Screaming in the Cloud

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.They get into everything: surviving 100% year-over-year growth, why running on two tailnets at once is pure chaos, and how Tailscale makes “secure by default” feel effortless. Plus, they dig into why FreeBSD firewalls needed some tough love, the uncomfortable truth behind POCs, and even the surprisingly useful trick of turning your Apple TV into an exit node.About Avery: Avery Pennarun is the co-founder and CEO of Tailscale, where he’s redefining secure networking with a simple, Zero Trust approach. A veteran software engineer with experience ranging from startups to Google, he’s known for turning complex systems into approachable, user-friendly tools. His contributions to projects like wvdial, bup, and sshuttle reflect his belief that great technology should be both powerful and easy to use. With a mix of technical depth and dry humor, Avery shares insights on modern networking, internet evolution, and the realities of scaling a startup.Highlights:(0:00) Introduction to Tailscale and Security(00:52) Sponsorship and Personal Experiences(02:07) Technical Deep Dive into Tail Scale(06:10) Challenges and Future of Tail Scale(22:45) Building the Tail Net's API(23:54) Connecting Cloud Providers with Tailscale(25:22) Tailscale as a Security Solution(26:44) Innovations and Future of TailscaleSponsored by: duckbillhq.com

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.Jeremy Price, VP of Technology at Grokability talks with Corey Quinn about how they built a business that makes enough money without chasing endless growth. From why they use simple technology to how they run thousands of separate installations for customers, Jeremy explains what happens when you care more about making a good product than explosive growth.Show Highlights: (00:51) Welcoming Jeremy Price from Grokability(03:34) How Snipe-IT Started With a Bet(05:30) Paying for Software Can Change Everything(07:40) When AWS Competes With Open Source(10:10) Boring Businesses Make Money(15:30) Balancing Hosting Needs and Product Quality(18:00) Pricing That Avoids Big Customer Problems(21:06) Better Than a Google Sheet(27:02) The Psychology of Buying(29:33) Where to Find Jeremy and GrokabilityLinks: https://jermops.com/about/https://www.linkedin.com/in/jeremygprice/https://snipeitapp.com/companySponsored by: duckbillhq.com

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.About Keith TownsendKeith Townsend is an enterprise technologist and founder of The Advisor Bench LLC, where he helps major IT vendors refine their go-to-market strategies through practitioner-driven insights from CIOs, CTOs, and enterprise architects. Known as “The CTO Advisor,” Keith blends deep expertise in IT infrastructure, AI, and cloud with a talent for translating complex technology into clear business strategy.With more than 20 years of experience, including roles as a systems engineer, enterprise architect, and PwC consultant, Keith has advised clients such as HPE, Google Cloud, Adobe, Intel, and AWS. His content series, 100 Days of AI and CloudEveryday.dev, provide practical, plainspoken guidance for IT leaders. A frequent speaker at VMware Explore, Interop, and Tech Field Day, Keith is a trusted voice on cloud and infrastructure transformation.Show Highlights(01:25) Life After the Futurum Group Acquisition(03:56) Building Apps You're Not Qualified to Build with Cursor(05:45)Creating an AI-Powered RSS Reader(09:01) Why AI is Great at Language But Not Intelligence(11:39) Are You Looking for Advice or Just Validation?(13:49) Why Startups Can Risk AI Disasters and AWS Can't(17:28) You Can't Outsource Responsibility(19:52) Business Users Are Scared of AI Too(23:00) LinkedIn's AI Writing Tool Misses the Point(26:42) Private AI is Starting to Look Appealing(29:00) Never Going Back to Pre-AI Development(34:27) AI for Jobs You'd Never Hire Someone to Do(39:09) Where to Find Keith and Closing ThoughtsLinksThe CTO Advisor:  https://thectoadvisor.comSponsor: https://www.sumologic.com/solutions/dojo-aihttps://wiz.io/crying-out-cloud

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.Show Highlights(00:25) Understanding Rubrik and Agent Rewind(00:50) Challenges in AI and Disaster Recovery(01:27) Guest Introduction: Dev Rishi from Rubrik(01:44) The Evolution of AI in Enterprises(02:33) Starting an AI Company: The Backstory(05:10) Generative AI and Its Impact(07:15) Enterprise AI Trends and Challenges(08:56) The Future of Agentic AI(18:03) AI in Customer Support(22:03) Rubrik's Acquisition and AI Strategy(29:30) Launching Rubrik Agent Cloud(31:26) Lessons from Starting a Machine Learning Company(35:25) Conclusion and Contact InformationSponsor:Rubrik: https://www.rubrik.com/sitc

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.Show Highlights:(03:50) Introducing RV(05:12) The RVM vs rbenv Wars and Why They All Break Bundler(09:00) Why Your Mac Still Shows Ruby 3.0.0 in Your Prompt(11:00) The Chef vs Puppet Philosophy Divide(16:30) Installing Ruby in One Second vs 40 Minutes(18:13) Apple’s Ancient System Ruby Problem(22:20) RV’s Incremental Approach (24:23) Is Ruby Dead? (28:44) Why RV Is Written in Rust, Not Ruby(31:10) The Bundler Problem(32:15) The Financial Reality(38:00) Spinel’s Plans to Make Money(39:23) How to Stay In Contact with AndréLinks:André Arko: https://arko.netBlue Sky: https://bsky.app/profile/indirect.ioSpinel Cooperative: https://spinel.coopSponsor: Rubrik: https://www.rubrik.com/sitc