Tailscale and Market Segmentation with Avery Pennarun
The Business of Open Source25 Touko 2022

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

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