How to Grow Licensing Revenue to $1.5B/yr Tailscale CEO, Avery Pennarun

What does it really take to go from startup to category leader? In this episode of The Jess Larsen Show: Innovation & Leadership, Jess sits down with Avery Pennarun, CEO of Tailscale, to break down the real mechanics behind product-market fit, scaling to a billion-dollar company, and becoming the default choice in your industry. Avery shares hard-earned lessons from building Tailscale into one of the most respected infrastructure companies in tech—used by thousands of teams worldwide. From why most founders think about markets the wrong way, to how focusing on a tiny niche can unlock massive growth, this conversation is a masterclass in strategy, execution, and discipline. Learn more about your ad choices. Visit megaphone.fm/adchoices

You can listen to How to Grow Licensing Revenue to $1.5B/yr Tailscale CEO, Avery Pennarun online on Radio and Podcast. Open the player on this page to stream the available audio.

How to Grow Licensing Revenue to $1.5B/yr Tailscale CEO, Avery Pennarun is an episode from Innovation and Leadership with Jess Larsen by Graystoke Networks.

This episode is 48:43 long.

This episode was published on Apr 9, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Innovation and Leadership with Jess Larsen when more episodes are available from the podcast feed.