Imagine this: You’re deep into a book, maybe cozied up on the couch. Maybe you’re sitting at your desk, highlighting passages and writing down notes.

But what if you could actually ask the book questions directly? Questions like, “What’s the historical context in which this book was written?” Or, “What might the author have been trying to convey through this metaphor?”

A new startup is making that a reality.

John Kaag is a philosophy professor at UMass Lowell and founder of Rebind . With Rebind, readers can engage directly with expert commentary from today’s smartest minds by using artificial intelligence to distribute answers derived from hours and hours of extensive — and exclusive — interviews.

Kaag joined GBH’s All Things Considered host Arun Rath to share how Rebind lets readers have interactive conversations to deepen their understanding and challenge their perspectives. What follows is a lightly edited transcript.

Arun Rath: First of all, tell us the story of Rebind. It’s a wonderful concept. How did it come together?

John Kaag: Two years ago, my co-founder — and the principal financial backer of Rebind — contacted me and said, “Why don’t we make a new reading experience?” ChatGPT had just come out, and he had said, “What if we inserted conversations with readers into a new type of digital book, or e-reader?”

These conversations would be funded by — not Chat GPT, but extensive interviews by today’s greatest luminaries, like Margaret Atwood, John Banville…

John Banville, pre-recorded: Hello, I’m John Banville, an Irish novelist, book reviewer and screenwriter. I’m here to introduce James Joyce’s “Dubliners.” ... We go to art in order to have a more vivid sense of what it is to be alive, what it is to be a human being.

Kaag: What we would do is interview these individuals about their favorite books, about classic works of literature in order to sort of breathe new life into the classics, both literary classics and also spiritual classics.

In so doing, what you get when you do a Rebind is basically an interactive guided experience with both films and a conversation. They’re sort of infused with this original commentary from the experts that we contract.

Four headshots.
Sadie Stein, Roxane Gay, Deb Olin Unferth, and Bill McKibben are all “Rebinders” who offer expert commentary on a specific book over hours of interviews.
Courtesy of Rebind

Rath: It reminds me of — you know, going back to my college days — the Norton Critical Editions, where you might get a work of literature, like Alfred Tennyson’s “In Memoriam,” footnoted all up and down, and then, these great essays from scholars. This is making it so that you can just do that directly with the text itself.

Kaag: That’s right. But we’re also trying to sort of stay to the mantra — read this together. Let’s read this together. I’m passionate, as a professor, about the tutorial method of education. And, at least in part, Rebind is an attempt to bring this method of education to the masses, to scale conversations about great books.

What we’re doing is providing readers with personalized, intimate experiences that enrich understanding and make it possible for basically everyone to enjoy some of the most challenging and meaningful works of our time — of any time.

Rath: John, you listed a few of the major thinkers who are part of this project providing commentary and answers. Tell us about the full range of people.

Kaag: Wow. Well, we’ve contracted 26 books, and we really think about this as a sort of growing library. We opened our doors — our bookstore for Rebind — at the beginning of October. We opened with five books. The next five books are really exciting. Roxane Gay…

Roxane Gay, pre-recorded: My name is Roxane Gay, and I’m a writer, editor and professor. ... I’m often asked about my favorite book — Edith Wharton’s “The Age of Innocence.” I’m excited to talk about my love for this incredible novel, the brilliant writing and sharp wit Wharton brings to the page.

Kaag: Darren Brown, who wrote a bestselling book on happiness, is going to provide commentary on Stoicism.

Darren Brown, pre-recorded: Hello, I’m Darren Brown. Welcome to Marcus Aurelius’ “Mediations” on Rebind. ... How do you keep your mind solid? How do you remain sane in this mad world? And that is such a universal human question.

Kaag: I just finished work with Marlon James, who won the Man Booker Prize, on “Huckleberry Finn.” What we’re really trying to do is match commentators with great books with diversity in mind.

“Everybody knows that when reading a tough book, discussions are so critical to understanding this type of literature. I believe — and my colleagues at Rebind believe — that you’re only two stupid questions away from understanding something.”
John Kaag, co-founder of Rebind

Rath: It’s really striking because while you’re a philosophy professor — and obviously you’re someone who’s devoted to the humanities from all of your work — that you’ve managed to pull off something with AI that keeps a really human element in it. It’s not data scraping or intellectual property theft. These are actual scholars and intellectuals.

Kaag: That’s right. When you have a conversation in a Rebind book, you actually get to see, verbatim, what the scholars or experts said during their interviews — we call it the “X-ray feature.”

One of the discoveries at Rebind is that we can use AI to distribute original commentary.

Everybody knows that when reading a tough book, discussions are so critical to understanding this type of literature. I believe — and my colleagues at Rebind believe — that you’re only two stupid questions away from understanding something, especially when it comes to a book.

Rath: You are a Rebinder yourself, for “Walden” by Henry David Thoreau. If you could use that as an example: Say, if I were to engage with reading “Walden,” what are the kind of ways I could engage with the AI — or, indirectly, with you — to find out more.

Kaag: You can ask me questions — or rather, my AI counterpart — within the book. You can say, “John, when did you read this book first?” It would source my interview where I described the process of swimming in Walden when I was 14, and my Latin teacher took me up from Pennsylvania to see Walden for the first time.

You can ask questions like, “What do you think about Thoreau’s cynicism?” And I have a particular take on Thoreau, the cynic. You would get to interact with my thoughts about this book, so you’re not getting a generic interpretation of a book when you do a Rebind. You’re getting a unique perspective from a commentator who’s really fallen in love with this particular text.

Rath: So, I could ask you, say, “How does his relationship with Emerson affect this particular passage?”

Kaag: Precisely. And I, for example, would say something like, “Well, I think that ‘Self Reliance’ and ‘Compensation’ — two of Ralph Waldo Emerson’s essays — really impacted Thoreau in staying at Walden in particular ways.” That would be a different interpretation if we had asked a different Rebinder. That’s really crucial in thinking through what we’re trying to offer here.

In addition, we have films embedded into these texts, which bring the texts alive, in a way, to remind a reader: “Oh, this is a commentator who really cares about the text.”

Rath: You know, I realize I’m getting all excited about this as someone who loves literature, but I want to think about this in terms of what this could mean for students — particularly, students who might struggle with deep, dense texts like these.

Kaag: I know. I mean, 50% of Americans struggle with literacy in one way or another, and that means that they probably struggle with reading books generally, and definitely classic books.

What we’re trying to do is lower the bar of accessibility to enter challenging but incredibly meaningful text. We think about this as an offering for classics newcomers to venture into literature for the first time with the confidence and clarity they need that really only expert guidance can provide.