Peter: Today I'm joined by Haile Wilson, an incredible photographer based in Missouri. Haile, give us a quick intro.

Haile: I've been shooting photography for about six years and weddings full-time for about four. It's always been my passion, and doing this has been the best decision I've ever made.

Peter: What stood out to me when we first connected was how unorthodox your style is. How did you develop it?

Haile: It started with portraits. When you first pick up a camera, you ask friends to let you photograph them, and your creative mind starts going to different places. What if I add a color? What if I light it this way? That drive to create something I hadn't seen anyone else do shaped my style.

Peter: People say the wedding industry is saturated, but a unique style really sets you apart. We built that into your marketing, and it's a big factor in your results.

Haile: I was using sites like Thumbtack and WeddingWire to get leads, and they weren't getting the results I wanted. All I'd ever done on Instagram was boost posts. I'm more on the creative side, and I didn't have the business and marketing side figured out.

Peter: Why not just keep using those sites?

Haile: There's a ceiling with them. I didn't want a cap. I wanted to get to the point where I'm turning down leads, not scraping them together.

Haile: My Instagram has grown steadily since we started, with quality followers who didn't know who I was before and now want to hire me. The community has also been huge. Everyone asks questions, everyone answers them, and you know you're not going through this alone. Portrait clients have even found me through the wedding ads, so it's cross-pollinating, and every side of my business has grown.

Peter: You're averaging 80 to 100 new Instagram followers a month. These aren't random followers. They're people who are engaged, planning a wedding, and looking for vendors. How many weddings have you booked since we started?

Haile: Around 26 weddings across 2024, 2025, and 2026.

Peter: Twenty-six weddings in four months. That's seriously epic.

Haile: St. Louis isn't an expensive market like Chicago or LA. I was priced about average for my area, and you told me I should raise my prices based on the quality of my work. I was super scared to, but I did it, and I'm now making almost double or triple what I used to per wedding. It's been the best season I've ever had.

Peter: We've also been running ads outside your local market, and you're booking in Chicago. How do you handle couples who'd rather hire someone local?

Haile: Chicago is only about four hours away, so I position myself as a Midwest photographer. When they ask, I say, "I travel. I'm not just a St. Louis photographer. I'll be anywhere you need me to be to capture your vows and your first kiss."

I'm upfront about the travel fee when they ask, but I don't lead with it. Nobody has balked, because I can drive there, and my prices are St. Louis prices. Chicago couples look at me like I'm a god, because photographers there are charging $10K.

Peter: It hasn't been easy for you. First there were bank issues that delayed your ads for a couple of weeks. Then, about two months ago, you got hit by a scam that was a huge financial blow. A lot of people would have hung it up, but you didn't.

Haile: When you see your bank account go to zero, it's crushing in the moment. But you take some time, breathe, and tell yourself, "If I'm confident in myself, I should be able to come back from this." Money comes and goes. When you're scrambling at 7 a.m. trying to figure everything out, it's humbling, but it's also motivating, because it can't get worse than this. I chose to stay positive and keep moving forward, because dwelling on it won't make it any better.

Peter: Practically, what do you do in that moment?

Haile: I do what I was already doing, but at a much higher level. If I used to follow up with a lead once or twice, now I'm sending another message. I had to secure those leads, because a deposit was literally going to save me. I didn't leave my computer until I'd secured two or three leads.

Peter: It's humbling to realize that most of us could work that hard if we needed to, yet we choose not to. If you need to grow your business, use that sense of urgency. Massive action works.

Haile: I have 21 weddings booked for 2025 so far, which is about $87,000 to $90,000 already. I'd love to get to 50 weddings this year.

Peter: If you book four or five weddings a month through July, you're there. Fifty weddings would put you at $150K, maybe closer to $200K. You did $75K last year.

Haile: I'm very confident. I have two discovery calls right after this. Bookings have been way more consistent than ever. My website views have skyrocketed, because people follow me on Instagram and then go to my website. They have so many touchpoints that they feel like they have to book.

Peter: People want more leads from their website, but a website doesn't exist in a vacuum. It's like a billboard on a highway with no traffic. We drive people to your Instagram, they visit your website and inquire, and then you get them on the phone.

Haile: I recently brought on a videographer, so we're now booking photo and video. When we started, it was photo only. Once I hit my number for my own weddings, around 45, I want to hire another photographer so we can cover more weddings on the same day. I'm only 28, so I can shoot a lot of weddings, but once popular dates start piling up, I'll need someone who delivers the same quality my clients expect. I'd also love to travel to other destinations.

Haile: First, verify every client and make sure they are who they say they are. Just because someone wants to give you money doesn't mean they have your best interests at heart. I learned that the hard way.

Second, ask questions. I learned so much by speaking up in the meetings. If I'd been a wallflower, I wouldn't have learned nearly as much.

Third, be persistent. Couples want someone who will make the effort to talk to them. Maybe they missed your text. Once I started double and triple texting, they'd think, "Oh, he's serious. Let's start this conversation up again."

Peter: Everybody wants the $10,000 clients, but those people have options. You don't find those clients. You earn them.

Haile: I ran track in college, which is an individual sport. It's just you in the blocks, and nobody is coming to save you. You have to put in all your effort.

Peter: What's been the most transformational part of working together?

Haile: The community, and all the information you share. Before, I had a small view of what was possible. Once I went to the meetings and talked to everybody, I realized this could go so much bigger.

Peter: Sometimes it takes someone else seeing it in you before you can see it in yourself. What would you say to someone on the fence about joining us?

Haile: Always invest in yourself. If you can get the money together, do it. This is a huge investment in yourself, for the information, the community, and the growth. As long as you're willing to put in the work, you will see growth. I guarantee it.