:50:00 -070016:21falsefull“How Todd Merrill Went from Cable Modems to Scaling AI Without Breaking Security”“How Todd Merrill Went from Cable Modems to Scaling AI Without Breaking Security”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Todd Merrill, Partner and Fractional CTO at TechCXO, Global Top 25 Consultant, and AI investor with more than 30 years of experience building mission-critical systems.

Todd shares his journey from holding patents on the first cable modem and deploying software on space-shuttle-launched satellites, to running early AWS production workloads, and now advising startups and enterprises on scaling AI securely. He explains how his background in telecom, cybersecurity, and embedded systems shaped his disciplined approach to reliability and risk.

The conversation explores AI and automation at scale, including why Todd was initially skeptical of large language models and what changed his perspective. He discusses how tool-augmented AI, connected to real enterprise systems, is unlocking hyper-productivity—while also introducing new security and operational challenges.

Finally, Todd shares practical advice for leaders adopting AI, emphasizing human-in-the-loop systems, strong change management, and protecting customer data as non-negotiables when moving fast

Key Takeaways:

  1. How AI has changed the economics of building and scaling software
  2. Why security gets harder as systems become more complex
  3. The role of human-in-the-loop AI in high-stakes environments
  4. Common security shortcuts that put fast-growing companies at risk
  5. Why change management—not technology—derails most transformations

Golden Nugget:

“AI won’t replace people, but it will make capable people dramatically more powerful when security and judgment come first.”

Connect with Todd Merrill:

  1. LinkedIn: linkedin.com/in/toddmerrill
  2. Company: techcxo.com/partners/todd-merrill/

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Todd Merrill, Partner and Fractional CTO at TechCXO, Global Top 25 Consultant, and AI investor with more than 30 years of experience building mission-critical systems.

Todd shares his journey from holding patents on the first cable modem and deploying software on space-shuttle-launched satellites, to running early AWS production workloads, and now advising startups and enterprises on scaling AI securely. He explains how his background in telecom, cybersecurity, and embedded systems shaped his disciplined approach to reliability and risk.

The conversation explores AI and automation at scale, including why Todd was initially skeptical of large language models and what changed his perspective. He discusses how tool-augmented AI, connected to real enterprise systems, is unlocking hyper-productivity—while also introducing new security and operational challenges.

Finally, Todd shares practical advice for leaders adopting AI, emphasizing human-in-the-loop systems, strong change management, and protecting customer data as non-negotiables when moving fast

Key Takeaways:

  1. How AI has changed the economics of building and scaling software
  2. Why security gets harder as systems become more complex
  3. The role of human-in-the-loop AI in high-stakes environments
  4. Common security shortcuts that put fast-growing companies at risk
  5. Why change management—not technology—derails most transformations

Golden Nugget:

“AI won’t replace people, but it will make capable people dramatically more powerful when security and judgment come first.”

Connect with Todd Merrill:

  1. LinkedIn: linkedin.com/in/toddmerrill
  2. Company: techcxo.com/partners/todd-merrill/

Listen Now & Subscribe:

Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>2c501f4d-7ac0-46d3-ba38-ef5b0d4478d3Mon, 05 Jan 2026 09:00:00 -070026:21falsefull“How Sunil Sharma Went from AI and XR Innovation to Transforming Trauma Care”“How Sunil Sharma Went from AI and XR Innovation to Transforming Trauma Care” Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Sunil Sharma, CTO and CEO at a stealth-mode AI MedTech startup focused on XR and data science. Sunil shares his journey from leading data science and platform engineering at companies like Thermo Fisher Scientific and ADP to building systems that scale, innovate, and save lives.

The conversation dives into how his team is transforming the “golden hour” into “golden minutes” for trauma victims, enabling first responders, even non-medical personnel to triage patients effectively in high-stakes environments. Sunil discusses predictive models, XR-enabled glasses that monitor vitals remotely, and hybrid AI systems designed for safety, speed, and accuracy. He also reflects on lessons learned scaling enterprise systems, implementing agile transformations, and building high-quality, actionable AI data pipelines.

Finally, Sunil shares practical advice for leaders developing AI-driven medical solutions, emphasizing collaboration, context-aware AI, and rigorous testing to ensure life-saving impact.

Key Takeaways:

  • How AI and XR compress the “golden hour” in trauma care
  • Designing AI systems for high-stakes environments with robust fail-safes
  • Scaling enterprise-grade systems for speed, precision, and reliability
  • Ensuring data quality and context-awareness in hybrid AI models
  • Lessons from leading innovation labs and accelerating product development cycles
  • The role of humans in AI-assisted decision-making and emergency triage

Golden Nugget:

“Technology can save lives, but it works best when humans remain in the loop. The right AI, in the right hands, can turn minutes into miracles.”

Connect with Sunil Sharma:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]> Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Sunil Sharma, CTO and CEO at a stealth-mode AI MedTech startup focused on XR and data science. Sunil shares his journey from leading data science and platform engineering at companies like Thermo Fisher Scientific and ADP to building systems that scale, innovate, and save lives.

The conversation dives into how his team is transforming the “golden hour” into “golden minutes” for trauma victims, enabling first responders, even non-medical personnel to triage patients effectively in high-stakes environments. Sunil discusses predictive models, XR-enabled glasses that monitor vitals remotely, and hybrid AI systems designed for safety, speed, and accuracy. He also reflects on lessons learned scaling enterprise systems, implementing agile transformations, and building high-quality, actionable AI data pipelines.

Finally, Sunil shares practical advice for leaders developing AI-driven medical solutions, emphasizing collaboration, context-aware AI, and rigorous testing to ensure life-saving impact.

Key Takeaways:

  • How AI and XR compress the “golden hour” in trauma care
  • Designing AI systems for high-stakes environments with robust fail-safes
  • Scaling enterprise-grade systems for speed, precision, and reliability
  • Ensuring data quality and context-awareness in hybrid AI models
  • Lessons from leading innovation labs and accelerating product development cycles
  • The role of humans in AI-assisted decision-making and emergency triage

Golden Nugget:

“Technology can save lives, but it works best when humans remain in the loop. The right AI, in the right hands, can turn minutes into miracles.”

Connect with Sunil Sharma:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>a46f303e-e40e-4f27-9ce2-4c10f8a188eeTue, 16 Dec 2025 09:00:00 -070042:40falsefull“How Bob Fabien “BZ” Zinga Went from Navy Cyber Warfare to Turning Security into a Growth Engine”“How Bob Fabien “BZ” Zinga Went from Navy Cyber Warfare to Turning Security into a Growth Engine”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Bob Fabien “BZ” Zinga, a trusted cybersecurity executive, servant leader, boardroom strategist, and Navy Commander whose career spans defending global military networks and enabling hypergrowth inside AI and SaaS companies. Ranked in the Top 3% of LinkedIn worldwide and the #1 U.S. content creator for #GlobalLeaders and #RiskandResilience, BZ brings a rare blend of military discipline, startup speed, and human-centered leadership.

BZ shares his journey from commanding Navy cyber operations and safeguarding mission-critical global systems to adapting his leadership style for engineering-driven Silicon Valley environments. He opens up about the culture shock of transitioning from authority-based leadership to influence-based leadership and explains why security only matters when it enhances speed, predictability, and trust.

The conversation dives deep into how BZ built security programs that empower developers rather than block them, embedding guardrails directly into engineering workflows to support rapid innovation. He breaks down how he helped an AI automation startup scale 50x in revenue, shorten sales cycles by 39 days, and use security as a competitive advantage to win enterprise customers.

Finally, BZ reflects on the personal evolution required to lead across radically different cultures, balancing mission assurance, business outcomes, relationship-building, and resilience. He shares why the safest path must also be the fastest path and how security becomes a true multiplier for growth when leaders focus on clarity, collaboration, and customer trust.

Key Takeaways:

  • Why modern security must function as a velocity engine, not a barrier
  • How to lead engineering teams through influence, empathy, and credibility
  • The power of embedding security guardrails into high-speed development workflows
  • How security can accelerate sales cycles and drive enterprise revenue
  • A practical framework for risk modeling based on impact, velocity, and blast radius
  • Why relationship-building is a core competency for security leaders
  • How evidence automation and trust signaling create measurable business value
  • Lessons from leading at global military scale and in high-growth startups
  • Why “the safest path must be the fastest path” for responsible innovation

Golden Nugget:

“Security should give your organization the confidence to move faster, not slow it down. When you build the right guardrails, you unlock velocity, trust, and sustainable innovation.”

Connect with Bob Fabien “BZ” Zinga:

  • LinkedIn: linkedin.com/in/bobfabienzinga
  • Website: bobfabienzinga.com
  • Linktree: linktr.ee/bobfabienzinga
  • Creator Spotlight: spotlight.favikon.com/bobfabienzinga/

Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Bob Fabien “BZ” Zinga, a trusted cybersecurity executive, servant leader, boardroom strategist, and Navy Commander whose career spans defending global military networks and enabling hypergrowth inside AI and SaaS companies. Ranked in the Top 3% of LinkedIn worldwide and the #1 U.S. content creator for #GlobalLeaders and #RiskandResilience, BZ brings a rare blend of military discipline, startup speed, and human-centered leadership.

BZ shares his journey from commanding Navy cyber operations and safeguarding mission-critical global systems to adapting his leadership style for engineering-driven Silicon Valley environments. He opens up about the culture shock of transitioning from authority-based leadership to influence-based leadership and explains why security only matters when it enhances speed, predictability, and trust.

The conversation dives deep into how BZ built security programs that empower developers rather than block them, embedding guardrails directly into engineering workflows to support rapid innovation. He breaks down how he helped an AI automation startup scale 50x in revenue, shorten sales cycles by 39 days, and use security as a competitive advantage to win enterprise customers.

Finally, BZ reflects on the personal evolution required to lead across radically different cultures, balancing mission assurance, business outcomes, relationship-building, and resilience. He shares why the safest path must also be the fastest path and how security becomes a true multiplier for growth when leaders focus on clarity, collaboration, and customer trust.

Key Takeaways:

  • Why modern security must function as a velocity engine, not a barrier
  • How to lead engineering teams through influence, empathy, and credibility
  • The power of embedding security guardrails into high-speed development workflows
  • How security can accelerate sales cycles and drive enterprise revenue
  • A practical framework for risk modeling based on impact, velocity, and blast radius
  • Why relationship-building is a core competency for security leaders
  • How evidence automation and trust signaling create measurable business value
  • Lessons from leading at global military scale and in high-growth startups
  • Why “the safest path must be the fastest path” for responsible innovation

Golden Nugget:

“Security should give your organization the confidence to move faster, not slow it down. When you build the right guardrails, you unlock velocity, trust, and sustainable innovation.”

Connect with Bob Fabien “BZ” Zinga:

  • LinkedIn: linkedin.com/in/bobfabienzinga
  • Website: bobfabienzinga.com
  • Linktree: linktr.ee/bobfabienzinga
  • Creator Spotlight: spotlight.favikon.com/bobfabienzinga/

Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>57b520eb-25a1-4991-88c6-be39e5c59ac9Mon, 15 Dec 2025 09:00:00 -070031:39falsefull“How Meade Kincke Became the Recalibrator for Elite Veterans & High-Performance Leaders”“How Meade Kincke Became the Recalibrator for Elite Veterans & High-Performance Leaders”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Meade Kincke, better known as The Recalibrator, a keynote speaker, transformation coach, and trusted advisor to elite veterans, former agency professionals, founders, and Fortune 500 executives from companies like AT&T, eBay, and Yum! Brands.

Meade shares his unconventional journey from hacking in basements to becoming a strategic coach for some of the most disciplined minds in the world. For more than two decades, he has helped special operations veterans transition into meaningful civilian careers, guided executives through high-stakes leadership challenges, and supported entrepreneurs seeking clarity, purpose, and performance at scale.

The conversation dives deep into identity, reinvention, and the psychological reset required to shift from one intense chapter of life to the next. Meade breaks down the emotional realities veterans face when leaving service, describing it as a strange kind of death, and explains how he helps them rebuild purpose, confidence, and direction.

He also unpacks his philosophy on simplicity in engineering and leadership, arguing that the most resilient systems and the most resilient people are the ones built on boredom, consistency, and disciplined fundamentals. Flashy tools do not build trust; predictable systems do.

Meade discusses the importance of environment when working with top performers, explaining why he uses his Pint Test to evaluate whether people should actually work together. Talent matters, but trust, compatibility, and emotional safety matter more. When those elements align, teams move faster, make smarter decisions, and prevent burnout before it starts.

The episode also explores veterans in tech, how companies can better support high-pressure transitions, and why automation, compliance, and security often fail when leaders assume the work is set and forget. Meade emphasizes that real security, whether technical or personal, requires relentless recalibration, not checkboxes.

Finally, Meade shares practical advice for executives, veterans, and founders who are looking to make major shifts in their lives. Whether navigating identity loss, career pivots, or overwhelming leadership responsibility, Meade’s framework helps people slow down, reassess, and rebuild from a place of clarity and strength.

Key Takeaways:

  • Why elite veterans struggle with identity loss after service and how recalibration restores purpose
  • How disciplined curiosity and boring consistency build stronger engineering and leadership systems
  • Why simplicity is more secure than complexity, especially in high-stakes environments
  • How the Pint Test helps leaders build trust-based, high-performance teams
  • Why more companies are hiring fewer people and paying them more to get better results
  • The difference between compliance checkboxes and real security
  • Why major life transitions require psychological decomposition before reconstruction
  • Practical steps for leaders, veterans, and founders seeking clarity, confidence, and direction

Golden Nugget:

“Recalibration is not about starting over. It is about stripping away what no longer serves you so you can rebuild with purpose, discipline, and clarity.”

Connect with Meade Kincke:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Meade Kincke, better known as The Recalibrator, a keynote speaker, transformation coach, and trusted advisor to elite veterans, former agency professionals, founders, and Fortune 500 executives from companies like AT&T, eBay, and Yum! Brands.

Meade shares his unconventional journey from hacking in basements to becoming a strategic coach for some of the most disciplined minds in the world. For more than two decades, he has helped special operations veterans transition into meaningful civilian careers, guided executives through high-stakes leadership challenges, and supported entrepreneurs seeking clarity, purpose, and performance at scale.

The conversation dives deep into identity, reinvention, and the psychological reset required to shift from one intense chapter of life to the next. Meade breaks down the emotional realities veterans face when leaving service, describing it as a strange kind of death, and explains how he helps them rebuild purpose, confidence, and direction.

He also unpacks his philosophy on simplicity in engineering and leadership, arguing that the most resilient systems and the most resilient people are the ones built on boredom, consistency, and disciplined fundamentals. Flashy tools do not build trust; predictable systems do.

Meade discusses the importance of environment when working with top performers, explaining why he uses his Pint Test to evaluate whether people should actually work together. Talent matters, but trust, compatibility, and emotional safety matter more. When those elements align, teams move faster, make smarter decisions, and prevent burnout before it starts.

The episode also explores veterans in tech, how companies can better support high-pressure transitions, and why automation, compliance, and security often fail when leaders assume the work is set and forget. Meade emphasizes that real security, whether technical or personal, requires relentless recalibration, not checkboxes.

Finally, Meade shares practical advice for executives, veterans, and founders who are looking to make major shifts in their lives. Whether navigating identity loss, career pivots, or overwhelming leadership responsibility, Meade’s framework helps people slow down, reassess, and rebuild from a place of clarity and strength.

Key Takeaways:

  • Why elite veterans struggle with identity loss after service and how recalibration restores purpose
  • How disciplined curiosity and boring consistency build stronger engineering and leadership systems
  • Why simplicity is more secure than complexity, especially in high-stakes environments
  • How the Pint Test helps leaders build trust-based, high-performance teams
  • Why more companies are hiring fewer people and paying them more to get better results
  • The difference between compliance checkboxes and real security
  • Why major life transitions require psychological decomposition before reconstruction
  • Practical steps for leaders, veterans, and founders seeking clarity, confidence, and direction

Golden Nugget:

“Recalibration is not about starting over. It is about stripping away what no longer serves you so you can rebuild with purpose, discipline, and clarity.”

Connect with Meade Kincke:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>49f5df9e-b0cd-402b-9d30-1f541bff2931Thu, 04 Dec 2025 09:05:00 -070032:03falsefull“How Brian Shea Went from Defense to Disrupting the AI Industry”“How Brian Shea Went from Defense to Disrupting the AI Industry”Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Brian Shea, a security executive, published author, and trusted leader in security, compliance, and technology. Brian shares his journey from military service to leading technology and security teams at Fortune 50 companies like Bank of America, Microsoft, and Salesforce, and now helping professionals pivot into new career opportunities through AI and “vibe coding.”

The conversation dives into the balance between speed and security in technology, the challenges of AI-assisted coding, and the importance of prompt specificity. Brian reflects on his career path, emphasizing transferable skills, adaptability, and the value of disciplined experimentation. He also explores trust in engineering teams, proactive vs. reactive security, and the role of humans in AI-assisted decision-making.

Finally, Brian discusses his AI startup, inspired by helping his wife’s Pilates business, and shares practical advice for leaders seeking to move fast without breaking things, highlighting ethical and thoughtful approaches to AI implementation.

Key Takeaways:

  • Why balancing speed and security is critical in tech at scale
  • How AI can accelerate coding while requiring disciplined engineering practices
  • The importance of prompt specificity to guide AI output effectively
  • Lessons from a non-linear career: leveraging transferable skills and curiosity
  • Building trust in engineering teams through guardrails, monitoring, and transparency
  • Balancing proactive and reactive security strategies in high-stakes environments
  • Why humans remain essential in AI-assisted decision-making
  • Practical advice for moving fast without breaking systems: plan first, act second
  • The inspiration and vision behind Brian’s AI startup to support career pivots

Golden Nugget:

“AI can do amazing things, but humans are still the final line of defense. Plan carefully, act thoughtfully, and use technology to amplify, not replace, our judgment.”

Connect with Brian Shea:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Brian Shea, a security executive, published author, and trusted leader in security, compliance, and technology. Brian shares his journey from military service to leading technology and security teams at Fortune 50 companies like Bank of America, Microsoft, and Salesforce, and now helping professionals pivot into new career opportunities through AI and “vibe coding.”

The conversation dives into the balance between speed and security in technology, the challenges of AI-assisted coding, and the importance of prompt specificity. Brian reflects on his career path, emphasizing transferable skills, adaptability, and the value of disciplined experimentation. He also explores trust in engineering teams, proactive vs. reactive security, and the role of humans in AI-assisted decision-making.

Finally, Brian discusses his AI startup, inspired by helping his wife’s Pilates business, and shares practical advice for leaders seeking to move fast without breaking things, highlighting ethical and thoughtful approaches to AI implementation.

Key Takeaways:

  • Why balancing speed and security is critical in tech at scale
  • How AI can accelerate coding while requiring disciplined engineering practices
  • The importance of prompt specificity to guide AI output effectively
  • Lessons from a non-linear career: leveraging transferable skills and curiosity
  • Building trust in engineering teams through guardrails, monitoring, and transparency
  • Balancing proactive and reactive security strategies in high-stakes environments
  • Why humans remain essential in AI-assisted decision-making
  • Practical advice for moving fast without breaking systems: plan first, act second
  • The inspiration and vision behind Brian’s AI startup to support career pivots

Golden Nugget:

“AI can do amazing things, but humans are still the final line of defense. Plan carefully, act thoughtfully, and use technology to amplify, not replace, our judgment.”

Connect with Brian Shea:


Listen Now & Subscribe:

Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts.

Powered by cybersecurityprivacy.com

Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

]]>bff33b5d-cf40-4d4a-a60d-062efe2d233fWed, 03 Dec 2025 19:45:00 -070032:43falsefull