In college, Jesse Israel knew that his major didn't really matter so much because he wanted to pursue a life in entertainment and media and early experiences landed him on the path right away. With a career that saw him in every sort of producing role, eventually developing major star vehicles, he realized that there might be another way to use the full range of skills he'd honed over two decades. Find out how tapping into relationships and dealing with rejection can be quite transferable.
In college, Jesse Israel knew that his major didn't really matter so much because he wanted to pursue a life in entertainment and media and early experiences landed him on the path right away. An out-of-season internship at NBC Sports landed him in the president’s office, with access to top executives and the inner workings of things. And when graduation coincided with the Atlanta Olympics, he had a job waiting, albeit a few flights down from the head office. With a career that saw him in every sort of producing role, eventually developing major star vehicles, he realized—in an industry that had transformed thoroughly since he began in it—that there might be another way to use the full range of skills he’d honed over two decades.
In this episode, find out from Jesse how tapping into relationships and dealing with rejection can be quite transferable…on Roads Taken with Leslie Jennings Rowley.
About This Episode’s Guest
Jesse Israel is a certified financial planner, wealth manager, and insurance expert, who currently advises at Capstone Partners Financial and Insurance Services in Los Angeles, where he previously spent a career in the entertainment industry that spanned two decades with stints at NBC Sports and Dateline, and development roles for numerous feature film deals. Being a very proud husband and father of two girls, he is cofounder of the Dad Club, which is just the coolest.
Jesse Israel:And I said, you know what, I'm going to give this a shot. And really was the best thing I ever did. I wish I had done it 10 years before what I didn't realize. And I tell a lot of my friends in the entertainment business who are thinking about leaving that it actually gives you skills that translate really well that you don't realize. I mean, number one, you know how to talk to people and number two, you know how to deal with rejection. And number three, you know, you know how to network .
Leslie Jennings Rowley: In college, Jesse Israel knew that his major didn't really matter so much because he wanted to pursue a life in entertainment and media and early experiences landed him on the path right away with a career that saw him in every sort of producing role, eventually developing major star vehicles. He realized that there might be another way to use the full range of skills he'd honed over two decades. Find out how tapping into relationships and dealing with rejection can be quite transferable on today's roads taken with me, Leslie Jennings Rowley. Today, I'm here with Jesse Israel, and we are going to talk about the power of relationships and whether that is to facilitate something really big that's good for the masses or really personal along the way. So Jesse, thanks so much for being here.
JI: Of course. Thanks for having me.
LJR: So when I talk to a guest for the first time on this program, I ask two questions and they are these: When we were in college, who were you? And when we were getting ready to leave, who did you think you would become?
JI: Sure. So at Dartmouth, I was a history major, a government minor. I was in Alpha Chi. I was the Rush Chairman. I was on the rugby team. I was a DJ on 99 Rock, known as The Jester, which is cringe-inducing at this point. I think my kids still make fun of that.
LJR: And so that's part one, who you were. Actually, how had you gotten to Dartmouth? What was your kind of background?
JI: Yeah, so I…it's funny, I looked at a lot of different schools and I remember going to Duke and I'm a big sports fan and I remember seeing Christian Leitner, Thomas Hill, and Grant Hill when I took a tour and I was like, I really want to go to Duke. And it's funny, my mother said, you know what, you should really go up and look at Dartmouth. And I had been there before, not to, not in any official capacity, but my best friend from high school, his parents had a, like a ski house slash, you know, lake house up in that area. So I'd been to Hanover. And I said, okay, you know, I'll go take a tour. And I remember being on the tour and the tour guide talking about all the different things you can do. And I kind of looked around and I said, this is what college is supposed to be like. And I was still, you know, I remember making a list of pros and cons of Dartmouth versus Duke and Dartmouth won out and I applied early and got in. And it's funny, over the years, how many people I've met who have gone to Duke, who said Dartmouth was their other, you know, top choice.
LJR: Someone just said that to me yesterday, actually. And I remember saying to my father when we visited, this is what college should be like. So very, very similar. All right. So that's who you were. And did your experiences there or the things that you were finding in either your history or anything else kind of give you a glimmer of what those years would look like specifically right after we graduated?
JI: So it's funny, you know, I really had no idea what I wanted to do with my life when I got to Dartmouth. And, you know, I tried a lot of different things, you know, academically and ended up just really loving my history professors. And I think that's why I majored there. And I also knew that, you know, as I always had an interest in media, you know, sports, media, entertainment, you know, kind of a wide ranging thing. But I also knew that after a while that whatever I majored in wasn't really going to affect my career. And so I just figured I'd go with what I enjoyed. I started off as a government major and didn't end up loving a lot of my classes, which is why I switched to history. And then, yeah, I had a, you know, if you had asked me at the time, I had an internship my junior year working for the president of NBC sports, which is really the value of the D plan because, you know, I had a connection to get an interview and they said, well, you know, we don't get a lot of interns in the winter. What do you want to do? And I said, well, what are my choices? They said, well, you can work for the president. And I said, sure, I'll do that. [LJR: Okay.] And so, you know, I thought, you know, I thought, okay, I'm going to be in sports broadcasting.
LJR: Wow. And that was in Manhattan?
JI: That was in Manhattan. Yeah. So I was living at the 92nd Street Y, you know, for 200 a month you know, shared kitchen, shared bathroom. And they gave me subway tokens. That's, you know, internships are a lot different now. You get paid for them.
LJR: Yeah. Well, but what an experience. I mean, you couldn't pay for that now, right?
JI: Yeah. It was fantastic.
LJR: So did that mean that you, Had your eye set on that level and, and that particular thing in New York and that life?
JI: Yeah. So I parlayed that internship. I worked at the Olympics in 96 in Atlanta and I was what's called a logger, which basically means, so I worked in gymnastics and they set me up, you know, with like five different monitors and it was my job to keep track of when everything happened. And Atlanta being in one of the first East Coast time Olympics, we were on a two hour turnaround. So the event would air and we'd be on the air two hours later. And so I would sit in the editing booth with the producer and the editor and tell them when everything happened and when all the good shots were. And at the time it was really exciting. I mean, I didn't know much about gymnastics, but that was Carrie Strug and the Magnificent Seven. And so you couldn't have written anything more dramatic than that.
LJR: Right. I had just written to myself, Carrie Strug. That's so. Okay, but, okay, let's back up a second because an internship working in the president's office sounds really exciting, but it does not sound like you're getting your hands dirty in media.
JI: No, I mean, it was more just doing whatever needs to be done. I mean, literally I would ride around with, you know, Dick Ebersole was the president of NBC sports at the time and I would ride around with his driver so he could double park and run errands for Dick or, you know, just, you know, answering the phone, whatever needed to be done. But I had access to a lot of the big executives there.
LJR: Yeah. And so then though, you're put in like the sports of sports with the Olympics and this quick turnaround. And so you just, you're learning on the job.
JI: Yeah. I mean, it's just, you know, most people were like me. I mean, you know, a lot of, you know, very young people just wanting to get their hands dirty and they say, here's a logging chart, here's what you do and we'll figure it out.
LJR: Got it. All right. So then where, tell me all about this. Where does it go?
JI: Sure. So then you know, all of this led to a job as an NBC page. So I was giving tours at 30 rock, like Kenneth. [LJR: Nice.] You know, I had the uniform. You know, it was interesting because, you know, all of my friends from Dartmouth were investment banking analysts and, you know, making a decent amount of money and I'm making 10 an hour.
LJR: Right.
JI: So the deal was, you know, they would pay for drinks and I'd get them SNL tickets.
LJR: Oh, I don't know that that's a fair shake for you, Jesse, come on, you could have a couple dinners and a couple drinks.
JI: Yeah, it worked out. I mean, it was, you know, unspoken deal.
LJR: I love it.
JI: But it was fun. I mean, it was nice to do things for my friends.
I would work SNL every weekend, helping seek the audience and being there. And I worked on Conan O'Brien and the Rosie O'Donnell show. And then, you know, as a page, you could get assignments, you know, at various departments. And then I would work every weekend as a logger. I was working seven days a week, so Saturday and Sunday…Saturday I would do, you know, college football or golf or whatever NBC had, and then Sunday I would do football. And this is before the era of NFL Sunday Ticket, so as a Patriots fan, I couldn't watch my Patriots in New York. But working for NBC, I could, and they had to deal with Domino's Pizza, where they bring in hundreds of pizzas, you know, for us, so it was like, I'm doing what I would do anyway, which is sit around and watch football and eating pizza, but I'm actually, you know, getting experience and getting paid to do it.
LJR: Awesome, awesome. So that is an interesting existence, though. In New York when we had all these banker friends and all of that. So the quality of life is pretty high. And how do you decide, okay, is this a long-term thing? And
JI: Yeah, so, you know, I, I, I did that for about a year and I looked around and I saw all of these people that had been working weekends for their entire lives, you know, and, and I looked at rent and all these people were miserable. And, you know, I didn't see myself wanting to do that in the long run. And I lucked out, you know, one day when I was a page, I was sitting in the page lounge between giving tours and somebody came down and said, you know, is anybody here good with computers and, you know, Dartmouth, you know, we were very advanced computer-wise. You know, I think I look at Blitzmail as like pre Microsoft Outlook, you know, and, and anyway, and I just sort of put my hand up and said, yeah, I'll figure it out. And I got sent up to the office of this woman who was the vice president of NBC News, who hired all the on air talent and all the producers. And she somehow had been tasked with sending holiday cards to, you know, everybody from—I'm not sure why she volunteered for this, probably political, but, you know, the president of NBC at the time. And so I helped her figure out how to print labels using Microsoft Word. And she and her assistant liked me and they kept bringing me back, you know, so I never had to give another tour. I basically worked there full time for the last three months of my pageship. Then they kept me on and, you know, after about six months total of working for her, she came to me and she said, look, you know, Dateline NBC is now on five nights a week. It's kind of all hands on deck. We need help and we need somebody to open the viewer mail. Because nobody has done this job for a year. So it's basically like, let's see if you like news and whether news likes you. [LJR: Okay.] And so, you know, I said yes and realized very quickly that, you know, I did not want opening the mail to be my job. But one of the things you had to do was send a postcard to everybody who had sent you mail. And I'm like, I'm not handwriting thousands of postcards. So I convinced them to give me a windows-based computer. Whereas most of the producers there had what was called a Basie's machine, which is a pre windows like news terminal. It was, you know, green. Looked like the Matrix, you know, green and black and, you know, no mouse, no nothing. And so I started, you know, I printed out labels, got caught up very quickly and actually found about, I would say, 10 stories that Dateline produced. And because I, you know, I pitched the story, I got to help. And so, you know, within a year, they made me an official assistant producer at Dateline. And, you know, I was there for about four and a half years, got promoted to an associate producer. And at the time Dateline was much more like a traditional news magazine. You know, so I worked on the 2000 election. I worked on a Columbine. I worked on 9-11. I worked on Celebrity Profiles, John F. Kennedy Jr. 's plane going down. That's actually a funny story. I was invited to a Dartmouth friend's place in the Hamptons that weekend. Got there and spent, you know, a lot of money buying groceries for the weekend because I was the guest. It was, you know, and then as soon as we got to the house, my pager went off. I saw that the plane had gone down and got called back into work. So I missed the entire weekend. But anyway, worked on a lot of different things at Dateline was a really exciting time. You know, when I'm 22, 23 years old, flying around the country, you know, worked on all these different stories and just kind of learning on the fly. Met a woman who's now my wife, who is still at Dateline 25 years later. It's the only job she's ever had, which is pretty crazy.
LJR: Wow. Okay.
JI: Yeah. And so, you know, I'd been there for a while and the show started turning into what it is now, which is true crime. And, you know, it doesn't particularly interest me. And, you know, I sort of got to the point where it's like, okay, like, is this really what I want to do for the rest of my life? And I found myself working on all the entertainment stories. Yeah, that's really what I was drawn to. And I was always a huge movie and TV fan. And it sort of gave me the confidence. Well, okay. I figured out how to be a news producer without any real training. You know, my wife went to Columbia journalism school and was editor in chief of the daily paper at Tufts. And, you know, I just sort of figured it out. So I wanted to make the transition, but I didn't really know how to do it. And my best friend on the show had gone to Yale with a guy who was doing a program at USC called the Peter Stark Producing Program, which is basically film school for producers. And they only let in 25 people a year. So as I was talking to him, he was saying, Oh, you know, I have a creative partner at this program that I'm working with a guy named Jeff Wadlow, who I had known from Dartmouth who was a 98 and I played rugby with his older brother, Ray. And so I got Jeff on the phone and he, you know, he told me about the program too. And I said, you know what, I'll apply. And if I get in, I'll move to LA. And I'd been to LA for two days in my entire life.
LJR: Oh my gosh.
JI: And applied and got in and leased a car and threw everything in my car and moved cross country 22 years ago. And so I worked, you know, full time during my second year of that program at a management company called Circle of Confusion, which repped the Wachowski brothers and people like that. And then I worked at Joel Silver's company. Joel's the producer of The Matrix, Lethal Weapon, you know, kind of a legendary Hollywood figure for good and for bad. That's all I'll say about that. And then I worked for about five years at a production and financing company called Alcon Entertainment. And while I was there, we did movies like The Blind Side and The Book of Eli. I was a development exec there. Sister of the Traveling Pants, things like that. Kind of hit my ceiling there. Left because I had two movies of my own that I thought I, you know, would get a chance to produce. Unfortunately, it was a terrible time. There was a writer's strike. The industry basically shut down. So ended up taking a job with a kind of more entrepreneurial production company. Did that for a few years, ended up producing a movie that's based on a dateline story I did about a guy who went through puberty at age 30. It's called The Late Bloomer. It's. Still on I think it's, you can get it on Amazon prime. It's not great. You'll get some laughs, but a lot of very recognizable people JK Simmons, who won an Oscar for Whiplash and Kamail Nanjiani and Beck Bennett from SNL and anyway, a lot of, a lot of recognizable faces.
LJR: Okay. Wait a minute. There's like a little dangling thread to this story. So Dateline, does Dateline move to LA?
JI: Yes. So after I graduate, well, I graduated. Six months before I graduated, I flew into New York, surprised my wife, proposed to her, and she was able to, so she ended up planning our wedding before she moved to LA, and then was able to transfer her job. Also during that time, because they knew both of us, there was a woman on the Today Show who was on maternity leave and they needed somebody to fill in. And so they basically sent my wife to work in LA for three months. So that definitely helped the relationship.
LJR: Yeah. Excellent. Excellent. Yeah. Thank goodness for babies.
JI: Yes.
LJR: And we'll get to that a little bit later too. Okay, so then there you are in LA living this kind of producer lifestyle and are you like kind of looking back going I knew I didn't need to use my major and I wanted to do something in entertainment and look oh my gosh I'm doing it.
JI: Yeah, it was you know, it's it was kind of crazy. But the road was was strange but honestly that so the connection really was…so when I got that internship at NBC, I was taking a course at, I took a bunch of, you know, film classes like introduction to television and I was taking an introduction to television class and I found out that my internship required college credit and Dartmouth does not give college credit. So I went to my professor and I explained the situation. He's like, don't worry, I got this. And so he wrote basically a bogus letter saying that I would get credit for this. And the funny thing was my boss at, at NBC sports kept asking me like, is there anything you need for your class for me? Or I was like, no, it's, it's okay. It's all taken care of. And then a couple of years later, when I was a dateline, he called me up and he was like, look, I got this other Dartmouth intern. Like, how did you get that bogus letter?
LJR: I asked nicely?
JI: You know, he had sort of figured it out.
LJR: Yeah. Good. All right. So you'd had your kind of movie taste and you'd had all these things. There's like one more little push and then things get a little nutty.
JI: Yeah. So about eight years ago I had a pretty good job. I was working for these two big producers. One of them has produced everything from Saving Private Ryan to Grey's Anatomy, things like that. The other one was a legend in the business who, you know, was head of the academy, was like the first AD on Chinatown, produced Wayne's World and variety of things, Heaven Can Wait. And, you know, I was the only executive and we were partnered with this Chinese conglomerate called Wanda. And basically the head of Wanda wanted to win an Oscar. So we were going to try to make the movies that Hollywood wasn't really making anymore. You know, the sort of like mass market, but still Oscar quality movies. And I had put a project together. You know, we had Russell Crowe attached and David Yellow attached and, you know, this is going great. I mean, the office is 10 minutes from my house, which in LA is a huge deal. And I remember I was on vacation visiting my family in the East coast. And I woke up to find out that I went from a great job to no job because the Chinese conglomerate had run afoul of the government and we couldn't get money out of the country anymore.
When I got back, I started looking at the opportunities available to me. And I realized like, it wasn't really going to get any better for me. You know, unfortunately when you're a development executive, you have no quantifiable skills. It's really about, you know, relationships and, and, you know, what franchises have you been associated with? And unfortunately I, you know, hadn't worked on any franchises. And so I started thinking, you know, look, if I don't get out now, you know, you're going to regret it for the rest of your life. And it's funny because a lot of my friends in the business now tell me that they wish I had gotten that when I did.
LJR: Yeah, cause it really has evolved into something that's almost not recognizable from people that moved there 23 years ago.
JI: Yeah, it's a very, exactly. It's a very different place. The middle has really been cut out. You know, you're either wildly successful or you're struggling to make ends meet. And so it's funny, I didn't know what I was going to do.
And, you know, one day just, you know, I was having lots of informational conversations with people in various industries. And one day I just said, you know what, I'm just going to like put my resume online, just to maybe something will come up that I never thought about. And I got a call from New York life the next day. And I started laughing because my dad's an insurance broker. He's been retired for years, but you know, self-made, you know, his father died when he was five, you know, he put himself through college, you know, built his business, you know, at the time he sent out postcards to people like, do you need life insurance? And, you know, I was never particularly interested in what my dad did. I thought it was really boring, but I said, you know what? Look, my dad's a really good guy and he worked really hard and was able to build a wonderful life for, you know, look, I'll be honest. I had no college loans or anything. And, you know, if I want to give my kids half of what my dad was able to give me, maybe I should suck it up and take a meeting. And the meeting was a lot different than I thought it was going to be. It was much more about financial planning. And I said, you know, I thought about it and I said, you know what? I'll at least go through the training program and kind of see how I feel. Training went well and I said, you know what, I'm going to give this a shot. And really was the best thing I ever did. I wish I had done it 10 years before.
LJR: Really?
JI: Yeah, I mean It turns out I what I didn't realize and I tell a lot of my friends in the entertainment business who were You know kind of Thinking about leaving that it actually gives you skills that translate really well that you don't realize I mean number one You know how to talk to people and number two, you know how to deal with rejection, hich is way worse than entertainment, you know, because it's so much more personal. [LJR: Yeah] And number three, you know, you know how to network, you know when I first started, you know You you're supposed to put together a project 200 of okay who are the 200 people that you know might take a meeting with you and hear what you have to say? I had a project 1000, you know, because entertainment is so social. And so since then, you know, I switched firms about four years ago because I really wanted to do much more than just insurance. So I'm fully licensed now. I'm a certified financial planner. I'm a certified life underwriter, which means I'm also a life insurance expert. I do wealth management. So it's really now we sit down with clients and we, you know, we get to know their financial situation and we figure out, you know, what do you need and how can we help?
LJR: I love this, Jesse, because it kind of does that. part thing. Yes you have all these transferable skills that you could not have really figured out, like, Oh, if I go into this entertainment industry, later I'll be able to do this because that does just doesn't compute right? But at the same time, you were saying this kind of job doesn't have the quantitative or the, you know that kind of skills, but you learned how to learn. And so you were able to say, okay, I know how to put a deal together too. And I must be able to figure out the little parts of it through some just learning really quickly. And I love that you realized, okay, I can parlay what I did into something that feels right for the moment.
JI: Absolutely. And you know, it's funny, people always ask me like, how did you go from entertainment to finance? And really what I do is not finance. I mean, it's seventh grade math. You know, it's, yeah, I learned, I mean, I learned everything that I need to learn and I'm constantly learning. However, you know, it's a big company, you know, there are experts in all sorts of different situations and we have all the software to run the numbers for us. Really my job is, is client relationships. You know, it's really understanding my clients, you know, what do they want now? Five years from now? Twenty years from now? What do they want to pass along to the next generation? How do they grow their money, but also how do they protect themselves in a variety of different situations? Because all of that is really part of the same conversation, you know, and it's really, you can't make recommendations to people until you really understand who they are and what they want.
LJR: Totally, totally. And it feels like you're in a much better position to figure that out with the kind of the level and the depth of the relationships you can make now versus probably what you could make in that thousand person project of like, I need to have a very wide Rolodex, [JI: Yes.] you know, for this kind of project, because it's going to be different from that kind of project, you know. People's needs and their legacy are pretty similar, but they're just like nuanced on the edges. And so it must be fun to kind of, delve into different…
JI: Look, it's, it's fun to help people or it's rewarding. You know, I'm, I'm basically my own boss. The nice thing about my business also is you can, you know, the way it's structured is you can see the future. You know, and, and my kids get to see, you know, not only that I help people, but also like they've seen that life and a career isn't linear. You know, like part of life is how you deal with setbacks.
LJR: Yeah. Yeah. And maybe not even setbacks, maybe just deciding, okay, now's the time to try something new.
JI: Yeah. Yeah. You never going to stop learning and you're never going to, you know, stop testing. And I mean, I've been basically taking tests for like the last seven years, although I think I'm good for now.
LJR: Good. All right. Now that you have that extra time, how do you feel life outside of work then?
JI: Sure. I mean, you know, my kid, my daughters are 16 and 12. And so it's really just trying to keep. All the trains running on time out here, you know, my older daughter's competitive dancer. She's also a cheerleader at high school, which is more of a dance team. So that takes up a lot. You know, my younger one is a soccer goalie and into musical theater, you know, so just a lot going on. You know, I also, I started a dad's club at my daughter's high school. You know, that's a lot of work.
LJR: No, no, no, no, no. I don't, I have not heard of this sweeping the nation. Tell me.
JI: So it's funny. So, you know, we…My daughter was in public school for nine years and then we ended up sending her to private for high school. And you know, I was sitting at one of the basketball games talking to one of the other cheer dads who ironically his oldest son just graduated from Dartmouth. But he was saying, you know, look, there's all these clubs at this school. There's a cooking club and a hiking club and you know, but they're kind of all dominated by moms and I never get to meet other dads. So I was thinking about starting a dad's club. Would you help me? And I said sure and you know, we thought you know, we went to the school. They gave us a little bit of money and you know we thought maybe we'd get 50 people at our first event which was like, you know beer and tacos. 250 people signed up for the first event and so we had to go back to the school and get more money and find a Bigger location and you know, it's kind of gone on from there. But what's funny is I found out that there were all these Dartmouth alums that I knew that I had no idea had kids at the school, like a couple of fraternity brothers of mine that I'd lost touch with and some other people. So it all comes back to Dartmouth.
LJR: Yeah. Yeah. But it is great that again, even when you're on your off hours, it really is all about relationships, right?
JI: Yes.
LJR: Yeah. And what, and figuring out what is important to people and being part of that. Yeah.
JI: Exactly. Yeah. And you know, I'm on the board of my temple, which is nice. And it's a really wonderful place. My kids are very involved. Yeah. But yeah, it's mostly the kids’ stuff right now.
LJR: Yeah. Excellent. All right. Well, Jesse, this has been, I had no idea. This just is a fun romp through like, let's, let's try to figure out how I can have this great career. And then what else do you do with it? I just love it. So I'm glad it seems that you're where you're supposed to be right now. And who knows what's next.
JI: Yeah. Absolutely. Thank you so much. This was great. I really enjoyed it.
LJR: That was Jesse Israel, who after a career in the entertainment industry that spanned two decades and stints at NBC Sports, Dateline and development roles for numerous feature film deals, has parlayed his skills into financial services. He's a certified financial planner, wealth manager, and insurance expert who currently advises at Capstone Partners Financial and Insurance Services in Los Angeles. Being a very proud husband and father of two girls, he's a co-founder of the Dad Club, which is just the coolest.
You know what else is cool? The fact that you listeners keep coming back to listen to all these great tales. You can find out more and drop us a line at Roadstakenshow.com and follow us wherever you get your podcasts so you don't miss anything new with my guests and me on the Leslie Jennings Rowley on Roads Taken.