Summary
Highlights
Avery describes the process of 'shopping around' their solution and ideas to hundreds of people, not to sell but to understand their problems. He explains that initially, they were looking for people who resonated with the idea of simplifying networking, focusing on the 'anti-persona' of those who didn't want to deal with networking complexities.
Avery recounts a crucial question from a VC: "Do they like your product or do they love your product?" This became Tailscale's mission for the next 12 months, focusing on transforming customer sentiment from liking to loving the product to drive word-of-mouth growth.
Avery emphasizes the importance of listening to customer feedback, actively monitoring social media for mentions of Tailscale. He discusses the concept of Net Promoter Score, aiming to eliminate detractors and move more users from merely satisfied to passionate advocates, even offering free, high-quality support to all users.
Tailscale has grown to over 80 employees and raised $113 million. Avery reflects on the company's relatively smooth journey compared to his first startup, which struggled with funding and strategic mistakes. He highlights Tailscale's strategic decision to overraise funds before a market downturn.
Tailscale's first concrete product came from solving a Canadian bank's problem with adding two-factor authentication to legacy banking software. Avery and his team quickly developed a WireGuard-based VPN solution that provided secure access, demonstrating the need for simpler networking solutions.
While initially not aiming for VC funding, conversations with investors revealed Tailscale's potential for a hybrid product-led growth model. The product appeals to developers (bottom-up adoption) and enterprises (top-down buying), with developers advocating for the product's adoption due to its effectiveness in simplifying networking and security.
Avery reiterates that ensuring customers 'love' Tailscale has been the primary driver of its success and financial growth. When users are passionate about the product, they naturally become advocates, and the financial returns follow, especially in the developer infrastructure space.
The greatest lever for cultivating customer love is active listening to feedback across various channels, including social media. Tailscale prioritizes addressing even minor complaints to improve the overall user experience and move more users from being indifferent to being passionate promoters of the product.
Avery discusses the 'Crossing the Chasm' framework, explaining how his first company excelled with early adopters but failed to engage pragmatic buyers. Tailscale, in contrast, focused on solving a specific problem exceptionally well, aiming to meet the needs of pragmatic buyers from the outset.
The idea for Tailscale emerged from Avery's observation that most projects, even within large companies, are not 'billion-user' problems. He aimed to create a solution for 'small problems' for teams of 30, which led him to co-found Tailscale as the 'opposite of Internet scale'.