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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.