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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