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Daily Inspiration: Meet Reese Oliver

Today we’d like to introduce you to Reese Oliver.

Hi Reese, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My origin story:

I served in the Army reserves for 6 years and my best friend in my unit at the time was gifted photography equipment. We picked a random day to head to Detroit and went to explore the old Woodmere cemetery, an abandoned old Detroit Police Office and an old high school. It was in that high school where we were approached by a random man and decided it was time to get out of there and we took off. During that adventure, she told me to only use manual mode and changed the settings. I was extremely frustrated as I could not figure out how to get my photos in focus. By the end of the day, I had figured out how to use the camera and get photos in focus. Upon returning home, said I wanted to do this everyday forever. At home, I decided to make business cards on Vistaprint. I, quite literally, called myself a photographer, while not owning a laptop or camera, but I made up my mind that this was going to be my life. That was November 2014. January 2015, I photographed my very first wedding at The Whitney in Detroit for $500 (I had purchased a Canon Rebel T5 and T5I).

Now, with over 500 weddings under my belt (my own plus second and associate shooting), I have traveled across the US (about half of the country, to date), the Dominican Republic, Mexico, Paris and Scotland!!!

Word of mouth got me started, honestly. I photographed a few of my high school friends weddings and they mentioned Facebook groups. I joined them and spent some money using Thumbtack. Everything for me started with social media. It wasn’t until Covid when I got my first website!!

At the time of all of this, I was running a cell phone store full time. When I could, I would choose not to take lunch and leave an hour early to have sessions or I would use my lunch break for photo sessions. Eventually I left the store and was working other jobs while slowly picking up more and more photo work. Including local proms, events and graduations for the local newspapers.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
My biggest mistake and learning experience was not having boundaries or set working hours. I also had no clue what I was doing business wise. So my biggest tip to anyone wanting to get into this industry is to have a thorough understanding of business, a business plan and goals. Please do not ever shoot a wedding without insurance, that is non-negotiable.

Please have boundaries. No one needs to be texting you at 9pm, 10pm or 6am unless it is an emergency the day of their event or session. You are allowed to separate yourself from your work and I wholeheartedly believe you will be much better off when you have established business hours, systems and boundaries.

I have endured things that I thought were career ending. I have been defeated more days than I’d like to admit. Not because my heart wasn’t/isn’t in it or because my work was bad, it was truly because there were never any systems in place. Working a full time job 5 days a week and using every available moment and weekend I had for photography is extremely taxing and unsustainable. I’ve had colleagues (other photographers) intentionally lie about me and their experience with me on social media to “get my attention” when I wasn’t communicating back fast enough for them (on Thanksgiving, nonetheless).

Do not ever delete text messages, emails or contracts. You never know when you will need receipts. Social media is both a blessing and a curse and it makes it too easy for a mob mentality to form without the “mob” having a clue what the situation actually was or the details and inclusions that were listed in the contract. People will always have something to say, let them talk and keep doing what you do best! Being a human and having empathy is important, so is sticking to your contract.

Thankfully, I was able to leave my day job four years ago and have been able to dedicate and devote myself to this craft and it was truly the best thing I have ever done. Make sure you have substantial savings before making that move. Some months bookings will be multiple times per week and some months will be slow. Preparation is key!!! Think about what you want your business want to feel and be in 5+ years, then take action steps to make it happen. Little by little.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
The majority of my work are weddings and elopements. Halloween sessions are my favorite type of sessions and it’s one of my busiest seasons each year.

I am most proud of the fact that this kind of fell into my lap, completely unexpected and unplanned and now I’m almost coming up on my 12th year of doing what I love. I’ve had both travel (Egypt) and couples work published and featured across many platforms. Archipelago presets featured work I created in Paris, Beyond The Shutter (which was owned by Sal CIncotta) published a handful of my Egypt travel photos, WeddingDay Magazine just invited me to photograph their cover shoot, many halloween sessions have been featured on Unscripted, the list goes on. The features and publications are amazing, but that’s not why I love this work.

I think my origin story sets me apart as well as the fact that the love of what I do stems from grief, loss and regret. It’s not your typical story.
When I came out of boot camp, I wanted a photo with myself, my mother and my gramma (as I lovingly spell it), my mother didn’t want to get in front of the camera so it never happened. Then, I lost my gramma who was my best friend and that photo will never be able to be created. I don’t want anyone to feel that way. My about me on my website highlights this and the importance of photography in my life. I have lost so many people that were such integral parts of my childhood and seeing them immortalized forever in print is so special. It also reminds me that I really need to be encouraging wedding albums.

What was your favorite childhood memory?
I was with my Gramma 5 days a week until I was a freshman in high school. During the school year, mom would drop me off, Gramma would pick me up. In the summer, mom would drop me off and we had adventures. I was at the bowling alley twice a week with them, playing all the video games I could as I was not allowed to have any at home.

I was so spoiled by everyone, but my Gramma was such a sucker for me, her only biological grandchild. I was just talking Sunday about how she would take me to Montgomery Ward to get me Lee Pipes jeans and JNCO jeans (mom did not approve). I spent summers dragging her to Toys R Us to get Pokemon cards, Macomb mall for all sorts of things and we loved the Little Caesars inside of KMart (crazy bread forever).

There was a lot of love in my childhood, especially around the holidays. The majority of those people were older (in their 70s when I was a kid) and have now passed on. I am so grateful for the photos and cards I have from the people that made sure I felt loved.

Pricing:

  • Weddings begin at $3,495
  • Sessions begin at $550
  • Elopements begin at $995

Contact Info:

Person standing on a wooden dock by a body of water, holding a drink, with a boat in the background.

Man crouching on sandy beach taking a photo with a camera, ocean and shoreline in background

Person balancing on one leg on the beach, raising one arm, holding a camera, with water in the background.

Two people taking a mirror selfie in a room with blue curtains and a window, one adult and one child, both holding cameras.

A bride and groom kiss on a rocky landscape at sunset, with a photographer capturing the moment, and mountains in the background.

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