Alright – so today we’ve got the honor of introducing you to Ben Sturdivant. We think you’ll enjoy our conversation, we’ve shared it below.

Ben, looking forward to hearing all of your stories today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.

When I started Legacy Property Media, it was the biggest risk I’d ever taken because I stepped into an industry I didn’t actually know how to work in yet.

I’d always wanted to build something that could scale. My family has a long history in real estate, and after years in the music industry, I realized the one thing I missed most was creating. When real estate and media finally clicked together in my head, it felt like the right lane for me. I understood the real estate world well because of my family, and I understood the creative world because of my career. Even though I’d never run a business before, I trusted that I could adapt.

Financially, my wife and I were in that early-marriage phase where you’re stable, but you’re definitely not floating in extra money. We were about eight months in, had a good savings, and I had just received a semi-annual publishing check from my music catalog. Normally we’d save that or use it for a major bill, but I felt this itch to take a shot. I talked it through with my wife, told her what I wanted to build, and she backed me completely. That meant everything.

Starting the business took more than I expected. By the time I bought the gear and the basics I needed, I had put over seven thousand dollars into something I wasn’t even sure I could do well yet. I had zero confidence starting out. I barely knew cameras, barely knew anything about real estate media, but I forced myself into the deep end. I basically removed the safety net and told myself I’d figure it out before I sank.

There were plenty of moments that made me question it. Slow weeks. Outreach that went ignored. Days where I felt like I had no idea what I was doing. When you take a big financial swing without proof you’ll ever make it back, those quiet stretches hit different.

But in July, my third month in business, everything shifted. I hit a financial goal I originally thought was unrealistic to hit even once by the end of the year. Then I doubled it the next month. That was the moment I realized, “Yeah, this is real. This is working.”

Taking that risk changed everything. It gave me a business, a mission, and a sense of confidence that I didn’t have before. It showed me I could build something from scratch, serve people well, and actually make a living doing it. Looking back, dumping almost all of that check into Legacy was the scariest decision I’ve ever made, but it was also the most important one.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m Ben Sturdivant, the founder of Legacy Property Media, a real estate media and marketing agency serving agents across Arkansas. Legacy was born from two parts of my background finally lining up. I’ve always been creative, and I grew up around real estate. When I stepped into this space and started working with agents directly, I realized pretty quickly that this is where I belonged. The relationships, the impact, the ability to help someone present their listings at a higher level — it all clicked for me.

Legacy provides everything an agent needs to market a property well: interior and exterior listing photos, aerial drone photo and video, premium video tours, agent feature videos, 2D and 3D floor plans, Zillow and Matterport 3D tours, and virtual enhancements like virtual twilight and virtual staging.

A lot of agents come to me because they’re dealing with inconsistent media, unreliable scheduling, or photographers who aren’t great around their clients. I try to eliminate those headaches by being someone they can trust with their listings and their homeowners. Fast turnaround, clear communication, and professionalism are the things I get complimented on the most.

What sets Legacy apart is how personal the partnership is. I don’t just show up to take pictures. I try to be part of the team. I want agents to feel like they have someone in their corner who genuinely cares about how their listings perform.

The thing I’m most proud of is seeing my clients win. When an agent tells me a home went under contract in a day, or refreshed media brought new attention to a stale listing, that’s the most rewarding part of this work. At the end of the day, I want people to know that Legacy isn’t just a media service. It’s a business built to help agents succeed, and I take that seriously every single day.

Where do you think you get most of your clients from?

Referrals have easily been the best source of new clients for me. Most of the time, it’s agents telling another agent, “You need to check out my media guy.” They usually highlight a mix of things: the quality, the turnaround time, and that I’m easy to work with around their homeowners. Hearing that from them carries a lot of weight.

What means the most is that most referrals come from my top clients and top producers. These are people who have been in the industry long enough to know good media when they see it. They’re real players, and the fact that they vouch for me tells me I’m doing something right.

One of the best examples is actually how I got into ERA. One of my earliest clients was a top broker at their office. After the first shoot went really well, we kept working together and her results started to get attention. Other agents saw what she was doing, heard what she was saying, and the word spread through the whole office. It eventually reached their sister offices across the state. That one relationship ended up opening a ton of doors for me.

How about pivoting – can you share the story of a time you’ve had to pivot?

A major pivot for me came when I realized I had to stop thinking like a creative and start thinking like an actual business owner.
When I launched Legacy, my entire pricing structure was built around photo count: 20, 40, or 60 images. It sounded simple at first, but in reality it caused more problems than it solved. Agents were booking 20 photos for homes that needed way more, or booking 60 for homes that didn’t need even half of that. I’d shoot everything the home needed, then cap myself at whatever number they purchased, and that’s where it started to break down.

One specific moment that made everything click was a home where the agent booked only 20 photos. I shot the whole property, narrowed it down to the best 20, deleted the rest, delivered them… and immediately got a message asking for a certain angle. I had shot it. I had deleted it. They ended up taking the photo themselves. That was a gut punch. It was the first time I said, “This can’t be the right way to do this.”

And it wasn’t just the booking side that was broken. The editing process became a nightmare. I’d spend 20 extra minutes per home I shot just counting photos, narrowing them down, rechecking what could be trimmed, second-guessing shots, and basically trying to solve a self-created puzzle that had nothing to do with quality. It made delivery slower, more stressful, and completely inconsistent. Instead of focusing on the best photos, I was focused on hitting a number.

Then I had a week with multiple shoots where agents underbooked what the home needed. Back to back to back. I hit my breaking point.

That’s when the pivot happened.
But it wasn’t only the pricing model that changed, it forced a mindset shift. I realized I couldn’t keep treating Legacy like a creative passion project. I had to start treating it like a real business. I started asking myself harder questions. Is this sustainable? Is this profitable? If someone bought this business tomorrow, would the systems make sense or would they wonder what on earth I was doing?

Switching to a pricing model based on the home’s square footage instead of the photo count changed everything. Now I walk into a shoot and just capture what the listing needs. I don’t have clients missing angles. I don’t worry about trimming sets down to arbitrary numbers. Editing is faster, cleaner, and way less stressful because I’m not playing “what do I cut.” And clients never have to worry about booking the wrong package ever again.

That combined pivot, changing my pricing and changing my mindset, is one of the biggest reasons Legacy feels like a real, scalable business now instead of a creative hustle I was trying to hold together.

Contact Info:

• Website: https://www.legacypropertymedia.com/
• Instagram: https://www.instagram.com/legacypropertymedia/
• Facebook: https://www.facebook.com/legacypropertymedia