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 Tailscale

Sponsored by:
duckbillhq.com

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

Screaming in the Cloud

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