Peter: All right, what's going on, everyone? Peter here, and I'm back today with another incredible client. We're joined by Jordan Gresham of JKG Photography. Jordan has an awesome story, and he's an incredible photographer. We're going to get into all of that. But Jordan, before we do, kick us off with a little intro. How long have you been in the industry?

Jordan: My name is Jordan, and I'm based in Denver, Colorado. I've been in the industry for about four to five years now. Before I got into weddings, I started as a hobbyist, finding joy in photography like most people do. Like a lot of people, I was hustling and shooting everything from family photos to engagement photos, really just trying to find my niche. It wasn't until 2019 that I was asked to shoot my first wedding. After that, I did some second shooting, and then I launched my business in 2020, the best year to start.

Honestly, I saw it as a learning experience, because I was matched with a mentor in the industry who was at a much higher tier than me. She was the one who taught me how to approach and run a business. She would send me referrals, brides she wasn't a good fit for, and I would end up booking them. By 2021, I had a full stack of weddings, mostly from referrals. That's how I got most of my business when I was in St. Louis.

Peter: So you relocated to Denver in 2022, when COVID was sort of dying off. What was going on in the business when you moved?

Jordan: Business was really slow. I was still going back to St. Louis for weddings, but I only had maybe four or five booked there, because I knew I was moving and didn't want to take on too much. I was anxious and excited to get into the Colorado market, but I really didn't know how. I'd met a few wedding friends, like John Mueller, who's been on here, but beyond that, I was trying to figure out how to get in front of people. I thought posting on Instagram and using hashtags could work, but I slowly learned there's more to it than posting all the time and relying on hashtags.

Peter: I usually say Instagram isn't a great lead generation tool. It's a great lead nurture tool. When people use it for lead generation, they tend to run into the same problem: they get frustrated because they're posting all the time without seeing results. Wedding photography is such a niche service that you're unlikely to attract the exact type of person you want to work with through organic content. Instagram is really a pay-to-play platform.

Jordan: That's exactly what I experienced. Every so often a bride would find me through a hashtag, but it wasn't consistent, maybe once every few months. That wasn't getting me anywhere.

Peter: Why did you finally decide to pull the trigger and sign up? You knew John, which is awesome, but you were on the fence. I think you and I talked about a year earlier, and it just wasn't the right time. What was going on when you decided, "I have to do this now"?

Jordan: In 2023, I invested in several workshops and courses, and I wasn't seeing the ROI. I'd go to a workshop geared toward the luxury space that taught you how to enter the luxury market and get luxury clients. It was a lot of good information, but I had no one to apply it to, because I wasn't getting the leads I needed. After my last workshop, which I paid for in January 2024, I left with a sour taste in my mouth. I felt like I was throwing money away and still not getting enough leads to book jobs.

John had told me a lot about the program and said it's a place where you get a lot of leads. In sales, that's how you find success. You need a healthy pipeline, a large number of leads to talk to, because your average close rate might be 30% or even less. I was getting one or two leads a month, and I wasn't closing those. That wasn't enough to build a good talk track or work out the kinks through trial and error, the way you do in a normal sales cycle. So I decided to give this a shot. If it didn't work, photography would always be part of me, but I'd stop investing in courses and workshops, maybe stop marketing altogether, keep my website up, and pivot to something else.

Peter: You also have an interesting background. When we started working together, you were working a sales job for a tech company, and I believe you still are.

Jordan: I have seven years of sales experience, and I'm currently an account executive. My job is to take a deal through the full sales process, from discovery to close, and then make sure my client is happy. It lines up with my photography business, but honestly, I wasn't thinking of it that way until I joined your program.

Peter: And you're selling high-ticket deals in that job, right?

Jordan: I'm on the senior account executive team, so I sell to everything from mid-market companies up to enterprise level.

Peter: So these could be $50,000 deals, give or take?

Jordan: Way more than that. My threshold starts at a million and goes up to $50 million, sometimes higher.

Peter: Let's cut to the chase. What have the results been over the last few months?

Jordan: I pulled the trigger, and the timing was a little weird because I was about to go on vacation. After I came back, the beginning was some trial and error. I was finding my voice and figuring out how to make the system work for me. By the end of month one and into month two, I found my mojo and thought, "Okay, I can do this now." The first month, I booked four weddings. The next month it was four, and the month after that it was four again. I thought, "Wow, this is consistent now."

I'm talking to a lot of brides, and I can tweak my messaging if something isn't working. Going back to sales, that's the biggest thing. You can be given a script or the tools, but in sales you constantly have to tweak and figure out what works, and what works today won't necessarily keep working down the road. You have to keep refining. That's been really powerful, because I keep getting better now that I'm talking to so many brides and have a good system in place.

Peter: So when we started, how many weddings did you have booked for 2025?

Jordan: I don't think I had any.

Peter: And now you have 12?

Jordan: Yes.

Jordan: Some brides aren't ready to book today. Maybe they got engaged four days ago and they're suddenly in front of me. That's sales too. You nurture them by sending more information, like a view book or something that tells them more about me. Going back to my sales roots, we take advantage of the seasons. Fall is huge for engagement photos right now, so I'll say, "It doesn't sound like you're quite ready yet, but do you want to get engagement photos this fall, or wait an entire year?" And they say, "Actually, yes, I do want photos now." So asking a few questions creates another source of income, which may eventually lead to a full wedding booking.

Peter: That's massive. People listening, take note, especially clients who are actively generating leads. Use what's happening right now to get clients. There's always a reason for people to act now. Think about all the holiday promotions car companies run, or how Apple leverages back-to-school. If you ask yourself what advantage your couple gets from booking now, you can really capitalize on that.

Peter: For the photographer who's getting leads but struggling because those couples don't always have a date, a venue, or a budget figured out, how do you handle that?

Jordan: Build a relationship with them. While they're finding a venue and a date, you can be a good resource. You can create resources to send them, like, "I know this venue. I've shot there. If you're touring it, here's a gallery you can look through." If you keep building those relationships, they'll think of you when they're finally ready to buy. The same thing happens in my sales career. I had a business that wasn't a good fit last year, and suddenly I got an email saying, "We're ready to move forward." I'd done all the work a year earlier, and now they were finally ready. So put in the work now, build the relationship, and follow up.

Peter: How do you do that tactically? Do you manage leads in a CRM, set reminders, schedule time for it?

Jordan: A CRM for sure. I keep going back through my CRM for brides who haven't responded in a few days. For brides who told me they're getting married in 2026, I keep a separate list, and I follow up every couple of weeks to see where they're at, whether they want engagement photos or just need more support and advice. I want to be an advocate for them and help however I can.

Peter: What do you say to the creative who says, "I don't want to sell. I just don't like sales"?

Jordan: Sales is everywhere in your life, whether you like it or not. At the end of the day, we're business owners, and we need to generate income to survive. But something I learned in my sales career is to think of yourself as a consultant, because we really are. Your job is to educate the prospect and see whether it's a good fit. Listen to what they're looking for and what their needs are. All we're doing is trying to solve a problem, whether that's photo or video for their wedding or whatever you're selling.

Then go deeper so you can pick up on the important details during the call. The biggest part is listening. When a bride says, "I don't want to feel stressed out," or "I have a big family," your job is to say, "Okay, my job is to make sure your day is stress-free, and here's how I do that." You're not doing a hard sell of "Here are my packages, here are my services." Just listen to them, stop talking, and figure out whether you're a good fit. Throughout this program, I've told several brides, "I don't think we'd be a good fit, but I still want to help you in some way."

Peter: When you honestly take the approach of trying to find a fit rather than trying to close someone or get them to do something, it takes so much pressure off. It's a skill you have to practice, which you might not expect, but that's what I've seen. And when you don't pitch everyone or assume you're the right fit for everyone, you're in integrity. So when you do make an offer, it's genuine, and your words carry more weight because you don't say them to everyone. The active listening piece is massive too. Everyone has this cartoonish image of sales in their mind, when really it's about relationships and listening.

Jordan: And if you can help someone, you just say, "I think I can help you." People see the value in you, and that makes it easier to get them to book. Yesterday, for example, I talked to a bride from the program, and we had a really good conversation. When it came to budget, I was a little over what she'd planned, but she said, "You know what? I think we can stretch to it." We have a follow-up call next week, and I feel really good that she'll choose me as her photographer.

Jordan: I'll be transparent: I was the artist who thinks, "If I build it, they will come," but that's because so many people were telling me that. They'd say, "Your work is so beautiful. How are you not getting leads? You should be charging more." I fell for all of it. I thought, "You're right. I have a great website and a great portfolio. I'm worth it." But then it was crickets.

Your program helped me see that I need to run a business. I know I'm a good artist, but if I want to make a living from this, I need to follow some simple practices, like following up, sending people resources, or posting helpful information on social media and pointing people to it. For example, "I just posted something educational on Instagram, go check it out," or "I have a blog post on the top five venues, here it is." I wasn't doing any of that. I was stuck in a world where everyone gives you fluff: "You're worth it, charge more." Now I realize I have to put in the effort. I can't just sit here and expect people to come to me.

Peter: Where do you think that mindset comes from? "You're worth it, raise your prices, you should be charging three times as much," when you're not even booking at your current price?

Jordan: I still go to networking events, and I heard it at the last one. Someone told a planner, "Bookings are slow. Should I change my pricing?" And the planner said, "I think you're worth it. Stick to your pricing. Go for it, girl." At the end of the day, we have to put food on the table, and if we want a good life where we're not thinking about work all the time, we have to make money somehow. I think it's an industry thing where everyone repeats the same advice, and it's a loop we all need to get out of.

Now that I've been booking weddings at a certain price point, I'm testing whether I can raise it by 10%. If it doesn't work, I can go back. That approach has really helped me, instead of jumping to a big number.

Peter: "You're worth it" is a nice sentiment, and of course you're intrinsically worth it as a human being. But there's another variable, which is the market, and people in our space don't think about it. Imagine Apple saying, "We sell iPhones for $1,000, but we're worth it, so we're charging $10,000." The market might say, "We don't want to pay that," and suddenly the $1,000 Samsung looks pretty good. If you're charging $6,000 to $10,000 and Susie down the street is 24, grateful to shoot anything, really good at what she does, and charging $4,000, the market is going to weigh the two. You can say, "I don't care, I'm worth it," but that's like being mad at the rain. You're still going to get wet.

That doesn't mean you can't charge those prices. I want everyone to hear that. It just means you have to consider all the variables, including the market itself. And I agree with being strategic about price increases. If you're closing one out of three consultations, does that conversion rate hold after a 10% increase? Be scientific about it instead of doing what sounds good.

Peter: So what's next for you? Are you going to quit your job?

Jordan: It's definitely coming. I want to book more, of course. Right now, I'm finally getting some support and hiring a virtual assistant, because so many leads are coming through and I'm still working my sales job, so it's been a lot to balance. That extra support will give me some time back. I feel confident that within the next three months, I'll be saying goodbye to my sales career and doing this full throttle.

Peter: That's the dream for so many photographers and videographers I talk to. And we haven't even touched on the fact that you've done this while working a full-time job.

Jordan: Yes, and then some. There have been lots of long nights. Sometimes you have to put in the work if you're really hungry and want to take the next step in your life. In the beginning, I was looking for shortcuts. I didn't want to be doing all this. Now my mindset is, "This is my goal, and to reach it, I have to make some sacrifices, but it won't be forever." You might be in a season of grinding for four or six months, and you'll be a little more tired. Is that worth it to be your own boss for the rest of your life? Having that light at the end of the tunnel is what helps me push through.

Peter: What hours are you working at your job right now?

Jordan: Typically 7:30 to 4:30, but some days are longer.

Peter: So how do you fit in messaging brides?

Jordan: I keep my personal laptop open right next to me and message throughout the day. Then I do consults in the evenings. I tell couples, "I'm free in the evenings. Let's talk on a call."

Peter: What would you say has been the most transformative thing since working with us?

Jordan: Being able to talk to so many brides, and being able to keep learning through trial and error in an iterative process.

Peter: Now, say someone watching is on the fence. They've been watching these interviews for a while and they're thinking about doing this, but they've spent money on other things before. What would you say to them?

Jordan: Just do it. But also figure out what you can control. A lot of people have had hardships because of the presidential election or the economy, but ask yourself, "What can I do today? What can I control today?" This program showed me that getting in front of people through marketing is something I can control. Everyone is still on Instagram and Facebook. So figure out what you can control and what you can do to get to the next step toward your goal.

My last piece of advice is not to fall into the negative thought loop we all go through. There's a new idea going around the wedding industry that fewer people are getting married, and that's a big concern for people. But it doesn't feel that way to me, because I'm getting lead after lead after lead.