Tailscale is a company that provides a zero-configuration and software-defined mesh VPN based on WireGuard that enables secure, direct, peer-to-peer connectivity between devices, servers, and cloud resources. Pulse 2.0 interviewed Tailscale co-founder and CEO Avery Pennarun to learn more.
Avery Pennarun’s Background
Could you tell me more about your background? Pennarun said:
“I grew up in Thunder Bay, Ontario, where the winter is long, and the Internet was originally a dial‑up line in the corner of a room. In university, I co‑founded Net Integration Technologies to make networking ‘just work’ for small businesses; IBM acquired it later. I spent seven‑plus years at Google on things like Google Wallet and Google Fiber, learned a lot about scale, and then intentionally built Tailscale to solve the opposite problem: the long tail of everyday networking.”
Formation Of The Company
How did the idea for the company come together? Pennarun shared:
“A Canadian bank needed phishing‑resistant 2FA for a Windows client app that nobody wanted to rewrite. We glued modern identity (SSO) to WireGuard and made a network you log into instead of babysitting. It worked so well for that ‘one weird trick’ that we repackaged it for everyone and Tailscale was born. Today my job is keeping the product small and coherent, picking the right “no’s,” and making sure we never break what customers already depend on.”
Favorite Memory
What has been your favorite memory working for the company so far? Pennarun reflected:
“The night our launch blog post hit #1 on Hacker News, my inbox turned into a firehose. I spent 24 hours straight manually approving accounts and emailing early users for feedback. That was when it clicked that this wasn’t just a bank solution — it was a new way to think about private networking.”
Core Products
What are the company’s core products and features? Pennarun explained:
“Tailscale is a secure mesh network built on WireGuard with SSO‑based identity. Key features include MagicDNS (human‑readable names for your devices), Funnel (one‑click, secure sharing to the public Internet when you need it), device posture checks (integrations with endpoint tools to gate sensitive access), and node sharing across tailnets. Most importantly, connections are peer‑to‑peer, end‑to‑end encrypted, and avoid centralized relays for speed and privacy.”
Challenges Faced
Have you faced any challenges in your sector recently? Pennarun acknowledged:
“Security buyers want power; developers want simplicity. Balancing those is hard. We tackled it by staying bottom-up and adding the minimum enterprise surface area, things like posture checks and better admin controls, without turning the product into a maze. We also formalized “lightweight sales” to hear blockers earlier while keeping product led growth at the core.”
Evolution Of The Company’s Technology
How has the company’s technology evolved since launching? Pennarun noted:
“Under the hood we’ve iterated the protocol relentlessly while keeping old clients working. We added identity‑aware policy, posture, better NAT traversal, and ways to safely share resources across teams. The north star is unchanged: you install Tailscale, log in, and your devices can talk as if they’re on the same LAN — without the usual setup headaches.”
Significant Milestones
What have been some of the company’s most significant milestones? Pennarun cited:
“Crossing 20,000 paying business customers and hundreds of thousands of weekly active users felt like a proof point for developer‑led networking. Shipping MagicDNS and Funnel showed we can make the “New Internet” feel like the old one — simple and personal — without compromising security.”
Customer Success Stories
Can you share any specific customer success stories? Pennarun highlighted:
“We see three common arcs: (1) A single engineer uses Tailscale at home, then connects a small team at work, then it grows company‑wide. (2) A security team replaces a brittle hub‑and‑spoke VPN with policy‑driven, identity‑first access and cuts support tickets. (3) An ops team uses Tailscale for machine‑to‑machine, Kubernetes clusters, labs, or fleets, and gets reliable connectivity without opening holes to the Internet.”
“We have a lot of success stories from remote access VPN replacement to managing automated robotics from anywhere in the world. It’s hard to pick just a couple.”
Funding/Revenue
Are you able to discuss funding and/or revenue metrics? Pennarun revealed:
“We are backed by some of the biggest names in the VC world – firms like Accel, CRV, Heavybit, Insight Partners and Uncork Capital. We raised our Series C in 2025. We don’t share revenue figures publicly. What I can say: growth has been durable and mostly inbound; churn is low; and we continue to invest ahead of demand while keeping the product surface small. The model works because networking has real network effects — each new teammate makes Tailscale more useful.”
Total Addressable Market (TAM)
What total addressable market (TAM) size is the company pursuing? Pennarun assessed:
“I don’t love spreadsheet TAM theater. Practically, our market is ‘any device that should talk to any other device securely,’ which keeps expanding: developers, small businesses, enterprises, AI agents, and IoT fleets. If it runs an IP stack and has an identity, it’s in scope.”
Differentiation From The Competition
What differentiates the company from its competition? Pennarun affirmed:
“Peer‑to‑peer by default, identity‑first, and unbelievably easy to start. Traditional VPNs force all traffic through a choke point and layers of config; we orchestrate direct, encrypted paths and let your SSO be the source of truth. That combination means less latency, fewer foot‑guns, and a product developers actually choose voluntarily.”
Future Company Goals
What are some of the company’s future goals? Pennarun emphasized:
“Make inter‑company sharing as easy as intra‑company: policy‑driven, identity‑aware links across tailnets. Keep hardening posture and machine‑to‑machine use cases without adding cognitive load. And hold the line on backward compatibility so people can build on Tailscale like a platform — not a moving target. Ultimately, we believe the Internet needs rebuilding, with a different approach that is actually the same as it started, and to do that, we need to have everyone in the world using Tailscale. It’s a vision, but also something very much achievable.”
Additional Thoughts
Any other topics you would like to discuss? Pennarun concluded:
“I get asked a lot about whether Tailscale is looking to be acquired or has had offers. The short answer is no, the long answer is that most acquisitions don’t make products better; they make roadmaps fuzzier. Our plan is to stay anobsessively refined core that other tools can build on. Think plumbing, not a palace. If we do our job right, the Internet feels like it used to — simple, safe, and personal — except it works for everyone this time.”
