Rob Eshman

publisher I editor I columnist

Rob Eshman is the former Publisher and Editor-in-Chief of the The Jewish Journal. Under his leadership, it became the largest independent American Jewish weekly, and, with upwards of 4 million unique visitors, the largest Jewish news website outside of Israel. Eshman brought The Jewish Journal into prominence by presenting distinguished columnists and guest contributors whose intelligent, thought-provoking and often controversial opinions addressed the range of issues relevant to the Jewish world. Under his leadership, The Jewish Journal received numerous national and local awards for journalism, design, and community service. 

Rob now continues to actively pursue writing on a variety of fronts, namely for the screen and publishing worlds.


Drew Kugler: As I start thinking about what is going to be the central focus of all the podcast regardless of who the guest is—the thought that keeps keeps hitting me in such a good way is something I wrote on my website and it just makes so much darn sense. And that is our lives are largely determined by the conversations that we engage in during those lives right? That how those go for us become turning points...

Rob Eshman: Right; it's not the what conversation is; how the conversation...

DK: It's the how. It's the, it's the very act. If I—as I'm going to try to do in these conversations—if I'm able to have people think about junctures in their life, I bet will be able not only to find a conversation that was important to that juncture in the life; but, and most importantly to me, the whole goal of these of these podcasts is to help the listener. And I am hunchin’ pretty strong that the listener is going to pick up and see themselves in the podcast, regardless of who the guest is. I'm going to very purposely do a very eclectic list of people. And in a moment, we'll talk about what you do and we'll go from there. However, life turns on conversations. With that in mind, Rob is the publisher of the The Jewish Journal, a very influential, widely read publication around the country—around the world. Has been doing that for a long time. Many, many, many folks in this city and around the world learned lots of interesting things from reading the stuff that Rob and his colleagues put out. And they had made just logical sense, as I said, for me to be able to begin this idea of getting people to talk about their careers and their lives through conversations by starting with Rob... But the question I want to start every one of these podcasts with is a seemingly easy one, I hope. And that is, when you were a little kid, what did you want to be when you grew up?

RE: A writer.

DK: So you knew from what age that you wanted to be a writer, and why? What was so intriguing about it to get your attention then?

RE: I liked to write from a young age. From I mean at least from second grade; I remember writing a book in second grade. It was... seven pages and it was mostly pictures. But my teacher read it to the class and I think I was hooked. But I, the funny thing for me... here's the funny thing starting with me is I don't think of myself as a conversationalist. I think of myself more as somebody who's more comfortable in front of a pen and paper or screen, and expressing myself much better on print, on paper, than I ever do in conversation. I find that the best writers—the writers I admire the most—tend to be also great storytellers and great conversationalists. I don't put myself in that category and I think that there is a connection between the ability to have great conversations and also express yourself really well and fluently in print. Having said that I just feel, I always felt more comfortable writing. To this day I have to—and this is something I credit you with—if I have an issue I have to deal with, I have to remember the words of Drew Kugler who says, “Email is bullshit.” And that anything important has to be done over the phone or face to face. So my temptation sometimes, if I'm having a conflict or an issue or I want to settle something with somebody is to—I know I'll express myself better in an e-mail or a text, but I know if it's supposed to have a lasting effect and really help build a relationship it's got to be a person to person. So, yeah, it was a writer, and I, you know, it was a very amorphous thing. I learned later on to say you want to be a writer is not saying that much. It's really what kind of writing and how you go about creating that career. But that's what I wanted to do.

DK: And when you think about your writing career—and again staying at least in my mind with the theme about conversation—what's in your mind's eye when you think about important conversations you've been in that have contributed to either your best writing or writing that you remember?

RE: I had a professor at Dartmouth named Noel Perrin who was a really accomplished essayists. He wrote for The New Yorker. He had a couple of successful books back when people read these kind of books. One is called First Person Rural. In the other one, Second Person Rural about a city boy who goes to live in the country is based on his life. So he was the perfect—we didn't have a journalism department. so I couldn't be a journalism major. But I created a kind of environmental journalism minor out of different classes and because I thought I wanted to go into environmental journalism. And I asked him for advice and he told me, he said, “There's only two things you need to do.” He said, “Write about what you love, or what your passionate about... because life is short. And feel free to turn anything in after the eleventh draft.”

DK: And did you eventually write stuff for him in that....

RE: Yeah,

DK: that you loved...

RE: Yeah I loved writing for him. He was exacting. He was a superb line editor. He had that kind of E. B. White—he came out of that school, The New Yorker sensibility. And he was great teacher and and it really taught me that just don't ever think anything you write is good until you've polished it. And then also to write about things you really care about. And that's good advice and bad advice, I found out. Because a lot of times when you're building a career, you probably will write about a lot of stuff you don't care that about deeply about, but you have to care about the writing, nevertheless. You care about what you're doing, nevertheless.

DK: Right.

RE: But you can't always write about what you care about.

DK: Yeah, because you write—at least what I know, right?—you write a weekly column of some length.

RE: Eight hundred fifty words.

DK: Thank you, not that anyone counts. But I'm biased in our friendship. Every time that I read them, I can hear you; it’s special kind of writing that you do. So that then leads to—maybe it's about a conversation with yourself. Is there even close to any sort of process or way that you get yourself to that point where you can create that kind of writing that borders on the passion? Because anybody who reads you gets that. Do you—what do you go through to get there—to be able to produce that?

RE: I think it's an internal experience and also an external. Externally, I talk to people and I have those conversations; like what are you, what's going on? What do you think is important this week with—what's bugging you this week? What are people talking about in your lives? Like, we have our, we're sitting in the conference room of the The Jewish Journal where we have editorial meetings, and I always like to ask people, you know, what were people talking about at your Shabbat table? Or talking about at your Seder table? What are people talking about? And that will kind of give me a sense of what people seem to be—what's on people's minds. And it may not be what's on my mind, but at least it gives me something to go from. But it's also, you know,  I read everything that needs to be read: The Atlantic, Washington Post, New York Times, Breitbart; everything that's out there. And then I just let it kind of sit with myself; probably for too long, pushing right up against the Tuesday deadline, and try to figure out what I really care about, you know? In other words I do take what Noel Perrin said to heart. Like, I I don't know how many more columns I'll get to write and I think it's a real privilege to be able to have an audience that's going to read what I'm going to write; that's going to take it seriously. So, what do I want to tell them? What I want to communicate? It's my chance to say something that I really care about. So, that sometimes takes me a while to figure out what's really... And sometimes it means you know writing one column and feeling like there's no passion in it and tossing it and writing something else.

DK: Do you literally ever get to the point, say on Monday or whenever, that deadline is on Tuesday, where you have to remind yourself—other than that the column's due—of this notion of OK, is there a dialogue with yourself; this is OK. What is it that I care about? Or does that just flow at the point when you decide to write?

RE: At this point, it kind of flows. And I just have to trust it. And I sat down to write a column last—a couple weeks ago... and when it's not coming out, when it's like I feel like I'm pushing and pulling it, I'm just forcing it; then I know something's amiss.

DK: Right.

RE: And so what will happen is I'll do that, because you have something on paper. And that and inevitably I walk into the office and the managing editor will say, “Where's your column.” And I'll say, “I don't like it.” And I'll sit down at my computer and then, within ten minutes, something that I really care about comes out. And I just live with it. Sometimes I think you know it could be... I just have to trust myself. Sometimes those are my best columns, and sometimes not. But at least honest to myself.

DK: So, I have thought often, and seen, through real experience that the notion of trusting oneself and what you bring, what you can bring, is a key to successfully communicating in general. There's an old saying that I remind some clients of—that it's hard to lead a cavalry if you think you look funny on a horse. Meaning that you've got to be in the right frame of mind to produce something worth following. So what I wonder is do you ever have to get to Tuesday and you've written somethin' and you've turned it in and like you said you're probably gonna let it go, but where you're not as happy as you'd like to be.

RE: I’d say every Tuesday.

DK: Every Tuesday.

RE: I wish I had more time... I mean doesn't everybody have this problem? I know I do with conversations, as well. I mean isn't the thing you wish you had said—the conversation you wish you had had... so there's a sentence you left out or... the deeper thought that you didn't quite get to in the piece? Also I’m limited to eight hundred fifty words in print and we have to which is this thing a few people still publish on and still read and so eight hundred fifty words is not much.

DK: No, no.

RE: Online I could write longer, but I tend to leave it alone once I've done it.

DK: Yeah.

RE: So yeah it happened. I don't think I'm really ever that satisfied, but then I thought you know if I had a month to write a column would it be that much different; I don't know.

DK: Yeah. So what were people as you sat around this conference table what are people talking about around the Seder table or in conversations that even your colleagues are hearing about? Just give us a little time frame.

RE: Well this Passover was about what the President's press secretary said about Hitler and gassing, when Hitler didn't gas people.

DK: Right.

RE: And then. I think there was some Trump talk. That was the big thing this Passover; a lot of dropped jaws over that.

DK: Yeah.

RE: And then you know the other thing is—like at our Seder table, we really didn't talk about Trump.

DK: What did you talk about?

RE: Family. You know, we had family. You don't see your family that much, and when you do, you're always busy. And so, when you finally have a chance to get together, and just catch up with the kids and what's going on in their lives and... brother, and with your friends and it wasn't—it felt like it was too good for Trump.

DK: Don't waste it on him, right?

RE: We don’t want to waste another minute, another conversation on him... so we just talked about other stuff. And we're also doing a Seder—and I have this advantage of having been married to somebody who really knows a lot about that stuff—so we asked questions about Passover and about spirituality, and liberation, and what it means, and it got good.

DK: Yeah, and the people around you want to live—I've said it many Seder tables where a certain member of our family forces us to try to converse in a certain way. Yeah, asked the big question; let's go around and hear everybody's answer. And the kids somehow are able to go to the bathroom at that point and the whole thing dies off quick, and we all resist.

RE: I have to say, I'm married to a rabbi, Naomi Levy. And the second-night Seder, my brother was there with his family. And his daughter's a teacher—she teaches fourth grade. She's been doing it for several years now at a tough school in the Bay Area. And so, when it got to the time of the four children where you get to a part of the Passover Seder where you read about the four different types of children; the wicked child, the smart child, the child, the simple child, and worst of all this one, and the fourth one right there: Rick Perry.

DK: Yeah, that’ll get you a job some day.

RE: Some Secretary of Energy right now. Lies, wicked...

DK: We’ll edit that in later.

RE: So she turned to my niece and she said, “You're a teacher. What do you think of the pedagogy? How did you deal with a child who's obstreperous, or how do you deal with a child?” And she said something that you would love—she said, “You build a relationship and you find out what motivates that child. And use that to get them through work.” And then she told me hysterical stories about teaching these kids... So it got very real... the T. word wasn't mentioned.

DK: That's a rare table. But speaking of passions—I know because we've built a friendship around two passions of ours. One of those is food. And the other is Howard Stern. So how I can—I don't even need to fit conversations on top of this, but those things are so consistent, only talk about your life for a second. What is it about those two things? You can tie them together—or keep them separate—that keeps you so diligent in your consumption of them.

RE: Well, in the case of food, as long as I've been passionate about writing, I've been passionate about food. And I think one of the challenges in my life is figuring out how much time I devote in my life to writing and how much I get to integrate them somewhat by blogging about food in assigning food stories or in editing stories and living in kind of the Jewish food world to some extent. But I kind of feel torn sometimes about my passions in those worlds.... for decades. I started life as a baker at Il Fornaio. Actually Yellin's Chocolate Fudge Cake Bakery—I was a baker at the age of fourteen.

DK: Where was that?

RE: Encino.

DK: Encino.

RE: Encino and Ventura. So I started my first job was in bakeries all... my job after that was at Miss Grace Lemon Cakes in a bakery. Then in college, I supported myself making sourdough bread at a local bakery in the food service industry. And then when I graduated, I wanted to do catering and have my own catering... was a cook, a line cook and then they had my own catering company in San Francisco—I mean in Los Angeles. So I made a living at it and then it was also my passion and then I think part of me just felt like I couldn't get to the part of cooking it felt like it was right for me as a career. I don't think I wanted to be in the kitchen nineteen or twenty hours a day, which I guess is a sign of true passion.  I didn't really know. And writing always seemed to be the thing that I always wanted to do as a career. And Howard, you know Howard's one of those people that he's a teacher. I mean it's like in a weird way—it's demented to people that don't listen to him or that only know him through his public image, but in some ways, I've learned so much from him. And not only is he funny and I enjoy it, and I always am guaranteed at least a laugh in my twenty, twenty five minute commute. I will laugh on the way to work and that's amazing.

DK: In and of itself, right?

RE: And you can watch a two hour comedy and not crack a smile. But I am always diverted and entertained by what goes on that show and then—I'm always—I always get something out of just listening to Howard. For one thing, he's in an industry or the part of the media that is really the worst. I mean radio, and he always talks about that, but he made it into something amazing. And frankly I see a parallel. I mean being in Jewish journalism, you're not considered mainstream. You're not considered like— it's kind of the junk bond of journalism, or whatever, the kind of marginal ethnic press in journalism. But I've learned from Howard, if you take what you have and you make it really good... and that's what we're trying... I've tried to do here at The Journal. I don't know they succeeded but just because you're an FM station, just because you're doing morning drive time—you know, you listen to any other morning drive, it's pretty lousy.

DK: Yep.

RE: Howard's raised it. So you can work to raise the bar. And then how does he do it? You know, like bringing every bit of the strengths to the people on his staff, like really bringing them to bear. So even if it's the guy who cuts his TV clips, like, he becomes part of the staff. You pull out the most you can from him; so it's really pulling out the most you can from everybody. And kind of learning where you can break barriers and trying to break them. And I don't know that we've succeeded beyond my wildest dreams here, but I think we've done better than people expect from a Jewish paper, a Jewish publication. And a lot of that is just Howard's modeling—what he's done in his career.

DK: And it's such an easy segue to understanding Stern. I mean you write a blog about it, an occasional blog. I've actually got to help you on a couple Serious Sterns, Serious Stern on the Jewish

RE: It's been a while since I've kept it up on a regular basis, like that I would like every other blogger out there.

DK: That's right. Amen to that. So but the issue is one of the issues with Howard—which which again takes us on this path of conversation—is that over the years, he's changed. He relies—some people criticize him for it, but a lot of people are commending him for it—that he relies much more heavily on the notion of the interview.

RE: Yeah.

DK: That and his skill is an interviewer is beyond.

RE: I mean, I've learned so much listening to him doing interviews. And he's got to do a show... there's this company called Master Class and they have, like, Steve Martin teach comedy, and Aaron Sorkin teach screenwriting, and they've got to have Howard teach interviewing and storytelling. I think those are two things he excels at. I mean, he could keep a story going about his father ordering blueberries and decaf coffee. He could keep that story going on—for Dunkin Donuts—for fifteen minutes have you on the edge of the seat; make it seem better than the most exciting thing that ever happened in your life. And he knows how to do it. He knows how to control his voice. He knows how to create tension. And then also interviewing; there's just nobody better. And I have to say, I was blogging about Howard years ago before he became recognized for that. But the thing I saw in him was just that particular skill of creating a relationship and drawing people out. And there's nobody close to it.

DK: Yeah, I was wondering though—

RE: Except you, Drew. You’re getting there.

DK: ...I’ve got a long way to go. But I am wondering what could a listener—if they were able to suspend the disbelief about Howard—what they could learn, since this show is ultimately about thinking and learning in my show is and that is where I can grab on to to Howard a little bit. What could a listener who's running a business—and you began to answer the question a few minutes ago—what could they learn from Howard about communication, about conversation? I often think of that because I listen to him as much as you do. What's the application?

RE: Well I would say first you have to separate. I don't know Howard. I just know the Howard Stern on the radio. So I don't know what you learn from that Howard Stern in his private life and how he really is. But I do know that one thing is he's always working on himself. He’s big in the self-improvement: therapy and coaches, and hobbies, and hiring people to make him better at things. And I think that's one thing. The other is that at least on the show he goes toward the conflict; not away from it. And this is something that I think you’ve really helped me with, and I think it's what you help your clients with, and I think what people really have the hardest time with. It's like—conversation's easy. I mean if you're saying people what makes a conversation critical, what makes a productive—is usually to go through a difficult thing, and how do you get through that difficult thing. How do you—you're going to have conversations as a boss where you have to let people go, or you have to improve people's behavior, or you have to get people on board and those are not—I don't know anybody who's naturally good at that. And most of us, because we're not naturally good at it, we avoid it.

DK: And that's how we met. Our friend introduced us because you were looking at an issue here at The Journal. And you were stuck. And just and a couple of senior folks here.

RE: Right.

DK: And we had I don't know where the space was, but we had this conversation where it came down to that.

RE: And to get through those things, I mean if you don't grow as a person, and you don't grow as an organization. And you're not really doing—I know it's easy to say this because it was probably a harder time for the person we had to have the conversation with—but you're not doing them any favors either in the long run.

DK: That's right, yeah.

RE: Because they can't really grow here if you're not going to take them on is as part of the team. You know what it is, but dealing with those conversations—so Howard, his show is really about conflict and it's about interpersonal conflict and that's where the humor comes from. It could be drama, but it's always humor. So one thing he's taught me—I've blogged about this—is whenever there's conflict, don't turn around. Turn into it. And  you're going to find—you're going to grow from it. You're going to learn from it and your organization is going to. And I think I still don’t like it, but I think also even listening to Howard in the morning kind of accustoms me to it.

DK: Knowing that may present itself—

RE: Yeah.

DK: —in the day. Do you think you're better at it?

RE: Marginally. I don't think I'm much better at it. I think I'm marginally better at it. There's always the next challenge. Like, I'm good at one level of it, but then life presents higher levels of it... so no; I don’t think I’m that good at it.


RE: To be honest. I’m much better than I was though. I got to get a B for improvement.

DK: That's right. That's right. And you at least have admitted over the years that that's something—as people will find out from my other guests in these days and months and maybe years go on—that it's something that ties a number of my clients together. And nobody likes it. Nobody.

RE: I think I'm an introvert by nature. And I think as an introvert, I just have a hard time with even non-conflict interactions sometimes. Left to my own devices, I'd be alone a lot. So even friendly conversation sometimes just feels like too much for me, much less unfriendly conversation. But like you said, there's a book that came out years ago, a famous anthropological book called Life is With People, and it was about Kibbutz movement. Every time I'm kind of walking away from a conflict and I just remember that; like, you don't get anything done without them.

DK: For the show notes on this thing title was?

RE: Life is With People.

DK: Well that's the irony, right?

RE: My book could be called Life is With People, Unfortunately.

DK: But that's the irony to all this as we, to quote my rabbi as we begin to conclude here. All the good that comes in in your life—knowing how much you love your wife, and you love your kids, and you do love your job, and your writing and everything—has come and is driven by conversations. Ones you would rather avoid. Ones that maybe, you could say, could be alone. But if you lived alone, we certainly wouldn't have met.

RE: Well, I was going to say—when you mention my wife, I was going say—I think it's interesting that when you asked about it, I didn't go into personal conversations. Partly because you're an executive coach, you do in people's professional lives. And I don't know how much they get when they talk to you—how much they get into their personal lives. But in some ways it's the exact same problem.

DK: Totally the same

RE: And, you know, the ability to sit with the person you love and have a difficult conversation with them, that's going to do more to determine your life happiness. And I found that with Naomi, every time we've had a difficult time and every time we've faced it, the love deepens. The marriage gets better. Everything's better. But man, those are things we're also not built to do.

DK: That's right.

RE: And I know people who are great in a boardroom; and I have specific people in mind who are at the top of their game when it comes to being tough in a boardroom, and and helping people grow in their business and having tough conversations. But their relationships are for shit. And so... I guess it's not you could do both, but it's important to keep—those are most critical conversations. And the ones with your kids are a little tough.

DK: That's right.

RE: Drew you're going to keep busy.

DK: I am going to say between getting people to talk about this on on air, so to speak. And also I couldn't agree more. Probably the thing that's changed the most about my practice just in the last couple of years—maybe when President Trump got elected—is people want to talk about more things about their life than just about the boardroom. So I spent—in the last day, I've sat with three different entrepreneurs who have all talked in equal amounts about their business challenges and the challenges in their marriage. And your point about it being less and less, or more of a finer line between home and work... I've decided to accept that. I never wanted to be called a life coach, but this is life. And this is this is what I'm going to help them deal with.

RE: If you could go into conflict in your personal in your professional life and you learn how to do that and you certainly have tools, you'll be offering any bill then you're going to take those and literally into the bedroom too, and I think that you're just going to be happier all around.

DK: Well, Rob thank you.

RE: Thank you Drew.

DK: I don't I don't know how long—

RE: As they say in The Jewish Journal, mazel tov on your first episode.

DK: —my first episode, and we will see. Oh, do tell them one thing. Hold on one more minute. I was debating with Rob... he was sitting, listening to me think through this podcast. And I was talking about the different guests who you'll be finding out about in in the near future. But Rob, pretty much in a very friendly way, insisted on taking on a certain role—which I'm going to have him describe—on how to think about your first guest.

RE: Oh, you told people that I was always into cooking. And when you're making crêpes or pancakes, the first one never comes out that good. It's something to do with the stickiness of the pan and the amount of butter in it, or whatever. For whatever reason—I'm sure Harold McGee would have a scientific reason—but they call it, so you throw it away, so it's called the dog crêpe. And the first crêpe—you give the dog—is not going to be that pretty. So I told Drew, let me be your dog crêpe.

DK: Right.

RE: So you might never even hear this.

DK: I was going to say you have performed much better at least than any dog I could have gotten.

RE: That’s high honors.

DK: So on that note, thank you for taking the time today. And we'll talk again soon.