Avery Pennarun, co-founder and CEO of Tailscale, describes how organic developer word-of-mouth and technical blogging drove early customer acquisition.
“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 would often get to the front page of Hacker News. I still can't explain why that happens. It's really not a voting block, even though we're accused of that sometimes.”
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More from Avery Pennarun
Insight
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…”
Avery PennarunJun 9, 2025▶ 28:37How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale · PMF Show
Opinion
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.”
Avery PennarunJun 9, 2025▶ 7:53How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale · PMF Show
Insight
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.”
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Opinion
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…”
Avery PennarunJun 9, 2025▶ 10:20How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale · PMF Show
Insight
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.”
Avery PennarunJun 9, 2025▶ 11:43How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale · PMF Show
Disclosure
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.”
Avery PennarunJun 9, 2025▶ 22:52How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale · PMF Show
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