Insightful conversations. Less snark.

When your website stops working at 3 AM, you need to answer one question fast: Is it my code or is a big cloud provider having problems? Omri Sass from Datadog explains updog.ai, a tool that monitors whether major services like AWS, CloudFlare, and others are actually working. Instead of asking people to report problems like Down Detector does, updog uses real data from thousands of computers to detect when services go down. Omri shares why this took 6 years to build, how they process massive amounts of data with machine learning, and why cloud providers have been strangely upset about these tools existing.

Hunter Leath, CEO of Archil, spent 8 years building Amazon's EFS file storage system, learning exactly why making cloud storage act like a hard drive always fails. Old programs need hard drives, but cloud storage doesn't work like hard drives—a problem that's existed for 20 years.

When AWS has a major outage, what actually happens behind the scenes? Ben Hartshorne, a principal engineer at Honeycomb, joins Corey Quinn to discuss a recent AWS outage and how they kept customer data safe even when their systems couldn't fully work. Ben explains why building services that expect things to break is the only way to survive these outages. Ben also shares how Honeycomb used its own tools to cut their AWS Lambda costs in half by tracking five different things in a spreadsheet and making small changes to all of them.

R. Tyler Croy, a principal engineer at Scribd, joins Corey Quinn to explain what happens when simple tasks cost $100,000. Checking if files are damaged? $100K. Using newer S3 tools? Way too expensive. Normal solutions don't work anymore. Tyler shares how with this much data, you can't just throw money at the problem, but rather you have to engineer your way out.

Corey Quinn sits down with Avery Pennarun, co-founder and CEO of Tailscale, for a deep dive into how the company is reinventing networking for the modern era. From finally making VPNs behave the way they should to tackling AI security with zero-click authentication, Avery shares candid insights on building infrastructure people actually love using, and love talking about.

Most open source companies do the same thing. They take investor money, lock their best features behind paywalls, sell the company, and disappoint everyone. Grokability did something different.

Corey Quinn reconnects with Keith Townsend, founder of The CTO Advisor, for a candid conversation about the massive gap between AI hype and enterprise reality. Keith shares why a biopharma company gave Microsoft Copilot a hard no, and why AI has genuinely 10x’d his personal productivity while Fortune 500 companies treat it like radioactive material. From building apps with Cursor to watching enterprises freeze in fear of being the next AI disaster in the news, Keith and Corey dig into why the tools transforming solo founders and small teams are dead on arrival in the enterprise, and what it'll actually take to bridge that gap.

In this episode of Screaming in the Cloud, Corey Quinn sits down with Rubrik’s GM of AI, Dev Rishi, to unpack the real story behind enterprise AI adoption, the rise of agentic systems, and why most organizations are still stuck in read-only mode. Dev breaks down how Rubrik’s Agent Rewind brings safety, observability, and resilience to AI-driven actions, solving the “Oh no, the agent deleted production data” problem before it happens. From deep learning’s evolution to the massive gap between consumer AI enthusiasm and enterprise risk posture, this conversation is a candid, insightful look at the AI future Global 2000 companies are racing toward… or cautiously tiptoeing into.

André Arko, CEO of Spinel Cooperative and longtime Bundler maintainer, joins Corey Quinn to introduce RV, a new Ruby tool that installs Ruby in one second instead of 10-40 minutes by using precompiled binaries. Inspired by Python's UV, RV aims to simplify Ruby dependency management without the complexity of older tools like RVM and rbenv. They talk about why Ruby isn't actually dead, Apple's problem with shipping a five-year-old end-of-life Ruby in macOS, and the challenges of writing dependency managers in the language they manage. André also shares how he transitioned from a struggling nonprofit model to a cooperative that charges companies for expertise, proving that open source maintainers can build sustainable businesses without relying on donations.

When attackers are smart enough to hit your backups, recovery becomes your best defense. Rubrik’s Chief Product Officer, Anneka Gupta, joins host Corey Quinn to break down what true cyber resilience looks like in today’s multi-cloud world. From AI-driven recovery to surviving ransomware with your data (and reputation) intact, this episode covers what it really takes to bounce back when everything goes sideways.

Deana Solis, 2022 FinOps Foundation Evangelist of the Year, joins Corey Quinn to discuss her winding career path from electrical engineering to healthcare IT to FinOps. She shares why certifications are "largely performative," warns that AI can turn your AWS bill into "a telephone number," and explains why NAT Gateway costs hit everyone from hobbyists to enterprises. The episode covers cloud repatriation conspiracy theories, translating between engineering and finance teams, and why good FinOps work is really just getting humans in a room to talk.

On this episode of Screaming in the Cloud, Corey welcomes back Chris Weichel, CTO of Ona (formerly Gitpod). Chris explains the rebrand and why Ona is building for a future where coding agents, not just humans, write software.