E127: Reimagining VPNs with Tailscale

E127: Reimagining VPNs with Tailscale

Author: Robby (MTF); Tim (Essence VC) April 17, 2024 Duration: 43:19

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!


Building a company around open source software is a unique and often misunderstood path, full of specific challenges and rare opportunities. The Open Source Startup Podcast digs into that journey directly with the people who have navigated it, moving beyond theory to the practical realities shared in conversation. Hosts Robby and Tim bring their distinct perspectives from MTF and Essence VC to these discussions, creating a space where founders speak candidly. You’ll hear from the architects behind names like HashiCorp, MongoDB, and Vercel, as well as leaders from Chronosphere, DBT, and mobile.dev, as they unpack their experiences. This podcast focuses on the pivotal decisions around community building, monetization strategies, and maintaining project ethos under the pressures of scaling a business. Each episode serves as a detailed case study, revealing how these companies turned publicly available code into sustainable, impactful enterprises. The dialogue naturally explores the tensions between open collaboration and commercial needs, offering a real-world blueprint that is both instructive and nuanced. For anyone curious about the intersection of community-driven development and venture-scale growth, this series provides an essential and unfiltered resource.
Author: Language: English Episodes: 100

Open Source Startup Podcast
Podcast Episodes
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