We were lucky to catch up with Kaylee Gresh recently and have shared our conversation below.
Hi Kaylee , we’re so appreciative of you taking the time to share your nuggets of wisdom with our community. One of the topics we think is most important for folks looking to level up their lives is building up their self-confidence and self-esteem. Can you share how you developed your confidence?
Before I became a business owner, I always struggled with my confidence and self-esteem. Whether it was with my weight, my appearance, working with the public at my jobs, you name it and I struggled with it. When I started taking pictures, it was of my sister playing basketball and softball in high school. Some of the other parents had noticed that I was doing so, and had asked if I could also do some of their kids. So I thought to myself “Okay, I must be doing something right” and that gave me a small boost of confidence. Fast forward to when I decided to dive head first into my business of Timeless Treasures Photography. I was still struggling with the confidence of if my photos were good enough. My self-esteem was also taking a hit with the fact that so many other photographers in my area were getting contracted to do events and sessions, but I couldn’t get anything as an up-and-coming photog. But that just drove me to work harder, push myself to make a name that everyone knew. I built up my portfolio, reached out to local arenas for weeknight jackpots, and did a couple session giveaways to start getting my name out there. And soon enough, I was being contacted by different associations to come do shows for them. And in different states to boot! As I was getting contacted more and more, my confidence level was rising along with my self-esteem. I was good enough and my hard work was finally shining through.


Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
So as I had mentioned previously, I started my photography journey doing pictures of my sister and her teammates playing sports in high school. I have always gone after more of the “action” side of things. I had tried my hand with portrait sessions and had quickly decided that that avenue was not meant for me, and that’s okay. I could always revisit that option. But I had always loved horses, and I had one of my own, so I thought to myself “Why not combine my love of both horses and photography?” So I decided to dive into the world of Equine Sports Photography. I started out with more of your contesting events like Barrel Racing and Pole Bending and did that for the first several years. I also did several rodeos and covered our local county fair for the 4H kids as well. But then after some time, I was starting to get bored with the same things over and over. I decided why not branch out? There are so many different disciplines in the equine industry, why limit myself to just one? So I learned about timing and lighting and added every other discipline I possibly could to my resume. Any equine discipline that shows today, I can photograph it. And I am very proud to say that I can do that, and pride myself on that as well. Not many people are able to go from the slow pleasure horses to the fast barrel racers and time everything. I have also got more confident with portrait sessions and have added those back into my work. Over the last year, I have learned a great deal about editing and all the great and fun things you can do with it and have enjoyed adding that in for my clients as well!


If you had to pick three qualities that are most important to develop, which three would you say matter most?
Oh man, this is a tough one. I’ve worked with some top notch people as well as helped new ones coming up so I guess going off of that I would say Confidence, Work Ethic, and Knowledge of what you are photographing. First and foremost, you have to be confident. You have to be confident in your work, in your people skills when talking to clients, communications with your workers, literally everything you do for your business requires confidence. And it’s okay if you don’t have it starting out! You can build as you go, that’s what I did. But you at least need to have confidence in the work you are putting out. Secondly, you need a work ethic no matter what your business brand will be. As for photography and my business, I work very long hours sometimes. Then you add in the hours of processing orders and editing photos after the end of the show. You have to want to work, and you have to want it bad. Otherwise, what is the point of owning a business if you have no work ethic, no grind? You did this to make a name for yourself. That’s why I made my business. And lastly, you have to have knowledge of what you are photographing. Pleasure Horses are way different to photograph than a Cutter or a Reiner, and each discipline has that “shot” they are always working or looking for. You have to make sure you know what each is looking for. The same goes for sessions. You have to know how to pose, how to light, how to edit properly so that your client is happy with their photos.
My advice for anyone early in their journey, is to find someone established and ask to mentor or shadow them. Get a first hand experience so you know what it is truly like. Ask questions! Research things and learn the sport. Make sure you know your camera and gear inside and out. There is a wealth of knowledge out there for beginners and lots of established photogs that are willing to help teach. You are not alone in this industry.


Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?
My dad actually let me use his camera when I was doing pictures of my sister when she was playing sports through high school. I got to use that camera for 2 or so years before he asked for it back. But my mom has been my saving grace when it comes to purchasing cameras and helping get me my start. She bought me my first camera kit from Amazon one year for Christmas. She has also helped me upgrade my cameras and lenses a couple times over the years, that way I didn’t have to deal with credit card debt and interest rates. She has always been my biggest supporter with my photography business journey and I truly don’t know what I would do without her.
Contact Info:
- Website: https://timelesstreasuresphoto.shootproof.com
- Instagram: https://www.instagram.com/timelesstreasures.p/
- Facebook: https://www.facebook.com/timelesstreasures.p


Image Credits
Chelsea Lease Photography – photo of Kaylee sitting in truck
so if you or someone you know deserves recognition please let us know here.
