Summary
Highlights
Avery, founder of Tailscale, recounts a pivotal moment where a VC asked if users 'liked' or 'loved' their product. This question became their mission for the next 12 months, emphasizing that genuine love for a product leads to organic word-of-mouth growth. Tailscale focused heavily on this, resulting in a huge community of passionate users who actively advocate for the product.
The most crucial lever for transforming 'liking' to 'loving' is actively listening to customer feedback. Avery personally monitors social media for any mention of Tailscale to gauge user sentiment. He highlights that addressing even minor complaints for $0 plan users is vital, as one person's problem often reflects a wider issue that needs swift resolution. This dedication aims to convert neutral users into enthusiastic promoters.
Tailscale has grown to over 80 employees and raised $113 million ($3M seed, $12M Series A, $100M Series B). Avery acknowledges the company's continuous growth but highlights past startup challenges. They strategically raised more capital ($100M Series B in early 2022) to navigate anticipated market tightening, a decision that proved prescient.
Avery reflects on a key mistake from his first startup: failing to 'Crossing the Chasm' from early adopters to pragmatic buyers. Tailscale, in contrast, focused on solving one problem exceptionally well rather than many problems adequately. This allowed them to resonate deeply with early adopters and build a foundation for attracting pragmatic buyers by positioning Tailscale as a serious and long-term solution.
Avery conceived Tailscale to address 'tailscale' problems – the numerous small-scale issues that developers and teams face, often overlooked in the push for 'internet scale' solutions. The name itself represents the opposite of internet scale, focusing on making things easy for smaller teams. This philosophy predated the specific product, with the idea attracting his co-founders and leading to a solution that made 'easy things easy'.
Tailscale's product, a secure VPN for small teams, was born from solving a specific problem for a banking CEO: enabling two-factor authentication for legacy banking software. What started as a 'weekend' Wireguard solution evolved into a product solving a huge, unrecognized problem around secure connectivity for internal tools. This accidentally stumbled upon a critical need for almost every team, providing both connectivity and security without complex setup.
Tailscale's business model is a 'modern hybrid product-led growth' approach. While initially not intending to raise money, investors recognized their dual appeal: developers loved their product, and enterprises (like the banking client) found significant value. This model allows developers to adopt the product easily, and their love for it then influences organizational buying decisions, leading to full enterprise adoption. The money follows when users genuinely love and use the software daily.
Avery advises founders to prioritize fostering deep product love rather than obsessing over immediate financial gains. When users genuinely love a product, they become advocates, creating powerful word-of-mouth marketing. In the developer infrastructure space, if developers are using a tool more and more each day, the financial success will naturally follow. This approach ensures continuous iteration based on user feedback to maintain that love.