Recorded: Welcome to The ReWork with Allison Tyler Jones. A podcast dedicated to inspiring portrait photographers to uniquely brand, profitably price, and confidently sell their best work. Allison has been doing just that for the last 15 years, and she’s proven that it’s possible to create unforgettable art and run a portrait business that supports your family and your dreams. All it takes is a little ReWork. Episodes will include interviews with experts from in and outside of the photo industry, many workshops and behind the scenes secrets that Allison uses in her portrait studio every single day. She will challenge your thinking and inspire your confidence to create a profitable, sustainable portrait business you love through continually refining and reworking your business. Let’s do the ReWork.

Allison Tyler Jones: Hi friends, and welcome back to The Rework. You know this is a podcast geared toward portrait photographers, but I also know that many of us are also doing commercial work, headshots, business portraits, that sort of thing. And one of the trends that I’ve noticed recently in the last few years is this trend toward branding portraits. And it’s awesome, but I see a lot of photographers working really, really hard shooting what would be the equivalent of a wedding or an elaborate senior session, if you will, and not getting paid what that time is worth.

Allison Tyler Jones: So how do you make headshots and branding portraits profitable? Well, I didn’t want you to only hear from me. I wanted you to hear from a portrait photographer who is killing it in this arena, and she has made very intentional steps toward profitability, sustainability, efficiency in her business. Today’s guest is Kira Derryberry from Tallahassee, Florida, who also happens to be the Vice President of Professional Photographers of America. And she has created a sustainable, profitable product line in her business, in the area of headshots and branding. There are so many good tips from software to workflow to how she runs a session. You are going to get so many great tips today. So I always tell you, get out your notebook, get out your pen and take some notes. Let’s do it.

Allison Tyler Jones: All right. So I wanted to welcome to the Rework podcast today, my friend Kira Derryberry from Florida.

Kira Derryberry: Yep.

Allison Tyler Jones: Where in Florida are you? Tampa.

Kira Derryberry: Tallahassee.

Allison Tyler Jones: Tallahassee, okay.

Kira Derryberry: Tallahassee is one of those oddities where it’s like everyone’s like, “Oh, you live in Florida.” And I really live in South Georgia. It’s much less glamorous, not what you think of when you think of Florida. You think of Florida beaches and things like that. And Tallahassee, it’s like right at the very top northern part in what’s called the Big Bend. So we’re basically just… I’m a 30 minute drive to Georgia.

Allison Tyler Jones: I love it. So you’re not on the Redneck Riviera?

Kira Derryberry: No, I’m not on the Redneck Riviera, but I have been many times.

Allison Tyler Jones: Okay.

Kira Derryberry: Because I am from redneck areas for sure.

Allison Tyler Jones: Right. I love it. Same. Though we’re the Western true rednecks out here for sure. Okay, well what I wanted to talk to you about today is that you’re killing it with headshots and stuff, and so I want to talk about that, but I have been had a burning question for you that I want to discuss. And my question is, I can see that there are so many, kind of the new big thing right now is this personal branding product line that people are getting into. Like, okay, I’m going to do all this personal branding. And as I look at that, I just think, “Okay, I love the idea of that. I see the need for it.” How does it benefit the photographer? Because I totally see how it benefits the person that’s hiring the photographer.

Kira Derryberry: Right.

Allison Tyler Jones: Because they get a ton of images, a ton of digital files, and they need that because they either are an influencer or they need a lot of different looks and a lot of different things. So it’s like 55 senior portrait sessions, outfit changes, and props, and backgrounds and all that kind of stuff. But how do you make that not be a soul suck and how do you make that profitable?

Kira Derryberry: Well, I have a secret to reveal to you and just so just brace yourself.

Allison Tyler Jones: I’m ready.

Kira Derryberry: Personal branding, in my studio anyway, personal branding, images and headshots, it’s the exact same thing. So I treat it volume, I treat it like I would anybody coming in for just a head and shoulders headshot because every time I’m doing a headshot session, I’m just basically adding on different types of styles. I’m like, “Oh, do you want, you think you might want to be sitting at a desk and do whatever?” I’ll do all that in a session and then we’ll call it personal branding. Where it becomes not beneficial for me is when they go, “Well, I want to be seen outside walking down the street looking casual with my cup of coffee and whatever.” You know what I mean?

Allison Tyler Jones: Laughing to the side, giggling to the side, giggling to the side while looking to the side with your cup of coffee. Yeah.

Kira Derryberry: And by the way, I don’t want to be posed, I want to look natural, but you have to tell me how to look natural.

Allison Tyler Jones: But I have my angles and you can only photograph me from this one side ever. I have to be looking exactly like this and I can never turn my head straight on. It has to be from this particular angle, but I don’t want to be posed.

Kira Derryberry: But just, and make sure it looks casual. I don’t-

Allison Tyler Jones: And totally natural

Kira Derryberry: Tell me what to do with my face also, because I don’t know what to do with my face. So I don’t do those.

Allison Tyler Jones: Authentic. I think authentic is the word we’re looking for.

Kira Derryberry: Looking for authentic.

Allison Tyler Jones: Vulnerable. I need to be vulnerably authentic.

Kira Derryberry: I need to be vulnerably authentic.

Allison Tyler Jones: And candid and post with my six-inch eyelashes and my face that doesn’t move. Okay, anyway, sorry we’re digressing.

Kira Derryberry: So I can’t figure out, I’m going to tell you this, I cannot figure out how to make that going on location, doing all these different looks, outfit changes, whatever. I cannot figure out, unless you put a crazy big price tag on it, how to make that beneficial to me in the studio because… So I don’t offer it. If somebody says “I want to do branding shots.” I go, “Great. So tell me what kind of marketing pieces we’re going to be working on so I can get an idea of your vision.” And half the time they’re like, “Well I just want to be able to put my… I’d like some extra space on the left or right so I can put some text on or whatever.” The ones, the influencers and the things they don’t want to spend, in my market anyway. I can’t speak to everyone, they don’t want to spend the money on actually having a photographer follow them around and do that thing.

Kira Derryberry: Because my price tag for that would be much higher than my volume work in the studio. So I just try as best I can to keep everyone coming to me. That’s the best way I can say. That is if you want to come to me and do a branding session in the studio, if you want to have a seat on this little table that we put into the studio session with your cup of coffee or your notebook or your whatever, we’ve staged those type of looks here and that falls under personal branding and marketing. But I don’t go and follow somebody around with their cute cozy scarf and in the coffee shop, I don’t do that.

Allison Tyler Jones: Right, right. Okay, that’s interesting.

Kira Derryberry: I’m not hating on it. It takes up so much time. I can’t make money that way.

Allison Tyler Jones: Right. And I think honestly, what you’re also talking about, I think you know who your clients are. So people that have actual businesses, I’m not saying influencers who don’t have actual businesses because I know they do, but there are people that want to be influencers that just want a bunch of stuff and don’t want to pay for it. But then there are attorneys or people that actually have either brick and mortar businesses or whatever and they need it to be super professional and they are printing it on collateral or-

Kira Derryberry: Yes.

Allison Tyler Jones: … Trade show booth graphics or that sort of thing. And they do need it. It was way better if they have it in studio where you have a featureless background that they can lay graphic type into.

Kira Derryberry: That either their graphic designer could do or I can do or however they want to do it. But that is most of my clientele. You’re exactly right. I know exactly who the clients are. They are realtors, they are lawyers, they are in the medical profession, they are entrepreneurs opening a business, they are dentists. I mean I’ve got all of those kind of things. And the most popular thing that they want is a white background, just a solid white background that will match anything and that looks nice and bright.

Kira Derryberry: And those people, I get and understand. I have tried to figure out a way that I could make an influencer market work and there are so many traps that are good for the influencer but bad for the photographer. Like, well, I’ll set up a package subscription deal where they have to have some, I’ll shoot for them every month or every two weeks or whatever. But then it becomes you’re now tethered to them whenever they need you and you’re not able to schedule things. I’m all about just scheduling blocks of time in the studio for when I am doing certain things so that I can pack as much of that one… So if it’s headshots, we do that twice a week here in the studio and we pack as many of them as we can back to back in the day. I can’t do that if I’m going to leave.

Allison Tyler Jones: Right. Right. And to leave is, if you’re in any kind of a metro area, it’s a minimum of three hours. It’s like, because you got to pack up and get ready and get your head right and then you got to get where you’re going and then you got to shoot. And that’s if you’re shooting for an hour and then you got to do all of that in reverse and usually at rush hour. So again, we’re not saying that… We’re not hating on anybody that is doing influencer…

Kira Derryberry: There are people who make it work. There are people who make it work.

Allison Tyler Jones: Yeah. We don’t know how.

Kira Derryberry: Well, I could surmise how, especially if you’re a photographer out there who doesn’t have a brick and mortar studio like you and I do. You know what I mean? I could figure out that maybe you’re setting up a mini-session day or maybe you’re scheduling time with people and going out with them. But I mean I know it can work, but I don’t think it can work in my business model because my business model is designed around bringing people to the studio and getting as many as I can done in a block of time.

Allison Tyler Jones: And the reason I’m asking this question of you and wanting to have this conversation is because how long have you been in business?

Kira Derryberry: Going on 13 years.

Allison Tyler Jones: And I’m 17, so we’re really close to the same amount of time. So we’ve been in a while, but not as long as… Longer than some, not as long as others. But I see these darling little young, maybe not even young, new photographers that are coming in are so excited and then they get some influencer, it might be somebody that’s big in their area, might be somebody that really is really big on Instagram or whatever, and they’re just so grateful to be able to work with somebody and they’re getting that old thing that we all got when we first started, which is I’m going to refer a million people to you. And if all you’re getting referrals are is other influencers that only want to give you referrals to other influencers, you’re never going to make the money that you need to make to support your family and your dreams.

Kira Derryberry: Yeah, a hundred percent. I find that business by referral, it really matters how that person who booked you, booked you is because their value system is all of the people they’re referring you to are their value systems are all the same. But it works the same with my family portraits too. I mean, if I have a client that I super, super pleased in the headshot world, they’re going to go tell all their friends and also they don’t have to tell all their friends because they’re going to post it everywhere and all of the people in their circles have the same value system. It’s tough to work on exposure. I know we all know that.

Allison Tyler Jones: And we’ve all done it and realize that actually usually almost never pans out.

Kira Derryberry: Almost never. Yeah.

Allison Tyler Jones: Yeah. So my goal, and I know you and Mary have the same goal for your podcast, is I want to build up photographers to realize the value of what it is that they’re bringing to the world and to be able to have real businesses where they’re not just editing till 3:00 AM every morning and not being able to spend time with their family or their kids and being able to support their family. So that’s just one area where I really am seeing people doing a ton of work for not a lot of return.

Kira Derryberry: For not a lot of return.

Allison Tyler Jones: Yeah.

Kira Derryberry: The thing is that I’ve been the photographer doing a ton of work for not a lot of money for… I have worked for hopefully for exposure to the right people before and I have been up on weekends and nights until 3:00 AM working. The reason that I’ve made all these changes to be more efficient in the studio with my time is because there’s a breaking point. I couldn’t do that anymore. And so yeah, maybe I don’t leave and go on location and do a bunch of location shoots that are really exciting and fun all the time. And maybe I am being super consistent with white background work, but honestly it’s super profitable and it’s cost effective and it’s efficient use of my time. And I’m able to go home at 5:30 or so and then come back in and start the day again and work like a normal business hour. So all of those things were out of necessity for the longevity of my business in my mental health.

Allison Tyler Jones: Your personal sustainability.

Kira Derryberry: Yeah. And I need to be able to know that I can go pick up my daughter from school at a certain time of day. I need to know that I am available to go to a birthday party at a bouncy house place or whatever on a Saturday. You know what I mean? Because I know what my schedule is at work. And I think in the beginning when you’re a photographer, you’re so hungry for the opportunities and for the work that you’re just available all the time. This actually just happened yesterday or a couple days ago.

Kira Derryberry: I had a session, somebody wanted to do a maternity session and I don’t do a ton of maternity sessions, but she wanted a very specific kind of studio look, which is in my wheelhouse. And so she contacted us and we tried to suss out what it was she was hoping to do with the photos. And it turns out she really just wanted three images to announce her pregnancy. She really wanted it for her social and because that’s the age demographic that she’s in too. And it became, I’m not going to do this like I would do a big family session where we’re creating wall art or whatever because the spend isn’t there. You know what I mean? That’s not what she needs.

Kira Derryberry: And so I offered her, just because I want to be able to accommodate people and the shoot wouldn’t take me long, I said, “Well, we can do this as a headshot session and I don’t mind treating it that way. You’ll have two different looks.” I mean it’s basically the same as a headshot. One of my branding headshot sessions, it’s just in maternity clothes and we’ll do it that way. And she’s like, “Great, can we do it on Sunday?” Well no, we can’t do it on Sunday because I only do these sessions on Tuesdays and Wednesdays and that’s how I’m able to offer them at this price and it’s only an hour long. She’s like, “Well, but I work, I can’t do it.” And I said, “I’m so sorry, the latest appointment I can do is a 4:00, the link where you can book, I hope it works out.” She booked and she figured out a way to make it work for 4:00.

Allison Tyler Jones: Yep. Okay. So I think there’s so many good takeaways in what you just said, and for those of you who are listening that are newer in your career and are maybe being run around the block a little bit by clients, again, when you first start, you’re so grateful that anybody would hire you to do anything and you’re so also so excited about the craft and learning your gear and you need to shoot a lot so that you can learn. And so there’s nothing wrong with that. There’s nothing wrong with any of this, but at some point you have to look and go, “Okay, is this working out the way that I want it to? Am I getting out of this what I need to get out of it?” If you’re, you’re replacing your income, you’re quitting your nine to five and you need to replace that.

Allison Tyler Jones: Or if you’ve, you’ve been shooting for a while, you’re going into brick-and-mortar studio and you need to make up the difference on your rent or whatever for whatever reason, then you start to look and what you said that’s so valuable is that you look and go, “Okay, what am I really good at?” You’re really, I mean, your headshots are beautiful. It’s not just like, “Oh, it’s a white background. Here’s somebody…” The lighting is masterful, they’re so well crafted, they’re just well done. And then you see the true personality of that person, which is really hard to do in that arena. I think people come in and it’s not a long shoot. You don’t have a lot of time to make them comfortable. And you obviously have nailed that.

Kira Derryberry: Thank you.

Allison Tyler Jones: And then you also realize, okay, once you’re shooting this studio, you’re like, “Dude, I don’t have to leave here. I can do so much more. I can accommodate more clients in less time.” Also good for the clients because we live in hot, sweaty places so they can come in. It’s AC. So you’ve narrowed down what is really good. I know that you also do other kinds of portraits, but we’re talking about this headshot branding today. And then the thing that I think that you said that I think people really need to pay attention to is that you have decided that I am shooting this type of session on this day and this is the only time that that is available at that price. And so just because somebody asks you to come to their house on Christmas Eve at midnight doesn’t mean that you have to do that.

Kira Derryberry: No, no. Because they will make it work. If they really want to work with you and they really want the photos done, they will book when you say it’s available. And I’ve found too, with headshot sessions, you don’t want them to take a long time. Most of my clients, especially the lawyers and medical industry people, they really are very, very busy. And they need to scoot in, get this headshot done and scoot out. The ones that take a little longer are the entrepreneurs or the realtors ,people who are running their own business and they’re like, “Well, I really need all these different types of shot.” But once you kind of get in the bankers and those type of people, they really want to be in and out and so out. Yes, absolutely.

Allison Tyler Jones: It’s a feature that it doesn’t take long. It’s a benefit.

Kira Derryberry: And they don’t want to have… It’s a benefit. They don’t want to have a lot of back and forth about it. So setting up online booking for this has been something that my clients love. I love it because I don’t have to sit there on the phone with them and explain everything. And because normally we would handhold our bigger sale clients through every step of the process, but because these guys just know they need their headshot done, they’re like “I’m speaking at a conference and they’re asking me for a headshot and I haven’t had… I’m just using an iPhone picture. I’ve just got to get this done. And can you turn it around quickly?”

Kira Derryberry: We don’t have to handhold them at all. The answer is “Yes. Here’s the link to book. Find a time that works for you and come in, we’ll get it done and I’ll get it back to you in a couple of days.” So I found that, while I think the scary thing about that is it doesn’t sound sexy at all. I mean it is to me because of the amount of money that is making me. That’s awful. But-

Allison Tyler Jones: No, exactly. But this is, my sister and I talk about this all the time. We’re like, we need something non-sexy. We need a mini storage business or something that is not sexy at all, but that just brings in tons of cash because you can take the money that you make from the non-sexy thing and go do sexy things with it. You can go to Italy. We did that. We were in Italy.

Kira Derryberry: We did, we did that one time.

Allison Tyler Jones: So again, I think you are such a good example of this. It’s not like you just set up some umbrella and just crank them through and it all looks the same.

Kira Derryberry: No.

Allison Tyler Jones: These are very well-crafted business portraits. I would say they’re business portraits because they are beautiful.

Kira Derryberry: Thank you.

Allison Tyler Jones: So it’s not just a quickie down and dirty. You’ve mastered your craft so that you’re faster at it than you were when you first started. It used to take you probably a lot longer to set this stuff up. Now you can do it in your sleep.

Kira Derryberry: It did. I can’t credit… I’ll tell you somebody who kind of shook me into some sense for a little bit, because you know how much, I don’t know if you know this, but I love playing with lighting. I love experimenting.

Allison Tyler Jones: Yes.

Kira Derryberry: I love the craft of photography.

Allison Tyler Jones: Same.

Kira Derryberry: And our friend, Gregory Daniel one day, he was like, “How long has it taken you to… So how many lighting setups do you do in a session? And how long is it taking you to do all these different things?” This was a while ago, this was five years ago. And I was like, “Well, I don’t know. I guess I like to tweak the light. I like to try something new or I like to maybe change the modifier out and see how that’s going to look or whatever.” And he was like, “Aren’t you spending more time doing that than you are doing this session? I mean, how long is this session?” I was like, “Oh, sometimes we shoot for two hours, sometimes we whatever.” And he was like, “You really need to nail down three looks maybe, and then just offer those three looks. So you just come on and turn the lights on when you get there and then do your thing. And then they’re in and out.”

Kira Derryberry: And I was like, “That’s boring though. Where’s the art in that?” And the truth is that I have crafted three different… I haven’t invented them, but certainly crafted three different looks in the studio that are consistently asked for by the client. I have my lights in zones and I have my modifiers pretty consistently that I use throughout the whole thing with very little changing. And I can do a quick change. Somebody goes in the bathroom and I drop a new background down. Now we have the dark set turn, the two background lights off and it’s the dark set now.

Allison Tyler Jones: Yeah.

Kira Derryberry: And it’s a matter of you’re still being creative, you’re still doing what you love, but you’re being efficient with the setup, the breakdown, and the time so that you can spend more time making them feel comfortable.

Allison Tyler Jones: Right. That’s exactly what I was going to say because why your stuff stands out is okay, yes, it is beautifully lit, but we’ve all seen very boring, beautifully lit images, very boring. But you have the combination of that person is comfortable and you kind of feel like you know them when you look at it, that’s a goal. And you don’t always get it no matter how good you are. But if you don’t have any time, if your fussing around with your stuff, and this is with any portrait session and you can’t connect with the subject, you’re going to lose something in the translation.

Kira Derryberry: You lose confidence. I think that’s what it is. I think when you’re fussing around with your lights, when you’re moving things around, or if you’re just trying to get it dialed in, trying to get it dialed in, like, “Oh, let me just do a test shot 12 times over or whatever.” They start to lose patience and start to wonder if you know what you’re doing. And they start… And they may not say it and they may not, whatever, but it’s there. You start sweating, you start apologizing. “Oh, sorry, I’m just going to move this. I’m just going to, whatever.” The more you move things, by the way, the more they won’t work. I’m going to tell you that right now.

Allison Tyler Jones: Yeah. That is for sure.

Kira Derryberry: But the other thing that I do, this is my step two of making this efficient thing work, is I shoot tethered.

Allison Tyler Jones: Tell me.

Kira Derryberry: That’s the second part of what you’re calling that feeling that you know that person on camera. It does come from them having a confidence in you that they’re not having to worry that the pictures aren’t turning out because I shoot tethered, and the minute I start to think that somebody is overthinking how it’s looking, I just turn the screen around and I show them and I go, “Look, it looks so good.” And she goes, “Oh, thank God.”

Kira Derryberry: And then it’s like ah, their shoulders loosen enough just they breathe. And there are times where they look at it and they go, “Ugh.” And you go, “What’s ugh about it?” And they go, “Well, I don’t like my hair.” I’m like, “Let’s fix your hair. Let’s get that.” Because the worst thing would be to do a whole session and then them see the photos and then go, “Oh my God, my hair looked like that the whole time?”

Allison Tyler Jones: Right.

Kira Derryberry: I don’t want any of these photos. And so the tethering thing is great because it builds trust between the two people. The other nice thing about it is I can sell them there. We do… In this one hour-

Allison Tyler Jones: They can select it right then.

Kira Derryberry: I probably only shoot for 15 minutes, honestly, with these people. And then we spend the rest of the time looking at the photos and adding on additional photos to the package. And that’s the secret. That’s the secret to having a really good day. And then getting them out the door so that the next person can come in and you can start that process over again. And you’re not waiting around for weeks for somebody to look at their proofs online to get those choices to you. And then all of a sudden they need it right now, but they’ve…

Allison Tyler Jones: Right. And it’s a hot rush and it runs the freight train through everything else you’re doing. So you’re shooting tethered to a laptop or to an iMac, or what are you shooting?

Kira Derryberry: So I shoot tethered to a MacBook Pro.

Allison Tyler Jones: Okay.

Kira Derryberry: That I have set up in the studio. And then I also do airplay, Apple airplay to our big TV in the main room. So if somebody has brought people with them, sometimes I work with kids, I work with theater students. And so their parents will be there and the theater kid is like, “Mom, I don’t want you watching or whatever.” They can actually… Parents can sit on the couch and actually be out of view of the kid and watch the images come up as they go. And sometimes the mom will go, “Can I get in there and fix her hair or can I whatever?” And sure. But that way they’re not looming over your shoulder going “Smile to me. Smile. Okay.”

Allison Tyler Jones: Yeah.

Kira Derryberry: They’re in the other room and they’re actually participating, but not in the shoot at the same time.

Allison Tyler Jones: Yeah. No, I love that. Okay, so 15 minutes shooting. You’re spending what, 30 minutes selecting? 15 minutes selecting? 45?

Kira Derryberry: Yeah. Sometimes it’s very fast. It really depends on who it is.

Allison Tyler Jones: Yeah, of course.

Kira Derryberry: I’m going to tell you right now that realtors are the worst offenders for taking the longest to make a decision. But generally I try and leave as much time as I can for that order session portion of it without them feeling like they didn’t get enough value out of this shoot.

Allison Tyler Jones: Right.

Kira Derryberry: So I actually ask them before I moved them into the sales room, I go, “Hey, so I feel really great about what we got. Was there anything I didn’t get that you were really hoping for? Was there any look that you were hoping for? Or whatever?” And they go, “No man, God, I feel like we’ve taken a ton.” That’s usually what happens. “Oh, I feel like we’ve taken a ton. No, I’m ready.” Okay, let’s go look. I kind of ask for permission to finish so that they don’t feel like I rush them. I don’t want to be accused of rushing them out of the session. Because you know when you got it, you know what I mean?

Allison Tyler Jones: But you don’t quit… You don’t quit shooting until you’ve got it.

Kira Derryberry: Absolutely.

Allison Tyler Jones: I mean, you keep going until you… Yeah, for sure. So I want to ask a quick question. I want to back up just one second. On your online booking. What are you using for that? Are you using Calendly or?

Kira Derryberry: Yes.

Allison Tyler Jones: Okay.

Kira Derryberry: Yes. I am using Calendly. Love it. It’s hard to say.

Allison Tyler Jones: Calendly. C A L E N D L Y. We’ll link to it in the show notes.

Kira Derryberry: Yeah.

Allison Tyler Jones: Okay. Yeah. I love Calendly. We use that on our website also for people can schedule consultations that way.

Kira Derryberry: I use it for everything. We do it for exactly that. I mean, it’s literally, I have six different Calendly bookings links that we use for everything.

Allison Tyler Jones: That’s awesome. Okay. So shooting tethered. And then are you using Lightroom that you’re shooting tethered?

Kira Derryberry: Yes. Unpopular answer. But yes.

Allison Tyler Jones: Because everybody wants to use Capture One?

Kira Derryberry: Everyone wants to use Capture One. And I’m not hating on Capture One, but I tried to love Capture One, but it’s one of those times where I know I’m very fast and efficient with Lightroom and It just works for me.

Allison Tyler Jones: Yeah.

Kira Derryberry: But it’s not the most popular answer for sure.

Allison Tyler Jones: Yeah. But there are going to be people listening to us that are going to go, I feel so validated by Kira Derryberry today. So you’re welcome. And then Airplay too, are you airplaying to like an Apple TV?

Kira Derryberry: It’s a smart TV.

Allison Tyler Jones: A smart TV. Okay.

Kira Derryberry: Okay. Yeah. Most TVs that you buy nowadays have that built in.

Allison Tyler Jones: Yeah. Absolutely. Okay. I love that. All right. So what’s next? What else? That’s your whole process. I love it.

Kira Derryberry: That’s my whole process. But I feel like I get into these little ruts that I think are normal and natural when something is working really well, you know what I mean? So I try and give myself a little bit of creative time, or if I have a client that comes in and they have a great look or whatever, I will go, “Hey, I would love to try something.” And I might throw some different color in. I might do something a little above and beyond, out of the normal because I think it will really work for them. And I need to break up the monotony myself. It’s not monotonous for the client ever because it’s new to them every single time, but…

Allison Tyler Jones: Right. And they’re on the hot seat. It’s everything but monotonous. They’re freaking out because they’re worried about themselves.

Kira Derryberry: They’re totally worried about themselves. So I do that. The one thing we haven’t talked about that’s also part of this little business is composite work. I am, that is hot right now, ATJ, that is super hot right now. During the pandemic when people couldn’t stand shoulder to shoulder, these companies were all redoing their websites and all their marketing because they couldn’t do anything else. And so I started photographing people individually and then compositing them into one image and adding the little shadow work or whatever to make it look believable. And it has become now one of my signature things that I do because my studio is fairly small, I can’t photograph really more than five people, six people altogether in a group without it looking crammed and me having to do a bunch of work on the background to extend it.

Kira Derryberry: So pretty much if you’ve got over five people now I am saying, “You know what? This is actually super efficient for you.” I’m basically solving a problem they didn’t know they had.

Allison Tyler Jones: Absolutely.

Kira Derryberry: Look, every time you have an employee that leaves your group photo is no longer useful. Every time you add a new employee, your group photo is no longer useful. And then if you’ve got 10 plus employees getting them all together and having it redone over and over again, that’s a pain in the butt. You’re never going to get it done. So why not? Why don’t we just photograph everybody full length? And that way we’ll have a file image of every single person so that if Mary Smith ends up moving on to another job, we just take Mary Smith out of the group photo. We just push everybody together and no more Mary Smiths.

Allison Tyler Jones: Yep. Well because how many group shots had we done before now that somebody was like, I mean I have had people say, “Okay look, can you make sure that the secretary’s on the outside because she’s on her way out, but we don’t want her to know.” And so we are doing the same thing and it absolutely, it’s the hugest benefit for the client.

Kira Derryberry: A hundred percent. They really see it like, “Oh, I didn’t even think about that.” That is the answer we get most often is “I didn’t even think about that. That’ll be great.” It also creates a need for them to consistently come back to you forever. They’ve got to come back to you every single time they have a new employee they’ve got to add, they just set up a session. We have a special link just for those clients to book their new employees to come in. They come in and get photographed and then I send them the individual file of the headshot for the person and send them the new group photo and actually have that on my screen, on my other screen right now I’ve got one, but…

Allison Tyler Jones: I love it.

Kira Derryberry: And then I just send an invoice and it’s great. And I should mention that all of these sessions that I do, I always sell it we’re going to do this individual portrait of the person, we’re going to crop it to three quarter or to head and shoulders for their actual headshot. And that’s the one we’ll use in the thing. So it’s all like, “Oh, we just need one image of the person.” We don’t need 20 images of the person.

Allison Tyler Jones: And really, I’m always preaching about what is the value. And Tim Walden and so many of our friends are always talk about don’t sell the spark plug, sell that it’s actually starting your car, the result. And so the result of this is that you have a beautiful group shot, you have professional looking headshots on your website, and then at anytime if the staff changes, it can be quickly and inexpensively really shifted compared to having to set up a whole new thing and get all those people in. It’s just so much more convenient. But it’s also steady income for the photographer and it’s completely worth it. You become the keeper of the branding imagery of the people in the businesses.

Kira Derryberry: Right. Right. And even if you’re not excessively skilled at your Photoshop compositing skills, I mean there are retouching companies that you can send it out to. I use Retouch Up when the volume gets a little too big for me because lately I’ve got tons of these clients where we’re doing this. And so I have a few of them that are set up and I just send them out to the retoucher and to the group photo and then send it back to me. And I’m like, “Oh great. $10.” That was $10 for me to get done.

Kira Derryberry: So it’s great. The industries that are really great for this as far as repeat business is, I would say your spa and beauty industry is great for this. So hair salons…

Allison Tyler Jones: Estheticians.

Kira Derryberry: Big Estheticians, hair salons, I’ve got several clients like that where they have new stylists or new Estheticians come in all the time and people leaving. It works out really nicely for them. The banking industry, I find that to be a great revenue generator for this. Law firms, things like that. I mean just everybody needs a headshot these days. I mean, I can’t really think of a business that wouldn’t benefit from having it.

Allison Tyler Jones: Yeah, no, I think it’s amazing. So are you charging more for that because it’s time and effort and you’ve got to manage that?

Kira Derryberry: So I charge a larger fee for the initial composite photo, right?

Allison Tyler Jones: Yes.

Kira Derryberry: And then every time they have a new employee come in, they’re going to pay a session fee and a fee for that individual employee and a small fee to add them to the image. In fact, every single time they need to change the image there is a small fee. But typically if I’ve got this one client and every other month they’re sending me three new people and they’re having me remove three new people. Those little small line items add up to being very efficient use of time.

Allison Tyler Jones: Absolutely.

Kira Derryberry: Good money maker.

Allison Tyler Jones: Well, and I find that my best clients on the portrait side are clients that own their own businesses. And going business to business is so nice because there’s very little drama. It’s just like, “Hey, we need this for business. It’s clean and easy.” I feel like it’s just less angst. Although, I mean some people are worried about how they look. And then we had one law firm that sent in some girls that were dressed they were going to a rave and we had to re shoot it because they showed up very sexy.

Kira Derryberry: It is important to do a little wardrobe coaching as far as what the brand is. I have done that before too actually, where we’d established a look for the brand and we just have a little wardrobe list of do’s and don’ts and recommendations. That will help the group portrait continually looking good. Because there’s sometimes where the company picks a color scheme and then So and so comes in a full plaid suit and you’re like, “Oh, okay. That’s not going to… That’s going to look strange.”

Allison Tyler Jones: Or nine-inch plexiglass stilettos for example.

Kira Derryberry: What the plexiglass stilettos, Allison?

Allison Tyler Jones: I don’t know. It’s like the hooker shoes. I don’t know. It’s very strange.

Kira Derryberry: And then they ask you to Photoshop their feet smaller because they’re squeezing. I’ve literally, I’ve told this story a hundred times, look, I feel like in the last week, but I’ve literally had somebody come in some really tight high platform shoes that had tight bands around them and then I’ll deliver the image and then they come back to me with, “Could you Photoshop my toes so that they don’t look like they’re being squeezed by the shoes? Could you?” And you’re like one, you had to zoom into 800… At what point is 800% zoom ever going to happen for this photo in real life?

Allison Tyler Jones: I know. The proofing on the phone thing is a whole… That’s another reason to sell in person because it’s that whole when they zoom in on that phone and they’re… My third pore to the left of my nostril.

Kira Derryberry: Yeah.

Allison Tyler Jones: You’re just like, “Okay.”

Kira Derryberry: There’s a small hair in my eyebrows. I know my eyebrows have hair, but that hair, that one there’s, could you find that hair that’s in my eyebrow?

Allison Tyler Jones: Yeah, the third from the left.

Kira Derryberry: Yeah. Yeah. I mean that’s going to happen because of the phone. Even on delivery, it’s going to happen. I have always found that the longer somebody has to review and to pour over their proofs on their own at home or with friends or they send it out to 12 people, it’s bad. It’s a sale killer the second they walk out the door mean. I think it applies to pretty much every bit of photography that can be done that you’re selling to a client. The second they’re gone, it’s just like they’ll convince themselves that they’re a monster and they don’t want the photo anymore.

Allison Tyler Jones: Right. Yeah, no, I have one client that can’t make… She has a really hard time making decisions and so she has to consult literally her lawn guy, her housekeeper, all of her nearest and dear. Yeah. And then everything that she sends back that she wants to change, it’s like, “Well, even my lawn guy thought that my daughter’s face looked fat.” And you’re just like, “I don’t think your lawn guy thought your daughter’s face looked fat. But okay.” Anyway, just so funny. That’s another episode right there.

Kira Derryberry: I know. Well, okay, let me share my fun story though.

Allison Tyler Jones: Yeah.

Kira Derryberry: That just literally just happened. Delivered to a real estate client, realtor client. She’s gorgeous. Just gorgeous photos of her and delivered and out of sight out of mind. I get an email on Friday at 11:30 at night and she says, “I showed my friends my picture and they all think my necklace is weird and now I think my necklace is weird. So what can we do about it?” I said, “Oh well, for a fee,” and I give her the amount “We can remove that necklace for you. No problem.”

Kira Derryberry: And she’s like, “That seems like a lot.” Because it was two photos, just two photos. She goes… So I was like, “It’s per photo.” And she goes, “That seems like a lot per photo. Can you do it for the price of one?” She cut it in half, whatever. And I said “No.” And then she’s like, “Do you mind if I do it myself?” And I was like, “They’re yours, whatever.” And we moved on, but she’d shown her friends and her friends were like, “”What’s with the necklace? And then it just ruined… She loved her photos when she left here.

Allison Tyler Jones: Yeah.

Kira Derryberry: Loved them. So…

Allison Tyler Jones: I find that the more beautiful they are, sometimes the more complicated.

Kira Derryberry: That’s a hundred percent true. A hundred percent. A hundred percent true.

Allison Tyler Jones: Yep. I know. We’re just our own worst enemies for sure. Okay, well I love all of the things. So I want to just recap where we’ve been.

Kira Derryberry: Okay.

Allison Tyler Jones: Kind of the takeaway from this episode is that headshots and business to business portraits can be the most amazing thing ever and the personal branding, but maybe have some limits in your mind as far as when, where, how you want to do it and really think about even if you start off doing a lot for a little, you’re learning, but maybe don’t stay there. Where can we move forward? I love your idea of that limited availability because I think once you have your… Especially if you have a studio like what you’re saying, you’ve got this lighting set up and the way you’re going to shoot a family session is going to be different than the way you’re doing a headshot. So it behooves you to set up an entire day where you can just bring people in and out doing the same kinds of work.

Kira Derryberry: Yes, absolutely. Yeah. Because if you’re having to reset for a whole different kind of shoot after that, then you really have to book in time to do that and then it takes away from the time you could be shooting.

Allison Tyler Jones: Exactly. Yeah. So I love that. And then I love the idea that one of the selling features, one of the value of the way that you’re doing it is that it is quick so that it’s not giving less. You’re getting somebody in and out, some CEO that’s 245 pounds and making a couple million a year needs to be in and out. He doesn’t really care. He thinks he looks great. Make him not sweat and get him in and out.

Kira Derryberry: Yeah, yeah.

Allison Tyler Jones: Make it quick. And then your online booking, awesome. Because then they can set that up and you know I’m just going to be at the studio on those specific days. And so whoever’s coming in, they can book it. Are they paying for it then when they book it?

Kira Derryberry: They pay for it online, that is also a major, major. I’m glad you even said that. They pay ahead of time, the full session fee that includes-

Allison Tyler Jones: Absolutely.

Kira Derryberry: … Whatever it comes with. They pay it upfront because then they have skin in the game that eliminates, I mean eliminates no shows. Exactly. When somebody drops some money on it, they’re like, “Oh I’ve got to show up to this cause I’ve paid money for it.”

Allison Tyler Jones: Absolutely.

Kira Derryberry: If they haven’t done it they will definitely go…

Allison Tyler Jones: They can be flaky. So are they paying online with a link?

Kira Derryberry: They’re paying through Calendly. Pay Calendly. Yeah.

Allison Tyler Jones: Okay. I didn’t know that Calendly had that feature.

Kira Derryberry: Oh yeah. Yeah, you can. So this is another little hot tip. So for my individuals who are just coming in for their personal headshot or whatever, they have the Calendly link that books them for where they actually put in their credit card number and pay for my companies that I work with on a regular basis, they have their own special link so that the employee is not, because they’re not going to be the one that pays the bill, but the employee is just booking their session and then I invoice the company when we’re done just because it’s a different kind of relationship with the corporate client.

Allison Tyler Jones: Exactly. Okay, I love that. So invoice the company for the ones that have employees and then for the ones that are paying for it themselves, they can pay online. Love that. Then you’re shooting tethered and you are shooting maybe 15 to 20 minutes on one of these sessions. You have certain setups that you have dialed in and that look good so that you can spend your time connecting with your client and getting authentic expression from them and having them feel really comfortable.

Kira Derryberry: Yes.

Allison Tyler Jones: You shoot enough to where they feel like, “Okay, we’ve got this.” And you know you’ve got it. And then you’re asking, I like that idea of asking permission of “I feel great about what we’ve got. Is there anything specific that you think that we’ve missed?” Because I think then that gives them the chance to say, “Oh, actually I really wanted to be… I forgot the beach ball or whatever.” And then you spend the rest of the time looking at the images and then that gives you the time to say, “Okay, this is how we can retouch. This is what we would do in a typical retouching situation.”

Kira Derryberry: Yes.

Allison Tyler Jones: Putting them at ease with that and then picking out the images and adding images and then they leave and then you don’t have to talk to them again until the images… Well, you don’t have to talk to them again. You can just be like, “Here’s his link to your images.”

Kira Derryberry: Yeah. We just deliver them. And it’s totally different animal than selling physical products, which I’m very for. And that’s just a whole different part of my business. But I mean this part of it, the overhead is low, which makes it really, really great. The volume is high if you book it correctly. And then the interaction with the client is pretty quick. It’s very transactional and I feel like it’s the kind of thing where I can’t think of the wrong type of client for it really. Everybody needs a well-loved portrait.

Allison Tyler Jones: A good headshot. Yeah. Well, and I think what you’ve done is just taking a term from the tech industry is you’ve just made it frictionless for them to book, for them to have it to be photographed and then to select their photographs. And so when they leave that studio, everything is paid for. You don’t have to get more money from them. And all you’re doing is just then delivering the images, which I think is just absolutely genius.

Allison Tyler Jones: The one thing that I wanted to end with is a story, and you’ve probably heard this, but it makes me think that sometimes when you do something, you’ve gotten so good at it and it’s easy, easy for you. It can feel like, for example, when people come out of weddings, shooting weddings and they decide to go into the portrait world and they way under charge for family portraits because they’re just so grateful they don’t have to spend 15 hours with somebody.

Kira Derryberry: Right. Right.

Allison Tyler Jones: So they undervalue what exactly they’re bringing. And so it’s, I think going back to our very first part of this podcast, when I was saying I feel like there are a lot of people that are working a lot for a little because they think, “Well this is easy for me.” Or it’d be easy for you to say, “I’ve got my three setups. I know how to do this.” So the story I want to tell is that there’s this story about, I think it was a nuclear reactor, nuclear company, and they were having problems with one of their tanks. Have you heard this story?

Kira Derryberry: No.

Allison Tyler Jones: So there was something that was overheating or whatever, some nuclear company. And so they call this expert, he comes in, he’s looks around and walks over and picks a sharpie and puts a big X on one of the tanks and says, “This is the one that needs to be fixed.”

Allison Tyler Jones: And so they’re like, “Oh great, that’s awesome.” And so he sends him a bill for $10,000 and they send him back and they’re like, “What in the heck? Why would you charge me $10,000? You were here for five minutes and you put an X with a Sharpie on of tank.” And he is like, “Oh, I’ll revise the bill and send it to you.” And so he sent the bill and he is like, “X number of dollars, like say a hundred dollars for my five minutes of my time and then $9,900 for knowing which tank to put the X on.”

Kira Derryberry: Right, exactly.

Allison Tyler Jones: It’s the expertise. So it’s…

Kira Derryberry: The expertise.

Allison Tyler Jones: You have spent thousands, you’ve got your 10,000 hours in at going to PPA imaging, learning from practicing the lighting, having so many images that just totally sucked, that didn’t work or didn’t look good, or that you look back and think, “Can’t believe somebody paid you for it.” We’ve all put in the time. And so it’s getting it to this point and making a well-oiled machine in this one area that can feel really, really good. And then, like you said, you still have moments where you can say, “Ooh, this is really fun. Let’s try this and make it more creative.” And then you’re getting your creative also in other areas, other product lines that you have going on in your business.

Kira Derryberry: Yeah. Yeah. That’s the secret kids.

Allison Tyler Jones: I love it. I love it. Well, I thank you so much for being willing to share all of that info because I think that’s hard won knowledge and you’re always so good to share. Is there anything that you want to leave our friends and listeners with as we think it out?

Kira Derryberry: I would say if it’s a newer person into the industry or whatever, I would say that learning, that thing that you said, spending the hours, spending the time learning, that’s what in the long term makes you successful. I mean, you could be great at business and you could have a hard understanding, but if you have to even think… This doesn’t work if you’re having to sit there and calculate and think and do the math and figure out the angle of the light and do whatever.

Kira Derryberry: So practice, practice, practice, practice as much as you possibly can. Get it to where in your sleep you could turn that camera on and those lights on and know what you’re doing so that you could spend more time being with the client. Because the client has so many choices in photographers, there’s a lot of us out there. And so you want the client that wants to work with you because you make them feel great. They don’t care so much about… They really don’t want to know or care about your expertise. But if you’re having to think about that, you can’t be that person for them. So that’s what I’ll leave you with.

Allison Tyler Jones: I love it. I totally agree. Kira, you’re the best. I appreciate you taking the time. I know you’re so busy, and thank you so much for lending your expertise to The ReWork.

Kira Derryberry: Thank you for having me. This has been awesome.

Allison Tyler Jones: I hope you know how much I appreciate your time and your attention. And if you feel that something you learned today could benefit another fellow portrait photographer, please share this episode with them. We want to help as many portrait photographers as possible to build sustainable, enjoyable, profitable businesses that can help sustain their families and their dreams. And that’s what it’s all about. So please share if something was valuable and you feel like that it could help somebody else. And if you get a minute, please give us a review at iTunes or wherever you listen to your podcast. It makes a huge difference in other photographers being able to find us and get the information that can help them build better businesses. You’re awesome and I appreciate you. Have a great day.

Recorded: You can find more great resources from Allison at and on Instagram at Do.The.ReWork.


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