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 »