Peter: Today we're joined by Sean Brown of Move Mountains Co., a wedding studio based in Rhode Island. We want to talk about building, hiring, training and managing high-performing associate teams. Sean, introduce yourself.

Sean: I've been doing video for 10 years, and I started Move Mountains in 2016. I was going to school and needed a way to pay my bills, because I'd cut my hours at work from full-time to about 10 hours a week. I started answering Craigslist ads for second-shooter gigs, and that's how I got into the wedding industry. I realized it was pretty good money and I liked doing it, so I found a few other companies like that and got into the freelance world.

I did that for about three years, working for three different companies, doing some photo and some video. I didn't have my own gear. A friend had a camera and some lenses, and for every gig, I owed him 10%. He was super lenient about it. So I learned with very little investment, and I learned on someone else's reputation. When you work for bigger companies, there's not much of a vetting process. It's, "You're a person with a camera, go shoot this wedding." There's not a lot of training, which is unfortunate, but it was fortunate for me. It took about three years to figure out what I should be shooting and what gear I should use. First I learned on other people's reputations, and eventually on my own.

Peter: How did Move Mountains come about?

Sean: I launched the website while I was in school. I was thinking about leaving my job. It was a good job I felt unqualified for, since everyone around me had college degrees. I asked a mentor if it was foolish to leave and drive Uber in between gigs, and he said, "If that's what you feel called to do, you should do it." Full transparency, I ended up getting fired, so the leap was made for me. I started driving Uber and taking side gigs. Then in November, a client from out of state found the website, saw the pricing and booked us for about $4,500. In my head, I'd said, "If I land this client, I'll invest the $4,500 into advertising." And that's what I did.

Peter: What did you invest in?

Sean: The Knot. It was all the money I had. I was paying about $300 a month in rent, living with friends. I put up the whole $4,500, and I didn't get any leads for about two weeks. I was kicking myself, thinking I'd blown all that money. Then I realized I had no reviews on there. I got reviews from a few couples I'd shot for other companies, some friends, and some commercial clients, and shortly after that, people started reaching out. That made all the difference. In that first season, we booked about 25 weddings.

Peter: I bet you spend a lot more on The Knot now.

Sean: Probably at least $15,000, maybe $20,000. We also get a lot of organic traffic, and we put things in place with vendors in the early years that bring us consistent leads.

Sean: In 2016 we were in full swing as a company, which was really me and a friend from high school, still with no cameras. I borrowed gear until about 2018. We booked those 25 weddings, but there was no real vision for where we were going. I had almost no knowledge of anything.

I remember one defining moment when I was still freelancing. I was doing video at a wedding, and an older gentleman was doing photo. He seemed like a nice guy, but a bit out of touch, and he didn't really connect with the couple. I thought, "Man, I wouldn't want to be his age out here doing a long day like this on my feet in the hot sun." That's when I decided that if I did this, I didn't want it to be Sean Brown Photography. I wanted it under a company name, because I do think it's a younger person's game. I didn't want to shoot weddings forever. So I went into it wanting an associate team. That first year, with 25 weddings, I was already double-booking dates, so I had to have other people. I pulled in a lot of friends at the time.

Peter: How did you get your first associate?

Sean: That first round was really friends, people I knew who were interested in photography or videography. I had no concept of hiring or making job posts. I just leveraged my network, and I was fortunate to know a lot of artists and creative types. We did it that way for about two years.

Then I met someone at church who was a photographer. He said he'd love to shoot with me. I told him I already had photographers, but I really needed a video person, and he was up for whatever. So I took him out for an entire season. Whether I needed a second shooter for video or not, he came to train and shadow. I put him on literally every gig and invested in him for a full season, and he became my first lead videographer.

Around the same time, I met someone at a photography networking group. I checked out her work on Instagram and messaged her: "I love your work and the vision behind your photos. I'd love for you to come to an engagement session and shadow me." She came out, I let her take some photos, and after that she joined the team as a second shooter and eventually led. Both of those people now train my associates. I don't know if I got extremely lucky, but I found two very loyal people who understood the vision and mission of the company, and they've stuck with me and helped train everybody.

Peter: Was she already shooting weddings of her own?

Sean: She was naturally gifted. She had a lot of imagination and was very artistic. She had just graduated from photography school and was looking for an opportunity. She still says she doesn't want to own her own business or do finances. She likes being a shooter, and that's what she does.

Peter: People tell me all the time they're afraid to send someone else out because they won't do as good a job, and it's their name on it. How did you get past that?

Sean: That's a tough one. You're very attached to your brand, and you want people who care about it as much as you do. I have sent out people who were great photographers, but they mailed it in. There's a level of risk every time you send somebody, even when you send somebody you know. So you have to get comfortable with that, and we try not to send out anyone we haven't vetted. Now we have a training process, a system and a shot list. Everyone trains on that. They shadow for a certain amount, second shoot for a certain amount, and eventually lead. It's very systematic now, but in the early days it was not. We were just looking for people to fill gigs.

You have to find people who are likable. That gets overlooked, because the team has to like working with them, you have to like working with them, and your clients have to like them. Character really matters. And the talent has to be there, so vet their portfolio. I've hired top-tier talent, paid the most for it, and they still didn't deliver. So we hire more on ability and bring people through our system. We really care about quality.

Peter: What was going through your head before you sent your first associate out?

Sean: It was really scary. One that comes to mind was a bigger wedding with a bigger client, but I was already booked, so I sent another guy. The footage I got back was just terrible. I tried to edit it, and I couldn't. I sent it out, and luckily the client loved it. Sometimes clients' expectations are different from yours. They wanted a video of their wedding, and this was a video of their wedding. But in the early days, sending people out without a system was very anxiety-ridden.

Peter: Why did you do it anyway, despite the anxiety?

Sean: The limitation. I could only go so far by myself. Back then I was unaware of the luxury market, where you can charge $20,000. Even then, you'll do 10 or 20 of those, and you're still the one shooting the weddings. If you want to be 40 or 50 and still shooting, that's great. But you could also have an associate team that generates a lot more revenue. I guess I'm a bit of an opportunist. We did 25 weddings, and it was more money than I'd ever made doing something I love. People loved the work and kept booking. The second year, we did about 50 or 57. That was a big jump with no admin skills, no sales skills and no team-building skills. I was learning everything in real time. But people kept inquiring, so I had to keep building the team and get comfortable with it.

Peter: How did you handle couples who expected you to shoot their wedding?

Sean: In the early days, that was one of the biggest hurdles. Some days we have four or five weddings, and you can't have them all expecting you to be there. Some clients don't care. Others really connect with you and want you. In 2016 we did 25, in 2017 about 50, and in 2018 about 50 again, because I'd gone back to school that year. In 2019 we did 115, and that's when we hired someone to do our sales and timeline calls. With that separation, I was more behind the scenes. Couples still asked for me sometimes, but we were able to sell our other photographers, and as the portfolio grew, it wasn't all my work going out. At this point, I'm not even the best photographer. But it takes time to build your team and your portfolio.

Peter: In the early years, when couples were still talking to you, how did you sell it?

Sean: It wasn't easy. Transparency is important. I'd send them another shooter's work and be clear on the phone, getting ahead of it: "I have [shooter's name] available for your date." Set that expectation up front. The worst thing is getting on the call, having them ask who their photographer will be, and saying, "Someone from the team." Have an answer ready, and say it before they bring it up.

Peter: The clients I've seen make this transition are really confident in the person they're selling. They'll say, "Honestly, you're better off with this person than with me."

Sean: Right. If you only shoot video, you can say, "I shoot video. Your photographer will be this person." Or, "I just handle the calls." There are ways to pitch it so you're not even part of the equation.

Peter: What do you do if the associate you sold isn't available?

Sean: That's tough. Even with contracts, some people are flaky, so you have to weed that out early. In the early years, we didn't have agreements. It was mostly people I knew, and their word was their bond. But then people get overbooked, or they sell their own $4,000 package and say, "I'm going to take this instead." So hire slow, fire fast. When you see warning signs, like someone flaking on two dates, cut it. Establish a culture where everyone understands these are people's wedding days. Have a policy up front and be clear about expectations. Shooter agreements are really important: what you expect, and what happens if they don't deliver.

When I was freelancing, I wrote down all my dates, and in the hundred or so weddings I shot, I think I flaked on two in the very early days. I saw every gig as an opportunity to learn. I wasn't thinking, "I'll do my shots and collect my $350." I worked hard because I wanted the work to be great, whether my name was on it or the company's. I brought that same hustle to my own company.

Sean: Everything I've learned in business, I've learned in real time. When you make a mistake, it's a mistake with a client and a wedding. That's why having a mentor in the early days would have been valuable. I didn't seek anyone out. There are so many decisions: how to respond to a client, how to hire, which systems to use, how to make sure you got all the files when someone's shooting remotely. One season, we spent nine months fighting with a network storage server we'd bought and knew nothing about. You're trying to make sales, build social media, build your team and hire, and meanwhile you can't edit anything. You always lose money trying to save money.

Even now, I'm always looking for the company that's at the next level, to ask what they use and how they got there. At a certain scale, you have to bring in partners and people who know more than you.

Peter: You don't know what you don't know. You need to be around people who are where you want to be. Otherwise everyone thinks the same and does the same things.

Sean: Building a business has been extremely painful for me. Some seasons you're on the mountaintop, and some you're below ground, wondering if it's time to sell. But each season you learn something new, like building a muscle. What I thought would sink me in 2019 is probably just my day-to-day now.

From a 4-Month Edit Backlog to 2 Weeks (34:21)

Sean: A pain point since we started has been having more edits than bandwidth. Turnaround times in this industry are typically about four months for a video, and we were always editing into the next season. This year, we solved it so well that we're taking on other companies' work, including companies we look up to, and quality hasn't gone down. For a long time, our solution was working our people harder, and that's banging your head against a wall. To fix it, we had to build systems. We got 150 applications for video editors, and we built a system that automates the review and a process for hiring. We onboarded and vetted editors quickly. We had about 175 videos in our backlog, and we cleared it in about two months. Our turnaround for video is now about two weeks.

Peter: Growing a business is just solving the next problem, and you can't get past a certain size without systems and processes.

Sean: When we started, I had all our gigs written on a whiteboard. Then I thought, "What if someone erases it?" So I made my first Google Sheet, and I was super proud of it. Now it's all automated. The contract goes into our production sheet and onto the calendar. Almost every time we realized we needed something, or something went wrong, we built a system for it. This year we've been big on automations.

Peter: Break down hiring, training and managing for us at a high level.

Sean: We always need second shooters. Our core team has been fairly stable. We hired two core members around 2018 and a couple more in 2019. For hiring, we leverage our network first, because good people usually know good people. We ask, "Do you know anybody who does this?" We've moved away from hiring friends. It has advantages, but more disadvantages, and if you care about the friendship, you probably don't want to hire your friends.

Now we have an application. When someone fills it out, it goes into our project management software, which has a pipeline with stages for hiring. We have a PDF that breaks down our entire process. It's not, "Read this document and let's go shoot." You read it, then you shadow, then we review your work. If you pass, you second shoot for a while before you lead a wedding of your own.

We have a format for shooting and for editing. The shooting format came together around 2019 and the editing around 2020. When I was freelancing, I'd go to a wedding and shoot whatever looked nice: a vase of flowers, the flower girl, hair and makeup. I had no concept of the timeline or what shots the editor needed to tell the story. Once it clicked, we built a shot list: what shots we get, the order we get them in, when to leave one location for the next, and how we get them, including the principles and style choices we shoot by. You have to teach all of that.

With video, we had an all-star editor. If one person carries the whole vision of the company, that's a vulnerability. What happens if they leave, or need to be let go but you can't afford to lose them? Then they dictate the culture. We realized there's a storyline we follow for every video. The shooters in the field create the puzzle pieces, and the editor assembles the puzzle. As long as they have the shots, it's a repeatable format we can teach to other editors. If you have a company, it doesn't matter who shoots or edits. It has to look like the other videos and photo galleries.

Peter: How did you learn this kind of systems thinking?

Sean: It came to us in the field. One of the core team members and I realized we got the same important shots every time, so we decided to go in and get those shots. A system also gives you confidence, because every wedding is different. Some couples are relaxed, the weather's great and the timeline is easy. Others are stressed or demanding, the timeline is tight, or it's raining. With a system, it doesn't matter. I show up, say hello, put my gear in a certain spot, find the best light, shoot the details, check in with hair and makeup, and leave at a set time for the next shots. You know exactly what you're doing, and that confidence puts the couple at ease too.

Sean: The other thing that made me think in systems was when bad things happened. A contract didn't get logged, or a date was entered as 9/3 instead of 9/23. That's a small oversight, but it's a wedding. You can't just not show up. So wherever something can go wrong, we ask whether there's a workaround or an automation.

Peter: How do you prioritize what to fix?

Sean: Sometimes it's organic. If I have energy for something, even if it's not the top priority, I'll work on it, because it gives me energy for the other things. Other times, I meet with the core team and ask, "What issues are facing the company right now? Where are we most vulnerable?" We make a list together. Or something major happens. File management is a big one. If we have 20 weddings in a weekend and each video shooter goes out with six memory cards for four cameras, that's a lot of data every week. Before, it was, "Take your card case and bring it back." But maybe someone didn't take a card out of a camera. Now we track how many cards went out and came back, and how many files are on each, so the person importing can check that they match. Client data matters too. In 2016, I had everything on one portable hard drive. I literally had nightmares about someone stealing it or it failing. Now we have redundancies.

Peter: Creating processes is a skill in itself: identifying problems, prioritizing them, and solving them in a way that's repeatable and can be delegated.

Sean: And you have to set up your systems for the lowest common denominator. You'll have all-stars who are creative, great with clients and detail-oriented. You'll also have people who are very talented and great with clients, but organization isn't their strong suit. So your systems need to be dummy-proof. The hardest part is thinking through every "if this happens, then what?" It's mentally taxing, but at our level it's necessary.

Peter: When you need to fix something, how do you build the system?

Sean: Starting on the right foundation matters. In the early days, we spent a long time choosing project management software. If you build on the wrong foundation, it's hard to tear it down, because you're still using it. Over time, we've found software that works well for us. I keep looking for the one that does everything, and I'm not sure it exists yet. Long term, we'd like to build our own system. The software has to be simple enough for the team to understand and fit into their workflow, and it should integrate with other software. When I think through a problem, I ask which of our tools can solve it. We'll design a form that feeds a Google Sheet, which collects data or triggers an automation.

Gear check-in is an example. We send every shooter out with the same kit, four cameras and a drone, about $30,000 worth. If you have 20 weddings and every person loses a $100 battery, you just burned $2,000. So our studio manager checks out what went out and what came back. You could pay for check-out software, or build a checklist with an automation. Zapier does a lot of cool things. Start simple and grow as you learn. That's another place where having someone who's done it before helps.

Peter: What drives you?

Sean: I've always been driven. In bands, I wrote the songs and pushed for practice three times a week, and I made the website and graphics. Life is brief, and it's a gift. I want to do something worth being here for. If I took inventory of my life when I'm older, I want to know I used my time well. The money is good, and the wedding industry is lucrative, but money isn't what drives me. I like to build things.'

Peter: Say someone watching is making $50,000 to $100,000 a year and wants to bring on their first associate. What's your number one piece of advice?

Sean: First, mindset. In the early days, our whiteboard goal was 100 weddings, and I was a little embarrassed to put it up, because I felt like people would think, "Good luck with that." Last year, we did 325 weddings. Then I talked to another CEO whose goal from the beginning was 5,000 weddings, and he did about 1,500 in a season. He built his systems for 5,000 weddings, and I built mine for 100. So build your foundation for what you're going for, even if you fall short. Your systems will be that much stronger.

Whatever you feel called to do, whether it's 100, 500 or 5,000, have faith in it and ask how to do it. Success isn't overnight. It takes seasons. Bad things will happen. The pandemic hurt the wedding industry, but we grew during it, doubled year over year, and stayed profitable. If you stick with it, you pass that test and you're ready for the next one, and you can help the people coming up behind you.

Peter: Mental toughness doesn't get talked about enough with creatives. Every battle you fight through makes you stronger.

Sean: It can be very lonely. Even with a team, the problems are truly yours. Some things have brought me to my knees, where I wanted to shed a tear. I probably would have quit, but I had 150 weddings on the books for the next year, so I had to figure it out. And nothing feels better than winning, like crossing off that 100 weddings on the board and thinking, "I really did that."

Peter: How can people connect with you?

Sean: If you want to take your business to the next level, whether you want better systems and accountability or want to grow an associate team, there are a lot of pain points you'll run into and things you can put in place to make the journey smoother. My email is [email protected].

Peter: Thanks for jumping on, Sean.

Sean: Thank you. I really enjoyed the conversation.