What does it take to turn a bold idea into a billion-dollar company during one of the most unpredictable periods in recent history? In this episode of Startup Builders and Backers, we meet Avery Pennarun, Co-founder and CEO of Tailscale, who shares how a lean networking startup found its stride in the middle of a global pandemic and reshaped expectations for what secure connectivity can look like.

Before founding Tailscale in 2019, Avery had already built and sold a company to IBM, worked closely with senior leadership at Alphabet, and led engineering efforts at Google Fiber. His experience spans both massive tech enterprises and nimble, founder-led ventures. But Tailscale may be his most ambitious project yet. Designed to simplify secure networking, Tailscale removes the complexity and frustration that usually accompany corporate VPN setups, making it easier for teams of all sizes to connect devices across locations—without expensive infrastructure or weeks of onboarding.

As remote work surged and companies scrambled to secure distributed teams, Tailscale quietly gained traction. By delivering speed, usability, and compatibility with existing tools, the startup found its audience. In 2023, VentureBeat named it one of the top zero-trust startups to watch, and earlier this year, the team launched an enterprise-ready zero-trust VPN that’s already drawing attention from major customers.

In this conversation, Avery opens up about the personal and strategic decisions behind Tailscale’s rise. He reflects on product-market fit, the importance of saying no to unnecessary complexity, and how the team remained focused under pressure. For anyone building in the infrastructure or security space, this is a rare look behind the curtain.

We also zoom out to examine the growing interest in zero-trust security models. While the term often gets thrown around in sales decks and funding pitches, Avery provides clarity on what it really means, how Tailscale approaches it, and why simplicity is often the most powerful form of security.

From scaling smart to staying grounded, Avery’s story is one that early-stage founders and first-time builders will find relatable and energizing. It’s proof that you don’t need a huge team or deep pockets to build something impactful—you just need to solve a real problem better than anyone else.

If you're building in public, navigating investor conversations, or sketching out your MVP, this episode offers both perspective and encouragement. Where could simplicity take your startup?