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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.
20 Episodes
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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 »
In this sponsored episode, FluidCloud co-founders Sharad Kumar and Harshit Omar sit down with William and Eyvonne to discuss how FluidCloud tackles multi-cloud portability. They detail how FluidCloud acts as a cloning platform that scans an existing cloud or VMware environment, extracts complex infrastructure configurations (including compute and storage, as well as firewall rules and... 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 »
In this unplanned and unfiltered conversation, we dive deep into network automation realities with Ivan Pepelnjak, networking’s long standing and independent voice from ipSpace.net. We explore why automation projects fail, dissect the tooling landscape (Ansible vs. Terraform vs. Python), and discuss the cultural barriers preventing enterprises from modernizing their networks. Ivan delivers hard truths about... Read more »
Today we explore how to build sustainable tech companies with Brian Pontarelli, Founder of FusionAuth. Brian shares his path from early programming on an Apple IIe to creating innovative solutions in the complex world of customer identity and access management (CIAM). Brian argues that single-tenancy and local development capabilities are crucial for developers. He also... Read more »
How is Infrastructure-as-Code (IaC) evolving? How does user experience fit in? Today on The Cloud Gambit, Cory O’Daniel, Co-Founder & CEO of Massdriver, lends his experience as a coder, architect, and founder to help us answer these questions. Cory also discusses what it was like building and funding a startup in the 2021-2022 market, the... Read more »
The Cloud Gambit is joining the Packet Pushers network! Launched in 2023 as an independent podcast, The Cloud Gambit cuts through the hype to deliver what actually matters in cloud and AI. Hosts William Collins and Eyvonne Sharp decode the strategies, technologies, and market forces reshaping enterprise infrastructure. Built for engineers who lead, leaders who... Read more »
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