What started as a seemingly routine pull request to add LLM-friendly documentation to Tailwind CSS’s GitHub repository turned into something much bigger when co-founder Adam Wathan declined it and revealed that the company had just laid off 75% of its engineering team due to what he called "the brutal impact AI has had on our business."

The thread quickly went off the rails. After drawing hundreds of comments and going viral on Hacker News, it eventually had to be locked, but not before cracking open a broader conversation about the future of open source sustainability in the era of LLMs.

The revelation hit particularly hard given Tailwind’s ubiquity in the web development world. From NASA’s Jet Propulsion Laboratory to countless startups and Fortune 500 companies, Tailwind CSS has become infrastructure-level technology, the kind of foundational tool that major platforms like Claude.ai, Vercel, Cloudflare, Shopify, Cursor, GitLab, OpenAI, and Grok are built on. Yet even with that reach, the business built around it is struggling to survive.

PR to Add LLM-Friendly Docs Gets Rejected#

On November 18, 2025, a developer opened a pull request proposing to add an /llms.txt endpoint to Tailwind’s documentation site. The PR sat for nearly two months as comments piled up asking why it hadn’t been merged. The day after laying off 75% of his team, Wathan closed it with an explanation that cut to the heart of the crisis.

"Making it easier for LLMs to read our docs just means less traffic to our docs which means less people learning about our paid products and the business being even less sustainable," Wathan wrote, adding that the team was focused on figuring out how to pay the bills right now.

In a recent episode of his podcast titled "We had six months left," Wathan elaborated on the dilemma: "Traffic to our docs is down like 40% or something from peak, even though Tailwind is like three times as popular as it was when traffic was at its peak. And the only way people find out about our paid products is through the docs. That’s our entire distribution."

Tailwind Labs Revenue Down 80% with Six Months of Runway#

Wathan revealed he had finally done proper revenue forecasting over the holidays. "The situation was significantly worse than I realized," he said, describing it as a "boiling the frog situation" where revenue declined so slowly and steadily "you almost don’t really notice. You just get used to the lower revenue being sort of normal."

He said he was caught off guard realzing that "it was not stabilizing at all." This led to a brutal conclusion: "If absolutely nothing changed, then in about six months we would no longer be able to meet payroll obligations," Wathan said.

In follow-up comments, he shared specifics about Tailwind’s situation:

• Traffic down 40% from early 2023, despite Tailwind being "more popular than ever"
• Revenue down close to 80%
• 75% of the engineering team laid off the day before his response

"Tailwind is growing faster than it ever has and is bigger than it ever has been, and our revenue is down close to 80%," he explained. "Right now there’s just no correlation between making Tailwind easier to use and making development of the framework more sustainable."

Tailwind CSS was already running a lean crew. "To say that we had to let go three people doesn’t sound like we have to do much," Wathan explained in his podcast, "but in reality, we have four engineers on staff and now we have one. So it is a big change."

In the same podcast, Wathan described the emotional toll: "I feel like a fucking idiot for somehow being able to build this CSS framework that’s taken over the world and it’s used by everything and it’s super popular, but I can’t figure out how to have it make enough money that eight people can work on it."

The company’s business model relies on documentation traffic to drive awareness of its paid products: Tailwind UI (a component library) and the Insiders sponsorship program. As developers increasingly use LLMs to generate Tailwind code without visiting the documentation site, that discovery funnel has broken down.

"Tailwind CSS is facing economic troubles and could be on the ropes," Microsoft software engineer Marcos Rivas tweeted. "Just imagine if the most popular and widely used CSS framework is in such bad shape, how the others must be faring.

"Open source projects or those that are free as a hook to sell other things will always run the risk of becoming more popular and not generating much revenue to allow the project to continue... Without knowing if this is a critical factor in this case, it’s a point to consider because you no longer need to consume official documentation or resources to understand a tool."

In one of the most heartbreaking moments of the podcast, Wathan spent several minutes at the end recommending the engineers he’d just laid off to potential employers, detailing their specific talents and offering to provide references. "These are three of the most talented people I’ve ever worked with," he said. "I’m gonna be really jealous of any company that hires any of these guys." It was a poignant goodbye to people he clearly wanted to keep but couldn’t afford to pay.

OSS Business Models Can No Longer Rely on Documentation to Drive Revenue#

Tailwind’s situation isn’t isolated. When documentation-driven monetization strategies meet LLMs that can answer questions without users ever visiting a website, the traditional paths from open source adoption to commercial conversion break down.

"In this context, making documentation easier for LLMs to consume means accelerating the loss of the only real revenue source," software engineer Hugo Lassiege wrote in a blog post about the Tailwind layoffs.

"From a purely economic standpoint, the decision makes sense. It’s not anti-AI — it’s simply an economic reality."

Developers using LLMs can now generate Tailwind code without seeing ads for Tailwind UI, reading about the Insiders program, or even knowing paid products exist. The framework grows more popular while revenue plummets. It’s a paradox that’s becoming increasingly common across developer tools, though different projects are responding in different ways.

Nuxt, for instance, recently went the opposite direction after being acquired by Vercel, making their previously paid Nuxt UI Pro completely free and embracing AI-friendly documentation with llms.txt endpoints and MCP server integration.

The Tailwind thread attracted suggestions ranging from creating paid MCP (Model Context Protocol) servers to integrating with AI coding tools, implementing pay-per-API-call documentation access, and even acquisition by AI companies. Some pointed to Bun’s recent joining of Anthropic as a potential model, an outcome Wathan had previously joked about on social media.

One commenter summarized the challenge: "Tailwind’s paid product offering (prebuilt components with best practices) is being obviated by a technological disruption... Tailwind is in a dire spot because its product is a ‘text-output’, and worse, with low configuration needs, which is EXACTLY the most automateable thing."

It also doesn’t help that Tailwind’s pricing includes lifetime subscriptions, a model that trades long-term recurring revenue for one-time payments. At $299 for individuals and $979 for teams of up to 25, customers get lifetime access to all current and future components, meaning once someone buys in, they never pay again, no matter how much new content gets added.

What’s Next for Tailwind CSS#

The GitHub thread drew hundreds of comments before eventually being locked after attracting significant attention from Hacker News and other tech communities. Many expressed support for Tailwind Labs and purchased sponsorships or licenses, while others debated whether refusing to add LLM-friendly documentation would ultimately help or hurt the project’s sustainability.

Making Tailwind easier to use with LLMs could increase adoption and create indirect business value, but LLMs already have access to Tailwind’s documentation through normal web crawling, making the /llms.txt file largely symbolic.

Many commenters also pushed back on what they saw as entitled demands for features from a struggling company. The thread also raised deeper questions about whether an open source project’s documentation should be tied to commercial interests at all.

Wathan ended the discussion on a note of determination: "Just wanted to drop a quick note and say I appreciate all the support here, on Twitter, and on Hacker News. We’ll figure it out I’m sure."

In the days following the viral thread, the community rallied with tangible support. Gumroad announced they were becoming a Tailwind Partner, joining other companies in directly sponsoring the framework’s development. The response demonstrated that despite the challenges, there’s still strong willingness within the developer community to support the tools they depend on.

The incident puts a big spotlight on questions that extend far beyond this one PR that blew up in the Tailwind repo. How do open source projects sustain themselves when AI transforms how developers interact with documentation and code? What business models can survive when the traditional paths from open source usage to commercial conversion are disrupted? And what obligations, if any, do successful companies built on open source tools have to the projects they depend on?

As one commenter on the GitHub thread noted, "This story neither starts nor ends with Tailwind, it’s just among the most visible at the moment."

Lassiege’s commentary on the layoffs sums it up with a grim conclusion: "The problem isn’t AI. The problem is that the open source economic model was built for a world that no longer exists — and if usage has moved from the browser to the prompt, monetization will have to follow."