Avery Pennarun on Tailscale's Evolution: From Mesh VPN to AI Security Gateway

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 

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.Show Highlights(00:00) Introduction to Ransomware and Backups(00:25) Welcome to Screaming in the Cloud(00:32) Introducing Rubrik and Annika Gupta(01:26) What Does Rubrik Do?(02:18) Evolution of Backup and Recovery(03:37) Challenges in Cyber Recovery(05:33) Rubrik's Approach to Cyber Resilience(08:44) Importance of Cyber Recovery Simulations(09:40) Security vs. Operational Recovery(11:28) Assume Breach: A New Security Paradigm(14:29) Multi-Cloud Complexities and Security(27:45) Hybrid Cloud and Cyber Resilience(29:25) AI in Cyber Resilience(33:09) Conclusion and Contact InformationAbout Anneka GuptaAnneka Gupta is a senior executive leader with a proven track record of scaling successful B2B SaaS businesses from the ground up. She’s led across product, tech, go-to-market, and operations, always with a customer-first mindset. Known for turning complex challenges into big wins, Anneka brings energy, innovation, and real-world results to every team she leads.She’s been recognized as one of San Francisco Business Times’ Most Influential Women in Business and 40 Under 40, as well as a Rising Star by AdExchanger and Marketing EDGE. Oh, and AdAge once named her one of the Top 10 Digital Marketing Innovators.Linksrubrik.com/sitchttps://www.linkedin.com/in/annekagupta/Sponsor: Rubrik: https://www.rubrik.com/sitc 

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.Show Highlights: (02:36) FinOps Foundation (03:15) FinOps as Marriage Counseling Between Engineering and Finance(06:00) Deana’s Journey From Electrical Engineering to FinOps(12:41) The Performative Nature of Certifications(16:22) AI as Both a Threat and Tool in FinOps(20:41) Why AI Is Flooding the Job Market with Noise(25:09) Why FinOps Is Never Boring Despite Sounding Like It(29:10) The NAT Gateway Problem(33:09) The Generational Divide in Cloud Platform Preferences(37:23) Stay In Contact With Deana SolisAbout Deana Solis: Deana Solis is a senior FinOps engineer with more than 20 years of infrastructure management experience. Recognized as the FinOps Evangelist of the Year by the FinOps Foundation in 2022, she has become a leading voice in driving cloud financial accountability and culture.Beyond her technical expertise, Deana is passionate about humanizing technology. She serves as a FinOps Foundation ambassador and mentor, using her voice to elevate Women in FinOps and underrepresented folks in technology.Her unique journey, from electrical engineering to liberal studies to FinOps, embodies both analytical rigor and emotional intelligence. Deana isn’t just shaping the way organizations think about cloud costs; she’s helping reshape the culture of technology itself.Sponsor: https://www.wiz.io/

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.They discuss what changes when agents spin up environments, why multi-agent workflows feel addictive, and how Ona is solving the scaling and safety challenges behind it.If you’re curious about the next wave of software engineering and how AI will reshape developer tools, this episode is for you.About Chris: Chris Weichel is the Chief Technology Officer at Ona (formerly Gitpod), where he leads the engineering team behind the company’s cloud-native development platform. With more than two decades of experience spanning software engineering and human–computer interaction, Chris brings a rare combination of technical depth and user-centered perspective to the systems he helps design and build.He is passionate about creating technology that empowers people and tackling complex engineering challenges. His expertise in cloud-native architecture, programming, and digital fabrication has earned him multiple publications, patents, and industry awards. Chris is continually exploring new opportunities to apply his broad skill set and enthusiasm for building transformative technology in both commercial and research settings.Show Highlights(00:00) Introduction to Modern Software Interfaces(00:55) Welcome to Screaming in the Cloud(01:02) Introducing Chris Weichel and Ona(02:23) The Evolution from Git Pod to Ona(03:26) Challenges and Insights on Company Renaming(05:16) The Changing Landscape of Software Engineering(05:54) The Role of AI in Code Generation(12:04) The Importance of Development Environments(15:44) The Future of Software Development with Ona(21:31) Practical Applications and Challenges of AI Agents(30:01) The Economics of AI in Software Development(38:11) The Future Vision for Ona(39:41) Conclusion and Contact InformationLinks: Christian Weichel LinkedIn: https://www.linkedin.com/in/christian-weichel-740b4224/?originalSubdomain=deOna: https://ona.com/https://csweichel.de/Sponsor: Ona: https://ona.com/

Brian Scanlan, Senior Principal Engineer at Intercom, the company building Fin.ai, joins Corey Quinn on Screaming in the Cloud to discuss Intercom’s move from AWS Aurora to PlanetScale’s managed Vitess after years of scaling challenges with their Ruby on Rails monolith. He explains how 13 Aurora clusters created operational pain and why PlanetScale’s white-glove, partnership-driven model won out over Amazon’s building-block approach.The discussion also covers Intercom’s volunteer-based on-call system, their pivot to AI agents after ChatGPT’s launch, concerns about the shrinking pipeline of systems engineers, and how companies like PlanetScale and Snowflake are outpacing AWS by delivering superior user experiences.About Brian: Brian is an engineer based in Intercom’s Dublin office. He fixes problems, builds things, and grows people. Show Highlights(01:34) The Digital Clippy Rant(2:16) The Good Chatbot vs. Bad Chatbot (03:51) The AI Chatbot Revolution (04:33) Unexpected Consequences of Good Chatbots (05:42) AI Support vs. Human Support (05:59) The Alexa Problem and Feature Discoverability (19:03) Amazon's Struggles Moving Up the Stack (26:55) The Unix Networking Society Origins (34:43) The Global On-Call Challenge(42:09) LinkedIn: The World's Largest Porn Site LinksIntercom: intercom.comBrian on LinkedIn: https://www.linkedin.com/in/scanlanb/Brian on Bluesky: https://bsky.app/profile/bscanlan.bsky.socialSponsor Wiz - Listen to Crying Out Cloud: wiz.io/crying-out-cloud

AI is rewriting the rules of code review and CodeRabbit is leading the charge. In this featured episode of Screaming in the Cloud, Harjot Gill shares with Corey Quinn how his team built the most-installed AI app on GitHub and GitLab, nailed positive unit economics, and turned code review into a powerful guardrail for the AI era.Show Highlights(0:00) Entrepreneurial Journey and Code Rabbit's Origin (3:06) The Broken Nature of Code Reviews (5:47) Developer Feedback and the Future of Code Review (9:50) AI-Generated Code and the Code Review Burden (11:46) Traditional Tools vs. AI in Code Review (13:41) Keeping Up with State-of-the-Art Models (16:16) Cloud Architecture and Google Cloud Run(18:21) Context Engineering for Large Codebases (20:52) Taming LLMs and Balancing Feedback (22:30) Business Model and Open Source Strategy About Harjot Gill Harjot is the CEO of CodeRabbit, a leading AI-first developer tools company. LinksHarjot on LinkedIn: https://www.linkedin.com/in/harjotsgill/SponsorCodeRabbit: https://coderabbit.link/corey