Peter: Today I'm joined by Kelsey Sheehan of Kelsey Sheehan Photography. Kelsey has grown a lot over the last year, and I'm excited to dig into her story. Kelsey, give us a quick intro.

Kelsey: I started in 2019, right before the COVID lockdown. My son was born within the year before that, and I felt kind of lost about what I wanted to do. My husband asked me, "What's your passion? What do you really want to do?" I said I hadn't had my camera in my hand in a couple of years, and I'd love to start doing photography again. He said, "If it doesn't take off, we'll redirect, but go for it." So I went in guns blazing. I didn't have the chance to drag my feet. I had to give it 110%.

Peter: What was business like when you were getting started?

Kelsey: It was rough. There were a lot of crickets. I started as a family photographer because I thought that would be easier to navigate as a new mom. I was definitely undercutting myself drastically, because I just wanted the experience and to figure out what people wanted. I was also still teaching myself to shoot in manual.

Peter: When did you shift into weddings?

Kelsey: During the COVID lockdown, actually. A lot of friends, old high school friends, acquaintances and distant relatives were doing quick elopements at the church or the town hall, and they'd ask, "Can you just take a couple of quick pictures for an hour?" I said yes, and from there I started getting second-shooting gigs. Now I'm all in.

Peter: We first connected in fall 2023. Where was your business then?

Kelsey: Struggling. I wasn't really booking weddings. I think I had about four weddings of my own in total. I had a lot of second-shooting gigs keeping me semi-busy, but I was very in my own head. I couldn't figure out where to get clients. When I did get leads, they would enter my inquiry form and I'd never hear from them. I couldn't even get a conversation going. I knew there was some sort of disconnect, so I dove in headfirst and spent more money than I was making on education, trying to figure out where the leak in my bucket was.

Peter: A lot of photographers tell me they're slow, and when I ask how many inquiries they get, they say two a month. Where were your leads coming from?

Kelsey: Mostly Facebook groups and some vendor referrals, like DJ friends who sent couples my way.

Peter: So you signed up with us. What happened next?

Kelsey: It took a couple of months to get traction. I had to get used to all the inquiries coming in and the follow-up process. Then at the beginning of this year, within the first week, I booked three or four weddings. Since then it's kept going up. I'm at 11 weddings booked for next year and seven or eight for this year.

Peter: So 18 or 19 weddings booked in about six months. What was the struggle at first?

Kelsey: Going from stranger to couple. A lot of them hadn't seen my portfolio, and I was stumbling over my words on calls because I was super nervous. It was a mix of everything at the same time.

Peter: Was there a turning point when things really clicked?

Kelsey: I think it was around the middle of April. February and March were a really big lull. I was throwing everything at it. Leads were coming in, but nobody would respond, or they'd blow me off on calls. Then, around mid-April, leads started responding. Somebody would come out of the woodwork from months before and say, "I'm so sorry, stuff happened." From there, things kept going up.

Peter: Wasn't April your first big month?

Kelsey: Let me look. Yes, it was $19,600.

Peter: As long as you keep following the process, the wins come. You can't control outcomes. All you can control is that you do the process.

Peter: You didn't have much sales experience when we started, right?

Kelsey: Right. Most of my inquiries went from email straight to booking, and the engagement session was often the first time I saw the couple. I was just starting to do consultations before we worked together, so I had a bit of a script. The discovery calls were what I stumbled over most at first. Now I don't mind them. There have been a handful of couples I've weeded out in a 10-minute phone call, instead of spending an hour on a Zoom consultation.

Peter: Do couples book on the consultation?

Kelsey: I've had one. A lot of my couples say, "We're still locking down the venue, but we'll come right back," and they come back within a week or two. I ask when they think they'll know, then follow up a few days after.

Peter: Do you show them the price on the call?

Kelsey: I do custom proposals. I show them my three base collections and walk them through all of them. Then I suggest the one that I think fits their day and timeline best based on our conversation. From there, we can add extra time or other things to fit their day specifically. I don't think one size fits all.

Peter: Where are you right now, year to date?

Kelsey: About $73,000.

Peter: At the beginning of the year, I asked your goal, and you said $60K. I said mine for you was $100K. It's June 21st, and you're at $73,000. Last year you did $26,000. What would you say to someone where you were a year ago?

Kelsey: Don't give up. If it's something you really want, the dream isn't going to chase you. You have to chase the dream. Last year I threw everything into my business and stressed myself out to the max, but I'm seeing a total change in the business because of all the hard work in the background that people might not see. If it's a passion you really want, you have to fight for it.

Peter: What motivates you?

Kelsey: My son, honestly. He has one of my old cameras, and he's always saying, "I want to work with you, Mama." I want him to be able to say, "My mom chased a dream," and to know you don't have to take the normal nine-to-five job. You can go chase whatever dream it is. I want him to see somebody actually do it. It doesn't have to be photography. If he wants to be a professional baseball player, go for it.

Peter: Kids might not do everything you say, but they'll repeat the behavior they see from you. If your son sees you do this, you've opened that door for him.

Peter: A lot of photographers who've been shooting for 10 or 20 years tell me their calendar isn't full for next year. That's not your problem. What do you attribute that to?

Kelsey: I'm not 100% sure, but based on feedback from couples, a lot of them say that talking with me, and my brand as a whole, is a breath of fresh air compared to what they see scrolling social media. Sometimes on consultations, I'll ask a question based on their previous answer to dig a little deeper, and they'll say, "Wow, nobody's ever asked us that." Usually it's straight to the details. I try to connect with them on a more personal level.

Peter: People who struggle to book think they're selling packages, hours and albums. What they're really selling is the meaning the couple puts on the photos. How many consultations are you doing a month?

Kelsey: A couple a week. I had three this week, so about 10 to 15 a month.

Peter: How do you manage building your business and being there for your son?

Kelsey: It's not for the faint of heart. My whole family does martial arts, so I block off time to coach his kickboxing and jiu-jitsu classes. That's about eight hours a week. He also plays soccer, so all his sports are blocked off on my calendar. I don't want to miss a game, a stripe ceremony or a belt promotion. I want him to grow up and say, "My mom was always there for me. My mom was my biggest cheerleader." There have been times I couldn't make a soccer practice because of an engagement session, and I feel guilty. But family comes first. That's why I love owning my business. I can set my hours to be with him.

Last week, he had a half day on the last day of school, and the weather was nice. We have a summer bucket list, so I said, "Let's learn to ride your bike." By the end of the day he was riding it, and I started crying. If I'd said, "Screw this, I've got to work," I would have missed that moment.

Peter: How did you manage before he was in school?

Kelsey: We had a part-time nanny for the morning hours, and our town has a half-day preschool. That was the only way I could make it work. It was rough. Now I have set hours during the day. For a later consultation, I tell him, "I need an hour for this call, and then we'll play Legos. Just don't come down and bug me during the call." He understands.

Peter: What would you tell a mom who wants to make $100K a year but is struggling to manage it all?

Kelsey: Find a support system that will help you when you need it. My parents and my husband's parents are more than willing to help. If I have a wedding and my husband has to work, my son can sleep over at their house. During the week, find the times you can get a lot of work done undisturbed. When my son was younger, I had a lot of late nights editing after he went to bed, with the TV on so I was still spending time with my husband.

Peter: What's next for you?

Kelsey: I've moved on to the $100K goal. My 2025 calendar is almost completely booked. I can take about two more weddings, so I might open my 2026 calendar, since people are already asking. I'd also like to ask one of my second shooters to associate shoot for me, because I already have a couple of dates next year I need associates for. In 10 years, I'd like a team, so I can shoot the weddings I really want and also go on vacation and trust the team to take care of clients.

Peter: What was the mindset shift you had?

Kelsey: I'd get off a call thinking, "That went really well, I'm going to book them," and run upstairs to tell my husband. Then they'd say I was too much money or give some other reason, and it would bring me down even further. I was hyping up myself, my husband and my son, and then letting myself down. So I decided to take the pressure off and just have a conversation. I'm still offering my collections on the call, but I'm more relaxed. I'm not in my head about needing the booking. I used to sit stiffly with my script up. Now I sit back in my chair and just chat, and my hands go flying everywhere. Couples tell me, "This was so informative. We really connected with you, and we learned a lot about your process. We're definitely going to book you, we just have to sort out this first."

Peter: It's not just what you do. It's how you do it, and the intention behind it. And active listening matters: hearing what someone is really saying. People can sense that.

Peter: Say there's a photographer watching this who's making $20,000 and wants to make $100,000. They're thinking about signing up with us but they're on the fence. What would you tell them?

Kelsey: If you really want to make that leap, you have to spend money to make money. If you need leads, you should definitely give it a try. I went from $20K to $73K, so I don't have any regrets.

Peter: It's always a leap of faith, and there's a cost, financially and in the work. But it's worth it, wouldn't you say?

Kelsey: Absolutely. You have to put some skin in the game.

Peter: Thanks so much for jumping on today, Kelsey. I'm excited for what's next for you.

Kelsey: Thank you for having me. I hope I inspire at least one other person.