Avery Pennarun
Co-founder & CEO, Tailscale. On 1 show, 1 appearance. The Shows tab opens the full record on each.
founderexecutiveengineerauthor@apenwarr ↗LinkedIn ↗apenwarr.ca ↗
Avery Pennarun is the co-founder and CEO of Tailscale, a mesh VPN platform founded in 2019. Previously, he co-founded Net Integration Technologies, served as a software engineer on Google Fiber, and developed open-source tools including WvDial and Bup.
1shows
1appearances
20statements
1resolved
1supported
0contradicted
100%fully supported
Everything Avery Pennarun said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Pennarun: PLG fails in cybersecurity because users rarely adopt security voluntarily
“It's still pretty rare in the security and network infrastructure space, because very rarely do you get a good PLG motion working in like security for the simple reason that like no person wants security. Voluntarily, right? Most of the time, security is somet…”
Pennarun: A modern equivalent of Microsoft Access does not exist today
“Over time, that model went away, but, like, weirdly, nobody built the Microsoft Access of the future, right? It still doesn't exist today.”
Pennarun: App complexity requires a million users to amortize development costs
“It's so hard to build an app that now you have to amortize the cost over, like, a million users in order to make it worthwhile to build something.”
Pennarun: Deploying LLM-generated apps to the public internet is a security disaster
“The default world where people like ask an LLM to slap something together and then they publish on the public internet, it doesn't seem like a very good idea to me. Right. Right. Like, yes, you can do that. But you're going to get like your stuff broken into i…”
Pennarun: 90% of deploying internal tools is connectivity and security, not building
“And if you're deploying a dashboard, people who have done this at a company, they know that like, 90% of the work is somehow those two things. And then the remaining 10% is actually making the dashboard.”
Pennarun: Tailscale founders rejected building a pure enterprise software company
“Well, one of the realizations we as co-founders had is that we didn't want to be a pure enterprise software company just because of like, eh, that just doesn't sound that fun.”
Pennarun: Tailscale only does enterprise sales for inbound warm leads with internal champions
“And when you're doing this top-down sale, it's only for people who contacted you in the first place. So they're very warm leads. And there's somebody in the company who is what we call an internal champion. Like they really want you to win. Which is super diff…”
Pennarun: NATs and firewalls broke direct device connectivity, forcing cloud intermediaries
“The original internet, the whole point of it was I can connect any device to any other device. And yet, the way evolution has happened with NATs and firewalls and insecurity and logins and passwords and, you know, connect with Google and OAuth and everything e…”
Pennarun: Tailscale grew primarily through word of mouth and Hacker News hits
“And that was the number one way tail scale spread is just through word of mouth. And then yes, we kept on writing blog posts. We, for whatever reason, the early people at tail scale are popular blog post writers that seem to like. We would write something. It …”
Pennarun: Tailscale has more than doubled revenue and users every year
“So we've been more than a hundred percent doubling revenue every year since we started similarly with user count similarly with number of active nodes, and so it's growing really, really fast, and it's continuing to grow really, really fast.”
Pennarun: Tailscale Reached Enterprise Product-Market Fit in Late 2023 or Mid-2024
“You know, I would say we didn't really get to enterprise product market fit until maybe late, late, 20, 23 ish or mid 20, 24, at least for like really big deals.”
Pennarun: Tailscale monetizes when free users bring the product to work
“We have a generous free plan, but it's also people end up bringing it to work to solve all the connectivity problems at work. And that's where our business model is.”
Pennarun: Tailscale Assembled Founding Team Before Picking a Specific Product
“I mean, I started with the name TailScale. I'm like, ah, Somebody's got to do things that make stuff easier. And I guess the initial version was just me going around to my friends saying like, Hey, I'm going to start a startup doing this. What do you think? An…”
Pennarun: Tailscale Built Its First Prototype with WireGuard in Days
“There's this new thing called WireGuard. It just came out. It's a super reliable, super simple VPN. So it'll be perfectly fine to leave on all the time. We can run it only to your banking app. And then we just need to build a little key generator for it that t…”
Pennarun: Pre-COVID corporate VPNs were only provisioned for 20% remote capacity
“All of the VPN servers that these VPNs would connect to were suddenly overloaded because they provisioned them all for like a maximum of 20% of people being out of the office at a time, right?”
Pennarun manually approved hundreds of early Tailscale users by editing source code
“The secret of the waiting list was there was not actually a waiting list. It just sent me an email every time somebody put their email address in this form. And so I've got an email box now with like hundreds of, and I just like, I stayed up for like, Answerin…”
Pennarun: Tailscale raised a $3 million seed round with under $100K ARR
“We raised three million in the seed round. And I think our revenue was like, you know, less than a hundred K and it was from like one, I think one and a half customers.”
Pennarun: Tailscale's peer-to-peer architecture eliminates bandwidth fees, subsidizing its free tier
“Because tailscale makes a direct connection between your devices. We don't have to pay for the bytes, right? It's kind of like obvious in retrospect, but because we don't have to pay for the bytes, all we're paying for is just a little service that helps your …”
Pennarun: Tailscale operated for four years before hiring its first sales leader
“And eventually only at the beginning of 20, 23, four years into the life of the company, did we finally hire a head of sales.”
One line per show, most statements first. The link opens Avery's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 PRODUCT MARKET FITLEDGER | Co-founder & CEO, Tailscale | 1 | 20 | 100% 1/1 | full record on A Product Market Fit Show → |