Interview with Josh Szeps
Josh Szeps is a journalist and the host of Uncomfortable Conversations with Josh Szeps.
Interview Prep
Max Raskin: As I was prepping for this interview, I was wondering — how you prep for your interviews?
Contents
Josh Szeps: I have almost no consistent policy here, and I almost even have no consistent ideology about what the best strategy is. There seem to be two different poles of opinions in the interviewing game — about how much to prepare. There's an old Larry King adage — it may be apocryphal — that you shouldn't read anything about your guest because you want to come in with just as much ignorance as the viewer has. And you want to experience the journey of exploration the same way that a layperson would, and you want the surprise on your face to be as authentic as possible. That always struck me a little bit like an excuse for not working. It's convenient when your philosophy about work aligns perfectly with your ability to go and play golf or go to the beach, isn’t it. So I sometimes take that attitude when I'm busy in other arenas, and I don't have time to prep. And I can be like, "I'm not being lazy. I'm learning from the great man, Larry King."
On other occasions, I feel like I would be doing a disservice to the conversation if I didn't have an arsenal of information going in. Those are mostly cases where I feel like the person is either going to bamboozle me in some way or there's some point that needs to be extracted; if there's something that I think they need to be held accountable for — what journalists call an accountability interview. I don't do many of those on my podcast, but I did do as a broadcaster.
MR: What's it like quitting on air?
JS: It was the most traumatizing professional experience of my life. Like a marriage breakup, where a future you believed in is ripped from under you, all in public. It wasn’t related to Gaza, though. The problems pre-dated that. As they say in divorce court: “irreconcilable differences.” I believed in wrestling frankly with provocative issues. Management believed in avoiding controversy.
Now, it all feels like a weird dream. A huge weight has lifted off my shoulders. I can truly create a safe space for dangerous ideas, which is my purpose; it’s the point of Uncomfortable Conversations, and I hope your readers subscribe and join me on the adventure. It took time to back myself. But now I’m liberated. I can breathe, I can wrestle. I can debate, I can think. What a joy.
MR: I saw you interviewed Dick Cavett. Of the interviewers that you enjoy reading or watching, who is in your pantheon?
JS: Letterman would probably be the top. Dave Letterman was the person who inspired in me the love of the art of the jousting match, the wrestling ring, the parry and the dance of an adversarial but lighthearted comedic interview. I still remember when Madonna came on the show in the 90’s and just kept dropping the F-bomb because he'd made a lot of jokes about her being promiscuous, and she took the opportunity to come on and blow up his show. And seeing him handle that was so deft, and he combined this sort of misanthropic worldview and the kind of world-weary cynicism toward the artifice of broadcasting with one of the most razor-sharp minds on TV.
MR: It reminds me of when Joaquin Phoenix came to see him, Letterman said, "I’m sorry you couldn’t be here tonight.”
MR: What about adversarial? There’s all these videos on YouTube of people owning people in argument. Do you find yourself liking to watch these?
JS: No, I don't get anything out of the so-and-so owning so-and-so videos. There's a subtle difference here between being fearless, holding people to account, cutting through bullshit, not tolerating nonsense, versus being adversarial for the sake of being adversarial, which can often actually be just as superficial and glib as a sycophantic interview. Because in both cases, in the sycophantic interview and the hyper-adversarial-owning interview, you are playing a game. You're not authentic.
MR: But you don't get any pleasure out of watching that?
JS: Well, I mean, who doesn't…
Look, actually, the person who did both was Christopher Hitchens. I admire someone like that, who is both ferociously intelligent, deeply honest to their own principles, true to their own vision of what is authentic…and also capable of destroying somebody. So I mean, Sam Harris would be another person I admire. Richard Dawkins would be another person I admire.
The Four Horsemen
MR: All these people are atheists.
JS: I just noticed that as I was saying it.
That's partly coincidence, partly a historical anomaly because when I was coming of age, it was the post-9/11 period of a resurgence of those atheist voices finally having the balls to stand up and make an articulate argument for atheism. And so I was a fan of those guys in the early 2000s. It’s also partly a function of a way of thinking that goes along with a rejection of dogma that I think is useful. I come from a long line of philosophizing Jews on my dad's side — this kind of secular Jewish tradition of constant Talmudic self-questioning and men arguing about the universe.
MR: Are both your parents Jewish?
JS: No, only dad. Mom converted in the ‘70s, I think in London in a very reformed synagogue in a bout of hippie enthusiasm. But she would define herself as a lapsed Catholic.
MR: How do you define your religious beliefs?
JS: I try not to. I mean, agnosticism would be the closest thing. I'm an atheist towards the holy books. I don't think that there's any more reason to believe that the things that are claimed about what happened in the Middle East a couple of thousand years ago are more credible than anything else that people were scribbling down at the time, which we rightly reject as being probably made-up. But on the nature of the cosmos, I would be agnostic as to whether or not there's some vast ineffable purpose that you could call God.
MR: What do you think about the afterlife?
JS: When I was in my teens and early 20s, I would've said absolutely not. We're mammals. We're made up of material stuff. Consciousness is a function of things that are going on in between our ears. If you drill a hole into my head and poke your finger inside and wiggle it around, my consciousness is going to be massively impaired. So there's no reason to believe that if you put it all the way through my head, then suddenly my subjective consciousness is going to magically reassemble itself and be perfect again. You damage the brain, you damage my mind. So that seems to be a pretty hard stop.
As I've gotten older, I've gotten more perplexed by what the hell the whole thing is all about and perplexed by why it would be the case that materials would get ejected from stars and then assemble themselves in such a way that they can think about the universe and ponder spiritual questions. And in light of that, I would say the possibility of an afterlife — not an afterlife in which I cohere as Josh Szeps, but an afterlife in which there is some continuity of mystical self-awareness that could be considered to be me — has become non-zero. Whether that's the kind of flickering candle of consciousness coming alive in some other creature, or whether that's going back into some kind of cosmic swamp somewhere else in the cosmos, who knows? I would say that belief has been nudged up from 0% to 0.5%.
MR: Oh, so it's still extremely low.
JS: It's still low.
Turn On, Tune In
MR: And was there any experience that caused that change?
JS: Psychedelics didn't hurt. And meditation.
MR: Do you meditate today?
JS: I’m one of those guilty people who feels like they should.
MR: Why do you feel guilty?
JS: Because it's one of those areas where I know that it would enhance my life so much.
MR: So why don't you?
JS: Well, why is anyone overweight or falling short of their own aspirations for themselves? Why haven't I written the great novel that I have inside me? It's complicated, being a primate. And so for the same reasons why I carried too much weight for 10 years before I decided to get fit, I think if you check back in, in 20 years, I'd like to think that I have a daily meditation practice. But I have two kindergarten-age children and two jobs and a father with Alzheimer's disease and a lot of things going on in my life.
MR: There's a joke about this where a guy goes to a guru and the guru says, "After looking at your life, I decided you need to meditate for 15 minutes every day." And the guy says, "Listen, I don't have 15 minutes. I just don't have 15 minutes." The guru says, "Okay, then you need to meditate for 30 minutes every day."
JS: That's right. As far as any metaphysical insights are concerned, meditation is a long road. It’s a relatively quick road to peace of mind and lower stress levels. But I feel like it's a long hike to get to the profound spiritual insights that are available in a mushroom trip, for example, which is another thing that I haven't done in a while that I would like to do, especially in a clinical setting and in a high dose.
MR: Why in a clinical setting?
JS: Because I'm afraid of doing a high dose in a non-clinical setting.
MR: What's the fear?
JS: That it would be deeply unpleasant and scarring and traumatizing or something.
MR: I interviewed a federal judge who said that everyone has a natural inclination that if left unchecked would tend toward a certain mental illness. Some people would be depressive, some people schizoid — what would be yours?
JS: Do I get a multiple-choice suite of options?
It's easier to rule them out than rule them in. I wouldn't be manic depressive. I have a naturally upbeat temperament. I wouldn't have anxiety; it's hard to ruffle me. Sociopathy, potentially in the sense that I'm a highly logical and rational person, and so I can find it difficult to understand other people's emotions. I guess I'm a bit spectrum-y.
MR: Do you offend people easily?
JS: Yeah.
MR: When you look at your entire career is there anything you wish you could take back?
JS: One of the great things about being married is that I'm married to somebody who has softened that side of me so much. Prior to my meeting him, probably when I was in my 20s, there would've been plenty of things that I said after having six drinks at a cocktail party in New York that I would take back or blush at if I could see them.
Allen, Letterman, and Seinfeld
MR: Why New York?
JS: I spent most of my professional life in New York. I moved to New York after finishing university in Sydney and wanted to work in broadcasting there. I had been backpacking around the world when I was 18. And when I got to New York, I fell in love with it. My heroes had always been Woody Allen and David Letterman and Jerry Seinfeld, and I had this great iconic love of New York City from afar. And when I got there, it blew me away a thousandfold. And as the global center of broadcasting in the English-speaking world, I also wanted to get experience there.
MR: What's the first Woody Allen movie that comes to your mind right now?
JS: Annie Hall.
MR: What's the first Dave Top 10 that comes to your mind right now?
JS: I'll dodge the question and say the Madonna interview is his Annie Hall.
MR: And then what’s the first episode of Seinfeld that comes to your mind right now?
JS: “The Contest” and the “The Chinese Restaurant.”
MR: Why do you think both of those came to your mind right now?
JS: Well, “The Contest” is the easiest one to remember because it was shocking and courageous to put that on prime-time television in America in the 1990s. And the Chinese restaurant was actually cleverer because it had never been done before on TV. You couldn't do an entire episode of a sitcom where people were just waiting for a table at a Chinese restaurant. Doesn't make any sense.
MR: I feel like you would enjoy the original Twilight Zones.
JS: Oh, probably. I've been told that before. I don't think I have ever seen the originals.
Manhattan
MR: Do you have any apps on your phone or any tools that you use that you recommend that people might not have heard of?
JS: One that's purely for fun is called Everyday, which takes a photo of you every day and then compiles it into a video of you aging over that time.
It prompts you randomly at some random point during the day to take a photo and aligns your face with a shadow outline of the photo that you took the previous day. I've been doing that on and off for over 10 years, and you get a sense of all these different places that you were.
MR: In the last 10 years of your life, what do you think were the most important days?
JS: Well, the birth of my twin children and my marriage.
MR: Why do you live in Australia?
JS: New York was an incredible place to spend my 20s and a portion of my 30s. And then I felt that it was not an ideal place to be struggling with strollers down icy stairways to get into a subway and paying the kinds of prices that you have to pay for preschools and healthcare. America is a logistically complicated place to live. America has not constructed itself the way that Western Europe and Australia and New Zealand and Canada have, where there's less friction in life. There's a lot of friction in life in the United States.
MR: What do you miss about America?
JS: Oh, I miss so much about New York as a city. But some of the things that I miss about New York as a city, New Yorkers also miss about New York as a city of 10 years ago — the chaos and vibrancy of the independent art scene, of crazy cats getting up to whatever they want to do, the sheer number of different people you would bump into on a rooftop in Brooklyn while drinking cheap cocktails out of red Solo cups. I've lived in Los Angeles. I've lived in London. I've lived in Sydney. I've spent time in Washington D.C., and Chicago has a place in my heart as well. But of all the big American cities, New York is just such an international hub where everyone comes to do so many different things. And I miss that. I miss wandering down Eighth Avenue or through The Village and seeing the madness.
MR: You sound like Woody Allen in the beginning of Manhattan.
JS: Yeah. Every time I get to New York…honestly, I'm so schmaltzy about it. If I'm flying in — or if I'm in a cab from LaGuardia — and I see the skyline, I cry. It really is a home to me, that town. I lived there for 12 years.
MR: Do you have dream guests that you've never been able to get?
JS: There are some people who I would love to interview if I knew that they were going to really reveal themselves.
MR: Like who?
JS: Tucker Carlson.
Russell Brand of Humor
MR: Do you have any hobbies?
JS: I have a scuba diving license, which I don't do as much as I would like to. But that would be my number one hobby if I could get off my arse and do more of it.
MR: Do you floss?
JS: Do I floss? Yes. That's not a hobby, though.
You would be really boring if that was your hobby. I don't want to meet the person whose most exciting part of their day is flossing.
MR: What's the last book you read cover to cover?
JS: 2001: A Space Odyssey, actually.
MR: What’s the last album you listened to fully?
JS: Radiohead's OK Computer.
MR: Do you define yourself as a Generation X or a Millennial?
JS: I resent those.
MR: Oh, so Generation X.
JS: Well, I resent those labels because I fall between them. By some definitions, I’m one month off being the oldest millennial. But it feels like those of us who were little kids in the ‘80s don’t have a tribe. So neither. But if I had to, I would say I'm an old Millennial.
MR: What about the last show you binge-watched?
JS: I went back and rewatched Breaking Bad during the pandemic. That would be the last big show that I've binge-watched all of.
MR: Who is the first character that comes to mind right now.
JS: Walter White. I mean, just Walter White. Look, there are so many great characters, but what Cranston was able to do there was staggering. I mean, if you say what episode, I mean, the one scene that just keeps coming up is the, "I am the one who knocks" conversation.
MR: If someone has never seen one of your interviews, which one would you point them to?
JS: The juiciest interview I've ever done is with Russell Brand.
Unfortunately, people can't watch it. It was on HuffPost Live, which is no longer online. I do have that segment, though, on a hard drive, and I should probably upload it in contravention of all IP rules.
He's the type of person who will derail the interview completely and go rogue and can destroy you in the same way that Letterman could. Russell Brand is ferociously intelligent, incredibly quick, and very articulate. And about four or five minutes into the interview, I realized, "Oh, he's going to destroy me, or I'm going to ride this horse." And so then I had to figure out how to ride the horse. And it's this spar and repartee where, I mean, he clearly appreciated it. He ended the interview by saying, "You're good." He said, "You're like a young David Frost.” That was at a moment where I was just starting out on the television side of things. It's like jiujitsu or chess, jiujitsu combined with chess, interviewing someone like Russell Brand.
MR: I do both of them. Do you do either of them?
JS: No.
MR: What about something I can point them to without contravening IP laws?
JS: I would have them listen to my first Uncomfortable Conversations podcast episode with Tim Urban and my first with Sam Harris and my first with Stan Grant.
MR: Who have you interviewed that has charisma?
JS: Dick Cavett, Russell Brand, Norm MacDonald.
MR: Norm’s the best.
JS: Yes. Such a good comic. There's some clips online of him and me on HuffPost Live. [In Norm MacDonald impression:] And when he is doing those kind of long, shaggy dog stories, he kind of, kind of looks at you, and he pegs you in his eyes. And he's got that kind of grin on his face…
MR: Did you talk beforehand? Was it an act?
JS: No, I don't think it was. I think his life is an act. I think he just loved it. He was so nice. We exchanged numbers. We would text from time to time. I'd tell him when I was going to be in LA. He'd plan on meeting up and then make some excuse about why he couldn't, and I'd tease him for it. Amazing, amazing guy.
And you often don't get that. Often, there's a lot of artifice.
MR: Have you become friends with any of your guests ever?
JS: Yes. Tim Minchin is a great Australian musician and comedian. He wrote the Matilda musical on Broadway and the amazing songs in the recent movie adaptation, and the Groundhog Day musical and is someone I met, I think, originally through the show. But I won't name-drop every individual.
“So That’s Why I’m Australian”
MR: Did you officially change your name? I know two people with sz’s — Nick Szabo and Thomas Szasz.
JS: No, I never officially changed my name. My grandmother was a Holocaust survivor who came to Australia as a refugee on a boat. And so I don't know what the name was spelled like in her shtetl in Poland 150 years ago.
When I moved to the States and was getting a lot of television pilots and quite a lot of work in broadcasting, initially, it was just irritating to have people constantly going, "Oh, Schweppes?” And so I re-phoneticized it to Z-E-P-P-S. But then once I had kids and started having to fill out forms and everything, I was like, "Oh, it'll all be too difficult." By then I'd reached a certain level of success that I was able not to care.
MR: What was your grandmother’s story?
JS: She was in a little town in Poland and fell in love with a shady guy who ended up saving her life by telling her to get out of Dodge and suggesting when she was 19 that they leave Poland in 1938. And so she followed him to Paris just before the Nazi invasion of Poland. And they spent most of the war in Paris, evading the Nazis even after occupation — very narrowly on some occasions.
MR: Was he Jewish?
JS: They were both Jewish.
MR: So how did they get around being Jewish in Paris?
JS: Well, at the time, you could wear a yellow star and you wouldn't automatically be sent to a death camp. In the early '40s, you were able to live a discriminated-against life in occupied Paris. There was one occasion when my grandmother was out shopping, and she was rounded up and put into a holding cell for deportation to the east. And she was a very fiery woman and quite a beautiful woman apparently. And so she took off her shoe and started smashing it on the bars of the cell to attract the attention of the guards, one of whom she said came over. And she actually did have a child. She had my aunt in her apartment alone. And she told him, "I've got my daughter up there. Can I just go? I promise I'll come back. I promise I'll come back."
And all of the other Jewish people had been trying to get her to stop creating a ruckus and just shut up and do the right thing. She refused. And apparently, with a flirtatious twinkle in her eye, she managed to convince the French (not German) guard. They were apparently easier to get to go your way because they weren't committed Nazis anyway. And he said, "Yeah, be sure to come back." Presumably knowing full well that she of course wouldn't come back. And she went and grabbed her daughter and fled, and they left Paris immediately. They went down to Swiss border where my grandfather was running a smuggling ring for the French Resistance across the border into neutral Switzerland.
He knew some of the border guards and was able to get them some booze that they liked from Switzerland and essentially bribed them to look the other way when my grandmother snuck across the barbed wire fence into Switzerland with my aunt, who was four. My grandmother was pregnant with my dad at the time, and she had to beat my aunt over the head to get her to shut up crying. But they made it. And they got to a refugee camp in Switzerland in 1943, which is where my dad was born. Luckily, he was fostered out to a staunch Lutheran family in the mountains of Switzerland. And I'm still in touch with their kids. They're now a part of our family and God bless them because without them, I wouldn't be here.
MR: Do you think your grandmother banging on the bars of the jail sticks with you as a part of your personality?
JS: Definitely. We're a very resilient bunch of people. The end of the story is she fell ill when the war ended and had to go back to Paris, leaving my dad with the foster family in Switzerland. For the first eight years of his life, he was bounced between this idyllic Swiss village and a filthy orphanage in Paris.
Eventually they made it, in the early '50s, to the port in France where ships full of refugees were going to the U.S., Canada, and Australia. And she'd been through all of that, this penniless Polish peasant. They said, "Where do you want to go? You can go the United States or Canada or Australia." She said, "Which one is further away?"
So that's why I'm Australian.