One thing we like about working with repeat founders is that they’re decisive about how they do and do not want to build their company. Take Avery Pennarun, CEO of Tailscale. Even before he knew what Tailscale would be, he knew he wanted to: build products as simply as possible, avoid selling software only at the enterprise level, focus on winning small segments before expanding, and not waste time “innovating” executive team structure. Clearly, it’s working: the company is redefining the network security category, and recently hit 10,000 paid customers after doubling its customer base in 10 months. Listening to Amit Kumar’s conversation with Avery is like taking a crash course on how to build a successful tech company – give it a listen and let us know if you agree.

Conversation highlights:

0:00 – Avery’s background and how Tailscale was born by solving a customer’s problem

5:50 – The decision to sell directly to developers versus at the enterprise level

8:55 – “Listen to people, and give them what they want.”

10:22 – Why Tailscale’s made building simply a guiding principle

14:40 – Avery’s philosophy on failing quickly and cheaply

18:38 – How Tailscale’s adapting to the different ways customers use their products

21:46 – Building a growth strategy based on doing and winning at small things

26:00 – Winning the market with a bottoms-up approach

30:28 – Why it’s time to fix the internet

33:50 – What Avery’s learned about hiring the right executive team

Related reading:

How our free plan stays free
The Future of Private Networks: Our Series A in Tailscale
Crossing the Chasm, by Geoffrey A. Moore

It’s Time to Build a Better Internet, with Tailscale CEO Avery Pennarun

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