The Quiet Death of AskMyBook: What Happened to Sahil Lavingia’s AI-Powered Book Assistant?

Ever wondered why Askmybook.com disappeared—even though it seemed tailor-made for the AI age?

On the surface, AskMyBook had all the ingredients of a viral side project—an AI-powered tool from a well-known founder, open-source roots, and a minimalist premise. Yet, today, the site is offline. There’s no farewell post, no dramatic shutdown announcement—just silence. So, what truly happened to AskMyBook?

In short: AskMyBook was a clever experiment that perhaps ran its course. Built by Sahil Lavingia (the founder of Gumroad), it allowed readers to ask questions about his book The Minimalist Entrepreneur and receive instant, AI-generated responses—in his voice, no less. It was quirky, functional, and on-trend. But it never evolved beyond its initial scope, and now it’s gone.

Let’s break down the rise and fall of AskMyBook—because even side projects have stories worth telling.

What Was AskMyBook?

AskMyBook.com was an AI-powered Q&A tool created by Sahil Lavingia around 2022. At its core, it aimed to make reading more accessible by allowing users to “talk” to his book The Minimalist Entrepreneur. Instead of thumbing through the pages, users could type a question—like “How do I launch a startup without investors?”—and get an answer drawn from the book, presented in Sahil’s voice.

Key characteristics:

• Creator: Sahil Lavingia (founder of Gumroad)
• Launch: 2022 (exact date unclear)
• Purpose: Let users query The Minimalist Entrepreneur using natural language
• Tech Stack: AI-generated responses, likely using GPT-driven models
• Open Source: Code available publicly on GitHub
• Website: askmybook.com, now defunct

It was a fun, frictionless idea—perfect for readers short on time who still wanted the wisdom of a startup manual.

But while clever, the project never turned into a business. There were no visible monetization efforts, investor funding announcements, or aggressive growth plans. It was, by all signs, a one-author experiment.

Why Did AskMyBook Fail?

Short Answer:

AskMyBook quietly faded due to lack of sustained interest and focus—likely a case of a niche tool losing momentum as its creator moved on to bigger things.

Long Answer:

Let’s dive deeper into the contributing factors:

1. Limited Product Scope and Market Fit

AskMyBook’s utility was tightly tethered to The Minimalist Entrepreneur—a single book with a limited audience. Unlike tools that let users query entire libraries or multiple sources (like ChatGPT plugins or AskBooks.ai), AskMyBook offered no extensibility.

A cool demo? Yes. But a scalable utility? Arguably not.

2. No Monetization Plan

AskMyBook wasn’t just free—it didn’t even attempt monetization. No premium features, no subscription model, not even a donate button. As a solo side project, that’s understandable. But it meant there was no business incentive to maintain or grow it over time.

Once the novelty wore off, sustaining server costs and iteration likely felt unjustifiable.

3. Mounting Competition from AI-Powered Tools

By 2023, dozens of tools allowed users to query long documents or entire books using AI—some better funded, some smarter, some just more flexible.

Services like:

• AskBooks.ai – Allowed users to ask questions across a range of books.
• MyReader.ai – Enabled document uploads and interactive querying.
• ChatGPT Plugins – Gave power users direct access to book summaries and content-based Q&A.

Compared to these general-purpose platforms, AskMyBook—with its single-book constraint—fell behind fast.

4. Leadership & Prioritization

Sahil Lavingia is no stranger to pivoting. As the founder of Gumroad—and a vocal advocate for minimalist entrepreneurship—he often launches, experiments, and then moves on.

It appears AskMyBook was a genuine passion project, but not one he intended (nor needed) to scale. By late 2022, the GitHub repo saw its last update, and the website slowly faded out of operation, with no further mentions from Sahil.

5. Lack of Broad Adoption

Despite some early buzz (thanks largely to Sahil’s personal following), AskMyBook never found a large user base—at least not enough to justify an ongoing development cycle.

There were no app integrations, email signups, or traction metrics shared. The scarcity of feedback loops likely meant that there wasn’t enough data to improve or grow the tool. And without an active user community, the project faded naturally.

6. Not a Business—Just a Project

This is perhaps the clearest explanation.

AskMyBook wasn’t a startup. There were no pitch decks, investors, teams, or business models. It was an experiment in accessibility—a neat showcase of what happens when a book meets a language model.

Unlike a failed company, there’s little drama here. It worked, served its purpose, and then was archived—much like a blog post or tweet thread.

Why AskBooks Succeeded Where AskMyBook Didn’t

If you’ve tried tools like AskBooks.ai, you’ll immediately see why AskMyBook couldn’t compete in the long run. AskBooks lets users:

• Access a wide range of books across genres
• Ask questions across multiple titles
• Receive citations and summaries
• Easily share and export answers

Put simply: It's a product, not a project.

AskBooks focused on scale and user flexibility, while AskMyBook doubled down on minimalism and niche appeal. Philosophically brilliant—but commercially limiting. It's a reminder that product strategy matters just as much as innovation.

Final Thoughts: The Beauty (and Doom) of Side Projects

AskMyBook may be gone, but it wasn’t a failure in the traditional sense. It demonstrated what’s possible when authors embrace tech and rethink content access. In a way, Sahil Lavingia did what many tech founders preach: built something cool, shared it for free, and let it go when the time was right.

Still, its quiet fade is a useful case study in the limits of niche AI tools. Even good ideas—ones backed by brilliant founders—need a path to sustainability if they’re going to last.

So what’s the next AskMyBook? Likely something broader, smarter, and with just a bit more business sense.

FAQs

Who founded AskMyBook?
AskMyBook was created by Sahil Lavingia, the founder of Gumroad and author of The Minimalist Entrepreneur.

When did AskMyBook come out?
The project launched sometime in 2022, though the exact launch date is unclear.

When did AskMyBook shut down?
While there was no official shutdown announcement, the GitHub repository saw its last update in December 2022, and the website became nonfunctional by early 2024.

How much funding did AskMyBook raise?
None—it was a personal, open-source project with no external funding.

Why did AskMyBook fail?
Short answer: It didn’t evolve or scale beyond a single use case. Long answer: Lack of monetization, limited scope, shifting priorities, and growing competition all contributed to its quiet fade.

Can I still access AskMyBook?
The website is currently offline, but the open-source code is still available on GitHub for anyone interested in reviving or modifying the project.

Even minimalist experiments sometimes fade into maximal obscurity. But AskMyBook showed how merging authorship with AI can offer delightful, if fleeting, results.