Jesse Dittmar is a commercial portrait photographer based in Brooklyn who specializes in celebrities and other notable figures. Jesse had photographed celebrities like Tom Hanks, Denzel Washington, Jodie Foster, Sting, Charli D’Amelio, Tom Brady, George Takei, David Letterman, Uma Thurman and many many more. In this interview we chat about Jesses early start in photography, what he learned from assisting that he didnt in art school, and the transition to going out on his own and shooting for himself.

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In This Episode You'll Learn:

• When Jesse knew photography was going to be an important part of his life

• Struggles Jesse had with photography early on

• The magic of developing your own film

• What Jesse learned when going to art college

• Why Jesse started assisting other photographers after graduating

• Who books Jesse to take portraits of celebrities and notable figures

• How Jesse is able to connect with his subjects in an impossibly short amount of time

• The importance that music plays in Jesses life and in his photographs

• What kind of music Jesse plays when he photographs artists like Sting

• How Jesse approaches vision for his shoots when he just has minutes to grab the shot

• How much direction Jesse gives to his subjects

• The one thing Jesse needs from each shoot to consider it a success

• Why Jesse still shoots film and how he uses it to achieve a signature look

Premium Members Also Learn:

• How to nail your client meetings

• What Jesse was surprised to learn after going out on his own and how he handled the stress

• What Jesse outsourced in his business to make him a better photographer

• How to overdeliver to your client to ensure they keep calling you back

Resources:

• Celebrity Portrait Photographer Jesse Dittmar’s website

• Jesse Dittmar’s Instagram

• Jesse Dittmar’s book “Two”

Did you enjoy this episode? Check out more recent interviews with other great guests!

Full Episode Transcription:

Disclaimer: The transcript was transcribed electronically by Temi.com and may contain errors that do not reflect accurately what the speaker said. Because of this, please do not quote this automated transcript.

Raymond Hatfield: 00:00 You know, from a pretty early age, you were interested in photography after high school, you went to art college, but I want to know before you made that decision, tell me when you knew that photography was going to play an important part in your life.

Jesse Dittmar: 00:15 I would say Raymond that around 17, 16, 17, so mid, mid to late high school, I started really considering it something that I would want to do longterm which was really early actually in the grand scheme of things. But yeah, I think, I think that for me personally, I was always really artistic kid and I was always making videos with my friends and I, and this is back in the early, like at the turn of the century. So, you know, all this stuff wasn't as accessible as it is now. I was in bands, I was working really hard in bands. There was a, there was a moment where I thought I was going to be a musician professionally, but I realized that if you're in a, if you're in a rock band you know, and yeah, all four of you, aren't working as hard as you can. And one person's pulling a, pulling a card of people behind them you know, trying to get someplace. And I was also excelling at photography and I was kind of a big fish in a small pond in my small town. And, and I realized, Oh, I can get as far as, as, as, as I can work and nothing will really stand in the way of that. So I kind of started gravitating more towards photography because of, because of kind of the ability to control my destiny.

Raymond Hatfield: 01:34 Are you saying that the did I'm sorry, I'm not sure. Did you, were you born and raised in New York city or did you move to New York later?

Jesse Dittmar: 01:41 No, I was born in, I was, I grew up in Connecticut. I was in the suburbs in the suburbs of the city and and we're just an hour away. So I was in the city a lot as a kid.

Raymond Hatfield: 01:54 So when you say that you were a big fish in a small pond and that you knew that you could like essentially get to the top of your field without any hesitation, was that why you wanted to move to New York? You wanted some sort of pressure. You wanted a challenge, is that, is that what I'm?

Jesse Dittmar: 02:11 Well, no. I mean, I mean, I was, I was a big fish in a small pond, meaning like I was the photography kid in my, in my town and my school. Like I was the guy that did photography and, and so I didn't, you know, I, I, it was something that I was getting positively reinforced, you know, it was a thing that was being a positive reinforcement in my life. And so therefore I knew that as I worked really hard at, at it, unlike being in a band, like I could work super hard at being, at being a musician or being in a band with a group of other people. But if they're not working with me you know, the ceiling is only so high, you know, you can't force someone to kind of be as hardworking as you are. So in photography, I could work as hard, as hard as I could.

Jesse Dittmar: 02:54 And there wasn't, you know, I wasn't turning around and trying to motivate other people to get on my so that's what I mean, mean by the difference between being in a rock band and being a photographer is that it's much more solitary in an aspect of you know, you're working for yourself. And then I moved to New York because that's where everything was that's where all the photo shoots were happening. That's where all the photographers were. That's where NYU was that I wanted to go. I mean, I mean, you know, new, York's pretty much the center of the world, so not a better place to want to be a portrait photographer than New York city.

Raymond Hatfield: 03:27 For sure. For sure. So w I want to focus a little bit more on kind of those early days in photography. So you know, you had that interest in photography when you were younger, but it wasn't until you were like 17, as you said, that you thought, you know, maybe photography is going to be the Avenue for me, but when you were younger, you know, what were some of those first things that you were photographing?

Jesse Dittmar: 03:50 Yeah. So, I mean, you have to remember. I, so young, I probably got into photography in earnest in like 1999, 2000. So it was still film. It was still dark room. I was in the dark room a lot. I built my own dark room when I was a teenager at my house. So I could be printing when school wasn't in session. I think the thing that really caught me in the very beginning was the magic of the chemistry of it, the science behind it. I was so excited about literally seeing a print emerge from white paper, into an image, like seeing that kind of being in a dark room and seeing it, seeing it come from nothing was a really exciting process. And just the kind of the chemistry and the science behind it was really what got me in the beginning.

Jesse Dittmar: 04:38 So in the beginning I was doing, I mean, I've always been interested in people. But in the beginning I was just exploring a lot. I was doing a lot of taking pictures as I was traveling and taking pictures of friends, taking pictures of, of concerts and you know, shows that my friends were playing. Cause I, you know, I, again, I was like big in the music scene taking pictures of sports, you know, like my high school football team and you know, taking portraits of friends and my family and my sister. And and I was kind of just doing all kinds of stuff in the beginning, feeling out what was, what was right for me, but the, the very initial kind of connection and motivation was like just the mystery and mystery behind the science and kind of that magic of, of what photography is at a, at a base kind of scientific level.

Raymond Hatfield: 05:31 Did you, how did you get interested in, in the developing process? Because I know when I was younger, my parents just gave me like a disposable camera, I'd go out and I take some pictures and then, you know, two hours later or whatever, we'd go pick it up from CVS. And that was it. I just assumed that it was a machine that did it. And that was it. You know, when you're a teenager, how did you know that you had to invest in this dark room equipment and have more?

Jesse Dittmar: 05:54 I mean, my very first experience with photography was like a little class at camp, like summer at summer camp. So, I mean, I grew up in a privileged environment. I grew up in a, I was a sense of sleep-away summer camp. Like they had a photography program. There, it was something that I kind of just tried on a whim. The whole point of the photography program is to teach you how to develop black and white film in a dark room and then print. I mean, it was very basic. It was like a closet, but so that's where I got the first, you know, taste of developer, smell of developer there. And then I was in a high school that had a photography program, had a black man photography program. So I came back into high school, you know, freshman year and I took a photography class in which they were, you know, you were required to shoot your own black and white film. You were required to develop your own black and white film. You were required to print your own prints. And so I was you know, by the lock-in privilege of having a school that, you know, had that available to me at the age of 13, 14, that's what I was doing. And there was also disposable cameras in my life, obviously before that. But you know, I think, yeah, having, having a high quality school with our program was really what did it, that's part of the program.

Raymond Hatfield: 07:14 Yeah. Tell me about that transition from going from disposable camera, which is just literally point and shoot, like can't get any more basic them to having full control of the camera that you were using. What, was there anything early on that you felt that you really struggled with when it came to photography now that you had all this control?

Jesse Dittmar: 07:32 Well, the first thing is just like, it's just learning the, the machine, you know, I think, I think my very first role ever, I, I shot a tired 36 Springs, but the but the film wasn't loaded correctly, so no frames were taken and I had to reshoot it. And so just, just understanding the ergonomics and the process of loading film, and, and then focusing, I think one of the initial things, which is really interesting, it's just like the difference between a point and shoot camera and, and an a single reflex lens, a single lens reflex camera is is that you can focus. You can, you can change what your camera is focusing on. And so that the kind of like the focus pulling of the camera that like fluid kind of smooth action of your lens and deciding that like you have this whole scene in front of you, you're, you're experiencing the world, you put a camera in front of your eye, and then all of a sudden that world is broken down into a rectangle.

Jesse Dittmar: 08:32 And then within that rectangle, you have the ability to say, okay, this is what I want you to look at. You know, this is the thing that's going to be in focus. It's, you know, so you really have the ability to select very specifically what you want people to see. And so figuring that out and understanding that, Oh, wow, there I can, I have a voice, I have a, I can show people an opinion. I can show people what I want them to see out of all of the things that there is to see was, you know, something that was really attractive to me and something that was a tool to express myself.

Raymond Hatfield: 09:12 Yeah. That's very cool. I can, I can relate a lot to that to that story there. So when it you said early on you were shooting concerts, you were shooting your friends, you were just shooting kind of your everyday life. When did that affinity towards portraits really take off for you?

Jesse Dittmar: 09:29 Definitely in the middle, towards the end of high school. I started, you know, researching master photographers and spending a lot of time in the Barnes and noble looking through all of the photo books that they had, and just being enamored with Avedon and Irving Penn and Annie Liebowitz and Nigel Perry and Martin Schoeller and you know, contemporary and photographer, master photographers in the past. And I think that my evolution of the understanding of medium went from, okay, this is a really interesting scientific artistic process, which I can kind of tell people what I want them to see, and what's important to me to, Oh, wow. You can also use this art art as a as a turnkey, as a key as a window, as an opportunity to go photograph and represent and give your artistic take on the most important people in the world right now.

Jesse Dittmar: 10:36 And you know, here I was looking at these books, that was the roadmap. It was like, these people do this. These people go and meet the presidents of the United States and the Kings and Queens of the world and the biggest movie stars and the biggest writers and the biggest scientists, and literally anyone who's doing anything that matters. And then they get the ability to take that face and make art. And, and that, that when I, when I figured that out was when I went, I need to, I need to understand how this works. I need to understand how these books came into existence. How is that accomplished? Can I do it, let me go find that out. And that was when I, when I realized that around 17 probably is when I just started on this path, that I'm still on. And and now I'm here doing it.

Raymond Hatfield: 11:30 It's amazing. Yeah. I mean, somebody has got to photograph the president of the United States. Why not you? Yeah,

Jesse Dittmar: 11:36 Exactly. Why not me?

Raymond Hatfield: 11:38 That is so cool. But so few so few times do I think people really have that that mindset that was really cool that even at 17, you were able to, to kind of connect those dots and, and move forward with them. That's very cool. So,

Jesse Dittmar: 11:52 Yeah, I mean, I, a lot more questions

Raymond Hatfield: 11:54 At 17 than I had answers that's for sure. Didn't we all. Yeah. And I still got a lot of questions, Raymond. I think if you ever run out of questions, it's just a, I don't know, time to die, I suppose. Like you should just always be curious. Yeah, yeah, exactly. Exactly. So at that point you're sitting there and Barnes and noble, you're looking at these photo books and you're thinking, why not meet that next step for you? Is, is art college, right? So what was it that that made you think, you know, what, I'm sorry, let me rephrase the question. You had already had some sort of technical knowledge and knowhow for how to use your camera for you. What was the benefit of going to art college? What were you hoping to get out of that experience?

Jesse Dittmar: 12:44 Well, in the beginning, I was really hoping to get access to more technical knowledge, more, you know, there was, I had never used lighting equipment before I went to school. I had never been in a photo studio really before I had gone to college. There was so much I had there's so many cameras I had never used. I've never, I had never printed digitally. I mean, like I, there was just a lot to be explored technically that I really wanted to get at. I mean, I also wanted to go to college for the experience of going to college and I also wanted to become a smarter human. And, you know, I think that there was a lot of I was a very like lackadaisical, really good student in high school. It was, I didn't challenge myself. And because of that, it was very easy for me.

Jesse Dittmar: 13:30 And so I think I got to college and I quickly learned that most people there were much smarter than me and and that I, I needed to do a lot of work in order to kind of like up, you know, up my game and become a better writer and become a better reader and to become a better comprehender of the world and be able to speak about a lot of subjects and relate to a lot of things. You know, I wanted to become a generalist. I wanted to be able to talk to people about stuff that they, that they were experts at, that I could basically still be able to have a conversation with them and kind of try to learn from them. And, and and so I actually switched out of art school, mid in the middle of my college career to focus more on just becoming more learned and becoming a smarter person. And that, that, that became the focus of college for me was just to, to maximize my intellectual potential. And I realized that I was going to learn the more, I was going to learn more about photography eventually from being an apprentice and an intern and an assistant for the master photographers. And I was going to learn at art school. And that's what eventually I did.

Raymond Hatfield: 14:49 Wow. That's I, I feel like I was just like a dumb kid at like 20, 21 that there's no way that I would have that that sort of insight, but that's interesting that that, that you said, you know, learning photography, you were going to do that in the real world, because that was my next question. Having gone to art school, having gone to learn photography and then going on to become an assistant to some of these master photographers, you know, what was it that assisting did for you? Why not just straight out of school, just go out on your own and start from there.

Jesse Dittmar: 15:22 Cause I still felt, I still felt like I had so much to learn. I mean, I think every single part of this process boils down to the one concept of curiosity. I was just so I would see images in the world photographs. I would see photographs in art galleries. I would see photographs in magazines and in newspapers and in books and in museums. And I would just, I would just be like, how did this happen? Like I just needed, I needed to understand how the person made it because I just that's what was like, that was my driving force. My driving, you know, I was on photo shoots and I was in the beginning, a terrible photo assistant because all I wanted to figure out was having a thing was being made and that's not a good photo assistant. A good photo system is to help it get made, not to not to ask what the hell is happening everywhere.

Jesse Dittmar: 16:15 So I was a really bad photo assistant at the beginning because I was just, I was, I was trying to learn more than I was trying to do. But that was what drove me to go work for these people because I, I wanted to figure out how they did it. I wanted to figure out how I wanted it. It's like going, it's like, you know, working with the magician, you know, I wanted to figure out how the trick was being done. And, and it, you know, I just kept doing that until I felt like I knew enough to do it myself.

Raymond Hatfield: 16:44 So if being a good photo assistant is somebody who's trying to help get the photo made rather than making the photo, I suppose. Why did you think, why did you continue assisting then if you really wanted to learn the photography side of it rather than making the photo, I guess on the back end, is that a bad question? Am I, I don't, maybe I'm not afraid.

Jesse Dittmar: 17:04 No, what you're getting at is like it is, you know to me a good assistant is eventually a good assistant is someone who you know, treats, treats being an assistant as a job and brings value to the table as far as being able to help accomplish the goal of making, making the photograph and and and an intern and and kind of like a very green assistant, like the assistant I was, I was just much more interested in kind of just letting the experience wash over me and trying to take in as much of it as possible. So I could, you know, I wasn't trying to help. I was trying to learn and that in the beginning, if you're an intern, a green assistant is okay because, you know, you can't walk on set experienced, you know, unless you have that experience.

Jesse Dittmar: 17:58 But by the end of being an assistant, the thing is the more it's like anything, the more you learn about the, the easy stuff, then when, when you're getting asked to do the easy stuff, you can pay attention and you can understand the more nuance things that are happening that might not be being said. Or you can start to understand the dynamics, the interpersonal dynamics and the politics behind a photo shoot. You can understand a little bit, the more experience you have on set, the more sets you go on, the more photo shoots that you're experienced. You start to figure out that a photo shoot is so much more than understanding f-stop shutter speed, ISO you know, and you know, you can learn that, listen, you don't have to be assistant in order to go be a photographer. You can learn all of those things on your own, but I would rather, I, I preferred to watch other people fail and watch other people succeed while I was in a lower stakes role. Then, you know, being, you know, like the higher the stakes are, if you fail the less likely you are to get another shot. And so by the time when I was a foot photographer, I was completely prepared to capitalize on, on the luck and the privilege of being asked to photograph someone important. I knew I was going to do a good job. And if I would've been asked to do that at a young age, I, I would've had a much lower chance of success.

Raymond Hatfield: 19:21 Wow. Okay. Yeah. Let's, let's talk about that because that's the next progression in your journey after you left college, after you started assisting, after you kind of learned the ropes of how a photo shoot works, I suppose you went out on your own and now where you're at today, you're shooting. I mean, many notable figures is anybody can see by going to your website or your Instagram heads of state pop culture icons as a wedding photographer like myself and engaged couple, they come to me, they reach out to me to ask me to photograph them with your style of photography and the portraits that you take. Do these notable figures reach out to you for portraits or explain to me how your side works.

Jesse Dittmar: 20:05 Yeah. I mean the most, there's lots of different ways that people find me and ask me to take pictures of people. There's no one there's no one way. But, but typically I have publications like the New York times, the Washington post and many others who reach out to me and they need a picture of a notable person for a story that that's being written. And they asked me to go make that happen. There's also brands and companies that can do the same thing. And then sometimes notable figures want pictures of themselves as well. That can happen too. So most often it's some combination of a publication or a brand or an advertising agency that says, Hey, we need, we need to photograph this person for a reason. And we're going to ask Jessie to do it.

Raymond Hatfield: 21:00 So even though, you know, you've photographed, I mean, just amazing people like Tom Hanks and Denzel Washington, they weren't the ones who reached out to you. There was a publication who needed photos for something that they were creating

Jesse Dittmar: 21:14 Pretty much. Yeah. I mean, what I mean, like for, for Tom Hanks, for example, he was when he was being awarded the Kennedy center honor presidential honor. And so you know, the Kennedy center wanted portraits of all the people that were getting that honor. And so they say, Hey mr. Hanks, Tom, you know, we, we want to take your portrait for this. And he's like, yeah, that makes sense. And then they were like, okay let me go ask Jesse if he can do it. And and that's kinda how it goes. And with Denzel Washington, I, I, you know, the, the Tony, he was getting he was nominated for a Tony award and and the New York times had me go and photograph all of the Tony award nominees or most of them for a story they were writing about all of the people who were up for Tony's. So, you know it's, it's typically there it's typically a newsworthy event, a newsworthy person or a brand or an agency that has a concept that they want to, you know, get out to the world and they need help doing that.

Raymond Hatfield: 22:20 So with the with the example there that you gave of Denzel Washington and the Tony award winners I read the story a little bit on Instagram that you had posted about having just like four or five minutes with him. And this isn't an uncommon thing for you. It's not like you have an hour, an hour and a half with each of of your subjects. So in that context, how do you connect with your subjects so that they trust you and that they open up with you to have their portrait taken?

Jesse Dittmar: 22:54 Yeah, there's a lot of, there's a lot of answers to that question. It's a multifaceted multi-tiered plan of attack to get a connection going. I mean, you know, not every shoot is as quick as the Denzel shoot. You know, sometimes I do have much longer with people, but I'm prepared for either scenario. You know, with someone like Denzel, the very first thing I'll do before he even walks in the room, the room is set and kind of laid out in a way to try to make it as intimate as possible. And and we have music going and there is it's, it's a scenario that we're trying to create a mood that will get someone to be as comfortable as they can be in an uncomfortable situation. And then the next thing I do is I show them, I show him work of previous people.

Jesse Dittmar: 23:43 I've taken pictures of. I mean, I photograph people that I know, know that I know that Denzel knows that I know that he's friends with. And so the first thing I'm gonna do is show him those people and be like, Oh, you know, since you've photographed, you know Tom Brady, I know Ty, you know, I've met Tommy, I'd go like, Oh, you have been, you're good. You can photograph me, you know, that's going on in his head at least ideally so to try to, to try to prove trust through previous, you know, showing, showing that I've done it before. And then, you know, it depends on who it is, but someone like Denzel, obviously I have a lot of history with him, organically having watched his movies, heard interviews with him, read things about him. I mean, he's very much in my orbit of, of knowledge.

Jesse Dittmar: 24:31 I know he's a sports fan. I know he's a new Yorker. I know he's into the Knicks. I know he's, I'm pretty sure he's a Yankee guy. And I know he's also kind of like one of these guys, it's like one of the most super famous people in the world, who's this, who's like, you know, the concept of him being photographed is a little bit like, all right, I'm running, you know, somebody told me I had to be here. You know, I'm going to humor, humor, everyone in here by doing this photo shoot. And so I just leaned into that and, and I started talking about the Knicks and I start asking him, you know, he's got kids, you know, I start talking about his kids, asking about kids. You know, I have a kid. I try to relate with him about being a new Yorker, being of Knicks, being a woeful Knicks fan.

Jesse Dittmar: 25:13 You know, I just started talking about stuff. You would talk to someone about, who's not Denzel Washington and start trying to figure out how can we connect quickly on a human level that that can give some veiled semblance of being a peer, even though we never will be. But you know, that doesn't mean I can't try. So I try and I typically succeed and I typically get a connection with someone and I can typically get a laugh and a smile and I can get a focused focus attention. And that's what I'm looking for. And that's, those are always my goals walking into a, into a portrait session.

Raymond Hatfield: 25:54 That's very cool. That's very cool. I can't imagine the amount of you know, obviously the amount of not worry, worry, isn't the right word, but I guess maybe adrenaline, that would be going through my system. If some, if I knew somebody like, you know, Denzel was coming in and I think for me, I would probably be focused on myself. Like, how can I not act like a, like a crazed fan or something like that. And I think that what you mentioned right there is trying to make the room, you know, comfortable for him playing some music, you know, so that he feels comfortable when he gets in there. Those are things that focuses that attention back on him and makes his experience better rather than just focusing on yourself. And that's a really interesting distinction there that I don't, but I hope that many listeners right now picked up on, because I think that's a big thing.

Raymond Hatfield: 26:46 Now. I know that your dad was actually in the music industry, right? Yeah. And your website talks a lot about the importance of music, you know, where you say actually on your website, that music defines most people's experiences. So, and then you go on to say that you use music as a tool. Would you kind of just explained right there, but I want to know now, like when you have to photograph somebody who like, like sting, who's been in the music industry for decades, what kind of music do you play for him? Like if somebody who is essentially is, is, is hard at all.

Jesse Dittmar: 27:20 I mean, I think that's good that he's heard it all. It means he's a fan. And the point of me playing music is not, I mean, the point of my music is not to show things, something he hasn't heard. My point is to play something he has heard and to play something that he's into. Because if, you know, if he has a positive association with a song and I play that song, and all of a sudden he subconsciously has a positive association with our interaction. And and therefore that will hopefully get them more focused and hopefully get a more present and hopefully get a more agreeable to what I want to do. So, you know, I prefer to have someone in mind who is a music aficionado cause that, you know, the more I know about, you know, everyone, everyone under the sun is off staying who his influences are and who he likes. And so that makes it very easy for me to play music that is going to, you know, be in his wheelhouse. You know, I'm not going to be going. And, and so I playing music for other musicians is easy. That's easy

Raymond Hatfield: 28:32 Really. Cause I would think like, I would think, I would think, you know, what if I was going to meet you know, I don't know a famous chef. The last thing that I would want to do is like, Hey, try this kick that I just made. You know what I mean? Like not, not, not patient trying to impress him.

Jesse Dittmar: 28:47 Yeah, yeah. But that experience is like, Oh, I'm not playing sing like my own music. That would be that feeling of me being like, Hey, stay here, listen to my track, listen to these hop beats. I just, I just laid down. You're like, no, no, no, I'm trying, I'm playing him Al green and James Brown. And and I'm playing him Sharon Jones or, or, you know, I think, or maybe Bob Marley, I was playing him, you know, like I'm playing him stuff that is going to connect with with his influences, with things that are, have a positive connotation for him that aren't, I'm not trying to be super obvious. You know, if this thing is the kind of guy that walks around and says to every interview that my biggest influence was Bob Marley, then I'm not going to play him that I'm going to play him something that might be a deeper cut

Jesse Dittmar: 29:39 In the same wheelhouse, I, you know, in the same Jamaican Island Island, music wheelhouse. But you know, it's, it's not me trying to impress, it's not me trying to, I'm not trying to make it about me. I'm trying to make it about him. Yeah. Yeah. And, and that's the whole point of the experience is for me to foster a a fertile ground for connection. That's all I care about is I am only gonna meet staying once medium one media, a couple of times in my life. If I get to photograph Rico more than once, there's a few people that I've been able to do that with. I I've got like 20 minutes, I got 20 minutes to connect with staying. It's the only 20 minutes am I ever going to get. So I'm going to try my freaking hardest to create a space to make that connection happen because then you'll see it in the picture. And so, no, I'm not going to show him my band from 2001. And then I show him his favorite, his favorite band from 1972.

Raymond Hatfield: 30:50 Yeah. No, that makes sense. I guess I don't know. Maybe it just like an insecurity thing that I was kind of looking through that lens of is like, you know, if somebody is so deep into that world I don't know, it must be a personal insecurity. I would feel like it would come off as totally disingenuous. If I tried to be like, Oh, you know, check out this music that you might anyway,

Jesse Dittmar: 31:13 Totally going off. I think there's a middle ground there, Raymond, right? Like, you know, I'm not playing him music that I don't like, you know, like I'm playing, like, I'm a thing. I think this is one of the advantages I have to, one of the reasons why I'm I'm successful and I'm good at my job is that I'm a huge music fan. And so, you know, like I'm playing him music that I'm into. I mean, it's songs that I listened to over and over and over again on my photo shoot. It's like, these are, these are songs that I get behind, you know? And, and when I talk to someone about travel or when I talk to Denzel Washington about the Knicks, like I feel his pain, like I hate being expanded. He hates being a Knicks fan. Like that's not faith, you know, I'm not trying to, I'm not trying to like, just find something to talk with these people about, because it's what I think I should, I think they want to talk about it. It's, I'm trying to find things that we both care about. And it's not, it's not a it's not a show. I mean, it's specific because I I'm trying, you know, I'm not going to talk to, you know, whatever. I'm not going to talk to staying about something that I know he doesn't care about. Just because I care about it. But I can't, you know, I wouldn't play music that I don't know anything about.

Raymond Hatfield: 32:35 Yeah, yeah, no, I think that you wrapped it up perfectly. They're saying that, you know, it's not a show finding something that you too can have some sort of common ground on is really something that is, is obviously what sets you apart and makes makes you, makes you unique. So that that's very cool. Thank you. Thank you for sharing that. Thank you for sharing that. I want to switch gears now and talk a little bit more about that first time, like your first client, right after you'd been assisting for years going out and getting that first client of yours. Tell me what that experience was like. How did you book it? How did it go?

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Raymond Hatfield: 33:36 That is, that is such a great tip to it, especially in a world where you don't really have the tangibles that you're delivering. That is such a great tip to on how to overdeliver and I guess continue to get those phone calls. So I love it. Thank you so much for sharing that. When you go to a shoot, when you find out that you have somebody who you're going to be shooting do you have a vision in your head for how you're going to shoot your subject, who shows up? And if so, how often are you giving your subject any sort of direction to achieve that vision versus just winging it and see what happens?

Jesse Dittmar: 34:14 I am very rarely winging it. I'm never winging it.

Raymond Hatfield: 34:17 Okay. Hold on, hold on. Hold on. That was the wrong word to use. I suppose what I mean is I guess my, my thought process when I wrote that question specifically was again, thinking back to that Denzel example, when, when I believe he didn't even know that he was going to show up, is that right? Okay. So when something like that happens, do you have a vision for the photo that you're going to get of him? Or how much are you just, and then, and then if you do, what kind of direction are you giving to him to achieve it?

Jesse Dittmar: 34:47 Yeah. So with the den, with the Denzel shoot, I had been practicing all day. I had photographed already about 30 people. I knew he, I knew he might show up. And so, you know, with him, everything was already set. I mean, I think what you're talking about is really is kind of like, do I, do I know what kind of backdrop I'm going to use and what kind of framing I want and what kind of composition and like, do I want them to be doing a specific thing? And like, th those that stuff was already planned out before he walked in. So, you know, I had made, I had made those decisions. They were very planned. So what I do is I, I try to visualize what the shoot might look like, understanding that things will change. And, you know, I just try to map out all the different possible scenarios that could happen so that they don't feel completely novel to me.

Jesse Dittmar: 35:43 And I map out, okay, what if I want to ask them to do, you know, I kind of had done the shoot already. And I had gotten the closeup picture. I like to get, I wanted to get a close and picture of him. I had gotten him laughing and kind of showing an exp being expressive, which I wanted to get. And at the end, I was like, you know what, just throw your hands at me. And, and cause I was, I was just like, let me try. Like if he says, no, I already got it. So, and he's like, what do you mean, throw your, hit my hands at you. I'm like, just throw your hands in my camera. And he's like, like this and that was the shot. And, and you know, I can't honestly recall if I had planned to ask him to do that.

Jesse Dittmar: 36:23 It might have been a, a pivot on, on, in the moment. But you know, I think the point of having the space to do that, to be, to be spontaneous and to ask him to do something that's a bit different is that I had the rest of it planned and I had accomplished the plan and I felt like the plan had been accomplished. So now I can just, I, now I can, I can freelance. Now I can ad lib. Now I can now I can do my, my saxophone solo and, and and, and, and not have plans what's going on here. And that's the point. I mean, I think the key is, you know, you, you talk about, if you ever, if you ever talk to really really successful professional athletes, they'll tell you about how they run through all the scenarios in their head of what might happen before it happens.

Jesse Dittmar: 37:19 So they're prepared to their body, their, their mental, it's the same thing with me. Like my men, the mental wiring in my brain has, has visualized and simulated what might happen so that when it does happen, it's not completely novel. And it, and it feels like it's not the first time I've done it. And that makes it easier. And that makes it, it makes, it makes things it makes things more natural and it then allows me to be creative and to deal with curve balls and to deal with the challenges that inevitably happen.

Raymond Hatfield: 38:00 Yeah. So as you said, you, you know, the, these curve balls, so they can come your way, these, these changes that will inevitably happen while these things are still obviously a possibility I want to know for you. Like, what's the goal, what's the one thing that you need from every photo shoot, no matter what the subject is, no matter who it is to consider that you a success for you,

Jesse Dittmar: 38:23 Then I got an image that looks like, that looks like we had a connection. That looks like we're connecting that we're, that we're, that, that the only thing that matters is, is the connection between my lens and the person that there's a, you know, it's like, it's like, it's like when you're, when you're having a conversation with someone and you just want to look them directly in the eyes and like, you're really getting it. Like, it's, it's that that's why most of my pictures, people are looking directly into the, into the lens because you know, I'm, I'm, I'm trying to represent and show the viewer and the people that are looking at my images, I'm trying to, to help them understand the connection I'm having with the person in front of me. And that's what my art is really about is, is connecting on a human level with some people who are extremely famous and some people who are not, and showing that there's a lot of similarities between those two people. The way that I got to know them, how do you,

Raymond Hatfield: 39:39 I'm always interested in this. This is something that sometimes I still struggle with when I go to an engagement session or even a wedding, and I go to get those camera aware photos, you know, I think what you're describing is kind of what, not only me, but every photographer is really looking for, but you're one of the only few who have actually put in the work to figure out how to actually get that connection between the subject and the lens when they're, when I'm trying to talk to somebody, I like to look at them. And for me, there's a bit of a disconnect with the camera. So when you're having a conversation with somebody and you're trying to get them directly to look directly into the lens, are you looking at them hoping that your cameras frame properly, or are you looking in your camera still talking to them, hoping that they're just looking at your lens, I'm going back and forth.

Jesse Dittmar: 40:26 And, and there is a lot of people, you know, when we do get engrossed in conversation, people will look at my forehead rather than at the lens automatically. So I do say a lot of, like, I do kind of interject and tell people to like, look into the lens while they're talking to me. But you know, those are those kinds of comments that get forgotten because, because they they, they click in, they click in people, click in you know so I do have to tell people to look into the lens because they do naturally look, try to look at my face when we're talking, it makes sense. And, and, you know, I do do a lot of pictures of people aren't looking directly in the lens too. There's, there's, there's all kinds, you know, there's different ways to represent the engagement that I'm talking about. But yeah, it's, it, it can be difficult to kind of, but it's, it's very, at this point, extremely second nature to me you know, after doing hundreds and hundreds of these

Raymond Hatfield: 41:27 Types of shoots. Yeah. So one thing that I think is unique about looking at your work is your mix and yet consistency of using both or between both film and digital. Unfortunately we don't really get to talk a lot about film here on the podcast. Not many photographers, still shoot a lot of film. But I love film. There's something about film, as you know, I mean, I don't have to tell you I was looking on your Instagram and you posted a photo of that you had shot with Sean Patrick Maloney, and your film had came back developed with very predominant light leaks in the photo. And as a photographer, I think that it looked absolutely beautiful, but when you're shooting for a publication, you know, what do you do in that situation? Is that something that, you know, the photo can't be used? What does that make you think twice about shooting film?

Jesse Dittmar: 42:23 Not at all. It's the reason why I shoot film. I mean, I'm looking for happy accidents with the film. I'm looking for something that's organic. I'm looking for something that's not perfect with film. I mean you know, I shoot, that's not, I'm, I'm only shooting 12 rolls of, excuse me, 12 frames, one roll, basically, usually on a typically I'm only shooting one roll of medium format film. It's only 12 frames. I'm looking for something that's different than organic. That's a, one of a kind picture that no one else will be able to replicate. And you know, if, even if they tried it, I couldn't take it again. And if, if the client thinks it's too artistic or too weird, then I gave him 10 other safe options. They can use Debra digital. So no, I, I get excited.

Jesse Dittmar: 43:14 I mean, I, I, I mess my film up on purpose. I grossly overexpose it. I I, I, I like to know why it light leaked you know, why there was a light leak, but I don't, I just, so I'm able to change that variable if I want to. But you know, I, I try to mess my film up. I don't care how old it is. I don't, I don't, you know, like it's, I can, I can get a perfect picture. It's called taking my digital camera and then going and getting a perfect picture. Like it's possible. I perfectly technically perfect. But you know, a lot of people can get a really quite quality, technically proficient image. It's very easy now because the machines are so great. So, you know, my, my focus is on getting organic human connection with the person and, and the, the con just the base concept of films.

Jesse Dittmar: 44:15 And he speaks to that and hits, hits those notes that I'm trying to get. So I absolutely lean into film, be able to get weird and be organic. Cause humans are weird and humans, organic and bodies are weird. Faces are weird and care, weird, and voices are weird. And like, there's no such thing as a, you know, there is, it's called a, it's called like a digital rendering you know, robot human face is what, you know, like, I don't need to see that. Like I, you know, I'm, I'm interested in the person in front of me. And I, I think that film does a really great job of underlying the concepts that I'm trying to highlight

Raymond Hatfield: 45:01 That is just something. Okay. I got one last question for you. That was gonna be the last one, but I got one last question for you when you said, you know, when you're talking about the grossly overexposing your film. And then, so when you develop the film, do you develop the film yourself?

Jesse Dittmar: 45:14 I do. Not anymore. I have I have a lab that does it not have a guy carry. He does it. So I do not, I mean, I know how he does it, but I, I don't do it. No, I don't have, I mean, I, frankly I don't have time. I mean, I w I mean, yeah, it would be nice to go to get back in the dark room, but the volume of shoots I do it's one of those things that you have to in order if the ultimate end goal of my work is to photograph as many of the people that I, that are in, in the realm and scope of my, of my mission. Then I have to let certain things go and develop one of them.

Raymond Hatfield: 45:49 Of course, of course. So when you send it out for development, do you pull it the full five stops, or are you doing it a little bit less than that? How does, how does that process work?

Jesse Dittmar: 45:58 Well, I mean, if you want, you want to get technical. I mean, I shoot 32, I shoot over 3,200 speed and film. You know, I think that the actual mathematic rating on it is, is, I mean, listen, there's, the factory rating is 3,200. I think that the actual rating is probably closer to 1250. So already you're at a stop and a half less than what it says on the box. And then I think that film has a lot of range and it depends on what you're shooting. If you're shooting something that's more that's that has darker tones then you're even lowering the rating even more. And so especially in the beginning of my work, I was shooting a lot on black backgrounds. So I think that, you know, shooting at ISO a hundred is really only overexposing it a couple stops maybe three.

Jesse Dittmar: 46:46 And and then the way the development works is that you are pulling it a little bit. You are leaving it in for a little less time than is, is rated on the developer. You know, that everyone says but I think the key for what we do is that we're using spent developer, we're using developer. That's not as potent as fresh new developer. And so yeah, so that way that it's developed the, the image is being developed at a much lower contrast than if you were using fresh developer. Just the way the chemical, like, listen, I don't want to pretend to be an expert on this because I am not, I'm sure that maybe someone listening to this might know more about this stuff than I do, because I'm out of practice. I am not doing development. I'm not nerding out on forums about the chemistry anymore.

Jesse Dittmar: 47:42 So I'm out of, I am off my game as far as being an expert in this, but the way that it works is that, you know, the development is, is agitating and washing away grain, it's taking it off that has been exposed to light. And so if you're a fresh developer, it kind of is the effect of bleaching your plastic negative. If you're using spent slower developer, then that bleaching is taking a longer period of time. And there are things there is tones that will stay on the negative that might not stay on the negative if you did everything to the book. And so what the negatives that I ended up getting are very dense, meaning that they're very, they're very thick. You know, it's hard to look through them and, and they're low contrast. And I'm bumping, bumping up the contrast in in the printmaking process.

Raymond Hatfield: 48:44 That is a, that is a whole world. That is you know, I honestly can't imagine what it must've been like in the, you know, in the eighties and even early nineties to to shoot commercial photography on film, because there really is just so many more variables that it that it comes down to, and the fact that that you're doing it, it is very smart to outsource some of the more technical more taxing processes out to somebody else and let you really focus on, on what it is that you do best. Jesse I, you know, we've come to the end of our time here and I cannot thank you enough for coming on and sharing everything that you did before I let you go. Can you let the listeners know where they can find and follow your work online?

Jesse Dittmar: 49:30 Yeah, the best place to see my new work is Instagram easily. My handle is my main Jessie Ditmar posting new work. I've been I've been posting and amplifying a lot of black photographer voices recently because I think it's really important that their voices are heard right now. So you're going to see, you're going to see a lot of my work. You're going to see other people's work that I consider to be good. And that is easily the way the best way to follow a follow with me. You know, I've made a couple of books, although I'm pretty much sold out of them. So you know hopefully if people stay tuned in my Instagram, they'll, there'll be able to be in the know when I have new new books and new work to show I do sell prints. Also if that's of interest to people they can just always email my my agents and, and make that happen. That's on my website, those that contact information. So there's lots of different ways to be in touch with me. I'm very accessible. Raymond photographers want to be found on very Googleable. Lots will come up if you type my name into the, into the internet mostly hopefully positive and and yeah, check me out on Instagram and you'll see all my new pictures.

Raymond Hatfield: 50:41 Jesse again, man. Thank you so much for sharing everything that you did and and lending your time to the listeners. I can't tell you how much I appreciate it.

Jesse Dittmar: 50:49 Thanks Raymond. Thanks for having me.