The Business of Open Source

Today I’m chatting with Avery Pennarun, CEO of Tailscale, a VPN service that makes devices and applications accessible anywhere in the world.

Show Notes

Today I’m chatting with Avery Pennarun, CEO of Tailscale. Tailscale is a VPN service that makes devices and applications accessible anywhere in the world by enabling encrypted point-to-point connections using the open source WireGuard protocol. Avery begins by talking about his experience building a start-up while he was a college student and how things have changed as he leads his current start-up. Avery recommends the book “Crossing the Chasm” and we discuss market segmentation as it relates to creating a successful start-up. Avery explains how Tailscale has been successful in implementing market segmentation strategies. We conclude our conversation by talking about goal setting and the importance of quality.

Highlights:
  • Avery talks about his first start-up experience as a college student (1:10)
  • Avery recommends “Crossing the Chasm” and discusses how it influenced his start-ups (7:54)
  • We discuss market segmentation strategy (13:29)
  • Specific marketing strategies used at Tailscale (18:41)
  • Avery talks about mistakes he’s made while building his start-ups (22:24)
  • Goal setting in start-ups (24:42)
  • We talk about the importance of quality in building word of mouth success (29:49)
  • Avery answers the question “How do you maintain an identity as an engineer when you are also a serial entrepreneur?” (33:23)

Links:
Avery
  • Twitter: @apenwarr @tailscale
  • Company: https://www.tailscale.com

What is The Business of Open Source?

Whether you're a founder of an open source startup, an open source maintainer or just an open source enthusiast, join host Emily Omier as she talks to the people who work at the intersection of open source and business, from startup founders to leaders of open source giants and all the people who help open source startups grow.