Tailscale

“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.”

“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…”

“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…”

“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.”

“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…”

“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.”

“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…”

“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…”

“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…”

“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…”

“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.”

“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 …”

“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 …”

“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.”

“Even today we're, like, only now getting into, like, the first million dollar deals, because we're intentionally, like, we start small, we're moving towards enterprise, we're scaling up over time, right?”

“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.”

“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.”