From building Linux drivers as a teenager to rethinking how networks should work, it’s a story about following an idea, sometimes obsessively, until it becomes infrastructure.
Below, we’ve pulled together the most pivotal moments from Avery’s recent Stratechery interview with Ben Thompson. It’s a tale of sibling rivalry, dusty modems, open-source detours, and a vision for a better Internet. You can read the full Stratechery interview here. And now, on with our origin story…
Sibling rivalry, serial cables, and a 386 that moonlighted as a router.
Like many great engineers, Avery's journey started with a simple problem: his sister wanted the modem too.
“We both really wanted to use it at the same time... I was playing with this thing called Linux, and I found out there was networking stuff inside. If you fiddled with enough settings, you could connect two computers through one modem and make it work.”
It wasn’t long before “just figuring it out” turned into writing Linux drivers for arcane network cards that hadn’t seen attention since 1980.
“I was in grade 10, trying to learn how to write network drivers. It turned out to be surprisingly doable.”
“These cards were so old and simple, they were a great platform to learn on. And because I was a high school student with nothing better to do than write a Linux driver, my tech support turnaround time was amazing.”
This wasn’t tinkering for the sake of it — this was a necessary tool to outsmart time-sharing rules with his sister. A surprisingly durable motivation.
Dial-up sharing appliances, zero support calls, and how a co-op job turned into IBM money.
At university, that same itch to make the network work better turned into Net Integration Technologies. The product? A box that let small offices share a single Internet connection—no IT team (or pesky siblings) required.
“We wanted something that was plug-and-play, zero tech support. And it worked. Too well, actually — people kept calling to buy more.”
The company scaled, got acquired by IBM, and taught Avery one very clear lesson: ease of use is strategy. Especially when your users have better things to do than figure out VPN configs.
From cheque processing to Google Fiber, and the moment Avery realized scale was overrated.
After a few stops — including a stint in fintech building secure check-processing systems—Avery landed at Google, first in payments, then in infrastructure. That’s where the contrast really hit him.
“Even small projects at Google needed big DevOps teams. Everyone was copying Google’s scale — but most people don’t need Google scale.”
Avery says, if infrastructure makes it harder to prototype, you’ve done it wrong.
“Tailscale, the name, came before the company. I wanted something that was the opposite of ‘Internet-scale.’ I’m more interested in solving the long tail of small problems that everyone has — the ones that don’t need Google-scale infrastructure.”
A VPN nobody hates
The real-world spark for Tailscale came from an old colleague at a Canadian bank with a now-familiar problem: how do you secure access without rewriting everything?
“We figured, what if we just move the servers to a separate network, and force a 2FA-enabled VPN tunnel to reach them? Then every server has 2FA.”
When Avery went looking for the tool to do that — he couldn’t find it. So he built it.
Tailscale launched quietly. Then loudly.
“We posted a blog, it hit the front page of Hacker News, and I stayed up for more than 24 hours activating accounts manually, replying to every email. That’s how I knew we were onto something — people really wanted this.”
Building the Internet, again
Tailscale isn’t just a VPN. It’s not even just a tool. It’s infrastructure — new infrastructure — for a world where you expect your phone, your laptop, your robot lawnmower, and your office NAS to all just work together.
“An actual customer once told me, ‘Tailscale makes the Internet work the way I thought it worked… until I learned how it actually worked.’ That’s the goal.”
That vision — of simple, secure, peer-to-peer networking — has resonated. With hobbyists wiring up Airbnbs and remote cabins. With CTOs at banks. With mobile devs, IT teams, even RV clubs.
Today, Tailscale powers millions of devices across 10,000+ organizations.
And it all started with a sibling squabble over a modem.
For the full conversation (trust us, it’s worth it), head to the Stratechery interview.
Or go install Tailscale. It takes less time than reading this post.
Will Moore
