Avery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving everyday developer headaches. Learn why your startup idea is probably wrong (and why that’s okay), how Tailscale found explosive product-market fit, and why the biggest opportunities are hiding in the “smallest” problems. If you’re an early-stage founder looking for practical insights, game-changing growth hacks, and lessons from someone who’s been through it all, this is the episode you can’t miss.

Why You Should Listen

Learn how Avery grew Tailscale from zero to millions in revenue purely through word-of-mouth.
Discover why chasing enterprise deals too early might actually slow you down.
Find out why solving “small, simple” problems can lead to billion-dollar outcomes.
Hear the counterintuitive reason why your product failing early users is actually a huge advantage.
Understand how Tailscale turned COVID lockdown into an explosive growth opportunity.

Podcast Keywords
product market fit, startup growth, product-led growth, Tailscale, word-of-mouth growth, startup fundraising, developer tools, network security, B2B SaaS, early-stage founder advice

(00:00:00) How Tailscale Raised $160M Without Chasing Investors

(00:01:48) Building a Billion-Dollar Idea From Scratch

(00:05:18) How to Find Real Problems Worth Solving

(00:13:14) Landing the Critical First Customer

(00:22:25) Why Great Founders Start Small, Not Big

(00:28:33) Turning Bottom-Up Adoption into Enterprise Deals

(00:36:55) Growing from Zero to $1M+ ARR Through Word-of-Mouth

(00:46:16) When Avery Knew Tailscale Had Product Market Fit

(00:48:27) Avery’s Most Important Advice for Early-Stage Founders

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