Tailscale and Market Segmentation with Avery Pennarun

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

Chris Hill