We recently connected with David Oliver and have shared our conversation below.
Alright, David thanks for taking the time to share your stories and insights with us today. If you could go back in time do you wish you had started your creative career sooner or later?
The Midnight Muralist
The door slams, Ollie has packed the vehicle to the ceiling of ladders, paints, drop clothes and a billion other things to get the job done. He leaves his family in the safety of the bed, with his wife. As the car starts and peels out into the night, you can hear an old Allman Brothers classic on the radio. “I got one more silver dollar, I’m not going to let them catch me, no. Not going to let them catch the Midnight Rider…” As the world closes its eyes and falls into the dream realm, Ollie loses sleep to make a dream come true.
In high school I saw an article in the Richmond Times Dispatch with a photo of Ed Trask. He had recently been on a spree of murals in downtown Richmond (around 1998). I thought it was so cool and unique. I wanted to do that, but how? There are no schools or lesson for that. It was the late 90’s, you would have to know someone and they would have to care enough to explain it to you. I was just a dumb high school kid, so I just made a mental note in the back of my head labeled, “Coolest job in the world, but probably wont happen for me,” and moved on. Soon I would be graduating and would have to head off to college to pursue “higher learning”. Of course, I would choose an art college (SCAD, with a scholarship, btw!) but I didn’t know what I wanted to do. It seemed you were suppose to have everything figured out but nothing in my life for me was ever figured out. I always just went with the flow, and life just seemed to happen. At first I studied graphic design, but soon a voice in the back of my head would say, “This ain’t you kid!”. Soon, I would drop out of school and start building houses. It was an honest living, but after a few years I would return with a new perspective. I started back at SCAD as an illustration major, and after a year I switched to Advertising and Branding. I loved it. It allowed me to do everything and meet everybody. Designing custom campaigns and selecting styles to best display and redefine products was so entertaining.
Soon I would graduate as it was time to relocate and start a career. After college I would fall back on another skill set to pay the bills. I would start coaching at an MMA Gym in Richmond, VA. called Total Victory MMA and Crossfit. I put all of my talents to use for the gym. I coached classes, designing programs, did graphics, wrote, copy, and created an after school program. At Total Victory I had a lot of freedom to experiment. I worked 8am to 9pm and kept a bar backing job on the side. I did this for 5 years. Dave Womack (if you know you know) and the Total Victory crew gave me an immense sense of brotherhood in a lost era of my life. I realized I loved people and watching them achieve their goals. While coaching there, I would meet a muralist (A true wall dog!) named Caesar. I possessed raw talent, but Caesar would explain the history of sign painting, graffiti, techniques and the tricks of the trade to me. I could relate to him more then my college professors. He had passion, talent, a sense of humor, and a magnetic ability to attract calamity. I had a blast riding the highs and lows with him. I owe him a special thank you.
I met my wife while working at Total Victory MMA, and she was offered a travel job in dialysis. It paid more then what we were both making together. We got married and started traveling. We had a child while on the road. She really changed me. Life on the road was bitter sweet. I loved being with my daughter all day and taking care of her. I got to take her on walks, explain things to her, teach her about art and the world around her. The price tag came with shame. My wife had to work so hard. I started getting up at 3 am and working on children’s books, logos, illustrations, and anything for anyone we met on the road. Caesar would occasionally fly me out to hop on some murals from time to time. I was perplexed how I would ever get us out of travel and replace my wife’s income.
Finally, we came to Washington and I got a job teaching Jiu Jitsu in Washougal, WA. My wife stopped working and we had our second child. My second child also changed me, he forced me to realize I have to do something bigger. I realized I have to starting betting on myself. I started doing murals here and there after work. I worked 7 days a week forever but when a mural was going on, sleep was nonexistent. I didn’t advertise. Things just unfolded by word of mouth. November 2024 would start a chaotic year for me. I would have my position at the gym cut back, which forced me to get a night job working security in Portland. I witnessed the lowest of the lows as I was guarding drug rehabilitation centers overnight. Administration changes effected the security job and they would loose contracts so I would loose employment. Such is life. I would then get a temp job doing office work. I had never really learned much about running a business and it was a good lesson about my strengths and weaknesses in those sectors. After 6 months my temp job was up and it was time to move on. I am grateful for all of these events and set backs. The ups and downs tempered me in all the ways I needed.
Ultimately it changed my state of mind. I love people and had invested in them, but when you have a family you must make sure you invest in yourself. Over the years I had painted some beautiful things and got my name out there. This year I have no set job. I’m just painting murals for companies and residents. I’m still coaching in the combative sports. I’m throwing myself out there and somehow I know the universe will catch me. I has been waiting on me to have the courage to be my best self. I was never really afraid of a particular failure, except the pressure of rising to my true potential. The higher you go the longer the fall. My wife is scared. I placed an ad out for mural work and in one day four businesses contacted me. I made a bunch of ads and over the month got a bunch of leads. I got multiple projects being scheduled from January – March 2026. This is the beginning of my success… like REAL success. If you see a teal Mitsubishi hatch back flying down the interstate, in the dead of night, with ladders, buckets, and brushes barely hanging on, know I got one more silver dollar and I wont let them catch the Midnight Muralist!
David, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I’m marketing myself as a muralist. I’m really a life long artist, illustrator and lover of anything art. I love illustration and I have a background in advertising. I am good at conveying messages through lettering, copy, photos and illustrations. Illustration can be so magical because less is more. You want to reduce things down to their core and just ad a flare of character. The simpler the image and the more you focus the essence or emotional common ground of a thing the more people can relate to a thing. Murals are just big illustrations. I want businesses to use me to create unique environments for their customers to go through. It could be eye catching to lore someone into the store or something to create a mood like a dark wall with a few massive Maroon pedals. It could be a realist piece of someone doing something noteworthy and just paying homage to it.
Looking back, are there any resources you wish you knew about earlier in your creative journey?
Yeah but it’s not a resource from the outside, it’s courage from the inside. It’s risk of a thing that brings you to life. That’s the moment your truly living. I was so afraid of all the things that could go wrong that I could not see all the things that could go right. I do believe the timing worked out for me but if I told you, you needed to fail a 100 times to succeed would you not just start failing and get it over with? That fear held me back for years! Your mistakes are your greatest teacher and offer the greatest change. The goal is not perfection but almost perfection. The eye, I believe sees the beauty in flaws, they just need to be micro flaws.
Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
In high school it took me forever to complete a piece. I would be about 75 percent done with a painting and suddenly fear would engulf me. This was later remedied my freshman year in college in a drawing 101 class. It was the beginning of my freshman year, first quarter. The first project, the professor informed us it would be a 2 week long project. The piece was to be a very large and super detailed still life. Students poured their hearts into it as everyone was trying to validate and prove themselves. The professor left the still life up and kids would come in after hours to draw from the set up. At the end of the two weeks the professor held a in class critic. There was one catch, you could only receive two scores, a 100 or a 0. If you got up, showed the class the work and then destroyed it in front of everyone, you would receive the 100, otherwise you earned yourself a 0. Remember, people worked for two weeks on these things. There were kids crying, angry, some walked out, and I would not be surprised if that moment ended a few art school journeys. In that moment I realized what he was doing and why I always has a hard time completing work. The professor then stated out loud, “Don’t fall in love with your work, fall in love with working!” It all made sense and if you are ever going to make money doing art you need to understand that. I laugh at that memory, it’s as if God himself came down in deguise and with a smirk said “Got cha!”.
Contact Info:
- Website: https://www.ollieillustrations.com
- Instagram: @ollieillustrations
- Facebook: https://www.facebook.com/share/1Au7YPipAQ/?mibextid=wwXIfr
- Linkedin: https://www.linkedin.com/in/david-oliver-46a0b4173
Image Credits
David Oliver