Corey Boyles: From Real Estate Investor to Building a Thriving Photography Empire
Can you please share a brief history about your photography business? What motivated you to start this venture?
I bought my first camera in 2015 (a Canon T5i) just for fun. At the time, I was a full-time real estate investor and wanted to start taking my own photos of the houses we flipped and rented out. I dove into YouTube tutorials and Facebook groups to learn as much as I could. Photography quickly became a hobby and a new frontier of learning for me.
After attending the ShutterFest conference in 2016, I began connecting with photographers and educators to explore where my interests in photography might lead. In 2018, I officially launched my business, “Corey Boyles Photography,” and started shooting anything I could—families, engagements, real estate, video, headshots. I was experimenting to find my niche and discovered that I really enjoyed working with business professionals the most.
By 2019, I transitioned full-time into real estate and headshot photography, gradually stepping away from my real estate investing endeavors to pursue my passion. In 2022, I began scaling my real estate photography business by adding more shooters, editors, and an assistant. Then, in 2023, I launched “The Headshot Company,” a dedicated headshot studio.
What kind of challenges did you face when building up your portfolio or setting up your studio? How did you overcome these challenges?
Knowing my value and how to communicate it was key. I had to find pricing that worked for both myself and my customers. After mastering the technical aspects of photography, I focused on learning how to work with people for headshots and how to handle common real estate photography challenges. I reduced much of that stress by outsourcing tasks I didn’t enjoy or wasn’t naturally skilled at.
I also did a lot of personal work to better understand how I was helping people through headshots. Coaching played a crucial role in my growth—I’ve hired several executive business coaches and three photography coaches along the way.
Could you describe the early days of your business? What were the initial reactions and feedback you received?
It was so much fun. I wasn’t making much money—I just loved what I was doing. I only charged enough to eventually upgrade my gear. People were incredibly supportive of me, even though my work was what you’d expect from someone just starting out. I believe that not being overly tied to a specific financial goal or success outcome allowed me the freedom to fully enjoy the process when I was starting out.
How did you manage to grow and expand your business? What strategies did you use to attract more clients?
I started by serving the sphere of influence I was already part of—the real estate network in St. Louis. Having already built connections with investors and agents, I simply needed to share what I was doing, and they began giving me opportunities. I also started sponsoring real estate investor clubs in St. Louis, aiming to become “The Guy” for real estate investors. Additionally, I run some Google advertising to expand my reach.
How has your business performed financially over the years? Can you share some milestones or achievements in terms of revenue?
Here is a snapshot of my yearly revenue for the last 6 years:
- 2018 : -$1,860
- 2019 : $18,874
- 2020 : $35,266
- 2021 : $99,548
- 2022 $131,966
- 2023 : $158,443
- 2024 : $339,978
What are some key lessons you've learned along your entrepreneurial journey? Is there anything you would do differently if given a chance?
What drives me and fuels my passion may change over time. I’ve learned that my path is easiest when I let go of things that no longer interest me and focus on what truly excites me.
Building a genuine human connection with my subjects is one of the most important things I can do—not just for my business, but for my current calling.
I’ve also discovered the value of setting clear expectations for clients, enforcing my policies, and standing up to bullies while showing grace to those who value a good working relationship.
Above all, relationships matter more than any marketing strategy. Reputation is everything, and staying true to my virtues and values is essential for long-term success.
Are there any tools or software that have been particularly useful in managing and growing your business? Give us a list of what you use in your kit.
For tools and software, several have been instrumental in managing and growing my business:
- Aryeo for real estate systems
- 17Hats for commercial, headshots, and other invoicing and scheduling
- A VA from the Philippines for miscellaneous business tasks
- Vietnam Editors for real estate editing
- The Voxer app for team field communication
- Novation for process documentation and new hire company requirements
Could you recommend any books, resources, or mentors that have significantly influenced your business journey?
Books that have shaped my mindset and approach:
- Atomic Habits by James Clear: A practical guide to building good habits, breaking bad ones, and mastering the small, consistent changes that lead to remarkable results.
- Breaking The Habit of Being Yourself by Dr. Joe Dispenza: A transformative book that combines neuroscience, quantum physics, and spirituality to help you reprogram your mind and create the life you truly want.
- Building a StoryBrand by Donald Miller: A must-read for anyone in business, this book teaches you how to clarify your message and connect with your audience by framing your brand as the guide in their story.
What advice would you give to budding entrepreneurs who wish to start their own photography business?
Try to find problems to solve for people—problems they don’t even realize they have. Being responsive, actually following up with leads, and sending quotes has put me miles ahead of most of the competition. Don’t be afraid to make calls or send out those “scary” quotes.
Know when to shift from being passion-minded to business-minded. Don’t let the joy of your work stop you from charging what you’re truly worth. You can be worth whatever you say you are—if you understand what people REALLY want and know how to communicate it effectively.
Take your time learning. Progress may feel slow, but it’s faster than you think. One day, you’re figuring out how to change the opacity of a Photoshop brush, and the next, you’re driving past your work on billboards and national advertising campaigns. Enjoy every moment in between.
Corey Boyles is a professional photographer and founder of The Headshot Company, based in St. Louis. With a passion for capturing authentic and confident images, he focuses on headshots and commercial photography, helping clients stand out and achieve their professional goals.
About Corey
- Country: United States
Specializes in
- Commercial Photography, Headshot photography, Real Estate Photography
Quote
Relationships are more important than any marketing strategy. Reputation is everything, and doing whatever it takes to maintain my virtues and values is crucial.