The Cloud Gambit Podcast unravels the state of cloud computing, markets, strategy, and emerging trends. Join William Collins and Eyvonne Sharp for valuable conversations with industry mavens that educate and empower listeners on the intricate field of innovation and opportunity.
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William Collins and Eyvonne Sharp dig into the latest AI headlines, from the largest copyright settlement in American history to stolen AI models and invisible watermarks on Claude output. Plus, they discuss why so many companies have rallied around NVIDIA’s support for open weight AI models. Our hosts also examine the biggest questions arising from... Read more »
William Collins is joined by guest co-host Eric Chou as well as Network Automation Forum founders Scott Robohn and Chris Grundemann to discuss how their community emerged from a simple question: Why haven’t we seen full adoption of network automation, yet? They discuss the growth of AutoCon and how its practitioner-focused, vendor-neutral approach has fostered... Read more »
What if your MCP server shipped with its own manual? Angie Jones, VP of Developer Experience at the Agentic AI Foundation, joins William and Eyvonne to break down the Skills Over MCP working group effort, which delivers Agent Skills through MCP’s existing resources primitive (think voice over IP, not skills versus MCP). Angie shares her... Read more »
Malcolm Matalka joins William and Eyvonne to challenge the narrative that Infrastructure as Code (IaC) is dead. Malcolm argues that the real value of IaC was never the syntax, but state and governance. Together they examine whether the state was a file problem at all, or a distributed systems problem in a JSON costume. Episode... Read more »
The Pope issued a recent encyclical on AI, urging developers to safeguard human agency in the age of artificial intelligence. Eyvonne and William explore this encyclical, moving beyond the headlines to the core message regarding human dignity. They examine how the document provides a values-based framework for evaluating technology and the need for a balanced... Read more »
William and Eyvonne discuss recent tech news, including the growing political and community opposition to AI data centers driven by fears over power and water usage. They also analyze the “AI Chip War” as hyperscalers such as AWS and Google invest in specialized silicon for training and inference. Episode Links: Amid backlash, O’Leary Digital CEO... Read more »
Today our Packet Pushers team assembles to discuss whether the grass is greener on the NetOps or DevOps side of the telemetry fence. William of The Cloud Gambit, Scott of Total Network Operations, and Ned and Kyler of Day Two DevOps discuss the difficulties and differences of getting telemetry and state from devices across different... Read more »
Eyvonne and William sit down with Joseph Nicholson, a Network Operations Engineer with NTT DATA, to share how public speaking transformed his career and technical experience. Joseph went from a terrifying ten minute lightning talk at AutoCon 2 to presenting 45-minute sessions at conferences like NANOG. Together they discuss how conversations in conference halls influenced... Read more »
Eyvonne Sharp and William Collins speak with Sif Baksh, Principal Solutions Architect at Tines, to discuss the power of automation. Sif shares some personal stories of how he has been able to use automation to innovate and modernize networking operations. They also discuss the importance of learning AI and using it as a tool, how... Read more »
Vibe coding: give AI a description of what you want, the model writes the code, you ship it, and then you hope for the best. It works great for side projects, but it can fall apart the moment you point an AI agent at production infrastructure. Today, William and Eyvonne sit down with John Capobianco,... Read more »
William Collins and Eyvonne Sharp invite Skylar Sands, Senior Automation Engineer at World Wide Technology, to discuss what it means to integrate AI into the daily workflow in a meaningful way. Together they break down the shift in the automation engineer’s role now that AI can instantly generate the “toolkit” of Python, Ansible, and Bash,... Read more »
The tech industry is split between two fantasies – that AI writes production software while you get coffee, and that everything AI touches is slop. The reality is messier and more interesting: AI tools are force multipliers for people who already know what good looks like, and an expertise amplifier disguised as an easy button. ... Read more »
William and Eyvonne tackle the biggest AI stories of early 2026. They dissect Matt Schumer’s viral “Something Big is Happening” essay – agreeing professionals need to skill up now while pushing back on the doomsday framing with real-world examples from engineering disciplines. The conversation takes a fascinating turn as Eyvonne draws a parallel between AI-assisted... Read more »
We’ve spent a decade figuring out how to (more or less) securely authenticate humans. Now AI agents are crashing the party, and identity just got a whole lot more complicated. Today we sit down with Dan Moore, Senior Director of CIAM Strategy and Identity Standards at FusionAuth, to explore the collision course between artificial intelligence... Read more »
In this episode, we sit down with Adam Zimman, author and VC advisor, to explore the world of progressive delivery and why shipping software is only the beginning. Adam shares his fascinating journey through tech—from his early days as a fire juggler to leadership roles at EMC, VMware, GitHub, and LaunchDarkly – and how those... Read more »
The industry has pivoted from scripting to automation to orchestration – and now to systems that can reason. Today we explore what AI agents mean for infrastructure with Chris Wade, Co-Founder and CTO of Itential. We also dive into the brownfield reality, the potential for vendor-specific LLMs trained on proprietary knowledge, and advice for the... Read more »
In this year-end episode, William and Eyvonne recap their experiences at AutoCon 4 in Austin, Texas. They discuss the conference’s new multi-track format, including Eyvonne’s presentation in the leadership track on why technical projects fail. The conversation dives into how AI tools like Google Gemini can augment – not replace – human creativity, from research... Read more »
In this sponsored episode recorded live at AutoCon 4 in Austin, we sit down with Peter Sprygada, Chief Architect at Itential, to discuss Itential’s on-stage announcement of FlowAI. Peter shares his journey from network engineering skeptic to AI advocate, explaining how Itential securely connects AI agents to infrastructure with enterprise-grade governance and traceability. We dive... Read more »
Recorded live at AutoCon4, William Collins and Eyvonne Sharp join forces with John Capobianco for some in the moment thoughts and reflections on the AutoCon experience – from the in-person connections to the workshops to the stage presentations. John gives us the inside story on his very own workshop and the latest version releases in... Read more »
Today we delve into the tech expertise deficit and why technical depth and decades of doing the work matter more than social media followers and content creation hype. Our guest is Russ White, engineer, author, teacher, and certification developer. We begin with current events in AI, and then investigate the differences between career and influence... Read more »
Join William Collins and Evyonne Sharp as they catch up on all things AI. They discuss the AI bubble and how it relates to venture capital, stock, and company evaluations. They talk about the AI experience for the average person, the adoption rate of AI tools, and how the AI infrastructure buildout might affect the... Read more »
Michael Reid went from studying aerospace engineering to becoming CEO at Megaport, a global network-as-a-service platform. How did he get there, and what can we learn from his journey? We walk his career path, including a pivotal role scaling ThousandEyes from 74 million to over 2.4x ARR post-acquisition, and how those experiences shaped his approach to... Read more »
Network automation has a data problem. Traditional tools may hit limitations when managing complex infrastructure relationships. We explore how OpsMill’s InfraHub uses graph databases and temporal versioning to create what our guest calls “the knowledge graph of infrastructure” – enabling true version control at the database level while maintaining the flexibility to model anything from... Read more »
In this deep dive episode, we explore the evolution of networking with Avery Pennarun, Co-Founder and CEO of Tailscale. Avery shares his extensive journey through VPN technologies, from writing his first mesh VPN protocol in 1997 called “Tunnel Vision” to building Tailscale, a zero-trust networking solution. We discuss how Tailscale reimagines the OSI stack by... Read more »
John Capobianco is back! Just months after our first Model Context Protocol (MCP) discussion, John returns to showcase how this “USB-C of software” has transformed from experimental technology to an enterprise-ready solutions. We explore the game-changing OAuth 2.1 security updates, witness live demonstrations of packet analysis through natural language with Gemini CLI, and discover how... Read more »
