At Web Summit Vancouver, Tailscale CEO Avery Pennarun told BetaKit’s Josh Scott that the pressure to adopt AI has created a “Wild West” for corporate cybersecurity.
The statement stood out for the obvious reason, but also because it’s rare to find founders with both the technical chops and the capacity to articulate those chops in a way that’s accessible to the average person.
“That’s the literal term several CISOs have used with me unprompted: ‘ticking time bomb.’ There’s no world in which this doesn’t explode the way it’s done right now.”
Avery Pennarun
Tailscale
I made a mental note to connect with Pennarun at ALL IN, Canada’s most prominent AI conference (BetaKit is an official media partner). Fortunately, Pennarun happened to be on the panel I was moderating at the conference, so I was able to convince him to explore the Wild West with me in podcast form.
The journey begins with the Model Context Protocol (MCP), an open source framework that standardizes how large language models and AI agents connect to external tools, data, and systems. MCP has become incredibly popular in a short period of time—so short that many companies are deploying without the requisite security and privacy steps.
Pennarun thinks the AI revolution has put a gun to the head of CISOs: embrace unsafe data practices or get fired. Those same CISOs have told him the false choice has created a “ticking time bomb.”
It’s a troubling circumstance, but not all bad news. The agentic AI explosion has put Tailscale in a position to provide significant value, leveraging its core skill of connecting any device anywhere to essentially become an air traffic control system for any agent accessing and acting on corporate data.
The thing is, knowing where the planes are going is important, but not as important as ensuring they land safely. Pennarun says all the current security protocols are still relevant in an AI era; they just need to be built into new tools.
Which leads to Pennarun’s pitch at the heart of this podcast: build the AI tools that will be “worth billions,” so Tailscale isn’t forced to. Who will answer the call?
Let’s dig in.
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Recorded live at ALL IN. Feature image courtesy Tailscale.