this post was submitted on 09 Jun 2025
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Corporate VPN startup Tailscale secures $230 million CAD Series C on back of “surprising” growth

Pennarun confirmed the company had been approached by potential acquirers, but told BetaKit that the company intends to grow as a private company and work towards an initial public offering (IPO).

“Tailscale intends to remain independent and we are on a likely IPO track, although any IPO is several years out,” Pennarun said. “Meanwhile, we have an extremely efficient business model, rapid revenue acceleration, and a long runway that allows us to become profitable when needed, which means we can weather all kinds of economic storms.”

Keep that in mind as you ponder whether and when to switch to self-hosting Headscale.

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[–] Trainguyrom@reddthat.com 2 points 1 day ago

Realistically Tailscale seems to currently be running on a model of get all of the self hosters to love running it at home so then they advocate to run it at work where all of the pricey enterprises licenses make the real money.

I've actually seen some real world usecases where if I had more political push, I would've put Tailscale onto the running as a potential solution

Hopefully they have the right people in place to push back at the VC firms about maintaining their current strategy rather than scaring away all of their best advocates before they can truly get off the ground. Having worked at a company owned by a hedgefund, part of the trick is having the right people in place in the company who can block the worst decisions by the capital-hungry owners