Founders / Avery Pennarun
Avery Pennarun
Avery Pennarun is the co-founder and CEO of Tailscale, an AI infrastructure and compute company based in Toronto. Avery Pennarun co-founded Tailscale with David Crawshaw, David Carney and Brad Fitzpatrick. Tailscale is listed in the portfolio of Panache Ventures.
Co-founder/CEO of Tailscale.
Tailscale
Secure networking; AI-era infra; acquired Border0.
- Role
- Co-founder/CEO
- HQ
- Toronto, ON
- Founded
- 2019
- Status
- Active
- Website
- tailscale.com
Co-founders: David Crawshaw, David Carney, Brad Fitzpatrick
Investors: Panache Ventures
In the newsletter
- CanadianAI: Anthropic signs on for a $10B data centre in Cape Breton, and Tenstorrent raises US$1.5BOct 20, 2026
- CanadianAI: OpenAI backs Biossil at US$1B, and B.C. sues OpenAI over Tumbler RidgeSep 29, 2026
- Canadian AI: $6.5B for a Calgary cooling company, another Vancouver acquisition and Canada's largest data centre to begin constructionMar 24, 2026
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Data as of November 10, 2026.