E127: Reimagining VPNs with Tailscale

Avery Pennarun is Co-Founder & CEO of Tailscale, the Wireguard-based VPN that reimagines secure, private networks. Tailscale has raised $115M from investors including Heavybit, Accel, CRV, and Insight. In this episode, we dig into what caused the team to reimagine zero trust security at the networking level, why they focus both on individual developers and large enterprises with a bottoms-up and top-down business model, why they leaned into the VPN comparison, how they create a personal tone for their blog & more!