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