Last week, several of us from Tailscale, including our CEO Avery Pennarun, headed to Vancouver for Web Summit — the first time the event has ever been hosted in Canada.
Personally, this was my first visit to Vancouver — and what a city! It felt like stepping into the future: electric buses humming quietly down hyper-modern streets, cutting-edge architecture at every corner, and seaplanes gracefully landing amid breathtaking vistas. Honestly, it wouldn't have surprised me to see flying cars zooming overhead or a bio-fueled rocket launching from a nearby mountain.
But we weren’t just there to admire the views. Avery took to the stage twice at Web Summit: first, a main-stage discussion alongside Ivan Zhang, co-founder of Cohere, on securing the future of AI; and then, a fireside chat with journalist Rob Pegoraro, digging into how we can build a simpler, safer internet — with some nostalgic jokes about Trumpet Winsock thrown in for good measure.
Both sessions were insightful, and you can catch the recordings below. Here are a few standout points that resonated:
- 1. AI Security: Slow Down to Speed Up Everyone is racing to integrate AI, but speed often leads to careless practices — like exposing sensitive APIs on the public internet. Avery emphasized that proper security isn’t just about software — it’s fundamentally about network isolation. As Ivan highlighted, secure AI adoption means providing safe, isolated environments where engineers can experiment without risking data leaks.
- 2. Treat AI Like a Very Enthusiastic Intern Avery offered a vivid analogy: think of AI as a high-energy, slightly naive intern. It’s eager to help but can inadvertently wreak havoc if not carefully managed. The key takeaway? Provide AI the right guardrails — limit access appropriately, audit its actions, and don’t rush to grant it full permissions. Incremental trust building is essential.
- 3. Multicloud Realities: AI’s Infrastructure Challenge Due to GPU shortages and cost factors, AI workloads are increasingly distributed across multiple clouds. This creates complex connectivity challenges, exactly the kind Tailscale solves by securely bridging disparate environments. Avery noted that while multicloud setups add complexity, having secure, seamless connectivity is crucial — and fortunately, Tailscale is uniquely positioned to help.
Beyond the talks, our team had a packed agenda. We sat down with journalists covering Canadian innovation, growth, and the future of AI — anyone else deep-diving into MCPs? Face-to-face discussions with industry analysts always provide invaluable perspectives.
We also hosted a VIP dinner in partnership with Web Summit, bringing together many exceptional CEOs, CTOs, and engineering leaders. Over delicious food and drinks, conversations flowed freely; from the complexities of leading people organizations through rapid growth and change, to the personal development required to navigate current and future challenges. We may not have solved every networking problem (the kind over dinner, and over the wire) in one night, but judging by the feedback, we're definitely a step closer!
Between events, we even squeezed in a rooftop soirée with 360-degree city views, connected with great people at the local AT Protocol/Bluesky meetup, and made a quick but inspiring visit to chat to Internet legend Brewster Kahle at The Internet Archive Canada.
Across all these interactions, a couple of clear themes emerged:
- There's palpable AI fatigue. People don’t want another generic product sprinkled with AI — they want tangible solutions addressing real problems, securely and privately.
- Amidst geopolitical tensions, the significance of hosting Web Summit in Canada resonated strongly. Privacy and security were top-of-mind for nearly everyone we met, reflecting a collective desire for secure, productive digital connections.
As a Web Summit veteran, walking the 2025 conference floor felt strangely familiar. Replace 2015’s "Uber for everything" buzz with AI-focused pitches, and you get the idea. Yet beneath the hype, real value is emerging where AI solves genuine problems.
We’re a remote-first company — and proudly so — but nothing replaces the energy and insights gained from in-person connections with industry peers. We returned inspired, energized, and more committed than ever to making networking simpler and safer.
Until next time, Vancouver! (Though you will see us at quite a few places before then!)
You can watch Avery's talks below:
Will Moore
