An A.I.-Powered App Helps Readers Make Sense of Classic Texts

For the past year, two philosophy professors have been calling around to prominent authors and public intellectuals with an unusual, perhaps heretical, proposal. They have been asking these thinkers if, for a handsome fee, they wouldn’t mind turning themselves into A.I. chatbots.

John Kaag, one of the academics, is a professor at the University of Massachusetts Lowell. He is known for writing books, such as “Hiking With Nietzsche” and “American Philosophy: A Love Story,” that blend philosophy and memoir.

Clancy Martin, Mr. Kaag’s partner in the endeavor, is a professor at the University of Missouri in Kansas City and the author of 10 books, including “How Not to Kill Yourself,” an unflinching memoir about his mental health struggles and 10 suicide attempts.

The two became friends 14 years ago, when Mr. Kaag was struck by an essay Mr. Martin had written for Harper’s and called him up. The two bonded over their disenchantment with the siloed world of academia and their belief that philosophy can be helpful to more people, if only they studied it.

Over time, Mr. Kaag, 44, and Mr. Martin, 57, also bonded over their personal struggles. Each has been married three times, and each has faced death. (In 2020, Mr. Kaag suffered full-blown cardiac arrest after a gym workout.)

How they wound up cold-calling renowned writers is another story.

In April 2023, Mr. Kaag received an email from John Dubuque, a businessman who had become a patron of sorts.

Before joining his family’s plumbing-supply business in St. Louis, Mr. Dubuque had been a philosophy major at the University of Southern California. Feeling that he was stagnating intellectually, he began paying philosophy professors to take him through “Being and Time” by Martin Heidegger and other works.

Mr. Dubuque, 40, hired Mr. Kaag for a six-week tutorial on “The Varieties of Religious Experience” by William James. The professor was the right person for the job, having published “Sick Souls, Healthy Minds: How William James Can Save Your Life” in 2020.

At the time, Mr. Dubuque’s family business had recently been sold, and he was looking for what to do next. During his talks with Mr. Kaag, he suggested that they team up to create a publishing company.

As Mr. Dubuque envisioned it, the imprint would pair a world-class expert with a classic work and use technology similar to ChatGPT to replicate the dialogue between a student and teacher. In theory, readers could ask, say, Doris Kearns Goodwin about presidential speeches or delve into Buddhist texts with Deepak Chopra.

Mr. Kaag jumped on board and brought his friend Mr. Martin to the project. The result is Rebind Publishing.

It will makes its debut June 17 as an interactive reading experience, available on mobile, desktop and tablet. Users will have free access during the rollout, with per-book pricing and a subscription model to follow later this year.

Mr. Kaag and Mr. Martin selected the authors who would offer commentary. They spent up to 20 hours interviewing each of these “Rebinders,” as they call them, about their chosen texts, trying to cover every possible question a lay reader might have. The recorded interviews were then fed into A.I. software.

On a recent afternoon, Mr. Kaag and Mr. Martin sat for an interview at the Boston Athenaeum, one of the nation’s oldest libraries. Mr. Martin wore jeans and a rumpled sweater over a T-shirt; his gray-brown hair was mussed, giving him the appearance of aging member of an indie rock band. In contrast, Mr. Kaag wore a crisp dress shirt, tan chinos and brown dress shoes with turquoise socks.

Both seemed not to believe their luck to have been given carte blanche to assemble an intellectual dream team.

“Man, this thing could be super cool,” Mr. Martin said, recalling his reaction when Mr. Kaag approached him with the idea. “Then we started brainstorming.” He said Mr. Kaag suggested, “Imagine if we could get Laura Kipnis on ‘Romeo and Juliet.’” (They ended up hiring Ms. Kipnis, a cultural critic and essayist, to do just that.)

Other writers participating in Rebind include Roxane Gay (“The Age of Innocence”), Marlon James (“Adventures of Huckleberry Finn”), Bill McKibben (selections from John Muir), Margaret Atwood (“A Tale of Two Cities”) and the biblical scholar and Princeton University professor Elaine Pagels (selections from the New Testament and Secret Gospels).

For “Dubliners,” the James Joyce classic, Mr. Kaag and Mr. Martin flew to Dublin to interview the Irish novelist John Banville, who delivered video and audio commentary.

“I first read ‘Dubliners’ when I was 12 or 13,” Mr. Banville said by phone. “I was absolutely enthralled by it. It wasn’t a Wild West story or an Agatha Christie story. It was the real thing, about life itself.”

There is a sense in literary circles that artificial intelligence is in opposition to art and the humanities. This is, after all, technology that some believe might nudge out writers and teachers.

The authors who have worked with Rebind allowed their voices to be cloned and agreed to let their words be manipulated by A.I.

Asked if he had reservations about that, Mr. Banville said: “My initial reaction was deep suspicion, of course. You read a book in your hand and you read it line by line, page by page. But this is a wonderful way to get people to read classic books and not be afraid of them.”

“I was paid well for it,” he added, declining to disclose the amount. “But you know, it wasn’t the money. I was interested in this project. At my age, I’m taking part in something new.” (The Rebind commentators will also receive a royalty.)

Ms. Gay said she had little interest in the tech that made Rebind possible. “I have a weird sort of comprehension block with A.I.,” she said. “The minute someone says ‘A.I.,’ I’m done.”

Nevertheless, she said: “What I did think was interesting was revisiting classic texts. And anything that will get people reading is generally wonderful.”

Mr. Martin and Mr. Kaag are bullish on the creative potential of A.I., viewing those who shun it as shortsighted. “It’s one of the great artistic opportunities of our time, to collaborate with this tool,” Mr. Martin said. They hope to give the Rebind treatment to 100 classics, all published before 1928 and therefore in the public domain.

Mr. Kaag and Mr. Martin took on canonical works themselves — “Walden” by Henry David Thoreau in the case of Mr. Kaag, and “Thus Spoke Zarathustra” by Nietzsche for Mr. Martin.

Mr. Martin encountered the 19th-century German philosopher as a high-school student in Calgary, Canada, after being tipped off by his English teacher. “Changed my life,” he said.

Growing up in central Pennsylvania, Mr. Kaag had a similar experience after his older brother left “Walden” on top of the toilet tank. He mentioned that he was reading the book to his Latin teacher, who later took him to Walden Pond, just outside Concord, Mass.

“I swam in the lake,” Mr. Kaag recalled. “I said to myself, ‘I’m going to become a philosophy professor, teach “Walden” and live in Concord.’ Today, I live 10 minutes away.”

Making that kind of experience with a book widely accessible is the driving idea behind Rebind, said Mr. Dubuque, who has put up his own money to fund the project, though he declined to say how much.

“I am attracted to the classics and to older books because they’re a different kind of escape than the escape of watching Netflix,” he said. “There’s this refreshing experience of stepping out of your time. These books create a lot of meaning in your life, too.”

Mr. Kaag likened the A.I.-powered author commentaries to the marginalia scribbled in a book by an expert reader, before citing a more pop-cultural reference.

“We also thought of it as those Hogwarts newspapers that speak back to you,” he said.