Automate or Die Trying

Episode Summary Everyone wants faster automation and better AI outcomes, but few organizations stop to examine the data foundations underneath them. In this episode of Automate or Die Trying , host Will talks with Keith Belanger about why acceleration alone is not a strategy—and why AI will amplify both the strengths and weaknesses already present in your data ecosystem. Drawing on three decades o...

Episode Summary: In this episode of Automate or Die Trying , host Wil Ramos sits down with Christopher Moravec , CTO and founder of Dymatic, to explore what it actually looks like to deploy AI agents into real-world government, GIS, and public sector workflows. Christopher shares how Dymatic helps cities and agencies modernize permitting, infrastructure management, zoning feedback, and operational...

Episode Summary: In this episode of Automate or Die Trying , host Wil Ramos sits down with Lawrence Pingree, Head of Security and AI Research at SACR (Software Analyst Cyber Research), to explore how AI agents are fundamentally reshaping cybersecurity, governance, and enterprise defense strategies. Lawrence shares insights from a career spent defining major cybersecurity categories including EDR,...

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-l...

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 ho...

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...

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 criti...

Episode Summary: In this episode of A utomate 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 deve...

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 s...

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, automate...

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 h...

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...

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 ri...

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...

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 ven...

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...

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 n...

Episode Summary: In this episode of A utomate 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. Vick...

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...

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 compani...

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 runn...

  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...

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 #Globa...

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 base...

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...