The Everything Feed - All Packet Pushers Pods TCG058: Creating the Internet Layer That Should Have Been With Avery Pennarun
Sep 17, 2025
Avery Pennarun, co-founder and CEO of Tailscale, shares his journey from creating his first mesh VPN to revolutionizing modern networking. He discusses how Tailscale aims to enhance the OSI model by introducing a new internet layer and its innovative use of WireGuard. The conversation reveals insights into Tailscale’s unique full-mesh architecture and how DERP relays facilitate NAT traversal. Avery also delves into the impact of AI on networking, identity delegation, and the practicalities of implementing zero-trust models.
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Early Dial-Up And First ISP Job
- Avery recounted getting his first dial-up through a university Freenet and networking a 386 and 486 to share one modem.
- He later worked for the first commercial ISP in Thunder Bay while still in high school, gaining hands-on internet experience.
Focus On Small-Scale Needs Wins Big
- Tailscale targets the majority of apps that never need internet-scale by simplifying connectivity and security for small internal tools.
- Solving the top two pains (connectivity and security) created unexpected product-market fit in corporate VPNs.
An Extra Layer To Restore IP's Role
- Tailscale intentionally adds a new tunneling layer that re-implements the internetwork (OSI layer 3) on top of existing IP.
- This layer restores global reachability and adds identity and security missing from IPv4/IPv6 rollouts.