In this episode of The Business Owner’s Journey, host Nick Berry interviews Daniel Wakefield, founder of Top Tier Headshots. Daniel shares his journey from a side hustle to building a six-figure photography business in just 12 months, offering insights into the strategies that helped him de-commoditize headshots, gain confidence in pricing, and leverage strategic partnerships. They also discuss meaningful networking and how Daniel’s business mindset propelled him to success, now mentoring other photographers through workshops and an upcoming book. Tune in to discover how to accelerate your own photography business growth.
Daniel realized that headshots don't have to be a simple, transactional service. By focusing on genuine human expression and delivering a high-end experience, he was able to transform what many see as a commodity into a premium service. His process, which includes "expression coaching," ensures that clients not only receive great images but also gain confidence in how they present themselves professionally.
Daniel emphasizes the importance of building genuine, meaningful relationships in business. Rather than focusing on instant transactions, he nurtures relationships with other business owners and collaborators, which has led to strategic partnerships and long-term growth. He highlights how surrounding himself with successful individuals has accelerated his own development.
One of Daniel's major breakthroughs was learning to confidently price his services well above the competition. He explains how understanding the true value of his work, combined with delivering a top-tier client experience, allowed him to charge 3 to 5 times more than others in his field—without discounting. He teaches other photographers this mindset shift as part of his coaching.
Daniel attributes much of his business growth to strategic partnerships and collaborations, such as his work with The Daily Drip and other local business communities. These partnerships not only brought him more clients but also expanded his reach and helped him grow as a business leader.
Daniel shares how he went from nervous sales calls to confidently closing high-ticket clients by focusing on the value he brings. He now guides clients through their goals and helps them understand why his premium pricing reflects the quality of service and results they can expect.
If you enjoyed this episode, please subscribe to the podcast on your favorite platform and leave a review. Your feedback helps us bring you more valuable content.
Daniel Wakefield (00:00)
from that point of launching into the market for 12 months, then yeah, we hit six figures. But that first month was $60 of revenue. And it was a
It was a wake up call of I can't just put together a website with a good portfolio and wait for people to find me. And I know there are photographers, there are businesses that do that. They kind of build the website and it looks great and they tell all their family and friends and then they just sit back and wait and hope that somebody calls.
Nick Berry (00:35)
The Business Owner's Journey. I'm Nick Berry and I've got real business owners telling their real stories, sharing their real lessons and strategies so you don't have to figure it all out on your
Nick Berry (00:47)
Daniel Wakefield went from a school teacher to a side hustle to owning a business that did six figures in his first 12 months, multiple six figures in year two. Now in year three, he's already exceeded this year's revenue goal, doing something that I probably considered to be a commodity, headshot photography. His company is Top Tier Headshots, which does professional headshots. He's very transparent with how he's done it, and now he's teaching others in his workshops and upcoming book.
We talked about clients saying that the headshot changed their life. We talked about him being an expression coach, about how he did $60 in revenue in his first month and rebounded to do six figures in the first year. His approach to networking, how he decommoditized headshots and about how he makes the sale when he's priced three to five times higher than his competitors. Enjoy this episode with Daniel Wakefield.
Nick Berry (01:43)
would assume that a lot of people are like this. but I thought that headshots were a commodity, you know, because if you've got a phone, I can take a selfie, I can do a headshot. And now I know that that's probably insulting to you. But now that I've seen your work and heard people talk about the effect that it's had on them, I understand why you would
look at somebody who says that and kind of like, So I was just uninformed, but in the last couple of weeks, I've learned that there, what you're doing is anything but a commodity. And I've heard some stories, but I want to hear you talk. First of all, tell me like, what is it about your headshots? What is it that you see differently that, that has totally broken the whole commodity frame?
Daniel Wakefield (02:24)
So, well, first of all, thank you for having me on the podcast. It's a pleasure to be here. So for me, it was about thinking about what kind of value does a headshot have for a professional? And for some people, they themselves may think, you know, well, I need to get it done because I need to have something on my LinkedIn. But for them, it's almost more like a placeholder.
Right? It's like something to put in there. For some people, it's just, me find a photo of me at a wedding and crop it down. So they've got the tux on and something like that. So those people aren't really viewing the value that it can have for their career. And when I started to think about, you know, what kind of value could this have for professionals? I started to realize that people with really good headshots on LinkedIn.
tend to get more profile views. LinkedIn actually did a study that demonstrated that their study was basically comparing profiles with at least a decent headshot versus profiles that I think had like a selfie or nothing and found that the ones with at least a decent quality headshot get 14 times more profile views.
than those who don't. So right there, we're immediately starting to see some value in terms of, you know, if I'm in any sense wanting to use my page for business development, marketing, things like that, you're immediately getting a return on that investment just by having that good quality headshot on your profile and really presenting your professionalism upfront. there's...
Nick Berry (03:52)
Okay.
Daniel Wakefield (04:19)
That is one thing I would say in terms of value. And then other things, know, stories that I've had from my clients and just what they're using these images for, things like a book cover or a podcast cover, magazine features when they're doing something cool and they're getting featured in a magazine because of it. And so just all of these different things that are really
you know, helping to further someone's career and put out this great image of themselves. And, you know, it's people are benefiting from that when it's a great quality image and really helps to show off who they are and their personality and all of these things. And so that, and this goes right into like this story, that this client of mine who
she got me to do a headshot for her that she put on her book. And she told me sometime afterwards, and not just me, she actually put this on LinkedIn, on Instagram. She said that that photo changed her life. And, you know, I think there's, you know, several different factors to that. One of them just being the self-confidence piece and how having this powerful image of yourself actually translates to
helping you feel more confident in your career. But then beyond that, she's telling me that now when she does keynote speaking, and she has audience members come up and talk to her after the event, and she's spoken to some very large crowds as well across the US. And she has said, these people are coming up to her and saying, as soon as we saw the photo of you on the cover of your book,
we felt like we had to come and hear what you had to say. There's something to that that goes beyond just like dollar value there. There's something that it's actually helping her in maybe not tangible, maybe intangible ways of like, it's actually promoting her while she's sleeping. know, somebody sees the cover of her book and they're like, I gotta go hear this woman speak.
because of the way that we were able to portray her with that image. So not only is it getting her more recognition, but it's getting her more revenue because it's selling more tickets and bringing more people out to these events. So to me, I don't like to view headshots as just a, yeah, it's something we have to get done, something we need for the company website or for a LinkedIn profile, but what...
could it be? What's the potential there for brand development and recognition, for increased business development and networking opportunities and just connecting with people, and then revenue opportunities? It's something that's, you've got a great photo of yourself and it opens doors for connection on LinkedIn.
Nick Berry (07:33)
Mm-hmm.
Daniel Wakefield (07:41)
there may be revenue opportunities that started with that moment.
Nick Berry (07:45)
the way that I was introduced to you was through some people who I heard they were like sharing how proud they were of their headshots, right? They weren't even talking about what they were using it for. They were proud of a headshot. And I thought, man, that's kind of odd. And then I heard it again.
Daniel Wakefield (07:58)
Right.
Nick Berry (08:05)
And so then I finally looked into it and I was like, wow, those like, those really are good. but there's more to it than it just being a good photograph. think it goes, it's into their perception of themselves, And then the opportunities that can come from, changing your perception of yourself and having that asset on hand to use,
you know, it changes the way that you think about yourself and about, your brand,
Daniel Wakefield (08:30)
Yeah. And I think that the part of the, there's a process to it, but there's also something intangible about it. The kind of my mentality when it comes to headshots is that it starts with rapport and connection with someone. And then I have this process, that I call expression coaching, which is, I always tell people.
What I do is not school picture day. Stand over here, say cheese, click, and then we're done. Because what does that tend to produce? Fake smiles. Forced, we all kind of remember those high school pictures that just were like, those aren't flattering of anybody. And so that's what people, that's what my clients were telling me their past headshot experience was like.
just school picture day, but for adults. And I was like, there's gotta be something better. And I was blessed to have some mentors to kind of start pointing me in the right direction. But essentially it's, you know, if you get in front of a camera and you're not an actor or a model, so you don't really know what to do in front of a camera. So, and that's my primary clientele are corporate professionals, not actors and models. So,
They get in front of my camera. They're maybe a bit nervous. They don't know what to do in front of a camera. And they'll tell me. They open up and they say, you know, 90 % of my clients tell me some version of I'm not photogenic or I'm not comfortable in front of the camera or I hate doing this. You know, all of the bad experiences come crashing in all at once. And I've just learned to say, don't worry about it. I got you.
because you may not be good at this, but I am good at this. It's kind of what I've become good at. And then it kind of goes into this expression coaching where I'm just teaching people these little tips about how to look confident even if you don't feel confident, which is huge. And you can take this and use it when you walk into a big meeting at your workplace and things like that. So it goes beyond just getting a great headshot, but...
So I'm teaching them these little things that they need to do about, you know, what makes a facial expression look confident or approachable or genuine. But then part of it is literally just me saying random things to get reactions out of people because, and this is something very interesting. We as human beings,
Unless somebody's out there listening and they have this superpower, but the rest of us don't. You can't consciously think of two different things at the same time. Your mind might bounce around a bit from one thing to another, but you can't consciously think about two different things at the same time. So if somebody is standing in front of a camera and they're thinking about how nervous they are, or like, I'm not sure what to do.
and then I tell them to do something that's so like, what? And then they realize it was a joke and they start laughing. What you get is pure authenticity because in that moment, they're no longer thinking about how nervous they are. They're just reacting to what I said. And so it's kind of a, you know, it's madness, but there's a method to the madness with that.
Nick Berry (12:11)
Mm-hmm.
Daniel Wakefield (12:20)
But the whole point of it is, I think with the development of AI and everybody doing business online and all of those related topics, people are just craving real human connection. And the AI may be great for coming up with new ideas or different things, but people I think already are sick of AI produce content.
of things that just seem plastic and not real. so now translate that to the facial expression that you're making in a headshot, which is going to go on LinkedIn. So that's your, in a sense, your digital handshake. That's your first impression. If that's just a fake forced smile, you're not doing yourself any favors. You're not connecting with anybody. But here's the thing.
If we can produce a headshot that looks like you're not smiling at a camera, but looks like you're smiling at a person that has just totally elevated your first impression. And it looks like they're smiling at a person because they are. They were smiling at me, right? It's not just a technical, yes, there's all the technical, the lighting, camera settings, all of those things.
Nick Berry (13:40)
I think that's the difference that I can see in your images.
Daniel Wakefield (13:49)
composition, all of that is very important. And without it, there would be a lot of the, you know, the lighting and stuff just would be off. Right. But if all of that's there, but then you just have somebody go in and click the button, then there's something terribly missing. And that's that authenticity that needs to be there so that when somebody total stranger visits your LinkedIn page,
they feel like there's a connection between you just by seeing your headshot.
Nick Berry (14:23)
Or if they see your picture on the cover of a book, they know like, have to go see this person speak. Yeah, I can, that's what it is. That's the difference with your, the headshots that I've seen of yours that, it's like they're there with you. They see you there,
Daniel Wakefield (14:26)
Yes.
Yes. Yes.
Nick Berry (14:42)
That's not the only story that you've got, there are a lot, I've heard a lot of comments about the effect that having these headshots done has had on people.
Daniel Wakefield (14:49)
Yeah, I got one that's more on the, and it's one of my favorite stories and it's actually, I got permission from her. This story is gonna be in my book
Nick Berry (14:50)
You got another one ready to go?
Daniel Wakefield (15:03)
I had this client come in just for one of my quick express sessions. So 30 minutes. It's more of a quick in and out thing. And she came in and you know, just kind of some small talk. You know, I said, how's your week going? And she said, actually not very good. So was like, man, I'm so sorry to hear that. You know, you know, I, know we're going to have a great session today. I know we're going to knock it out of the park. And so
She just kept telling me repeatedly, I need to look really confident in these headshots. Not just once, but several times she said that. So I'm like, okay, there's something here, but thankfully that's one of my favorite expressions to capture is this confidence. And so I was like, no problem. I love capturing that. And that helps me, can then...
kind of direct to you in that direction with the coaching. So got her in front of the camera, did my coaching, started coaching her through the whole process, getting a bunch of different shots. We shot in two different outfits. And then at the end of the session, we're reviewing all of them on my laptop. We're narrowing it down and we narrow it down to two images, one in each outfit, both of which she just looks like over the top.
confident like if you didn't know that she was having a bad week you would never tell that from the photos because she just looked like calm and peaceful and like you know kind of that little hint of approachability but just like confident like she's gonna go take over the world just amazing and we narrowed it down to the two and we got down to the two and she said those are the two that I want and she immediately burst into tears and I was like no what happened
And she said, I didn't want to tell you this before, but I got fired yesterday from my job. And by the way, she's also a Marine veteran. So, you know, not the kind of person that, you know, is like late and gets fired because they're late or lazy or anything like she is, she was, know, on the ball and kind of out of the blue, just got let go. And...
And it just was such a huge blow to her self-confidence. And she said, you got me looking so confident in these images. I feel like I can get back out there and just take on the world no matter what happens. And she took those images, she put them on LinkedIn. She got an amazing new job within a couple of weeks of that session.
And she's told me a couple of times that she credits those images as playing a role in her getting the job, which just, I'm so, you humble that that was the case. But I think kind of the, one of the takeaways that I've seen is that if you see yourself, you can, on the screen, looking super confident, it actually helps you feel more confident.
There's something about that psychologically, seeing yourself kind of in that, know, pun intended in the best light and with that really genuine and confident expression that it actually does something to you and it actually makes you feel more confident. And that was just like, it was almost a revelation for me of the power of what you can do with these images.
Nick Berry (18:45)
Yeah, I believe that. think it's been enlightening to me having the conversations with you and learning about your work. mean, I think whether we realize it or not, when you see a picture of yourself to a degree, it sticks with you like that's who I am. And so it just stands to reason, then you probably should try to be intentional about that. And these pictures that we choose to use of ourselves in different places are
I have more significance than we might've let on. It's like that part of it is not a commodity for sure. But there's more to what's going on with you than the magic of your headshots though, which I mean, obviously you're, you're very talented, but you haven't been doing this for that long. Right. And this isn't your original career path.
Daniel Wakefield (19:16)
Yeah. Yeah.
Nick Berry (19:35)
Well, tell your backstory quick and then we'll get into like the milestone that you just hit the book you just mentioned, like this trajectory that you're on
Daniel Wakefield (19:44)
Yeah, so backstory, I used to be a high school science teacher, so a little bit of a different career path there. You know, went to college from Canada originally, so went to college up there, got a degree in biology, a degree in education, and started teaching high school up there. And wasn't
planning on doing anything else for the rest of my life. mean, you there's definitely something fulfilling about teaching the next generation. The unfortunate thing is that it's very hard to make a good living doing that. And my wife wanted to at least while we have small children, she wanted to be a stay at home mom. And so that was, you know, it's kind of multifaceted, but there was
part of the impetus for like, how can I use this hobby that I had been developing of photography and start to, you know, just really, could I make a living out of this? Is that a, you know, viable career path? And I knew that I didn't want to be a wedding photographer. And, but I wasn't really sure how else to kind of break into the industry.
My, as a hobby, was just doing it, wildlife and nature photography. I've always, again, kind of that was the tie into biology and how I got into photography in the first place was I love wildlife.
But that doesn't, you know, unless you become super famous and people are willing to pay, you know, a ton of money for one of your prints, you know, that's kind of hard to make a living just shooting wildlife. So it really kind of forced me to think about, well, you know, are there other areas? And I was doing like people portraits on the side a bit just for, you know, side hustle, little cash on the side.
And really started to become fascinated by this topic of genuine human expression. And thing that really got me started thinking about that was my mom and taking pictures of my parents, you know.
would go home for the holidays, Dan, can you bring your camera and take some photos for us while you come? Sure, no problem. Well, my mom has a beautiful smile, but when you tell her to smile, it's the most fake smile in the world. And it's just like, mom, that's not what you look like. So trying to photograph her and trying to figure out ways to get great smiles out of her and also really realizing, you know,
Nick Berry (22:17)
Yeah.
Daniel Wakefield (22:31)
In that case, it wasn't for a business purpose. It was just for the purpose of memories. You you look back on these photos, you want to, you know, remember somebody as they were, which is them looking genuine, them looking authentic, not them trying to force something. And so that, that got me started thinking about the importance of genuine expression. And then also how to, well, how do we elicit that? How do we capture that? Things like that.
And yeah, so then I kind of met somebody that I had a mutual friend with who was doing headshots full time in Washington, DC and got connected with that guy. And he came, became a bit of a business mentor for me at the beginning of my business. And, and I jumped in with both feet and that was in January of 2021. So getting close to.
Getting close to four years ago.
Nick Berry (23:31)
And you just hit your revenue goal for this year and it is the 11th of October. still two months left in the year. the growth trajectory of the business as a whole has been steady and upward.
Right. And I mean, you went to six figures in your second year, right?
Daniel Wakefield (23:46)
It's... yeah.
Yeah,
from that point of launching into the market for 12 months, then yeah, we hit six figures. But that first month was $60 of revenue. And it was a
It was a wake up call of I can't just put together a website with a good portfolio and wait for people to find me. And I know there are photographers, there are small businesses that do that. They kind of build the website and it looks great and they tell all their family and friends and then they just sit back and wait and hope that somebody calls.
And I know I'm not the only one that did that. And
Yeah, it was that $60 month. That was a wake up call. You know, thankfully we had some we had some savings and some things so you know, we were fine but I was like, yeah, thankfully I woke up quickly and started to think I've got to go find people. But I didn't know how to do that. And I think it was maybe part way or three quarters of the way through that month.
Nick Berry (24:33)
Yeah.
Thankfully you woke up.
Daniel Wakefield (24:57)
one of my friends that's in commercial real estate said something about, you ever been to like a business luncheon or something like that, like a networking thing? And I was like, I have kind of heard of networking. I've never done it. You know, didn't really, wasn't really doing anything like that in my previous career, at least not in that way. And so I just said, I got to do whatever it takes. And that was kind of what led into the networking.
thing.
Nick Berry (25:28)
Yeah. And so, to kind of bring that full circle. So, first month, $60. Then at the end of 12 months, you'd hit six figures. Second year, multiple six figures. Third year, upwards, another 20%. And then this year, you've already exceeded your annual goal by the 11th of October.
And that's not just because of the wonderful talent that you have taking headshots. We've talked about your philosophy behind headshots. So talk about your, some of your business philosophy behind the trajectory of the business.
Daniel Wakefield (26:08)
So I think it was one of the things that I really started learning early on, especially once I got into networking. going to that first networking meeting, never done it before in my life, no idea what I was doing, just trying to be friendly and pass out business cards and everything. And this well-meaning friend of mine had said,
You know, it's not rocket science. just a photo shoot. So you should be going and like actually selling people, you know, at these meetings. And I just felt really like, that's just not me. Like I didn't feel, you know, to, to meet somebody and try to book them on the spot for my services just felt like really forced. And, you know, I appreciate that friend and he has given me some great advice, but that just didn't really feel like me. And so.
But I kept going to these networking things because I thought, well, I need to meet people, need to connect with people and really get to know people so that I become a known entity. Because how do you, you you try to start a business, how do you get clients when nobody knows you exist in your area? You know, and I think a lot of businesses serve local areas. So.
You know, if nobody in the business community knows that I exist and that's my target market. Like I said, I just can't wait around for them to, you know, Google because they had a need. So it was.
Nick Berry (27:41)
And they probably don't appreciate the benefit of having great headshots.
Daniel Wakefield (27:45)
Right, yeah, a lot of people don't. They haven't experienced it or they haven't learned about the benefits that other people have found. So that was part of it, was like, do I educate people on this? so, you know, I think that in terms of a principle, and again, this is not something that is new to business, but it was new to me, at least, as I was growing, was,
really the importance of building strong and personal relationships in business with other business owners and the value that that has for growing a business. And even if somebody, you know, doesn't use your services for whatever reason, it doesn't mean that you shouldn't, you know, pursue a relationship with them.
and so that, kind of became a core value of top tier headshots was that it's, it's all about genuine connection with people and then the different facets of that as it relates to different areas of marketing and sales and, client experience and all of those things. So
You know, if you are trying to grow a business, but you've not really put in the work to genuinely connect with people, then you're missing out at the very least, you're missing out on opportunity. And at the worst, you might be like floundering or, you know, your business might be dying because you don't have those connections. know Adam Grant talks about the difference between,
Nick Berry (29:32)
Yeah.
Daniel Wakefield (29:38)
transactional relationships and meaningful relationships. And essentially with a transactional relationship, somebody needs your service. They pay you for it. They come get the service done. You deliver the product and then you're done. And that's it. And then you have no interest in any sort of relationship. So really you're just in it for the money. That's all. With a meaningful relationship,
there may or may not be transactions present with that relationship, but guaranteed there's gonna be ongoing value. And so for me, part of it wasn't just I need more clients, part of it was I need to learn. Like I'm getting into this photography business and while the photography aspect, were aspects of that that I had already, you know,
learned and was doing very well with the business and the networking and the marketing and the sales and all of those different things. I didn't, I barely knew what I was doing. And so part of the benefit of networking was I get to surround myself with and learn from people who are crushing it. And, know, hopefully have some of that rub off on me or some of them were so gracious to pour into me and take me out for lunch.
You know, just allow me to pick their brain about different, you know, different topics related to business. And it made a huge impact on me. And so I think that, you know, the people who are like, I got to go network because I need more clients are missing out on a bigger picture that we need to have of the more of the overall kind of mindset as it relates to networking.
Nick Berry (31:15)
Mm-hmm.
Daniel Wakefield (31:34)
and just the importance of building those genuine connections with people. And I've had people that have still never, people in my network that I've built relationships with, they've still never used my services for whatever reason. And that's fine, but they've also sent me clients and I've also learned from them. And I've benefited from following them on LinkedIn and learning from the things that they're posting about.
It's not just about like, you know, if you don't come and use my services, you're dead to me type of thing, which, you know, for all intents and purposes, some business owners are, they have that mindset. Like if you're not.
Nick Berry (32:09)
you
Networking is purely a business development activity, nothing else.
Daniel Wakefield (32:19)
Yeah, that's it. If I don't get the sale, if you don't go to me, if you go to my competitor, then I want nothing to do with you. And that's a mistake, I believe. so networking and kind of this mindset of relationship building and building meaningful relationships, not transactional relationships was a huge paradigm shift for me.
Nick Berry (32:49)
It seems like you're, look at networking, it's not as a purely a business development activity. It's just a part of your, your development, In all facets. It's a thing that like nurtures you. Yep. And it's, that's part of like, you've kind of curated your support system to include a lot of connections that are, you know, like the people you surround yourself with, you're going to kind of.
Daniel Wakefield (33:00)
Yeah.
Yeah.
Nick Berry (33:17)
ascend or descend to their level. a lot of the people that you are connected to have helped you expedite your learning process, get you up to speed in a few different areas. And I think that's awesome. I think it's a great way to look at it. It just feels better too, right? It feels a lot better than the transactional.
Daniel Wakefield (33:31)
Yeah. Yeah, no, absolutely. Especially if that's kind of, you know, how you operate, which I think is a good way to operate in the rest of your life that, you know, relationships are good thing and that they shouldn't just be transactional, but, know, we should cultivate, you know, deeper, meaningful relationships. Just take that and apply it to business. And I think that one of the
things as well that business owners are missing out on is the opportunity for strategic partnerships and collaborations with other businesses
You know, when you take two different business owners that may have two, maybe they overlap somewhat, but maybe they have two different audiences and then you do a collaboration between those two brands, it opens the door for both audiences to see what's happening and to potentially drive a lot of hype, a lot of excitement around what's going on there. But even just from the...
perspective of, you know, maybe a lower level perspective of just getting referrals between businesses. I think there's a lot of opportunities. So when I go networking, I'm not just looking for new clients. I'm looking for potential new collaborators. And I think that is something that can, you know, in a good way, open a can of worms to
so many new and potential opportunities.
Nick Berry (35:12)
Have you had many of those projects? Like, that been behind some of your growth?
Daniel Wakefield (35:17)
Yes, I would say so. I think that, you know, I don't mind saying this publicly. I think that, you know, my partnership with the Daily Drip, if there's anybody listening here in South Florida, South Florida business women's professional community It's not a networking group. It's like a business growth development.
community. There's several different aspects to it, but just partnering with them has been very helpful in a multitude of ways. It has gotten me more clients. Yes. So that's obviously an immediate benefit, but the just, I think awareness of my business because of that. And then also
The learning that happens whenever I have a conversation with the co-founders, Nicole and Romy, is always just like this nuclear bomb of ideas and strategies and just all of these things that really have helped my business thinking and my marketing thinking to grow and develop. And then we've seen the results of that.
in just the growth of my business and then hopefully the growth of theirs as well. So that, mean, if you're out networking and you're just like, got to get a new client, I got to get that number, but then you're missing those opportunities or those possibilities for those potential opportunities, you're missing out on a lot.
Nick Berry (36:59)
You're leaving a lot out there. That's right. I agree. One of the things that I think that I've seen, that I think you do really well is how you positioned yourself with the, with the white glove service. I give me just kind of going back to breaking the whole commoditization frame around headshots. think you attribute it to a mindset shift around
don't discount, right? talk about the mindset and don't discount and how that your positioning and how all that relates.
Daniel Wakefield (37:30)
So part of that, that was that initial thinking about that was definitely influenced by my first business mentor, the headshot photographer in DC. And kind of his thought process around it was, you know, if you price yourself at a lower price point and then you discount that.
That's what the majority of photographers are doing. Their pricing is pretty low to begin with, and then it's a weekend special, it's a Christmas special, it's a Thanksgiving, whatever it may be, it's some discount. And essentially what you're training your audience to do is to wait until there's a discount. So there's no reason to go and pay the full price for their service.
If they do these discounts frequently enough, then, we'll just wait until he runs another discount and then we'll do that. But essentially, you're kind of tapping into a market in your business where people are generally looking for the best deal. And so it essentially becomes a race to the bottom in terms of pricing.
And it's basically whoever has the cheapest price and the best portfolio wins. And it's like, how low do you go before you're essentially working for free and just giving away your service? And when I was doing photography as a side hustle, that's essentially where I was at and I didn't really know any better.
Then transitioning into this business where my mentor was really trying to encourage me, like there's another market up here where people aren't price shopping. What they're looking for is quality and quality and experience and all of the things that go along with that. And there was a, there was a, you know, a mindset shift that had to happen.
where I was thinking who in the world is gonna pay this much for a headshot? And that real fear of what if I start this business and I do this and nobody books with me? What's gonna happen? And was kind of at a point where I needed to make this work. But I think one of the things that encouraged me was
My mentor was actually doing it. So it wasn't just talking about it, but he was actually doing it. And he was being transparent with me about the kind of revenue that he was seeing in his business. And even right down to how he broke down the pricing for that, for a session. And I was like, well, if he can do it there, why can't I do it here? You know, it's there. We've got a proof of concept. So why, why can't I.
you know, just apply that down here. and so that's what I started to do. And I was, I did start off lower than I'm at today, but it was still on the higher end of what someone might expect to pay for a headshot. And man, it was, tell you the, the fear associated with getting on a phone call with somebody and like, okay, now what's your price? You know, big swallow. Here it is. Yeah.
Nick Berry (41:04)
Are you sure you wanna know?
Daniel Wakefield (41:07)
And I tell you, again, something I write about in my book, the very first time, know, think it was in that first month of the business, website was live, we had made a Google business page, somebody got my number from somewhere, called me up and wanted to know how much it would be to get headshots done. And that was the worst sales conversation in the history of sales because it was so terrible.
And I was defensive about my price and I didn't know what to say. And I think in the book, I actually apologized to the guy because it was so bad. I was like, call me again. I can do better this time. But it was again that learning to recognize, okay, if I can not only create the quality that I can create, but then add on top of that, the experience.
Nick Berry (41:46)
Ha!
Daniel Wakefield (42:03)
And then what that's going to do for your personal brand, for your business and all of these things. That's that's valuable to people. And when I started really in my own brain connecting what I do with the potential revenue that somebody could earn because of my work, then I was like, well, then it makes sense.
Nick Berry (42:27)
Is that what it took for you to?
Daniel Wakefield (42:28)
I was a little bit of that. mean, was still like, there wasn't like an aha moment. It was kind of a bit more gradual than that. And part of it was just getting the reps in and having more sales calls and learning and taking one of my sales buddies out for lunch and just being like, how do I talk to a human being on the phone? What am I doing here?
Nick Berry (42:40)
Thank
Daniel Wakefield (42:50)
and then just kind of the learning and the practicing, but then also the growing realization of the value that this brings to the table. and so there, there, but there was that mindset shift, where, know, now I can get on the phone with somebody and I can talk through, their needs, how I can be a solution, what the pricing is going to be for a session like this.
Nick Berry (43:03)
Mm-hmm.
Daniel Wakefield (43:14)
and I'm excited about it. I'm excited to tell somebody because I know the value is there to back it up. It's not a, here's two guys and here's one guy charging X and here's another guy charging 10X, but their product and services are exactly the same. I'm doing all of this on top of what the typical photographer is doing when it comes to headshots.
but then also just at the same time, recognizing the value that it has. Like if you come into headshots and even if you can take the best headshot in the world, but if you don't understand business and you don't understand the value that it has, you yourself are going to be afraid to charge for that because you don't understand that value and you think it's a commodity and you just think like, well, in my past side hustle, people paid me.
you know, 150 bucks for 30 images or whatever, something like that, then, you know, there's, you're going to be like limiting yourself in terms of, you know, understanding the value that these have for business professionals.
Nick Berry (44:29)
the feeling of being able to state your prices without the anxiety, with the conviction and with the confidence and a belief, like it's every bit as big of a shift and a powerful, as powerful of a shift as the one that we talked about for like for your clients and for me realizing like, shit, this, mean,
this image of my head changes the way that I'm looking at myself. And I didn't even realize I was looking at myself in any kind of way before. there's a story that you told me about someone came to you comparing your pricing to some quotes that they'd gotten and they bought from you.
Daniel Wakefield (44:57)
Yeah. Yeah.
Nick Berry (45:12)
And your price is like, if I remember, it was like five or six times what the competitors were.
Daniel Wakefield (45:18)
Yeah, was maybe the next highest quote I was probably, when all was said and done, probably 4X what they were.
Nick Berry (45:30)
Yeah. getting to a place where you can go into that conversation and your confidence is not shaken before, during or after by any of what happens there. And then to be able to close those deals successfully. That's not an accident, I'm sure it was that mindset.
Daniel Wakefield (45:43)
Yeah. Yeah. I mean, it's been, I tell you, man, it's been a journey for sure because I did not have any sales training or anything before this. But to me, it's just kind of come down to, you know, how, how am I going to help somebody and you know, what problems are they facing and am I the best solution for their problem? And so, you know, when I got on this call with this specific
a company and they told me the price of, you know, the other, well, let me back up a second, you know, cause I was doing some discovery and just finding out, know, what are your goals for these images? You know, that's if there's photographers listening to this, do you ask your potential clients? What are their goals for this photo shoot? Or are you just treating the headshots like a commodity? Like, yep, you need this. I can give this.
this price done, that's it. May or may not get the job. But I was asking this potential client at the time, you know, what are your goals for this image? Who are your potential clients? What kind of an impression are you trying to make with these images, you know, on your website or your social media, things like that? And they told me their ideal clients are high net worth individuals and
they really liked the fact that one of the things that I want to help my clients with is to help them be ready for any opportunity that comes their way. If you need to look like the cover of Forbes magazine, I'm going to help you do that. And they liked that. They liked that, that presentation of themselves to their potential clients as themselves, a high end service provider. So when they told me,
the quotes that they had gotten from the other photographers, I was maybe a little bit nervous, like, wow, my price is gonna be way above this. I don't know if I'll ever get this job. But at the same time, I also felt kind of worried that they would go and spend money that would end up being a waste because from my experience and from what my clients have told me,
the level of service and quality that you get at the price points they told me from the other quotes tends to look more like school picture day and not like this kind of high end Forbes magazine kind of a feel to it. And so I just, told them that and I said, listen, if you just need this kind of simple, basic headshot for your website, then I may not be your guy, you know, but.
But what you just told me before was you've got high end clientele. You want to look high end. You want to appeal to that crowd. I know that I can help you look like that. And, I said, you don't have to go with me, but if you go with something that's quoted that low, I'm worried that you're not going to be able to achieve your goals with this. And there, there ended up being a couple of conversations back and forth.
but I ended up closing them at probably about 3x what their the next highest quote was. And by the end, they ended up adding on more images, more stuff that I did for them. And actually they're continuing to work with me in an ongoing way with all of their new hires. So there's ongoing revenue from that. But on that first day of working together,
because of the additional things, they probably ended up paying four to five X what the next highest quote was. But they saw the value in what I was bringing to the table. So.
Nick Berry (49:35)
And that just would not, could not have unfolded like that. If you would have gone into that conversation with them, about the quotes and instead of being anchored on your price, you're more anchored on theirs and the competitions, right?
Daniel Wakefield (49:47)
Yeah, yeah. And there's definitely some people, some potential clients that I lose out on because my pricing is is up there. But those are usually people that they their goals are just we just need a simple headshot. We just need and really any photographer can do that. But that's not what what I'm offering to people. So if somebody like connects with, my offer and like
Usually if somebody connects with my offer, they're not going anywhere else. Like this is the guy. And that's what I want. want when I have somebody that I connect with that's an ideal client, that my portfolio is at such a level and the connection that I make with them and the problem solving that I do for them, that it just becomes a no brainer despite the price point.
Nick Berry (50:40)
That's what gets people to fly across the country for a half a day to spend a few thousand dollars to get a handful of headshots and leave so happy that they're going to fly back soon with their spouse to put them through the same session.
Daniel Wakefield (50:58)
Yep, yep. And that's like people flying in or people flying me to other parts of the country to work with their executive teams. Like that's not something I was expecting when I started my business. I had heard about other photographers being like that and I was like, well, you probably just have to be famous or something for that to happen to you. And that's kind of like the bleed over into the power of LinkedIn
as a business development tool to have somebody see my work on LinkedIn.
and immediately think that's what I want. And then, you know, when I've had clients fly over from California to work with me, there's headshot photographers in California. Like you could just Google it, but they saw a headshot of somebody they were connected to and they loved it and they were immediately sold. And when I picked up the phone to talk with them, they, you know, I told them the price. It was like, yeah, yeah, that's great. Well, how soon can I get on your calendar?
And that's just like the greatest sales feeling in the world because you're not pushing anything. You're just like, this is what it's going to cost. And they're like, great. Yeah. When can this happen?
Nick Berry (52:09)
talk about business coaching. you've gotten a lot of attention, business is growing.
you're not just a skilled photographer. your business acumen is getting some notoriety. And, similar to the path that I went on, a while back, then people are like, tell me how to do it and I'll pay you. And then you find yourself in another line of business. but you've written a book, you're sharing, this is what, what I've done. This is what other people can do too.
Daniel Wakefield (52:29)
Yeah.
Nick Berry (52:36)
so tell me what's the direction with the business coaching.
Daniel Wakefield (52:40)
So I guess the genesis of that was, you know, when I started my business, I had no aspirations. I literally just wanted to put food on the table for my family. Like, if I can make a good income doing this, then that's great. And I'm so thankful that that's happening, obviously. So maybe it would think it was about two years into the business and was having some great success.
And I started to have other photographers reach out and just like you said, they were reaching out and saying, hey, can I pay you to hop on a call and pick your brain about business stuff? And my first response was like, sure. I still felt like I was figuring it out. But these people, were...
five, 10 steps behind me, but saw the success that I was having and they wanted to do that. So, but then it just kept happening again and again and again. And then some of those first kind of students, they, maybe a month or so after our first call would call back or just like say, can I pay you for another call? Like what you told me is working and we're making more money. We're getting more clients. You know, can we...
hop on another call and talk about other stuff, other business stuff. So that's kind of where it started. And then maybe about a year, little over a year ago, I started talking with my wife, Bethany, and just saying, should we be doing something more strategic? You know, used to be a high school teacher, so I do enjoy the teaching element of things and the,
quote unquote, unofficial students that I started to have. They were actually, you know, taking what I told them and going out and using it. And it was working and, you know, making them more money, which was awesome. And I had always loved writing, high school, college, any opportunity that I had to write, typically loved it. And so I thought, when should I write a book?
about this and just kind of tell the story of how my business got started and then bring out all of these practical strategies that I was using and continue to use in the growth of my business. And then, you know, we've got that book as an asset and maybe that will lead to more coaching opportunities, more speaking opportunities, things like that. So that's what we decided to do. So.
I started writing the book actually about a year ago and finished the first draft back in March of this year and then started working with a publisher in July and we're still in the midst of the editing process, but the book is scheduled to go to print early in 2025.
Nick Berry (55:43)
congratulations. And you've done a workshop, you've got several more workshops scheduled and you're doing workshops with a pretty prominent figure in the photography business, right?
Daniel Wakefield (55:44)
Thank you.
Yes. Yep.
Yeah, so one of kind of the part of the story of the business is that mentor in DC said, hey, if you want to do headshots, you need to go join this group called Headshot Crew, where this run by and started by this guy named Peter Hurley, who's widely considered to be the best in the world when it comes to headshots. And he pioneered this style of lighting and really
puts a lot of emphasis on getting great expression out of people. that was kind of my interest in like getting a good expression out of my mom and other people. Kind of when I went to start working with Peter, it was like, he's actually teaching about this. So kind of just fit really nicely. So I got into his crew, started learning the headshots.
And less than a year, he made me one of his associates, which was a huge honor and accomplishment. And then just this year actually elevated me to the status of mentor in his headshot crew as well. And so we were talking and doing just having some conversations about different stuff. And I pitched him on the idea of when he does.
his headshot workshop, which he teaches around the country. I said, what if some of the times where you do those, we add on another day and I teach business, like the photography business side of things. And he loved the idea. And so we did the first one back in June in my workshop and it sold out. We had people fly in from four different states, including, you know, local photographers here and.
He loved it so much. He was like, let's figure out how to keep doing this. So the next one is actually this month and just a couple of weeks, I'm flying up to New York City to teach the workshop in his studio in NYC. So definitely excited about that.
Nick Berry (58:00)
Is there availability still for that?
Daniel Wakefield (58:03)
There's some, yeah, we're like, got a couple weeks left and I think we're just a little bit over halfway sold out, so there's a little room.
and just kind of to clarify as well, this workshop is not limited to photographers.
I think could be beneficial to any creative entrepreneur.
Nick Berry (58:22)
Okay. Daniel, this is fantastic, man. Congratulations. I I
Daniel Wakefield (58:26)
Thank you.
Nick Berry is an accomplished entrepreneur and CEO, whose track record includes founding and leading numerous companies since 2002.
He is also a mentor and coach to other entrepreneurs and business owners who are looking for a trusted (and proven) advisor.
Among peers, colleagues, staff, and clients, Nick has been referred to as both 'The Business Guy' as well as 'The Anti-Guru', due to his pragmatic approach and principled leadership.
He shares his insights and lessons learned, along with those of his expert guests,
on his podcast, 'The Business Owner's Journey'.
