Uploading a Book to an AI Is Technically Illegal – $155B Problem

01 /The Concept

Imagine listening to a book through headphones on your commute and leaving voice notes mid-listen – without pausing playback. Imagine being able to challenge the book on a point while you're still in the chapter, and have it respond in real time.

Or, if you're reading on your phone, asking the book to visualize a section as a diagram, a timeline, or an animation – to make the ideas click faster.

Can’t you get all of this by uploading the book to ChatGPT, Gemini, or Claude? Actually, no – for two reasons. Uploading books to third-party AI services is a copyright violation, regardless of whether you own the book. And even where rights weren’t an issue, general-purpose AI assistants struggle with long books due to context window limits – they simply weren’t designed for deep analysis of extended texts.

Sinai has built a reading app – available on mobile and desktop – that does everything described above, plus more.

The key differentiator: the app comes with a growing catalog of books for which Sinai has secured proper licensing deals with authors and publishers, allowing their content to be processed by the AI. The catalog focuses on non-fiction – personal development, business, psychology, history, and related categories.

Sinai's AI engine is purpose-built for long-form content. It maintains full context across an entire book, surfaces what matters, finds specific passages on request, and always responds within the frame of the complete work.

Language is no longer a barrier either. Any book can be read or listened to in any language. You could read in English while asking clarifying questions in Arabic – about both the ideas and the phrasing.

Beyond personal reading, the app works as a learning tool: ask the AI to turn a book into a textbook, a quiz set, or a full exam – based on a single chapter or the whole volume.

Sinai was founded by Egyptian entrepreneurs based in the UK and the US. The app is in beta, and the startup has just closed its first $1.5 million funding round.

02 /Why It Matters

The copyright angle is genuinely interesting. Is uploading a book you legally own to ChatGPT or NotebookLM actually illegal?

It turns out it is. Uploading it means creating a copy on a third party's servers – which constitutes copyright infringement regardless of whether you purchased the book. Beyond that, the AI service receiving the upload may use the content to generate summaries, quotes, or derivative works – infringement the user technically initiated.

Some jurisdictions have narrow exceptions for uploading excerpts strictly for personal use under fair use doctrine – but uploading a complete book is not legal anywhere.

Sinai resolves this by executing formal licensing agreements with copyright holders and paying them royalties – creating a new income stream for authors and publishers.

One might assume books are a dying medium. They're not.

The global book publishing market reached $155 billion in 2024. For comparison, the global recorded music market is around $29 billion. These figures align with what Sinai cites, and they hold up to independent verification.

The market continues to grow at 3–4% annually, driven increasingly not by traditional publishers but by independent authors self-publishing in digital formats. For those authors, a platform like Sinai represents a meaningful new revenue channel on top of conventional book sales.

As the book market evolves around independent creators, new platforms are emerging to help authors write, publish, and distribute. French startup DashBook ([related review](/review/ideja-dnja-kniga-luchshij-podarok-infljuenseru)) raised €2 million for one such platform. American startup Spines ([related review](/review/jetot-rynok-ne-umer-naoborot-tut-sejchas-pojavilsja-shans)) raised $23.7 million.

There's even a reader app built specifically around book discussions – Fable ([related review](/review/chitat-ne-vredno)), which lets anyone create or join a book club and has raised $36 million.

03 /Opportunities

If Sinai went to the trouble of licensing books for AI-powered derivative use, the natural question is: what else could that model unlock?

Consider what Showrunner ([related review](/review/kak-budet-vygljadet-novyj-netfliks-jepohi-ii)) did – a startup that raised investment from Amazon. Showrunner built a platform where users can expand a licensed film into an entire universe: using its settings, plot, and characters to create their own video episodes, remix original and fan-made content, insert themselves as new characters, and more. Describe what you want, and the AI generates the script and footage.

Why not the same for books? Imagine a platform where readers could add their own chapters – grounded in personal experience – to a book that resonated with them. Or contribute their own stories that either reinforce or argue with the original. A single thought-provoking book could become an entire universe of derivative content: richer, more coherent, and far more interesting than the scattered quote reposts that pass for literary engagement on social media today.

Books, arguably, are richer raw material than films. They're a legitimate medium ready for reinvention in multiple directions. That reinvention could go somewhere genuinely unexpected.

What would you build around a great book? Go build it. Just make sure you've cleared it with the author first.