We recently connected with David Montgomery and have shared our conversation below.
David, appreciate you joining us today. Let’s jump back to the first dollar you earned as a creative? What can you share with us about how it happened?
It’s very funny how I came to be an artist, kind of a different path than most. I was in the entertainment industry and made great strides in a relatively short amount of time, but when the pandemic hit, I was not prepared in any way. I wasn’t pivoting – I was trying to stay sane. This is when my neighbor threw out her old paints and offered them to me. I had no intention of making money off of them, which is probably for the best. If I set out to learn the craft as a capitalist, I might’ve been discouraged right away and not have created so much out of love for the subject.
I suffered an unexpected family loss and was devastated being so far away from them in Pittsburgh. I poured myself into teaching myself how to paint, as it was such an escape. It kept my mind focused on a task, kept my eyes on something beautiful, and kept my hands moving toward recreating it. The hours passed and I had something to show for it. When I posted my second finished piece on social media, an old friend reached out to buy it, which was insane to me. First off, I didn’t see myself as a professional, as this was just a pastime. Second, it was just for me! I was painting to decorate my walls with things that I wished were open again in the neighborhood. I had taken a shot of Griffith Observatory and did a somewhat vague interpretation of it that felt right to me, but someone else wanted to offer me money for it. I was in no position to say no, but truly didn’t feel like I had earned it.
When I posted that the painting was sold, I had several people messaging me saying they didn’t realize they were available to purchase, and that they wanted to commission me. It turned out to be such a huge turning point in my life.

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 am a painter that works mainly in acrylics specializing in dramatic landscapes of local landmarks (my biggest inspiration being Los Feliz). Think of a whimsically updated Edward Hopper who drinks at the Dresden before walking to the Vista for a midnight screening. I’m an avid movie lover, so I bring a cinematic sense to landmarks you see every day, painting them in a dramatic, often moody light that you might not always have pictured for it. I sell prints of my works in addition to originals, and have expanded into printing the images on coasters and ornaments for the holidays.

How can we best help foster a strong, supportive environment for artists and creatives?
If you can’t financially support it, share it.
I love when someone reposts my work to their followers when they’ve got a seemingly siloed shared love of something. I gain new followers from those shares almost every time – and that is good for both me and the new follower. I can potentially find a new sale, and they light up when they dive into my catalogue. If they loved the neon vaporwave painting of the Los Feliz 3 theater, they’re going to love the blown-out opening night rendition of the Vista.

Any insights you can share with us about how you built up your social media presence?
Mine is a slow and organic process. I don’t consume a ton of social media, but I post pretty regularly in a way that gives people a window into my actual personality, not just my business. A lot of people feel like this creates a bond in a way that feels more personal than following some company that just posts what they sell. If people find my work through a hashtag and are touched at all by the whimsy of it, they are locked in when they find the goofiness in my Instagram stories.
Contact Info:
- Website: https://mayoroflosfeliz.com
- Instagram: @buymeahotdog




Image Credits
All images (c) David Montgomery, mayoroflosfeliz.com.

