Jay Shapiro is a writer, director, producer, and the man behind the documentary film for Sam Harris and Maajid Nawaz’s collaboration Islam and The Future of Tolerance. Based in NYC, he now co-hosts the Dilemma podcast with Quillette author and recent congressional testifier, Coleman Hughes. 


We spoke with Jay to get his thoughts on the utility of debating ethics in public and the benefit of presenting bite-sized philosophy to a general audience, among other topics.

Banter: You’re in the business of having ethically complex conversations for a living; for those who can’t even manage the task at Thanksgiving dinner, what sort of advice would you give? How do you accrue the patience needed to wade through nuanced topics and hone the blade of truth?


Shapiro: The truth about getting deeper into these kinds of conversations is that you aren’t likely to discover the “right” answer. So, if you are waiting with patience for those kinds of epiphanies to come, you’ll be disappointed. What you’ll get better at is noticing the subtleties to arguments that you might not even agree with. And you’ll get better at understanding the shape of your own moral conviction. That is why it is so worthwhile. 

What you realize is that creativity is so crucial to ethical conversations. Simply insisting “that’s just how I feel about it!” or “that’s just the way it is!” is not a good enough argument in moral philosophy. And those answers are also boring. What you are forced to contend with is a question much closer to something like, “What are the conditions in place for me to feel strongly about the moral stance I find myself in and what are the variables which would compel me to move?” Finding those conditions and variables requires tremendous creativity. It can be a lot of fun to come up with crazy scenarios and people who you often argue with at the Thanksgiving table might even enjoy it. 

I can’t promise it will work but you may actually find some hypothetical common ground with someone you feel hopelessly entangled with… and a hypothetical meeting point is a good place to start if you hope to find an actual meeting point.


Banter: In addition to your recent podcast Dilemma, you’ve also applied creative energy to a handful of film projects. Of the three: Islam and The Future of Tolerance, All Rise, and Opposite Field, of which are you most proud? 


Shapiro: It’s difficult to choose one on those grounds. I am extremely proud of delivering a promise to the viewer of Islam and The Future of Tolerance that we would treat the delicate subject matter with care. The aim of that film was not to offend or anger but to present open questions and I’m proud of what we did there. With Opposite Field I just couldn’t be more proud of the boys who actually played the games. I just felt privileged to be the one holding the camera near them.


Banter: When the IDW appeared as a loose intellectual cohort did you have any sense that you would come to feel akin to that movement?


Shapiro: I think I did actually because it felt like there was enough of a common handshake understanding of what a lot of seemingly different people agreed about... and that was something like “seeking truth and unafraid to ask uncomfortable questions to discover those truths”. I think naming it was a mistake and quickly spelled its doom as it has become an unnecessarily political movement rather than a philosophical one. I am friends with plenty of the “members” but at this point I think the label is more trouble than it’s worth.


Banter: Podcasting has engulfed the landscape of digital media in a way that no one fully expected, how would you sell Dilemma to someone who has a finite amount of listening hours in the day?


Shapiro: I hope the dilemmas themselves pull some folks in. Save the Mona Lisa or a person? Intentionally have a deaf child? Listen to a musician who has abused women? There is something inviting and relevant about those open questions. I think a lot of people have this idea that “philosophy” is something for nerds on college campuses or old dead dudes in robes. I really hope this podcast can change that perception. And then of course I hope the humor and charm of the co-hosts does all the rest of the work.

We’re also lucky to have an incredible list of guests with names of public intellectuals and authors with large followings. I hope some of those fans find us through those names and then take some time to explore some of the minds of the guests they hadn’t heard before.


Banter: Coleman Hughes has proven himself a formidable intellect on television, on YouTube, in print, and now in the highest house of legislature in America. How do you contend with such a co-host? 


Shapiro: Mostly I just make fun of how young he is. 


Banter: Do you view Twitter as net positive outlet for communicating with a wider audience? 


Shapiro: I think it’s a great place to meet other minds but it’s not a great place to hang out with them. I hope the podcast can be a catalyst for people in the real world to engage in these kinds of conversations. They’re really fun to just throw out in quiet moments over drinks and see how they land. Usually people really get a kick out of talking about these things. And you can really learn a lot about your friends and vice versa. It’s better than small talk about the weather or staring at your phone… probably scrolling Twitter.